Holiday houses in Windham

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Top-rated holiday rentals in Windham

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.

Home in Columbia

4.92 out of 5 average rating, 132 reviews

Breathtaking home with unforgettable views & pool!

This spacious peaceful and private home on 5 acres is great for unwinding & relaxing whether it is enjoying the day by the incredible pool/spa or stargazing at night. Far from the noise and pollution of city life. You can spend a weekend or a week away from work life because you deserve it. Close to Foxwoods casino and Mohegan sun casino, super Walmart and other stores. Please let us know before booking more than 4 people whether it is just for the day or night or both. No loud music no parties.

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Top Guest favourite

A contemporary lakefront home is surrounded by tall trees, with a spacious deck offering views of Middle Bolton Lake. A fire pit is situated on a stone patio, surrounded by Adirondack chairs. The lush green yard leads to the water's edge, enhancing the natural ambiance.

Home in Vernon

4.99 out of 5 average rating, 186 reviews

Luxe Bolton Lake

Stay at Luxe Bolton Lake and feel like you are a million miles from home! The Luxe features a BEAUTIFUL WATERFRONT, 3 bedrooms/3 full bathrooms and a year-round outdoor JACUZZI Also included: gorgeous primary bedroom suite, artistic furnishings, cozy FIREPLACE, coffee bar, complimentary snacks, speedy WiFi, large deck, fire pit, KAYAKS, board games, and much more. The Luxe is perfectly suited for families and guests of all ages, so come stay at Luxe and make memories that will last a lifetime!

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Superhost

An open-plan living area is highlighted by a sleek kitchen equipped with modern appliances. A comfortable gray sofa, adorned with cushions, faces a light wooden coffee table. A dining area with four black chairs is conveniently positioned near the kitchen.

Apartment in Windham

4.62 out of 5 average rating, 13 reviews

Apartment near UCONN and Eastern

Enjoy a stylish experience at this centrally-located apartment. This newly renovated 1 bedroom, 1 bathroom unit sits on a golf course and is close to Eastern, UConn, and downtown Willimantic. The bedroom sleeps 2 guests and 2 additional guests are accommodated by the pull-out sofa. This apartment is handicap accessible and includes a box fan and a sound machine. Whether you’re in town to visit colleges, your historical parts of CT, or just get some peace and quiet; this is the perfect spot!

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Top Guest favourite

The exterior of a lakefront cottage is illuminated by warm lighting at dusk. The structure features a vaulted roof with large windows, surrounded by trees. A deck extends around the cottage, reflecting on the calm water, creating a serene and inviting atmosphere.

Home in Coventry

4.99 out of 5 average rating, 178 reviews

Cozy cottage 5 minutes from UConn

Wake up to the morning sun over the lake in the loft, or rise after the sun in one of the two back bedrooms. Enjoy a morning coffee or tea while enjoying the lake view from the live edge bar top overlooking the water and watch for the Swans, Bald Eagles, and Blue Herons. After a hike on the trails, kayaking up the lake into conservation land, or fishing off the dock, relax in the hot tub. As the sun sets over the trees cuddle up on the couch with a good book and keep an ear out for the owls.

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Top Guest favourite

Home in Coventry

5.0 out of 5 average rating, 31 reviews

Hillside Haven

Enjoy a breathtaking view of the sunrise over the lake from the spacious deck or from the generously sized living room and bedroom windows. The lake is home to swans and bald eagles, as well as large and smallmouth bass. Relax in style in our spacious, beautifully furnished home featuring an arcade style game room, an exercise room including a home gym and two stationary bicycles positioned to overlook the lake, and a roomy kitchen stocked with all the cooking and baking equipment you need.

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Top Guest favourite

Tiny home in Mansfield

5.0 out of 5 average rating, 38 reviews

Handcrafted Timber Frame Cabin Retreat

Escape to the woods and slow things down at this beautifully handcrafted timber frame cabin, tucked away among towering trees and nature’s quiet. Built with exposed beams, natural wood, and timeless craftsmanship, this cabin blends rustic charm with modern comfort—perfect for a romantic getaway, creative retreat, or unplugged weekend escape. Whether you’re looking to reconnect, recharge, or simply enjoy the beauty of the forest, this timber frame cabin offers a warm and memorable escape.

