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.

Top guest favourite

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.

Top guest favourite

Loft in Tolland

4.97 out of 5 average rating, 258 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 favourite

Barn in Hampton

5 out of 5 average rating, 36 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

Guest suite in Brooklyn

4.92 out of 5 average rating, 195 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 Willimantic

5 out of 5 average rating, 10 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, 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.

Guest favourite

Cabin in Windham

4.85 out of 5 average rating, 169 reviews

Secluded Cabin on Golden Pond

• Cozy Cabin on Golden Pond! • Fire Pit, (free wood)! • Fishing! • Kayak, Paddle Boat Canoe, Row boat! • Hiking! • Swimming! • Sand Beach! • Picnic Table, Chairs! • Grill! • WiFi! • Cooking Utensils, Service 4 six! • Air Conditioning! . Soap Stone Fire Place! . Comfy Couch, Smart T.V.! . Beds: 2 Full, 2 Twin, 1 Queen on Porch! • 14x14 Tent platform at waters edge! (Camping gear not provided) • Secluded! • Wildlife!

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

Guest favourite

Treehouse in Willington

4.91 out of 5 average rating, 455 reviews

Treehouse - Countryside - Farm Animals - Fire Pit

Top guest favourite

Flat in Mansfield

5 out of 5 average rating, 72 reviews

Beautiful one bedroom in convenient location

Keep it simple at this peaceful, centrally-located spot just minutes from both UCONN and Eastern Connecticut State University. Easy access to many hiking trails and Mansfield Hollow State Park. Enjoy some solitude in eastern Connecticut. Our apartment is very well cared-for and has everything a guest might need. Our house is a home, including the space you occupy.

Guest favourite

Flat in Stafford Springs

4.94 out of 5 average rating, 157 reviews

Modern Industrial Apartment with rooftop access

* Modern industrial apartment with rooftop access. * Nestled in an old Mill Building/Artist Community. * Centrally located between Boston and NYC. * 15 mins to UConn, 20 mins to Brimfield Antique Show. * 40 mins to MGM Casino in Springfield, MA. * Walk to restaurants, boutiques, parks, and events. * On-site Yoga, Dance, Recording Studio & Vintage Shop.