
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

Country getaway - huge yard, pool
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.

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!

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!

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

Country retreat on 4 private acres
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.

Casino Stay & Play House
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

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!

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!

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!!

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

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
Great location. Great space. Everything was in excellent condition. Our family had a wonderful time.

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.

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

West Hartford Center Gem 2!
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!

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!

RiverView Oasis
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!

Farmhouse Broad Brook: Comfort & Charm.
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.

Happy hour
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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- 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
- Attawan Beach
- Groton Long Point South Beach
- Grove Beach
- Kent Falls State Park
- Giants Neck Beach
- Mystic Seaport Museum
- Shennecossett Beach
- Anchor Beach
- Clinton Beach