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Explore Similar Houses Within 10 Miles of Great Barrington, MA

  • /19

    $3,300 per month

    • 1 Bed
    • 1.5 Baths
    • 1,900 Sq Ft
    • House for Rent

    174 Weatogue Rd, Salisbury, CT 06068

    Enjoy a unique retreat at the Lodge! This fully furnished rental boasts a large open floor plan that includes kitchen/dining area, seating area in front of large stone fireplace, sleigh bed, tv area and a beautiful custom bar. One full bath and one half bath. Plenty of space for a gathering or just a few. Vacation at the Lodge and enjoy the beauty of the Northwest Corner of Connecticut.

    Agent Photo

    Wendy Eichman

    Raynard & Peirce Realty,LLC

    (860) 734-4642

    174 Weatogue Rd, Salisbury, CT 06068
  • /50

    $20,000 per month

    • 5 Beds
    • 7 Baths
    • 4,645 Sq Ft
    • House for Rent

    42 Golf Course Rd, Craryville, NY 12521

    Escape to Casa do Lago: A Luxurious Seasonal Retreat on Copake LakeSEASONAL VACATION RENTAL! Unwind in peace at this exquisite 5-bedroom, 6.5-bath lakefront home, nestled next to a picturesque 18-hole golf course and charming farm-to-table restaurant. Located in the heart of the Hudson Valley, Copake Lake offers the perfect backdrop for your seasonal getaway, with Casa do Lago providing the ideal

    Agent Photo

    Veronica Newton

    Compass Greater NY, LLC

    (518) 662-7619

    42 Golf Course Rd, Craryville, NY 12521
  • /32

    $22,000 per month

    • 6 Beds
    • 5.5 Baths
    • 5,400 Sq Ft
    • House for Rent

    61 Red Fox Ln, Craryville, NY 12521

    SEASONAL RENTAL - book your 2025 visits now! Set amongst the bucolic Berkshire foothills surrounding Lake Copake, this newly built and beautifully appointed modern farmhouse style vacation home offers exceptional indoor and outdoor living with a covered porch, pergola, grill kitchen, and hot tub overlooking the links of the Copake Country Club and the lake beyond. Full of amenities and

    Agent Photo

    Veronica Newton

    Compass Greater NY, LLC

    (518) 684-7165

    61 Red Fox Ln, Craryville, NY 12521
  • /17

    $12,500 per month

    • 3 Beds
    • 2 Baths
    • 1,861 Sq Ft
    • House for Rent

    5 Beachwood Dr, Stockbridge, MA 01262

    Delightful, classic Berkshires summer cottage in the Beachwood enclave. Shares in gorgeous community beach at south end of the Stockbridge Bowl (Lake Mahkeenac.) Enjoy swimming, kayaking, etc. Minutes to Tanglewood and all the cultural delights of the Berkshires. 3BR including primary suite with bath. 1 Queen BR, 1 Br with double bunk beds. Fantastic large screened porch with dining. LR with

    Agent Photo

    Selina Lamb

    Birch Properties

    (413) 610-3637

    5 Beachwood Dr, Stockbridge, MA 01262
  • /19

    $3,200 per month

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

    242 Pittsfield Rd, Lenox, MA 01240

    Property Id: 1949104Enjoy the comfort of this clean and spacious three-bedroom unit featuring high vaulted ceilings and plenty of natural light throughout. Conveniently located above a restaurant (currently closed but expected to reopen before the end of summer), this unit offers a unique blend of privacy and accessibility.Key Features:3 generously sized bedrooms with

    242 Pittsfield Rd, Lenox, MA 01240
  • /18

    $3,600 per month

    • 3 Beds
    • 1.5 Baths
    • 1,428 Sq Ft
    • House for Rent

    765 Harlemville Rd, Hillsdale, NY 12529

    Tucked up against hill and overlooking farmland, you'll find this peaceful retreat, a Harlemville hideaway. This home is available for an academic lease, September 1st to June 30th (10 months). The perfect spot if you are looking to get away to the country but still want to be within reach of amenities or you want or need to be close to Hawthorne Valley which is only a 2 min drive or 10 min walk

    Jennifer Sesma Beach & Bartolo Realtors

    765 Harlemville Rd, Hillsdale, NY 12529
  • /23

    $12,000 per month

    • 4 Beds
    • 3.5 Baths
    • 3,332 Sq Ft
    • House for Rent

    66 Fiddlehead Ln, Ghent, NY 12075

    If you would like an Upstate country get-a-way for the a entire season for the sake of privacy or for an entire year to write a novel or entertain guests around a pond with a canoe but need contemporary surroundings for convenience, then our Fiddlehead Lane listing, just south of the lovely little Spencertown NY hamlet, is perfect for you. The proximity and privacy of this compound is

    Parker Meyer Four Seasons Sotheby's Int.

    66 Fiddlehead Ln, Ghent, NY 12075
  • /18

    $8,500 per month

    • 3 Beds
    • 2 Baths
    • 1,858 Sq Ft
    • House for Rent

    1100 Harlemville Rd, Ghent, NY 12075

    If you want to amplify that summer feeling, driving the Upstate's country roads until you reach your Greek Revival farmhouse tucked away very privately from the road and adjacent to tall grass hay fields blowing in the breeze is probably high on your list. We are pleased to offer a 3 bedroom 2 full bathroom historic farm house for lease this summer season to help fulfill your Upstate lifestyle

    Parker Meyer Four Seasons Sotheby's Int.

