
House holiday rentals in Windsor
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Top-rated house rentals in Windsor
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Popular amenities for house rentals in Windsor
House rentals with a pool

Homestead Near Mystic, Casinos & Beaches
This was the perfect spot for what we were looking for as my son graduated from Conn College. The host was very responsive to my questions and flexible with check in times which we needed. House was exactly what was described and we had a wonderful time. Thank you!!

Casino Wine Down House
Beautiful, relaxing, clean Airbnb. Had an issue with the shower, which can happen anywhere, Mk was super responsive and came over quickly. Loved loved loved our stay here. Didn’t use the swimming pool due to weather but the screened deck with the Fire Pit and the superb game room saved the day. Thank you for hosting us will be back

The Getaway-HOST & Co.
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.

Pool House
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!

Garden Level Suite with Beautiful Pool
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

Cedar Ridge: House or House+Apartment
Very responsive hosts who helped us with restaurants. House was very clean, well appointed and had everything we needed. Great for families or a girls weekend!

4BR Private Indoor Heated Pool - Lux Mystic Home
Enjoyed our time at Jason’s house. My family really enjoyed the warm pool along with all the pool toys. Our host provided good information as well as being responsive to any questions. The house was very clean and beautiful.

Mountaintop Nirvana: Lake, Pool, Hot Tub, Nature
We had an amazing stay! David was quick to respond with any questions I had and even came out to hook up the propane tank for the heated pool. I saw in previous reviews about the tricky driveway but David’s description of it is perfectly accurate and not any trouble, just a little steep but nothing super tricky to deal with! The house has a beautiful setup and view, very clean and so much space. Even though it was cold and rainy we had the most fun and peaceful stay at this home. The bride of the bachelorette group said she wants to book with David on her own just for another stay/get-a-way! Highly recommend this beautiful space!
Weekly house rentals

Renovated & Modern Victorian in Historic West End
Excellent place to stay, especially due to its amenities and proximity to the University of Hartford. Antonio was super friendly and responsive - will look to stay here again in the future!

The Silhouette in Hartford
It's a well-furnished, comfortable stay tucked into a very large house. One block from St Francis hospital. Enjoyed my stay. Thank you!

Great Room Lake House
A beautiful location with unbelievable views of a small lake. 3 comfortable bedrooms, great bathrooms- everything clean, updated and well appointed. Plenty of parking. This is the top floor of a large split up home (with 2 other units). You go upstairs and there is large open room that serves living room/dining/kitchenette. The kitchenette is minimal (fridge, coffee maker, hot plate, toaster and microwave). Enough if you are just going to have lunch and breakfast at home but definitely not the rental for you if you want to do a lot of cooking. The foosball table was a ton of fun! We are eager to stay again on our next trip here. The hosts were friendly and responsive to any questions we had. Thanks for the great stay!

Prime West Hartford Center Location: Historic Gem
We had a great stay at Mark’s place. The location is spot-on—just a short walk to the center of West Hartford, a surprisingly charming little town. Whole Foods, cafes, restaurants—all five minutes away. The house is spacious, clean, and has a nice, fresh feel to it. What really stood out was Mark’s attention to detail. Everything you might need is there—extra towels, toiletries, laundry stuff, umbrellas, coffee and kitchen supplies. even charging cables neatly set up by each bed. You can tell it’s been thoughtfully put together. the mattresses are amazing. We all slept like rocks.

Private Woodland Sanctuary—3 mins to a lake beach!
this place is magical. my sisters and I have stayed here twice now, for her wedding and now for mine. both times the home has been clean and the overall experience has been wonderful.

Cheerful 3 bedroom home with large back yard
There was plenty of room for our whole family with space to be together and have privacy if needed. We loved the backyard where we played corn hole that we brought and had a fire. The roads are safe for walking. Andrew was responsive to one minor issue we had which was very much appreciated! I would highly recommend a stay at this spot!!

