5-Bedroom Rentals in Litchfield County, CT

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

2ND FLOOR APARTMENT IN A GOOD NEIGHBORHOOD. CLEAN 2 BEDROOM. QUIET STREET.

Barbara Peloquin G & W Real Estate

Wonderful opportunity to live in the heart of prestigious Roxbury in Litchfield County. Well preserved antique colonial filled with charm. Updates include kitchen, baths and open living area leading to primary bedroom. Brand new septic, 4 car garage with storage above and period outbuildings including a barn. Washer and dryer are located on the main level, upstairs bedrooms offer privacy for

Lisa Titcomb William Pitt Sotheby's Int'l

Spacious 5 bedroom 1600 square foot apartment featuring a large eat in kitchen and living room area. Laundry in unit (washer & dryer supplied by landlord) . Plenty of parking, convientent location. First & last month and secuirty depoist required. Tenant tracks will be utlized for credit, background and income vertifation. Available for immediate move in.

Jason Hogan West Wind Realty, LLC

West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open

Jill Sloane Brown Harris Stevens

Available Sept 1 - May 31, 2026 @ $9,500 per month. Inquire about custom terms, more time or annual terms. Inquire for details about use of Luxury pontoon boat for cruising and waterskiing. Enjoy this chic and renovated home on glamorous Lake Waramaug. Walk across the street to the fabulous dock with spacious lake side lawn. Canoe is available for use. 6 bedrooms (3 en-suite) with plenty of room

Stacey Matthews W. Raveis Lifestyles Realty

Available Aug - Sept 15, 2025 @ $30,000 total. Inquire about custom terms, more time or annual terms. Inquire for details about use of Luxury pontoon boat for cruising and waterskiing. Enjoy this chic and renovated home on glamorous Lake Waramaug. Walk across the street to the fabulous dock with spacious lake side lawn. Canoe is available for use. 6 bedrooms (3 en-suite) with plenty of room for

Stacey Matthews W. Raveis Lifestyles Realty

Enjoy country living in this stunning location with spectacular views and total privacy. Explore 142 acres. 6 Bedroom main house with a 2 bedroom plus loft guest house. Total 8 Bedrooms and 4 Full baths. Can sleep 19 with every bed filled. Explore 142 acres of open fields and forest. The house has a chic modern interior that is tastefully decorated. Enjoy the in ground gunite pool and take in the

Sharon McGuire William Pitt Sotheby's Int'l

Enjoy a 6 week vacation in this stunning location with spectacular views and total privacy. Explore 142 acres. 6 Bedroom main house with a 2 bedroom plus loft guest house. Total 8 Bedrooms and 4 Full baths. Can sleep 19 with every bed filled. Explore 142 acres of open fields and forest. The house has a chic modern interior that is tastefully decorated. Enjoy the in ground gunite pool and take in

Sharon McGuire William Pitt Sotheby's Int'l

Very, very unusual opportunity to "try out" living in Litchfield. Historic residence is less than one block from the Green, coffee shops, restaurants, library, one-of-a-kind boutique stores. Small patio has sitting area with space for flower and herb gardens while wonderful rear yard offers summer privacy. Home trades lack of state-of-the-art appointments for many original features.

Cleve Fuessenich Klemm Real Estate Inc

Bright and Open Unit on First floor. 3 spacious bedrooms, giant bathroom.

J Troy Morris Coldwell Banker Calabro

Academic or winter rental. Strawberry Ridge Chalet is nestled between pristine vineyards overlooking Lake Waramaug. Complete privacy down a long driveway past the pond is a 5 bedroom home. Top of the line eat-in kitchen with seating area and stone fireplace. Flooded with light the living room/dining has vaulted beamed ceilings, sliders out to the orchard, vineyard and stream. Office/5th bedroom

Joseph Lorino Klemm Real Estate Inc

Strawberry Ridge Chalet is nestled between two pristine vineyards overlooking Lake Waramaug. Complete privacy down a long driveway past the pond is the 4 to 5 bedroom home. Eat in kitchen with seating area and stone fireplace. Living room/dining has vaulted beamed ceilings, sliders out to the orchard, vineyard and stream. Office/5th bedroom and full bath complete the 1st floor. The 2nd floor

