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Oak Bluffs, MA Homes for Rent

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  • 39 Old Coach Rd, West Tisbury, MA 02568
    39 Old Coach Rd, West Tisbury, MA 02568
    39 Old Coach Rd, West Tisbury, MA 02568
    /14

    $8,400 per month

    • 4 Beds
    • 3 Baths
    • 2,148 Sq Ft
    • House for Rent

    39 Old Coach Rd, West Tisbury, MA 02568

    Summer weekly rental only! June weekly rate is $8,400 and July weekly rate is $10,000/week - Sunday to Saturday. Recently renovated 4 bedroom, 3 bathroom home that sits on a private 2 acre lot in West Tisbury MA! This large cape house has just been update with new stainless steel appliances, new kitchen cabinets and countertops. Other updates include, new bathroom vanities and hardware,

    Joseph D'Amico Dee Development Company

    39 Old Coach Rd, West Tisbury, MA 02568
  • 11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    11 Hammett Ln, Chilmark, MA 02535
    /20

    $4,250 per month

    • 2 Beds
    • 2 Baths
    • 1,152 Sq Ft
    • House for Rent

    11 Hammett Ln, Chilmark, MA 02535

    **BOOKING SUMMER 2024** Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime

    Allison Cameron Parry Douglas Elliman Real Estate - Nantucket

    11 Hammett Ln, Chilmark, MA 02535
  • 29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
    /10

    $8,500 per month

    • 3 Beds
    • 2 Baths
    • House for Rent

    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL PROPERTY!! Red Farm, Off Lambert's Cove Road West Tisbury. This newly built Contemporary Home is privately sited overlooking a peaceful meadow and wooded setting. The spacious floor plan features an open living, dining and a well equipped chef's kitchen, cathedral ceilings, wood floors and sliders that lead to a nicely landscaped yard. Three spacious bedrooms, the primary

    Karen Overtoom Karen M. Overtoom R.E.

    29 Bea Lane Wt160 Unit 1, West Tisbury, MA 02575
  • 5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
    /8

    $16,000 per month

    • 7 Beds
    • 3.5 Baths
    • 4,000 Sq Ft
    • House for Rent

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite.

    Karen Overtoom Karen M. Overtoom R.E.

    5 Wauwompauque Trail Unit 1 CH213, Chilmark, MA 02535
  • 46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
    /8

    $11,800 per month

    • 4 Beds
    • 4 Baths
    • 2,612 Sq Ft
    • House for Rent

    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL PROPERTY!! Beautifully updated contemporary home with impeccably landscaped lawns and gardens, a swimming pond and hot tub with two outdoor showers - one enclosed and one open to the hot tub and patio area on the side of the house. Gorgeous back deck with outdoor dining accessible through sliding glass doors from the dining room. Inside, enjoy the fully equipped and

    Karen Overtoom Karen M. Overtoom R.E.

    46 Buttonwood Farm Rd Unit 1, West Tisbury, MA 02575
  • 44 Music St Wt153, West Tisbury, MA 02575
    44 Music St Wt153, West Tisbury, MA 02575
    44 Music St Wt153, West Tisbury, MA 02575
    /12

    $6,180 per month

    • 3 Beds
    • 3.5 Baths
    • 1,872 Sq Ft
    • House for Rent

    44 Music St Wt153, West Tisbury, MA 02575

    PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

    Karen Overtoom Karen M. Overtoom R.E.

    44 Music St Wt153, West Tisbury, MA 02575
  • 227 S Gate Rd Wt120, West Tisbury, MA 02575
    227 S Gate Rd Wt120, West Tisbury, MA 02575
    227 S Gate Rd Wt120, West Tisbury, MA 02575
    /8

    $8,250 per month

    • 7 Beds
    • 5 Baths
    • 3,528 Sq Ft
    • House for Rent

    227 S Gate Rd Wt120, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY PROPERTY!! Set on 12 acres of peaceful woods, meadows, stone walls and its own pond, this charming 18th century 4 bedroom farmhouse and 3 bedroom rustic barn sleeps 12 and is perfect for larger groups wanting peace and tranquility all within a short distance to private swimming beaches. The setting, on exclusive Seven Gates Farm, offers miles of sandy trails through

    Karen Overtoom Karen M. Overtoom R.E.

