Vacation rentals in Windham

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!

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.

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!

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.

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.

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.

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.

Lakefront - King - W&D - PetsOK - Kayaks - SUPs

Indulge in lakeside luxury at The Lake View Cottage, offering exclusive beach access & amazing views to picturesque Coventry Lake. ● 360 Mbps Wi-Fi | 50” Smart HD TV | Washer & Dryer | Indoor Fireplace ● 2x Kayaks | 2x Stand Up Paddle Boards | Beach Toys ● Record Player w/ a 100+ Vinyl Collection | Board Games ● Sunroom | Patio w/ Gas Grill | Full Kitchen | Coffee (Keurig) Drive to: UCONN (10 Mins) | Hartford (20 Mins) | Boston (1 Hour) | NYC (2 Hours)

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.

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!

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

One bedroom newly renovated clean and quiet. Apt F

Your home away from home. Queen size bed. End unit facing the woods in a quiet 6 unit apartment building. Off street parking. Pay laundry. Food shopping only a 1 minute walk to Bob's Windham IGA "home of the giant grinder" for that emergency ice cream fix or last minute beverage. 5 minute drive to romantic Willimantic and 15 to Norwich. Casinos are 25 minutes away.