Joseph Lorino Klemm Real Estate Inc

$17,000 June, $22,000 July, $25,000 August 2025. Fallen Fence is a historic center hall colonial is located on 40 acres has modern day amenities including a large Chef's kitchen and a full first floor bathroom. The spacious dining room seats up to 12. The large 2nd floor primary suite features a newly renovated bath and private lanai which overlooks the pool and ponds. There are two additional

Joseph Lorino Klemm Real Estate Inc

Available August. Sunny, bright, and clean with a gorgeous heated spa/pool. The rear deck overlooks the pool, patio, and expansive lawn, which leads out to the old rail bed for peaceful walks along the Bantam River. Private, tucked away but central to both Washington and Bantam and Litchfield's restaurants, shops, and conveniences. Become acquainted with the lifestyle of Litchfield County and

WENDY WESTCOTT William Raveis Real Estate

Luxurious Estate With Breathtaking Views In Salisbury, Ct - (Availability: $75,000/term: July 2 - September 2, 2025. $40,000/month: July or August to September 1, 2025) Escape to luxury in Salisbury, CT, with this stunning 9,000 sq. ft. estate atop a hill, offering panoramic views of the Housatonic River Valley and the Taconic Mountain Range. This 6-bedroom, 7-full-bath, and 3-half-bath home

Elyse Morris Elyse Harney Real Estate

$7900/month for remainder of academic season 2025. $8500/month annual. $25,000/month summer 2025. Fallen Fence is a historic center hall colonial is located on 40 acres has modern day amenities including a large Chef's kitchen and a full first floor bathroom. The spacious dining room seats up to 12. The large 2nd floor primary suite features a newly renovated bath and private lanai which

Joseph Lorino Klemm Real Estate Inc

~Fair Rising~ Experience the grandeur of the past with this exquisite 1790 classic Georgian Colonial, nestled on a private 21-acre sanctuary just minutes from the charming center of Sharon. As you approach the residence via the elegant circular drive, you are welcomed by the breathtaking beauty of the meticulously maintained grounds. This historic gem boasts 5 well-appointed bedrooms upstairs,

Diana Bisselle William Pitt Sotheby's Int'l

~Fair Rising~ Experience the grandeur of the past with this exquisite 1790 classic Georgian Colonial, nestled on a private 21-acre sanctuary just minutes from the charming center of Sharon. As you approach the residence via the elegant circular drive, you are welcomed by the breathtaking beauty of the meticulously maintained grounds. This historic gem boasts 5 well-appointed bedrooms upstairs,

Diana Bisselle William Pitt Sotheby's Int'l

Available June 6 - July 30, 2025 @ $45K total. Inquire about custom terms, more time or annual terms. Inquire for details about use of Luxury pontoon boat for cruising and waterskiing. Enjoy this chic and renovated home on glamorous Lake Waramaug. Walk across the street to the fabulous dock with spacious lake side lawn. Canoe is available for use. 6 bedrooms (3 en-suite) with plenty of room for

Stacey Matthews W. Raveis Lifestyles Realty

FURNISHED RENTAL AVAILABLE @ $7,500k/month. Modern Country home filled with stylish designer furniture and art. Fabulous AAA South Kent location with expansive lawn and western exposures. 4-5 bedrooms, fabulous outdoor entertainment areas, pond and brook. Close to Lake Waramaug, Appalachian Trail, Mohawk Mtn skiing, Kent and New Preston. Not far from NYC metro north train. 90 min drive to

Rebecca Doh W. Raveis Lifestyles Realty

Major estate with the highest standards of construction located within the Sunny Ridge historic district. Situated on 10 private, park-like acres with an over-sized heated pool, fabulous stonewalls, giant dining terraces, pond and orchard. 7+ bedrooms, Billiard room, screening room, paneled library, sunroom, new country kitchen, 100-person party room boasts a restaurant size bar, sound system and

Peter Klemm Klemm Real Estate Inc

Mint 6 bedroom colonial reproduction on scenic dirt road. Walk, jog, bike into land preserve. Heated pool, outdoor play set, bbq, 3 acre lawn, 4 wood-burning fireplaces. SUMMER:June - August $30,900/month. Memorial - Labor Day $74,900.OFF-SEASON: September - May $13,900/month If over 3 months, subtract $1,000 per month and no tax is due. ANNUAL:$169,000. Inquire about other/shorter rental terms.

Peter Klemm Klemm Real Estate Inc