    227 S Gate Rd Wt120, West Tisbury, MA 02575
  • 15 Crowell Lane Wt119, West Tisbury, MA 02575
    15 Crowell Lane Wt119, West Tisbury, MA 02575
    /2

    $10,000 per month

    • 6 Beds
    • 3.5 Baths
    • 2,100 Sq Ft
    • House for Rent

    15 Crowell Lane Wt119, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!Seven Gates Farm. This property has three ponds, overlooks rolling meadows and is very charming. Located in Seven Gates Farm association, the property affords access to association tennis and two miles of private beach as well as miles of walking trails. Bookings for tennis are available at the office for a slight fee.There is a $25 trash charge per

    Karen Overtoom Karen M. Overtoom R.E.

    15 Crowell Lane Wt119, West Tisbury, MA 02575
  • 165 Christiantown Rd, West Tisbury, MA 02575
    165 Christiantown Rd, West Tisbury, MA 02575
    165 Christiantown Rd, West Tisbury, MA 02575
    /8

    $4,800 per month

    • 3 Beds
    • 3 Baths
    • 3,279 Sq Ft
    • House for Rent

    165 Christiantown Rd, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY PROPERTY!! The home is set on six beautifully landscaped acres with original stone walls. It is located in private historic Christiantown on the North Shore, a short distance from both Lambert’s Cove Beach and Cedar Tree Neck Wildlife Reserve. Cedar Tree is a habitat with tumbling streams and freshwater ponds, sandy beaches and rocky cliffs, tall oaks and cool beech

    Karen Overtoom Karen M. Overtoom R.E.

    165 Christiantown Rd, West Tisbury, MA 02575
  • 33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
    /8

    $4,500 per month

    • 2 Beds
    • 2 Baths
    • 1,393 Sq Ft
    • House for Rent

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535

    THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

    Karen Overtoom Karen M. Overtoom R.E.

    33 Menemsha Inn Rd Ch223 3, Chilmark, MA 02535
  • 56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    /8

    $8,000 per month

    • 4 Beds
    • 4.5 Baths
    • 3,600 Sq Ft
    • House for Rent

    56 Chilmark Rd, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • 40 Sweet William Way, West Tisbury, MA 02575
    40 Sweet William Way, West Tisbury, MA 02575
    40 Sweet William Way, West Tisbury, MA 02575
    /42

    $19,000 per month

    • 6 Beds
    • 6.5 Baths
    • 6,950 Sq Ft
    • House for Rent

    40 Sweet William Way, West Tisbury, MA 02575

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY! This stunning home is situated right in the heart of West Tisbury, yet set back enough for a completely private feel. On a property that encompasses 10 acres with your own private pond, you will feel the stress melt away as soon as you get to this luxury vacation home. Keys to private Quansoo Beach Association come with the house. Spend your days on the

    Karen Overtoom Karen M. Overtoom R.E.

    40 Sweet William Way, West Tisbury, MA 02575
  • 99 Pond Road Wt104, West Tisbury, MA 02575
    99 Pond Road Wt104, West Tisbury, MA 02575
    99 Pond Road Wt104, West Tisbury, MA 02575
    /39

    $46,000 per month

    • 6 Beds
    • 4.5 Baths
    • 3,800 Sq Ft
    • House for Rent

    99 Pond Road Wt104, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!! Beautiful bright sunny home with open concept living. Main floor features a gourmet kitchen with stainless appliances, breakfast bar and formal dining table to seat 10. Large glass sliders open up to expansive views of the deck, pool and pasture beyond. Also on the main level is a separate living area with large screen TV, powder room, and den with twin

    Karen Overtoom Karen M. Overtoom R.E.

    99 Pond Road Wt104, West Tisbury, MA 02575
  • 224 N Rd Ch248, Chilmark, MA 02535
    224 N Rd Ch248, Chilmark, MA 02535
    224 N Rd Ch248, Chilmark, MA 02535
    /3

    $13,200 per month

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • House for Rent

    224 N Rd Ch248, Chilmark, MA 02535

    THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room.

