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House holiday rentals in Windsor

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Windsor

House rentals with a pool

Guest favourite
Home in East Hampton
4.95 out of 5 average rating, 65 reviews

Country getaway - huge yard, pool

TressiaRating, 5 stars1 week ago
Lena was wonderful. She warmly welcomed me and my guest, making our stay very comfortable and easy. She even left me a note with birthday wishes, along with a box of delicious baked cookies. The apartment is charming and spacious, located on top of their home, with a large yard and peaceful scenery.
Superhost
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars9 months ago
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.
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 201 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars3 months ago
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!
Superhost
Home in New Hartford
4.79 out of 5 average rating, 42 reviews

Mountaintop Nirvana: Lake, Pool, Hot Tub, Nature

ColleenRating, 5 stars1 week ago
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!
Guest favourite
Home in Montville
4.93 out of 5 average rating, 162 reviews

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos

SamRating, 5 stars2 weeks ago
AJ's home was great for our one night stay. The hot tub and outdoor patio were our favorites, and the interior also did not disappoint! AJ was a friendly and communicative host.
Top guest favourite
Home in Kent
4.96 out of 5 average rating, 26 reviews

Country retreat on 4 private acres

CaseyRating, 5 stars1 month ago
We sought out a quiet and peaceful place we could stay after a long winter. We got exactly that with Monica's home in Kent, Connecticut. We traveled with two dogs and our toddler. This home was able to accommodate that. Our toddler has a lot of energy and seeking out a place where we could get all of his energy out but still maintain a peaceful atmosphere, so we thought, would be hard. But tucked away in the beautiful forest of Kent, we found a place where our toddler could run through the large property and he had plenty of activities inside as well. Monica had everything equipped for families with children. Due to weather, the internet went out the day before we were to check out and unfortunately remained that way the remainder of the trip. But Monica was quick to inform me and we were able to find plenty of activities to do in the home. We truly appreciated all the amenities that this home had to offer for a peaceful and relaxing stay.
Guest favourite
Home in Montville
4.95 out of 5 average rating, 151 reviews

Casino Stay & Play House

NurisRating, 5 stars1 week ago
I loved spending my birthday with my family. It was the perfect place for my family. Everything was so clean and organized. I am very grateful for everything. Thank you

Weekly house rentals

Guest favourite
Home in Hartford
4.91 out of 5 average rating, 76 reviews

Renovated & Modern Victorian in Historic West End

AmandaRating, 5 stars2 weeks ago
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!
Guest favourite
Home in West Hartford
4.88 out of 5 average rating, 86 reviews

Charming home in West Hartford.

ShavaunRating, 5 stars1 week ago
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!
Top guest favourite
Home in West Hartford
5 out of 5 average rating, 72 reviews

Prime West Hartford Center Location: Historic Gem

RomanRating, 5 stars1 week ago
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.
Top guest favourite
Home in New Hartford
4.96 out of 5 average rating, 69 reviews

Private Woodland Sanctuary—3 mins to a lake beach!

EmilyRating, 5 stars1 week ago
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.
Guest favourite
Home in Ellington
4.83 out of 5 average rating, 64 reviews

Cheerful 3 bedroom home with large back yard

SusanRating, 5 stars4 weeks ago
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!!
Guest favourite
Home in New Britain
5 out of 5 average rating, 37 reviews

Clean, Bright & Private WHOLE HOUSE 4 YOU. 7 Beds

AvariRating, 5 stars4 days ago
I really enjoyed my stay at this house in Connecticut. It was super clean, comfortable, and had everything I needed for a relaxing visit. I appreciated the little things—like having dishes, cups, and basic kitchen supplies already there. It made it feel more like home and less like just a rental. The location was easy to get to and felt safe and quiet. Overall, it was a really smooth and stress-free stay, and I’d definitely recommend it to anyone looking for a simple, well-kept place to stay!
Superhost
Home in Agawam
4.82 out of 5 average rating, 28 reviews

Home near Six Flags/ hot tub

MariaRating, 5 stars3 weeks ago
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.
Guest favourite
Home in South Windsor
4.95 out of 5 average rating, 22 reviews

5 Bd 2.5 Bth Home Away From Home

KristinaRating, 5 stars3 weeks ago
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

Guest favourite
Home in Rocky Hill
4.96 out of 5 average rating, 25 reviews

Cozy Waterfront Home, With Hot Tub~Rocky Hill, CT

AdamRating, 5 stars1 week ago
Great location. Great space. Everything was in excellent condition. Our family had a wonderful time.
Top guest favourite
Home in Plymouth
4.98 out of 5 average rating, 41 reviews

Don’t miss out on this cozy New England escape!

PriscillaRating, 5 stars2 days ago
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.
Top guest favourite
Home in Newington
5 out of 5 average rating, 39 reviews

Urban Luxury in Central CT w/ free RV parking

JosephRating, 5 stars2 weeks ago
Staying with Sal is simple and nice! We felt very taken care of and safe, would stay again if in the area
Top guest favourite
Home in West Hartford
5 out of 5 average rating, 12 reviews

West Hartford Center Gem 2!

SarahRating, 5 stars2 weeks ago
We had a lovely stay at Alison’s place over a long weekend. The location can’t be beat — just a few minutes off the highway and walking distance to lots of shops and restaurants. My family of three had plenty of space to relax when we came home each night. The beds were firm but comfortable and the kitchen and bathroom were updated and very clean. I would definitely recommend this place to any visitor to the West Hartford area. Thank you Alison!
Guest favourite
Home in Granby
5 out of 5 average rating, 6 reviews

Great Room Lake House

SarahRating, 5 stars5 months ago
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!
Superhost
Home in Enfield
4.77 out of 5 average rating, 31 reviews

RiverView Oasis

HeatherRating, 5 stars3 weeks ago
Great place to stay. This couple paid very good attention to detail and left all the little things that would help make your stay so much easier. The stocked mini-fridge, candy dish, welcome sign, even extra toiletries, made the stay so much smoother. The washer and dryer were so helpful and we were really grateful for that. The back yard was overgrown when we first got there and they were super responsive and sent someone out within a day or 2. They were so friendly and so quick to answer any questions or address any issues. We would definitely stay at their place again, as it really did have all the comforts of home. We met the neighbors on either side of us as well and they were so kind. We traveled to watch our daughter graduate from grad school and not having to constantly worry about the little things or our safety really made it a great few days!
Guest favourite
Home in Connecticut
4.97 out of 5 average rating, 62 reviews

Farmhouse Broad Brook: Comfort & Charm.

KristinaRating, 5 stars1 month ago
The home was exquisite and everything you need for a stay is provided. The description of the home is true in every aspect. It is easy to communicate with Jean Paul the host as he reaches out to see how things are going and if any supplies are required. It is definitely worth the money and visiting again.
Guest favourite
Home in Wethersfield
4.9 out of 5 average rating, 20 reviews

Happy hour

DavidRating, 5 stars1 week ago
The place was cute as can be and John was the best host I have ever had. He was very friendly and responsive. He had various beverages in the refrigerator for our use and even gave us a $50 gift card to a local restaurant, which served delicious cuisine. My wife and I cannot say enough good things about our accommodations and host.

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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