Holiday houses in Windham

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Top-rated holiday rentals in Windham

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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

4.91 out of 5 average rating, 117 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 vibrant sunrise casts shades of orange and pink across the sky, illuminating the expansive green fields. A white fence lines the foreground, while horses are visible grazing in the distance against a backdrop of tree-covered hills.

Guest suite in Lebanon

4.96 out of 5 average rating, 156 reviews

Rural Homestead Stay in Your a Private Suite

Relaxing country setting secluded off a long private driveway, on a dead end road, in historic Lebanon, Connecticut. Horses line the driveway, and chickens roam the yard. Sunrises over the backyard amongst the tree covered hills. The private accessory apartment, attached to the main home, includes one bedroom, living area, kitchen, bathroom, & porch. Witness the bustle of the active homestead. Relatively close to landmark casinos (Foxwoods & Mohegan Sun), hiking, the shoreline & historic sites.

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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

4.7 out of 5 average rating, 10 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 view features a small wooden cabin surrounded by vibrant green trees. A stone path leads to a seating area, comprising four metal chairs and a table. Inside, the cozy octagonal space is lit by natural light filtering through several windows, showcasing a full-sized bed adorned with a colorful patterned quilt.

Tiny home in Norwich

4.99 out of 5 average rating, 942 reviews

Water Forest Retreat -Octagon

Water Forest retreat is a very private 122ft.² electrified and heated cedar octagon next to a brook on 56 acres of forest with a pond, waterfall, marsh and hiking trails. Cozy up in this quiet comfortable space while listening to Goldmine brook while you sleep. Fire pit, heated outhouse with composting toilet, outdoor dining area, brook, pond and trail head are just steps away. We also have a TREE HOUSE and HIKER’S HAVEN house by the brook. Please click on our profile picture to read more.

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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

5 out of 5 average rating, 17 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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Top Guest favourite

The exterior of the cottage is characterized by a charming stone chimney and a vibrant green door. The white siding contrasts with lush greenery, while a small seating area features two colorful chairs on the well-maintained lawn. A stone pathway leads toward the entrance.

Cottage in East Haddam

5 out of 5 average rating, 100 reviews

Historic Hearthstone Cottage

Built in 1800 and thoughtfully renovated in 2024, this two-story guest cottage can be the retreat of your dreams. Surrounded by thousands of acres of nature preserve, short walks to scenic vistas, a raging waterfall and countless hiking trails, few places are as peaceful as Hearthstone. Whether you’re looking for a private oasis or romantic getaway, are a parent sharing the beauty of nature, or an artist looking for inspiration, this historic cottage is for you.

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Top Guest favourite

A charming two-story house is framed by lush green trees and manicured lawns. The front porch offers an inviting entrance, while large windows allow for natural light. The surroundings are peaceful, enhancing the serene country setting.

Apartment in Ashford

4.96 out of 5 average rating, 211 reviews

On The Run Farm

Quiet country setting, minutes from UCONN and easy access from RTE 84 makes this place perfect for visitors traveling through the "Quiet Corner" of CT. Spacious living room, bedroom. kitchen and bath are newly renovated with, hardwood floors, skylights, and windows that allow for lots of natural light. The entryway is private with a lovely porch that is a great place to sit with your morning coffee. Hiking trails can be accessed from the property.

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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, 29 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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Top Guest favourite

Guest suite in Mansfield

4.96 out of 5 average rating, 234 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

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Top Guest favourite

The treehouse is elevated on wooden stilts, surrounded by vibrant autumn foliage. Large windows reflect warm light, showcasing a rustic wooden exterior. A staircase leads up to the entrance, inviting guests to explore this serene retreat among the trees.

Treehouse in Willington

4.92 out of 5 average rating, 529 reviews

Treehouse - Countryside - Farm Animals - Fire Pit

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Guest favourite

Tiny home in East Lyme

4.99 out of 5 average rating, 150 reviews

Waterfront Bliss Tiny Home

Lakeside Bliss in a Tiny Package Step into a world of relaxation at this cozy tiny house on Pattagansett Lake. In addition to the huge picture window overlooking the beautiful natural lake setting, the tiny house is equipped with a queen bed, full kitchen, high speed Wi-Fi, and unmatched ambiance. Perfect for nature lovers or couples looking for a unique stay by the lake!

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Guest favourite

Home in Tolland

4.94 out of 5 average rating, 281 reviews

The Carriage House

Private 1BR carriage house apartment in Tolland, CT, 5 min to I-84 and 15 min to UConn. Separate entrance with no shared spaces. Includes full kitchen, Wi-Fi, laundry, parking, and Level 2 EV charging. Sleeps up to 4 with optional queen mattress. Quiet wooded setting. Self check-in. No pets, smoking, or parties. Some light noise possible from upstairs unit.

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