    Karen Overtoom Karen M. Overtoom R.E.

    224 N Rd Ch248, Chilmark, MA 02535
  • 37 Mempremagog Ave Vh410, Tisbury, MA 02568
    37 Mempremagog Ave Vh410, Tisbury, MA 02568
    37 Mempremagog Ave Vh410, Tisbury, MA 02568
    /28

    $32,000 per month

    • 4 Beds
    • 4 Baths
    • 3,200 Sq Ft
    • House for Rent

    37 Mempremagog Ave Vh410, Tisbury, MA 02568

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous custom designed and decorated four bedroom home is located in a wooded setting that offers total privacy and is with-in walking distance to a private association beach. And yet is only 3 miles from downtown Vineyard Haven. This lovely home offers a gourmet eat-in

    Karen Overtoom Karen M. Overtoom R.E.

    37 Mempremagog Ave Vh410, Tisbury, MA 02568
  • 6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    6 Trails End Ch241, Chilmark, MA 02535
    /26

    $50,700 per month

    • 4 Beds
    • 3 Baths
    • 2,346 Sq Ft
    • House for Rent

    6 Trails End Ch241, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for

    Karen Overtoom Karen M. Overtoom R.E.

    6 Trails End Ch241, Chilmark, MA 02535
  • 44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, Chilmark, MA 02535
    44 Flanders Ln, Chilmark, MA 02535
    /19

    $24,000 per month

    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft
    • House for Rent

    44 Flanders Ln, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

    Karen Overtoom Karen M. Overtoom R.E.

    44 Flanders Ln, Chilmark, MA 02535
  • 384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    384 Middle Rd Ch222, Chilmark, MA 02535
    /31

    $40,000 per month

    • 6 Beds
    • 6 Baths
    • 3,960 Sq Ft
    • House for Rent

    384 Middle Rd Ch222, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four

    Karen Overtoom Karen M. Overtoom R.E.

    384 Middle Rd Ch222, Chilmark, MA 02535
  • 31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    31 S Ridge Rd Ch218, Chilmark, MA 02535
    /20

    $16,800 per month

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft
    • House for Rent

    31 S Ridge Rd Ch218, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and

    Karen Overtoom Karen M. Overtoom R.E.

    31 S Ridge Rd Ch218, Chilmark, MA 02535
  • 29 Cemetery Rd Ch216, Chilmark, MA 02535
    29 Cemetery Rd Ch216, Chilmark, MA 02535
    29 Cemetery Rd Ch216, Chilmark, MA 02535
    /32

    $36,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,600 Sq Ft
    • House for Rent

    29 Cemetery Rd Ch216, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half

    Karen Overtoom Karen M. Overtoom R.E.

    29 Cemetery Rd Ch216, Chilmark, MA 02535
  • 2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    2 Strikers Way Ch211, Chilmark, MA 02535
    /33

    $22,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    2 Strikers Way Ch211, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable

    Karen Overtoom Karen M. Overtoom R.E.

    2 Strikers Way Ch211, Chilmark, MA 02535
  • 56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    56 Chilmark Rd, Chilmark, MA 02535
    /23

    $24,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,637 Sq Ft
    • House for Rent

    56 Chilmark Rd, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Relax and enjoy this majestic estate you will call home during your stay. This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation

    Karen Overtoom Karen M. Overtoom R.E.

    56 Chilmark Rd, Chilmark, MA 02535
  • 36 Henry Hough Lane Ch206, Chilmark, MA 02535
    36 Henry Hough Lane Ch206, Chilmark, MA 02535
    36 Henry Hough Lane Ch206, Chilmark, MA 02535
    /35

    $22,000 per month

    • 4 Beds
    • 2 Baths
    • 2,290 Sq Ft
    • House for Rent

    36 Henry Hough Lane Ch206, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four

    Karen Overtoom Karen M. Overtoom R.E.

