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

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!

Amazing Oasis Private Pool, BBQ, Pool Table.
Glenda was friendly and had great communication from Start to Finish. This was a nice location for a family fun weekend. Although the drive is close enough to stores if you need anything (target/stopnshop/bjs etc), the property is in a quiet and safe neighborhood. The yard is a great place to hang out and relax with the fire pit or have fun in the pool. And when the weather was crappy the pool table and hanging out in the basement den was nice. Everything in the house is labeled and easy to find. We enjoyed the space and would definitely recommend. Thanks again! đ

Garden Level Suite with Beautiful Pool
We had an amazing time at Marybethâs suiteâit 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 canât 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
We thoroughly enjoyed our short stay in Mystic at this great home. The pool was the biggest hit, but the kitchen/living room area was an amazing place for our group to gather for meals and games. Location is spectacular as you can just park at the house and walk to all the great restaurants the area has to offer and if you have kids, thereâs a great playground just a short walk away. We would definitely stay here again!

Hot Tub~Pool~Game Room~Fire Pit~BBQ~Casinos
We had a great time at AJ's place! The space is very spacious and comfortable, everything was clean, and the backyard was PERFECT for our group. Close to casinos and restaurants. Highly recommend for groups and families!

Stunning Views, Bucolic Bliss in 1790s Farmhouse
Only complaint would be the noise from road during the morning commute
Weekly house rentals

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!

Charming home in West Hartford.
Terrific water pressure in shower & windows. Loved the soft cushion mattress .Very clean and welcoming environment . Suggestion : provide a Keurig machine Would like to stay here again in future.

Charming Cape Home, Close to All
This house was perfect for our group of four old college friends gathering to mark major birthdays happening throughout the year. The location was very convenient and easy to locate, and we especially enjoyed the comfortable outdoor seating areas. Beds and rooms were all comfortable, all necessities supplied, and everything worked as intended. Our host was very easy to communicate with, and accommodating with our request for early checkin. It was a great spot to relax and enjoy the area.

West Hartford Center Gem 2!
We had a lovely time and are grateful for the wonderful accommodations. Alison really put a lot of thought into her property and it shows. All the USB chargers everywhere, the kitchen had everything one would need, the array of books was so inviting even to non-readers đ and the bathrooms were immaculate. And being right across the police station made our kids feel so safe.

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 Markâs place. The location is spot-onâjust a short walk to the center of West Hartford, a surprisingly charming little town. Whole Foods, cafes, restaurantsâall five minutes away. The house is spacious, clean, and has a nice, fresh feel to it. What really stood out was Markâs attention to detail. Everything you might need is thereâextra towels, toiletries, laundry stuff, umbrellas, coffee and kitchen supplies. even charging cables neatly set up by each bed. You can tell itâs been thoughtfully put together. the mattresses are amazing. We all slept like rocks.

Cheerful 3 bedroom home with large back yard
Mr. Andrew was great! Made sure we didn't go without. On my next trip I would LOVE to come back. I felt right at home.

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 bathroomâs 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 didnât 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.
Private house rentals

Cozy Waterfront Home, With Hot Tub~Rocky Hill, CT
I would like to stay Lisaâs 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 thoughtfulâŚ.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.

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!

Donât miss out on this cozy New England escape!
Would gladly stay here again. Shawn was responsive and the place had everything we needed. Hope to come back to this part of CT again

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD
wonderful stay by the lake in Ashford! Joe is a very nice host and very responsive if needed.

Urban Luxury in Central CT w/ free RV parking
The home was in a beautiful neighborhood, which made for nice walks, the kids were able to play ball in the yard, the check in directions were clear, we had 2 vehicles with plenty of additional space, the house was squeaky clean, the beds were comfortable and the photos were very accurate. The ping pong table was awesome distraction when it rained. It was easy to get to stores and restaurants. Laser tag, movies, bowling all a short drive. Host was easy to reach, responded quickly and had friendly attitude. We can recommend the âFlying Monkeysâ restaurant where we had dinner to live jazz band! Food was great. All in all despite clouds and rain we had a great time visiting with our grandkids!

4 BR Entire House w/Hot Tub
Highly recommend Lynne's home. Spotless, welcoming, and every detail covered for travelers. The 4 bedrooms were spacious, and meticulous. Absolutely no hesitation in rebooking when in the area.

The little house that could!
I had a great time here in the space, it felt very comfortable and safe.

RiverView Oasis
A couple of snafus were handily dealt with by Akudo, who is very responsive. The bed were comfy and the view is outstanding! It took no time at all to acclimate to the friendly rumbling trains speeding by. A nice place to stay.
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
Wi-Fi availability
40 properties include access to Wi-Fi
Popular amenities
Kitchen, Wi-Fi and Pool
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- Yale University
- Foxwoods Resort Casino
- Six Flags New England
- TPC River Highlands
- Ocean Beach Park
- Woodmont Beach
- Silver Sands Beach
- Bushnell Park
- Taconic State Park
- Quotonset Beach
- Catamount Mountain Ski Resort
- Groton Long Point South Beach
- Kent Falls State Park
- Bash Bish Falls State Park
- Groton Long Point Main Beach
- Clinton Town Beach
- Mystic Seaport Museum
- Bayview Beach
- Attawan Beach
- Brownstone Adventure Sports Park
- Anchor Beach
- Avery Point Beach
- Brimfield State Forest
- Grove Beach