Apartment holiday rentals in Windham County

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Windham County

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

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Guest favourite

Flat in Woodstock

4.93 out of 5 average rating, 416 reviews

“Tranquillity on the Lake ” Woodstock Valley, CT.

Summer is here !! Enjoy fun relaxing water activities on beautiful Lake Bungee. Enjoy direct waterfront sunrises , 1400 sq ft. Queen bed in Master. Queen sofa in living area. fireplace. Air conditioning, Kitchen stove, full refrigerator, microwave. Enjoy your own deck, propane fire pit, gaze at the stars.BBQ propane grill. Stroll around both lakes, see bird sightings,nature’s at its finest. Great local dining & wineries. Each season paints its own stunning beauty. Relax and enjoy Tranquility !!

Superhost

Flat in Windsor Locks

4.85 out of 5 average rating, 166 reviews

Apt near Big E, Six Flags, Bradley airport

Welcome to our charming and stylish upstairs apartment, perfect for a cozy retreat! Enjoy the privacy of having the entire space to yourself. Access the apartment directly through the back entrance, up the outdoor staircase. We're conveniently located just a 10-minute drive from Bradley International Airport. Inside, you'll find: - A comfortable bedroom with a Queen-sized bed, complete with fresh linens - A fully stocked kitchen, equipped: Pots, pans, baking dishes, etc Washer and dryer

Guest favourite

Flat in Chester

4.93 out of 5 average rating, 384 reviews

Chester Village 'Pied-à-terre' above art gallery

ONE night stays are available for last minute bookings, please message us. Our lovely, well designed place is in an ideal location. A sunshine filled living room w/high ceilings, a private bedroom in back, and large private deck overlooking Pattaconk Brook. A true gem, set up solely for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique. We're neighbor to some of the BEST restaurants, art and shopping in CT! We know you'll enjoy your stay!

Top guest favourite

Flat in Coventry

5 out of 5 average rating, 115 reviews

Hide Away at Rock Farm UConn Private BnB “5 Star”

Enjoy a peaceful stay at The “Hide Away” on Rock Farm. The family friendly 1000+ sf 2 bdrm apt is surrounded by woods 600ft from road. Well lit, all amenities of home. Enjoy the private deck on sunny mornings. 2 min drive to Bolton Lakes & beaches. Fishing, Kayaking & trails. See our VIP GUEST BOOK for The Get Away, The Hide Away and Family Ties on Rock Farm. A no-shoe, clean place, safe & comfortable home. 5⭐️ Needing less space? Visit the Get Away https://www.airbnb.com/h/onrockfarm

Guest favourite

Flat in Sturbridge

4.95 out of 5 average rating, 118 reviews

Main Street Suite

Enjoy a boutique hotel experience in a historic New England town. This private, well-equipped suite is housed in a mixed use building (with a few small businesses with daytime hours) next door to a popular craft beer pub, and across the street from a hopping neighborhood Japanese restaurant. Enjoy everything you need in a home base with quick access to Old Sturbridge Village, lakes, trails, wineries, breweries, restaurants, farmers’ markets, festivals, events, antiquing, and more!

Top guest favourite

Flat in Brimfield

4.98 out of 5 average rating, 176 reviews

Quiet & Cozy Main Street Retreat

Skip the traffic on the way to popular seasonal tourist destination, the Brimfield Flea Market, by staying here the night prior to your visit! Or, complement an off-season stay with an abundance of hiking trails, antique shops, lakes, farms, and even a winery just a 5 minute walk from your doorstep. Enjoy the ease of a convenience store, gas station, package store, and post office across the way, combined with the peace and quiet of this private suite tucked behind the main house.

Top guest favourite

Flat in Wilbraham

4.98 out of 5 average rating, 119 reviews

Western Mass Retreat!

Western Mass Retreat! Come relax and unwind in this updated retreat and check out all the amazing things that Western Mass and Northern CT have to offer. Enjoy the cozy reading nook, outdoor space, or a relaxing dinner in at the dinette table. Centrally located near multiple colleges and universities, two miles from Wilbraham & Monson Academy, ten minutes from GreatHorse and close to many one-of-a-kind events and experiences. Please message me with any questions.

Superhost

Flat in Brooklyn

4.85 out of 5 average rating, 228 reviews

8 Bedroom, 4 full bath residence with 40' pool

Fully appointed guest suite in renovated 150-year old post & beam barn. Exposed original wooden posts, beams and pegs. Three floors. 8 bedrooms (1 full and 7 queen beds) with A/C. 2 bedrooms have attached bathroom and 4 have cathedral ceiling.. 2 living rooms, 4 full bathrooms, full kitchen, separate kitchenette, large dining area and solarium. 4 stone-walled acres. Shaded 40 ft pool with screen house and outdoor cooking and dining area..

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.

Top guest favourite

Flat in New Britain

4.96 out of 5 average rating, 207 reviews

Spacious Cozy Guest Suite

This unique guest suite located in a newly constructed home offers over 600 sq ft of space. There is a private entrance in a quiet and safe location. Minutes from CCSU, UCONN Med Center, I-84, downtown, restaurants and shopping. West Hartford Center is only 10 minutes away. KITCHEN DOESN’T INCLUDED STOVE , fridge, microwave, fully stocked coffee bar. Smart TV, high speed internet and work space are perfect for remote work.

Guest favourite

Flat in Dudley

4.83 out of 5 average rating, 502 reviews

웃❤️유 PRIVATE STUDIO - SAFE GORGEOUS HIDEOUT

Excellent for couples; voyagers & professionals. Ideal for short or long terms stays, everything is incld. Cozy, bright and small very comfy bedroom, if business travel or just visiting the area, Kitchen, living room and Laptop Desk. Self-Check-In, Wi-Fi, free & safe on-street Parking, Lock on Door, Laundry available*, A/C, we are in a busy street during the day but really safe

Guest favourite

Flat in Stafford

4.94 out of 5 average rating, 158 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.