    36 Henry Hough Lane Ch206, Chilmark, MA 02535
  • 17 Otis Bassett Rd, West Tisbury, MA 02575
    17 Otis Bassett Rd, West Tisbury, MA 02575
    17 Otis Bassett Rd, West Tisbury, MA 02575
    /28

    $38,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    17 Otis Bassett Rd, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT MONTHLY. AUGUST WEEKLY IS $9,500. SEE OUR WEB SITE FOR WEEKLY PRICING!!!!!Are you looking for the perfect back yard Oasis? Well here it is!! Surrounding a large pool you will be able to relax on the expansive deck areas that include plenty of space for gathering. Inside is an amazing kitchen with every amenity you could want. Coffee lovers will appreciate a regular

    Karen Overtoom Karen M. Overtoom R.E.

    17 Otis Bassett Rd, West Tisbury, MA 02575
  • 71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
    /8

    $18,000 per month

    • 3 Beds
    • 2.5 Baths
    • House for Rent

    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Finest Views on the Island!! This house is set high on a hill surrounded by nature. The expansive views from the front of this house are spectacular. Enjoy the large deck or the screened porch and gaze upon one of the most amazing Vineyard Views available. It is a short

    Karen Overtoom Karen M. Overtoom R.E.

    71 Bartmus Luce Road Wt154, West Tisbury, MA 02575
  • 41 Oak Lane Wt147, West Tisbury, MA 02575
    41 Oak Lane Wt147, West Tisbury, MA 02575
    41 Oak Lane Wt147, West Tisbury, MA 02575
    /22

    $3,000 per month

    • 4 Beds
    • 2.5 Baths
    • 2,703 Sq Ft
    • House for Rent

    41 Oak Lane Wt147, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $3,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Inside the front entrance is a large open living room with a comfortable L-shaped couch facing the floor to ceiling windows which look out onto the spacious tree lined back yard and a wall mounted flat screen television. Off the open concept living/dining room is a large

    Karen Overtoom Karen M. Overtoom R.E.

    41 Oak Lane Wt147, West Tisbury, MA 02575
  • 50 Carls Way, West Tisbury, MA 02575
    50 Carls Way, West Tisbury, MA 02575
    50 Carls Way, West Tisbury, MA 02575
    /19

    $17,600 per month

    • 4 Beds
    • 2 Baths
    • 1,584 Sq Ft
    • House for Rent

    50 Carls Way, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Looking for that perfect setting with a water view? This is the one!!This cute cape is privately set with a water view and direct water access to Town Pond. You can dock your canoes and kyacks here and access Tisbury Great Pond and then right out to the beach. There are

    Karen Overtoom Karen M. Overtoom R.E.

    50 Carls Way, West Tisbury, MA 02575
  • 40 Summer Cir, West Tisbury, MA 02575
    40 Summer Cir, West Tisbury, MA 02575
    40 Summer Cir, West Tisbury, MA 02575
    /10

    $17,600 per month

    • 4 Beds
    • 3.5 Baths
    • 2,676 Sq Ft
    • House for Rent

    40 Summer Cir, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,400. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This beautiful tasteful modern home has many charming elements. The bright open airy floor plan offers a generous kitchen, welcoming dining room and living room surrounded by windows and decks with an outdoor table and extra seating. An "upside down" house with the living

    Karen Overtoom Karen M. Overtoom R.E.

    40 Summer Cir, West Tisbury, MA 02575
  • 267 Great Plains Road Wt117, West Tisbury, MA 02575
    267 Great Plains Road Wt117, West Tisbury, MA 02575
    267 Great Plains Road Wt117, West Tisbury, MA 02575
    /34

    $12,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,240 Sq Ft
    • House for Rent

    267 Great Plains Road Wt117, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Large spacious home with open concept living and dining area. This house has gorgeous hardwood floors throughout, separate media room, and loads of natural sunlight. It also features an exceptionally large master bedroom with en-suite bath, and private deck. There is

    Karen Overtoom Karen M. Overtoom R.E.

    267 Great Plains Road Wt117, West Tisbury, MA 02575
  • 24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
    24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
    24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
    /18

    $10,000 per month

    • 3 Beds
    • 2 Baths
    • 1,439 Sq Ft
    • House for Rent

    24 Nat's Farm Lane Wt113, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Charming three bedroom home located in a private neighborhood close to bike path, walking trails and public tennis courts. Just a short drive to Lambert's Cove Beach, West Tisbury Village and down island restaurants and shops.Amenities include High definition TV, wifi

    Karen Overtoom Karen M. Overtoom R.E.

