Vacation rentals in Ashford

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Top-rated vacation rentals in Ashford

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Guest favorite

A spacious deck overlooks the serene waterfront, featuring comfortable seating arrangements including a swing and lounge chairs. Potted plants with vibrant flowers add color, while an umbrella provides shade. The surrounding trees reflect autumn hues, enhancing the peaceful lakeside atmosphere.

Apartment in Woodstock Valley

4.93 out of 5 average rating, 406 reviews

“Tranquillity on the Lake ” Woodstock Valley, CT.

Summer is here !! Enjoy fun relaxing water activities on beautiful Lake Bungee. Enjoy direct waterfront sunrises , 1400 sq ft. Queen bed in Master. Queen sofa in living area. fireplace. Air conditioning, Kitchen stove, full refrigerator, microwave. Enjoy your own deck, propane fire pit, gaze at the stars.BBQ propane grill. Stroll around both lakes, see bird sightings,nature’s at its finest. Great local dining & wineries. Each season paints its own stunning beauty. Relax and enjoy Tranquility !!

Top guest favorite

The exterior of a rustic wooden house is surrounded by lush greenery and trees. A small fenced area is visible near the entrance, where a welcoming front door can be seen. The building features windows and a gabled roof, set in a tranquil natural environment.

Farm stay in Thompson

4.99 out of 5 average rating, 191 reviews

Rustic Farmette Studio w/Pool & yearround Hot Tub

Relax and rejuvenate at this unique getaway on 20 acres in CT’s Quiet Corner. Just an hour from Boston, Providence, & Hartford, enjoy this private in-law studio with beautiful forest views. Lounge in bath robes & soak in the hot tub, take a walk along the trails, enjoy local vineyards, or explore antiques. Folks from all backgrounds and identities are welcome at The Farmette. Ideal for couples, solo travelers, or a family with a young kid. Please include all individuals (&pets) in your booking.

Top guest favorite

The charming lake house features a sun-themed front entrance, flanked by dark shutters. A welcoming path leads to the door, surrounded by lush greenery and flower beds. The serene lake can be glimpsed through the trees in the background, enhancing the tranquil setting.

Home in Eastford

4.92 out of 5 average rating, 105 reviews

Serenity Ashford Lake

Brand new central air in 2025! Charming waterfront home with gazebo and hot tub! Welcome to Serenity Ashford Lake. This peaceful lake home is removed from the everyday hustle and bustle of life. Nestled on the shores of beautiful Ashford lake, your stay is bound to create lasting memories. Plush furniture, stainless steel appliances, cozy linens, washer/dryer, 3 kayaks and a canoe, paddleboat, firepit, boutique toiletries and a brand new kitchen space are all part of this beautiful lake home.

Top guest favorite

A bright bedroom features a queen size bed with light linens and decorative pillows. A small desk and chair are positioned beside the bed. A closet offers hanging space, and a floral artwork adorns the wall, adding a touch of color to the space.

Guest suite in Vernon

4.98 out of 5 average rating, 192 reviews

Laura's Loft and Gallery, private suite

Unique and roomy space with private entrance, two bedrooms, full bath with tub shower, and plenty of room to relax. Kitchen space has mini fridge, microwave, toaster oven, hot plate, and crock pot. Pleasant living area opening to 2nd floor deck. WiFi with Ethernet also, great remote work space. Quiet and private, only common area shared with us is first floor entry into breezeway. Free parking on premises. Full coffee setup for your breakfast included, and homemade scones in seasonal flavors.

Guest favorite

A spacious living area is furnished with a gray sectional sofa, accented with colorful throw pillows. A wooden coffee table is placed in front, on a soft area rug. Two large windows allow natural light to brighten the room, complemented by ceiling fans and tasteful decor.

Loft in Tolland

4.97 out of 5 average rating, 254 reviews

Cozy studio loft

Home away from home! In a serene, wooded area tucked away from the road, you'll find our studio loft mother-in-law apartment. Beautiful views with wildlife often spotted. Well-lit with many windows to let in the morning light. Suitable for a change of scenery while working remotely, a brief stay between locations, or your actual destination. UConn is minutes down the road. Looking for antiques? Stafford Speedway? Mohegan Sun or Foxwoods visits? Outdoor enthusiast? This place works for all!