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Guest favourite

A charming two-bedroom cottage is set amidst greenery, featuring a welcoming front porch with a railing. A stone pathway leads to the entrance, and landscaping is visible around the base of the home. Large windows allow natural light to enhance the inviting exterior.

Cottage in Hebron

4.87 out of 5 average rating, 207 reviews

Welcome to The Holly at Amston Lake

Welcome to The Holly at Amston Lake! Great two-bedroom cottage situated in a peaceful lake community. Great place to enjoy time with family and friends. Take a stroll down to the main beach or enjoy the great views of the lake from the deck! Don't forget about the gas fire pit for those chilly evenings. We are located near numerous vineyards, a brewery, the Connecticut Airline Trail, and great local restaurants! Guests have access to the grill, fire pit, kayaks, and two main beaches.

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Guest favourite

Home in Mansfield

4.9 out of 5 average rating, 41 reviews

Boondocks Oasis On The River

Relax with the whole family at this peaceful place to stay. There is a beautiful river on property where you can swim safely, fish and float down. Only 2-3 feet deep so fun for kids. Fire pit, lighted gazebo and lots of wildlife-nothing better than waking up to see deer in the orchard, hear the peeper frogs at night or watch birds making their nests. There is a shelter near the river with a campfire to enjoy. Located at the end of dead end road so safe for kids to play or ride bikes.

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Guest favourite

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, 157 reviews

Clark Cottage in the historic village in Chaplin

Up to 14 day stays are OK. This rustic cottage, circa 1850, has antique charm, yet modern comforts. In addition to a living and dining room, there is a vintage kitchen, 2 bedrooms, 1 bathroom, 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". An exterior camera is installed to observe wild life passing through the yard. A switch in the laundry turns it off.

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Guest favourite

A rustic shed is framed by colorful autumn foliage, with vibrant red and yellow leaves highlighting the scene. The wooden structure, featuring a weathered appearance and a metal roof, stands amidst an array of seasonal greenery, creating a serene outdoor setting.

Guesthouse in Windham

4.95 out of 5 average rating, 22 reviews

Windham Gardens

Our guesthouse is a newly-renovated bespoke cottage located on the grounds of the circa 1750 Windham Gardens estate in the heart of historic colonial Windham Center. The cottage sits in the midst of a private garden, with several intimate outdoor seating areas. The cottage has a bedroom, bathroom, and a orchid filled garden conservatory with a retro kitchenette. The garden cottage is just 15 minutes from UConn and close to numerous restaurants and antique shops.

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Guest favourite

The living room features a cozy arrangement of green couches around a coffee table. A stone fireplace serves as the focal point, surrounded by wooden paneling. Bright sunlight enters through large windows, illuminating the space and highlighting nearby decor.

Cabin in Coventry

4.89 out of 5 average rating, 195 reviews

Lakefront - King - W&D - Pets OK - Kayaks - SUPs

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Top Guest favourite

A cozy living room features a dark sectional couch adorned with colorful throw pillows. A round coffee table made of natural wood sits on an orange patterned rug. A wall-mounted TV is positioned opposite the seating area, with soft lighting enhancing the ambiance.

Home in Windham

4.97 out of 5 average rating, 35 reviews

4BR Willimantic House | Near ECSU, UConn & Casinos

Welcome to Thread City Escape! This beautifully updated 4-bed, 2-bath home offers 1-gig fiber WiFi, a Roku TV, a desk workspace, and a private yard. The kitchen features a pot filler, and the living room boasts a cozy L-shaped couch. Walk to Main Street, ECSU, and Windham Hospital. Minutes to UConn & Mohegan/Foxwoods Casino's. Enjoy a stand-up tile shower and an oversized soaking tub. Perfect for families, professionals & groups!

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