    24 Nat's Farm Lane Wt113, West Tisbury, MA 02575
  • 10 James Pond Way, West Tisbury, MA 02575
    10 James Pond Way, West Tisbury, MA 02575
    10 James Pond Way, West Tisbury, MA 02575
    /21

    $8,000 per month

    • 1 Bed
    • 1 Bath
    • 936 Sq Ft
    • House for Rent

    10 James Pond Way, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This spacious and well appointed one bedroom guest house has a cozy living area and kitchen which opens up to a large second story deck with outdoor furniture, table and chairs where you can enjoy dining amidst the trees. One A/C unit is in the bedroom along with a

    Karen Overtoom Karen M. Overtoom R.E.

    10 James Pond Way, West Tisbury, MA 02575
  • 58 Forest Rd Wt140, West Tisbury, MA 02575
    58 Forest Rd Wt140, West Tisbury, MA 02575
    58 Forest Rd Wt140, West Tisbury, MA 02575
    /29

    $10,900 per month

    • 3 Beds
    • 1 Bath
    • 936 Sq Ft
    • House for Rent

    58 Forest Rd Wt140, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,725.. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This charming rustic home is set within Seven Gates Farm in West Tisbury. Walk down your own path to a beautiful private association beach. There are shared tennis courts and miles of walking trails.

    Karen Overtoom Karen M. Overtoom R.E.

    58 Forest Rd Wt140, West Tisbury, MA 02575
  • 76 Ben Chase Rd Wt136, West Tisbury, MA 02575
    76 Ben Chase Rd Wt136, West Tisbury, MA 02575
    76 Ben Chase Rd Wt136, West Tisbury, MA 02575
    /20

    $12,000 per month

    • 3 Beds
    • 1 Bath
    • 1,068 Sq Ft
    • House for Rent

    76 Ben Chase Rd Wt136, West Tisbury, MA 02575

    Experience a wonderful glimpse of country living in the peaceful, quiet setting of Serene Pond Cottage! This charming Martha's Vineyard retreat features a cozy interior with ample natural light, a private deck where you can take your breakfast and coffee, and a tree-lined backyard to enjoy on lazy summer days. Comfortable three bedroom single story home with one brand new renovated full bath with

    Karen Overtoom Karen M. Overtoom R.E.

    76 Ben Chase Rd Wt136, West Tisbury, MA 02575
  • 709 Old County Rd Wt134, West Tisbury, MA 02575
    709 Old County Rd Wt134, West Tisbury, MA 02575
    709 Old County Rd Wt134, West Tisbury, MA 02575
    /22

    $20,000 per month

    • 4 Beds
    • 2.5 Baths
    • 2,400 Sq Ft
    • House for Rent

    709 Old County Rd Wt134, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY. The weekly price in August is $5,000. per week. See website for additional weekly pricing. Mill Pond House is a completely restored 1890s farmhouse on the old Mill Pond in historic West Tisbury. Remodeled by the present owner, an interior designer, it is beautifully appointed with antiques and charming accessories. An old pine floor and columns add to the

    Karen Overtoom Karen M. Overtoom R.E.

    709 Old County Rd Wt134, West Tisbury, MA 02575
  • 37 Sachem Cir, West Tisbury, MA 02575
    37 Sachem Cir, West Tisbury, MA 02575
    37 Sachem Cir, West Tisbury, MA 02575
    /19

    $30,000 per month

    • 5 Beds
    • 4 Baths
    • 3,600 Sq Ft
    • House for Rent

    37 Sachem Cir, West Tisbury, MA 02575

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $7,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Lovely pastoral setting with an elegant farm house and guest house. Abutting Land Bank property on two sides. Quiet privacy, yet just minutes to Lambert’s Cove Beach. The four bedroom house and separate guest house are impeccably decorated and the floor plan lends itself

    Karen Overtoom Karen M. Overtoom R.E.

