5-Bedroom Rentals in Litchfield County, CT

Enjoy the privacy and comfort of this beautifully maintained single family rental. Featuring renovated bright and airy rooms, and plenty of natural light throughout. The spacious kitchen offers stainless steel appliances, and ample cabinet space perfect for home cooking. Relax on the inviting front porch, or enjoy the peaceful setting of the surrounding neighborhood. Located close to schools,

Pedrocarlo Otarola The Washington Agency

** Available November 2025 through May 2026 **Classic New England Charm - Located on a mountainside offering privacy in an open setting, yet minutes to town. This historic cape offers 5 Bedrooms and 3 full baths. One small bedroom is on the main floor with an ensuite bath, and the primary bedroom is located on the second floor with an ensuite bath. The other three bedrooms on the second floor

Colleen Vigeant Elyse Harney Real Estate

Your perfect getaway awaits! Discover the best of the Litchfield Hills, where vibrant fall foliage paints the landscape and a picturesque winter wonderland emerges-culminating in the magic of the holiday season. This modern masterpiece, set amid rolling hills, offers breathtaking sunset vistas that extend all the way to the Catskill Mountains. Step inside to a dramatic floating steel and glass

Steve Pener William Pitt Sotheby's Int'l

Welcome to this freshly updated 2nd floor unit with a spacious 4-bedroom, 1 full bathroom rental. Features brand new flooring throughout, a bright living room, and a modern kitchen equipped with stainless steel appliances. The layout offers plenty of room to spread out, along with ample storage space for added convenience. Located on a quiet residential street with easy access to local shops and

Janeth Alvarez eXp Realty

Sept 2025 to May 2026 furnished rental with stunning long southern and western views of Lake Waramaug and the Litchfield Hills! 16 acre, 5 bedroom estate located minutes from the lake with access to Warren Town Beach, hiking trails at Steep Rock or the Warren Land Trust. Village of New Preston is only minutes away for dinning and shopping. Less than 30 minutes to skiing at Mohawk Mtn. 5 large

Pels Matthews W. Raveis Lifestyles Realty

Luxury summer rental with inground Gunite pool in the beautiful Litchfield Hills of Washington. It's long gracious driveway leads you to the formal yet comfortable country house privately set on the property for peaceful enjoyment. This location is ideal, allowing easy access to Lake Waramaug, restaurants, an abundance of hiking and walking trails, wineries, breweries and New Preston Village for

Maria Taylor Klemm Real Estate Inc

Charming Remodeled Colonial in one of the most sought out neighborhoods. 5 generous size Bdrms,2.5 bathrooms, Layout boosts a spacious open floor plan w/ Family room & Kitchen w dining area, Formal Dining room open to Living Room, Mud room/Laundry room off the Garage. Hardwood floors throughout, Central air, Central Vac, custom solid-wood cabinets, Center Island w/ corian countertops, Fireplace,

Christina Moulthrop Showcase Realty, Inc.

Annual furnished rental with stunning long southern and western views of Lake Waramaug and the Litchfield Hills! 16 acre, 5 bedroom estate located minutes from the lake with access to Warren Town Beach, hiking trails at Steep Rock or the Warren Land Trust. Village of New Preston is only minutes away for dinning and shopping. Less than 30 minutes to skiing at Mohawk Mtn. 5 large bedrooms with 3

Pels Matthews W. Raveis Lifestyles Realty

Spend your summer and fall at Bantam Lake as part of a private waterfront community with picturesque grounds, beach, swim platform, tennis court and basketball court. This large rental includes a main floor primary suite with 4 additional upstairs bedrooms and common area. Enjoy your private garden and patio from the 3 season room or a cozy evening in the main living room with a roaring fire. The

Devon O'Neill Litchfield Hills Properties LLC

Luxury summer rental with inground Gunite pool in the beautiful Litchfield Hills of Washington. It's long gracious driveway leads you to the formal yet comfortable country house privately set on the property for peaceful enjoyment. This location is ideal, allowing easy access to Lake Waramaug, restaurants, an abundance of hiking and walking trails, wineries, breweries and New Preston Village for

Maria Taylor Klemm Real Estate Inc

Available: Annual or Academic Year: Welcome to this well-located furnished 5-bedroom, 2.5-bath Colonial, fresh and clean, and ready for you to move in! Situated in a private and quiet area near the charming villages of Salisbury and Lakeville, this home offers proximity to the area's prestigious schools, such as Hotchkiss, Salisbury, and Indian Mountain. The spacious eat-in kitchen has modern

William Melnick Elyse Harney Real Estate

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

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

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 Nov 11, 2025-May 25, 2026 @ $8,500 per month. Inquire about custom terms, more time or annual terms. 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 guests and a welcoming open floor plan. Media/Game Room with Ping Pong. and

Stacey Matthews W. Raveis Lifestyles Realty

Aug 1- Sept 8 2025 @ 19,500 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 guests and a

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

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

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

~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 Aug 1- Sept 15 at 19,500. 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 guests and a

Stacey Matthews 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