House vacation rentals in Windsor

Find and book unique houses on Airbnb

Top-rated house rentals in Windsor

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

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Guest favourite

Home in Lyme

4.97 out of 5 average rating, 189 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“The Answer” is listed amongst the 15 best Airbnbs in Ct, from Travellers Worldwide 2022 and 2023 and featured in “Only In Your State” titled “This Riverfront House Will Be Your New Favorite” February 2024 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

May 9 – 16

$476 CAD per night

Guest favourite

Home in Coventry

4.94 out of 5 average rating, 160 reviews

Cozy Cottage * Coventry Lake* 15 min to UConn *

Enjoy this quaint lake cottage that is close to Uconn and all the area has to offer. It has been updated with new flooring and fresh paint. Access to a private association beach is only a three minute walk. This beach is for paid guests only. Please note the fireplace is not a working fireplace. The area offers hiking trails, antiquing, vineyards and access to the lake. In the winter there is ice fishing and ice skating. In the summer you can kayak, paddleboard or relax on the beach.

Mar. 28 – Apr. 4

$275 CAD per night

Guest favourite

Home in Granby

4.95 out of 5 average rating, 219 reviews

FULLY stocked Ranch Home, * Gardens* Gameroom

Clean refreshing three-bedroom , one floor living, centrally located, walk to town for fantastic dining ! Mexican, Sushi and Thai, Mediterranean, Italian, Continental, and Vegan ! 8 minutes to rt 91 and Bradley, minutes to Mass line! Downstairs living space with a gameroom and comfortable seating, and extra sofa bed and airbeds, if needed. Other than clothes, you will need nothing else...I provide everything from razors to coffee , tea and a HUGE snack basket ! Even have a heating pad .

Feb. 1 – 8

$326 CAD per night

Guest favourite

Home in Vernon

4.99 out of 5 average rating, 115 reviews

Luxe Bolton Lake!

Now booking for summer! Relax and savor the tranquil vistas of picturesque Middle Bolton Lake while enjoying stylish comfort in our 2000+ sq. ft. 3 bedroom/3 bathroom architecturally-designed home. Amenities include expansive waterfront, outdoor jacuzzi, gorgeous master bedroom suite w/ private en suite bath, boutique toiletries, artistic furniture, cozy fireplace, coffee bar, complimentary snacks, wifi, large deck, fire pit, kayaks, vintage canoe and much more. Come make lasting memories.

Mar. 6 – 13

$837 CAD per night

Guest favourite

Home in Chester

4.96 out of 5 average rating, 311 reviews

Riverfront Getaway

Our place is on a gentle flowing river, close to waterfalls, walks and the Berkshire cultural sites like Tanglewood and Jacobs Pillow . You’ll love our place because of the river, the deck, the hot tub; complete tranquility and a home away from home. Close to some great sites and activities, far enough away to escape. Our place is good for couples, friends and solo adventurers. Snowboarders/Skiers (or snow bunnies) and families can have great fun too! Sit back, relax and enjoy our home!

Sep. 6 – 13

$296 CAD per night

Guest favourite

Home in Ware

4.89 out of 5 average rating, 110 reviews

Little House Inn

NO CLEANING FEES - NO CHORE LIST Reconnect with loved ones in this family-friendly place. Our little house is situated on an acre and a half of land surrounded by wetlands and woods yet minutes from local colleges and amenities. Enjoy the beautiful night sky while relaxing by the fire pit. Or enjoy the woodland view from your deck with your morning coffee. Deer, turkeys, bunnies, and many native birds are regular visitors. Check out our guidebook for places to eat & things to do.

Sep. 19 – 26

$214 CAD per night

Guest favourite

Home in Feeding Hills

4.89 out of 5 average rating, 883 reviews

Farm Fresh Feeding Hills

Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, good for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

May 31 – Jun. 7

$176 CAD per night

Guest favourite

Home in Bristol

4.93 out of 5 average rating, 114 reviews

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Apr. 4 – 11

$241 CAD per night

Guest favourite

Home in New Hartford

4.89 out of 5 average rating, 133 reviews

Modern Farmhouse

This is a quaint, sun-filled farmhouse in the Farmington valley of Connecticut. Convenient to great antique shopping, Ski Sundown, farm stands, Farmington river inner-tubing and biking trails, kayak and canoe rentals, the sweet towns of Collinsville and New Hartford, and a 30 minute straight shot to Hartford itself. The house is also convenient to Torrington, Simsbury, Avon, Winsted, and a beautiful drive to Hartford-Bradley International Airport.

May 6 – 13

$255 CAD per night

Guest favourite

Home in Manchester

4.94 out of 5 average rating, 176 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.

Sep. 23 – 30

$167 CAD per night

Guest favourite

Home in Southwick

4.99 out of 5 average rating, 181 reviews

Linny's Lakeview Cottage

Linny's lakeview cottage is updated with beautiful hardwood floors. The kitchen is finished in white shaker cabinets, granite counter tops & new ss appliances. The counter joins the kitchen/living room & comfortably sits 6. This is a renovated 650 sq ft home. Access our online guidebook (a few day before your stay) for; house rules, local attractions, maps, and more, ensuring you make the most of your stay.

Oct. 3 – 10

$279 CAD per night

Guest favourite

Home in Coventry

5.0 out of 5 average rating, 105 reviews

Waterfront 10 min to Uconn outdoor tv gas fire pit

Waterfront on Coventry Lake - Outdoor TV - Gas Fire Pit - Gas Fire Table - Grill - Stand Up Paddle Board - Canoe - Hydrobikes - Dock - Private Sandy Beach - Open Floor Plan - Complimentary Nespresso Pods, Teas & Coffee Bar - TV In All Bedrooms - Laundry

Dec. 30 – Jan. 6

$412 CAD per night