Holiday rentals 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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Top guest favourite

Guest suite in Lebanon

4.96 out of 5 average rating, 138 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.

Guest favourite

Loft in Tolland

4.96 out of 5 average rating, 267 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!

Guest favourite

Apartment in Norwich

4.93 out of 5 average rating, 182 reviews

KINGbed-Casino-HotTub-Pool-Sauna-Massagechair-golf

Superhost

Flat in Windham

4.88 out of 5 average rating, 136 reviews

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 2 minute walk 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. All appliances are brand new as of 1/20/21. Glass top stove, fridge, microwave and dishwasher. Tile wood and carpet are also new and has central heat and air conditioning.

Top guest favourite

Barn in Hampton

5 out of 5 average rating, 41 reviews

Little Rest Studio

Little Rest Studio overlooks 100 acres of conservation land, primarily oak and hickory forest. Recently renovated by the owners and full of personal, handmade touches. The space was originally conceived as an artist's retreat and occupies the top story of an English-style BARN otherwise used as a photographer's workshop. Here is your chance to slow down by the fire, soak in the views from your private balcony, and gaze at the stars from your soaking tub in the cedar and pine bathroom.

Guest favourite

Cottage in Chaplin

4.88 out of 5 average rating, 147 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 favourite

Guest suite in Brooklyn

4.92 out of 5 average rating, 198 reviews

Affordable In-Law Apartment in Brooklyn, CT

This is a great in-law style apartment which was fully renovated in 2020. It can be booked for short stays or more lengthy visits to Northeast CT. The apartment is one minute from Scenic route 169 and Route 6. It is 30 minutes to UCONN and ECSU. We are close toThe Pomfret School/Rectory School. It is 35 mins to Mohegan Sun and Foxwoods. My place is rural and peaceful. It is good for couples, solo adventurers, business travelers, and families.

Top guest favourite

Home in Windham

5 out of 5 average rating, 13 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 with a monitor, 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 Casino. Enjoy a stand-up tile shower and an oversized soaking tub. Perfect for families, professionals & groups!

Guest favourite

Flat in Ashford

4.97 out of 5 average rating, 254 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.

Guest favourite

Guest house in Hampton

4.95 out of 5 average rating, 160 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.

Guest favourite

Home in Manchester

4.94 out of 5 average rating, 217 reviews

Paradise On The Hill Luxury Apartment.

Enjoy your own special and separated section of this beautiful, modern colonial home. This beautiful home includes an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large bathroom with spa like jets. His and hers closets. Beautiful kitchenette. 50 inch T.V., Free WiFi. , comfortable dining and more, all for the comfort and convenience of our guests.

Top guest favourite

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