Top guest favorite

The exterior of a red, two-story building is surrounded by a well-maintained lawn featuring trees and landscaped flower beds. A large window above the entrance and additional windows enhance the farmhouse aesthetic. Cloudy skies and natural light create a serene atmosphere.

Farm stay in Woodstock

4.99 out of 5 average rating, 201 reviews

Barn suite at Southwood Alpacas

Country living at its best. Renovated guest space on a working alpaca farm. This is a two story unit with a kitchenette, living room and bathroom on the first floor and a studio loft on the second floor. Two decks, one on each level overlook the farm. Recently renovated. Great light floods the unit. Central heat & AC. Enjoy the farm and the bucolic setting in Woodstock. Watch the alpaca from your windows or deck. Cafes for morning breakfast and fine dining await.

Guest favorite

The cottage features a charming blue exterior, framed by a manicured lawn with greenery. Windows are adorned with white shutters, and a welcoming front porch is accessible via a small set of steps. Tall trees provide a natural backdrop, enhancing the serene setting.

Cottage in Chaplin

4.89 out of 5 average rating, 145 reviews

Clark Cottage in the historic village in Chaplin

Up to 14 day stays are OK. Cottage is empty several days between guests. Virus cleaning protocol in use. This little rustic cottage, circa 1850, has antique charm, yet modern comforts. In addition to a living and dining room, there is a full vintage kitchen, 2 bedrooms, 1 bathroom, plus laundry facilities. Very tall people will have to duck under door ways. Not suitable for children under 12. WiFi and a smart TV. Kitchen ceiling is 6'3.5".

Guest favorite

The living room showcases a comfortable seating area with a dark couch, complemented by a glass dining table nearby. A wooden mantel above a decorative fireplace adds warmth, while natural light filters through the large windows, illuminating the soft white walls.

Apartment in Ashford

4.97 out of 5 average rating, 255 reviews

Enjoy a Farm Stay without the Work

This 3-room one-story apartment with private entrance is attached to the main 1850 farmhouse and also has that older farm charm. Only 10 minutes to Interstate 84 and midway between New York City and Boston, this location allows for ease of access to experiences in the northeast. The property is set back from the state road (Route 89) and allows for relaxed living on a beautiful farm bordered by stone walls and wooded area behind.

Superhost

A spacious barn is situated in a large field, surrounded by greenery. Its two-story structure features a combination of windows and a central door, offering access to the outdoors. Lush grass and various plant life contribute to the serene rural setting.

Guesthouse in Hampton

4.95 out of 5 average rating, 153 reviews

Spacious, unique barn with beautiful views.

Our barn is in a large field on lot next to our home. Our rental area is upstairs which offers beautiful views of our field and the visiting deer. The eclectic decor is accumulated from years of activism. Our guest room and bathroom are newly renovated. It is a quiet and peaceful area near two state parks. We operate a mail order business in the downstairs area but will not be working while guests are staying with us.

Top guest favorite

A cozy bedroom features a bed dressed in a floral comforter with a decorative pillow. A soft glow from a floor lamp illuminates the space, complemented by a window that offers natural light. A mini-fridge is present in the corner, adding convenience.

Guest suite in Mansfield

4.96 out of 5 average rating, 208 reviews

Cozy private apt 8 mins from UCONN - solar powered

Relax & unwind in this amply sized private studio suite, complete with large seating/tv area & study/desk space. Space comes w/ 2 beds (1 queen, 1 full sized pull out futon couch) a full private bath, mini-fridge, cooktop, microwave, dishware, & utensils. Beautiful rural wooded area with numerous hiking trails nearby. Longer term rentals may be considered starting from Summer of 2025

Top guest favorite

The charming stone cottage features a vibrant blue door and flower boxes filled with colorful plants. Lush greenery surrounds the entrance, and original brick walkways lead to the home. Sunlight filters through the trees, creating a welcoming atmosphere outside.

Guesthouse in Granby

4.99 out of 5 average rating, 831 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Guest favorite