Home near Six Flags/ hot tub
This home is just what the pictures show. It was a great first experience with Airbnb. Checking in and out was simple. The only thing we noticed is that one of the bathroom’s trash was not thrown out. Other than that, no other issues. The home is very nice and clean. Just an FYI for future renters, the house is in a Main Street but we didn’t mind the minimal traffic noise, mostly at night, since we live in a big city and are used to it. We would stay here again.

5 Bd 2.5 Bth Home Away From Home
Large, spacious inside and out. Very easy to get to from the highway and close to Hartford where we were going. Absolutely spotless and clean!!! Close to convenient stores, dunks. We had a wonderful stay and really appreciated his timely and quick responses. We would stay here again!
Private house rentals

Cozy Waterfront Home, With Hot Tub~Rocky Hill, CT
I would like to stay Lisa’s property looked just like the pictures, but it was honestly even better! We have been to many nice Airbnbs but this was the nicest. It was the special touches that were so thoughtful….beautiful fresh roses in the kitchen and bathroom, battery candles that came on in the evening, muffins, snacks, dog treats, shower steamers. So very welcoming. We had such a relaxing few days. The home is extremely clean with very comfortable decor and bedding and lovely thick bath towels. The master bath is spa like. We enjoyed sitting out on the huge deck while my son was fishing right across the street. If we get back to the area, we would stay here again in a heartbeat. Thanks so much Lisa for having us.

Don’t miss out on this cozy New England escape!
Shawn's home provided a perfect place for my husband, mother and myself spend time with my son and daughter-in-law that are now attending college in CT. The home was spacious and made it possible for us to cook and to gather around a table for a family meal. The hot tub, fire pit table and grill was a great addition. There are also plenty of games available. The beds are super comfy! We wanted to take advantage of the skatepark but no one brought a board :-( The property and home are very beautiful. We had such a great time and won't forget how peaceful our stay was. Shawn is very responsive, informative and polite. Thank you for a wonderful stay.

Charming home in West Hartford.
We stayed in West Hartford for a weekend getaway, having grown up in the area we couldn't wait to get back and reminisce. The area is just how I remembered it, right down to our fav pizza place being in walking distance. We enjoyed staying in the first night and sitting out on the porch. The 2nd night we ventured out to West Hartford Center and Hartford, both very close to the apartment. The surrounding area is very quiet, we felt safe and at home and would definitely stay here again when we return to visit. I would recommend staying here. The beds were very comfortable and the house very clean. We look forward to returning, thank you!

Lake Escape: Lake Cottage Charm, Lake Front, AC
What a wonderful stay! We loved the location - beautiful view of the lake. House is very comfortable, clean, and easy to get to. Tracie and Sean were excellent in communicating everything we needed to know to have an enjoyable stay. We'll be back again with life jackets and fishing poles so we can enjoy some time on the lake!

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
We had such a nice family trip with nice walks en lots of laughs from the board games!

Urban Luxury in Central CT w/ free RV parking
Staying with Sal is simple and nice! We felt very taken care of and safe, would stay again if in the area

4BR House- Central Location
Caroline was extremely responsive to our questions and really friendly. Great location near quaint “main” street town of Manchester. Awesome backyard with fire-pit and ample seating Spacious bedrooms Games, snacks, water and coffee station were extremely thoughtful. We would definitely rent from her again.

West Hartford Center Gem 2!
Great stay! Had a fun time and it was a very cute place!
Quick stats about house rentals in Windsor
Total rentals
40 properties
Total number of reviews
1.2K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
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- Yale University
- Foxwoods Resort Casino
- Six Flags New England
- TPC River Highlands
- Ocean Beach Park
- Woodmont Beach
- Quotonset Beach
- Bushnell Park
- Silver Sands Beach
- Bash Bish Falls State Park
- Taconic State Park
- Catamount Mountain Ski Resort
- Groton Long Point Main Beach
- Clinton Town Beach
- Bayview Beach
- Grove Beach
- Attawan Beach
- Groton Long Point South Beach
- Kent Falls State Park
- Giants Neck Beach
- Mystic Seaport Museum
- Shennecossett Beach
- Anchor Beach
- Clinton Beach