    37 Sachem Cir, West Tisbury, MA 02575
  • 64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
    /25

    $13,600 per month

    • 2 Beds
    • 2 Baths
    • 792 Sq Ft
    • House for Rent

    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!!!!!!!Idyllic location right above a sandy private beach on the North Shore. This beach cottage affords views of the Sound and the Elizabeth Islands with a front row seat on unrivaled sunsets. It is rustic and cozy with a large screened porch overlooking the view. Have a getaway like in days of yore when life was simple and the beach at your doorstep.Take

    Karen Overtoom Karen M. Overtoom R.E.

    64 Bartimus Luce Road Wt125, West Tisbury, MA 02575
  • 76 School House Lane Wt101, West Tisbury, MA 02575
    76 School House Lane Wt101, West Tisbury, MA 02575
    76 School House Lane Wt101, West Tisbury, MA 02575
    /41

    $14,500 per month

    • 5 Beds
    • 5.5 Baths
    • 3,392 Sq Ft
    • House for Rent

    76 School House Lane Wt101, West Tisbury, MA 02575

    THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!! An elegant, whimsical house full of color, quality and artistic touches. The grounds are sumptuous, nature at its apotheosis. There is gentle movement in the landscape with flowering trees and shrubs everywhere replete with a babbling brook flowing into a pond bordering the garden behind the house. The stonework is finely crafted with balanced

    Karen Overtoom Karen M. Overtoom R.E.

    76 School House Lane Wt101, West Tisbury, MA 02575
  • 141 N Rd Ch202, Chilmark, MA 02535
    141 N Rd Ch202, Chilmark, MA 02535
    141 N Rd Ch202, Chilmark, MA 02535
    /9

    $10,800 per month

    • 4 Beds
    • 2 Baths
    • 702 Sq Ft
    • House for Rent

    141 N Rd Ch202, Chilmark, MA 02535

    THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $2,700. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Chilmark Cottage Perfection!!! You will love this quaint Vineyard Style Cottage that has been meticulously designed to include all the amenities one could imagine. This vintage charmer really boasts a lot of Style. Inside you will find really beautiful hardwood floors, a

    Karen Overtoom Karen M. Overtoom R.E.

    141 N Rd Ch202, Chilmark, MA 02535
  • 55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575
    55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575
    55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575
    /21

    $11,000 per month

    • 2 Beds
    • 1.5 Baths
    • 800 Sq Ft
    • House for Rent

    55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575

    THIS IS A SUMMER RENTAL ONLY. Nestled on a quiet country lane, this charming two BR guest house will enchant you with its inviting character and custom features throughout. From the cathedral living area and newly furnished interior to the covered front porch and expansive deck, this lovely cottage has it all. Privately situated , yet convenient to the village, bike path and local

    Karen Overtoom Karen M. Overtoom R.E.

    55 Dr Fisher Rd Unit 1, West Tisbury, MA 02575
  • 21 Leona Lane Wt115, West Tisbury, MA 02575
    21 Leona Lane Wt115, West Tisbury, MA 02575
    21 Leona Lane Wt115, West Tisbury, MA 02575
    /22

    $10,000 per month

    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • House for Rent

    21 Leona Lane Wt115, West Tisbury, MA 02575

    THIS IS A SUMMER RENTAL ONLY. This very charming post & beam home is the perfect getaway for those who appreciate West Tisbury's rural character. The home is very nicely furnished and equipped, has a lovely, big yard, and the location, adjacent to the bike path, is central to up-Island shopping and the fantastic sandy beaches of Lambert's Cove and Long Point Reservation. There is no land line

    Karen Overtoom Karen M. Overtoom R.E.

    21 Leona Lane Wt115, West Tisbury, MA 02575

Showing Results 1 - 40, Page 1 of 2

Massachusetts Oak Bluffs

Homes for Rent in Oak Bluffs, MA

Frequently Asked Questions

What are the most popular neighborhoods in Oak Bluffs, MA for renters?
The most popular neighborhoods in Oak Bluffs, MA for renters are West Tisbury, Chilmark, Aquinnah, Edgartown and Tisbury.
What are the most popular zip codes in Oak Bluffs, MA for renters?
The most popular zip codes in Oak Bluffs, MA for renters include 02568, 02575, 02535, 02539 and 02740.
How to Rent a Home

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