    1100 Harlemville Rd, Ghent, NY 12075
  • /28

    $7,000 per month

    • 3 Beds
    • 1.5 Baths
    • 2,216 Sq Ft
    • House for Rent

    33 High St, Chatham, NY 12037

    Seasonal Rental with a pool in the Village of Chatham now available from July 1st to September 30th. One month minimum rental. Sitting up on a hill on a quiet street this 3 bed, 1.5 bath village home is fully furnished and sleeps 6. The first level features a living room, dining room, kitchen, mudroom, half bath and sunroom. Access the rear patio from either the mudroom or sunroom where you'll

    Jennifer Sesma Beach & Bartolo Realtors

    33 High St, Chatham, NY 12037
  • /17

    $25,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,490 Sq Ft
    • House for Rent

    35 Bird Ln, Copake, NY 12516

    Beautiful, open and sunny rental walking distance to Copake Lake. Vaulted great room, gourmet kitchen, inviting bedrooms make for the perfect place to spend some time.

    Emma French Gabel Real Estate

    35 Bird Ln, Copake, NY 12516
  • /16

    $4,100 per month

    • 3 Beds
    • 2.5 Baths
    • 2,012 Sq Ft
    • House for Rent

    136 Macedonia Rd, Chatham, NY 12037

    Your own Country Retreat! Beautiful Secluded Post and Beam home w/ large spring fed pond on 8 acres. Located only 10 minutes from the Village of Chatham. Open concept w/ rustic cozy feel with 3BR and 2 1/2 BA, large country kitchen, 2 family rooms, glass enclosed sun-room, field stone wood burning fireplace, pellet stove, laundry room with washer and dryer, first floor bedroom w/BA. Views of pond

    Elizabeth Hendler Berkshire Hathaway HomeService

    136 Macedonia Rd, Chatham, NY 12037
  • /14

    $3,700 per month

    • 2 Beds
    • 1 Bath
    • 868 Sq Ft
    • House for Rent

    61 Preston Ln, Salisbury, CT 06068

    Twin Lakes Lakefront Annual Rental Salisbury, CT Furnished Year-Round Rental with direct frontage on Lake Washinee, the smaller and quieter of the Twin Lakes, with a wide lawn and a Dock. $3700. per month starting June 1, 2025 (not by month or season). Features include a Front Deck, Living Room, Dining Area, Kitchen, Sunroom, Mudroom, 2 Bedrooms, 1 Full Bath, Loft, and 1-bay of the Garage. Close

    Juliet Moore Elyse Harney Real Estate

    61 Preston Ln, Salisbury, CT 06068
  • /29

    $6,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,800 Sq Ft
    • House for Rent

    332 Arcadia Dr, Ancramdale, NY 12503

    Pristine 4 bedroom 4 bath waterfront rental at the sublime community of Long Lake in Ancram, NY. Available August 1st - August 28 with possible extension through Labor Day. This casually elegant home is masterfully designed with a first floor guest suit, large family room, open floor plan with kitchen, living room, and dining area, and three more bedrooms and two full baths upstairs. The second

    Jennifer Capala William Pitt Sothebys Intn'l

    332 Arcadia Dr, Ancramdale, NY 12503
  • /15

    $7,000 per month

    • 6 Beds
    • 3 Baths
    • 3,144 Sq Ft
    • House for Rent

    264 Twin Lakes Rd, Salisbury, CT 06068

    Available: May 26, 2025 through September 30, 2025 - Twin Lakes Lodge - Twin Lakes Lodge is a Landmark building located next to O'Hara's Marina. Features of this rental include a primary suite on the first and second floor, living room with a wood burning fireplace and a recently renovated kitchen. Enjoy entertaining or relaxing on the wrap around porch there is also a boat slip available to use

    KATHLEEN DEVANEY Elyse Harney Real Estate

    264 Twin Lakes Rd, Salisbury, CT 06068
  • /17

    $40,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,326 Sq Ft
    • House for Rent

    23 Ravine Ridge Rd, Salisbury, CT 06068

    Secluded Salisbury Rental With Private Pool & Riverside Charm - Escape to this tranquil 3-bedroom, 2.5-bath cottage nestled at the end of a private road in Salisbury, CT. Thoughtfully furnished and brimming with charm, this home features three fireplaces, rustic brick flooring, and a three-season sunroom perfect for unwinding. Step outside to a riverside patio, where you can sip your morning

    Elyse Morris Elyse Harney Real Estate

    23 Ravine Ridge Rd, Salisbury, CT 06068
  • /34

    $25,000 per month

    • 6 Beds
    • 5.5 Baths
    • 6,000 Sq Ft
    • House for Rent

    61 Red Fox Ln, Craryville, NY 12521

    Book your 2025 ski season visits now! Set amongst the bucolic Berkshire foothills surrounding Lake Copake, this newly built and beautifully appointed 6 bedroom, 5.5 bathroom modern farmhouse style home offers exceptional indoor and outdoor living with an expansive covered porch, pergola, grill kitchen, and hot tub overlooking the links of the Copake Country Club and the lake beyond. Full of

    Susanna Scott-Mitchell Compass Greater NY, LLC

    61 Red Fox Ln, Craryville, NY 12521
  • /15

    $13,000 per month

    • 4 Beds
    • 3 Baths
    • 2,167 Sq Ft
    • House for Rent

    Unlisted Address

    Charming Twin Lakes Lakefront Retreat Nestled along the serene shores of Washining Lake, this beautiful 4 bedroom, 3 bath home offers a tranquil retreat for those seeking relaxation and natural beauty. With its spacious interior and breathtaking views, this rental property promises an unforgettable experience. This lake home is the perfect place to create lasting memories. Whether you seek a

    TAMI REID Northwest CT Realty

    Unlisted Address
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