House vacation rentals in Windsor

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Windsor house rentals

House rentals with a pool

Superhost
Home in Stonington
4.9 out of 5 average rating, 105 reviews

Homestead Near Mystic, Casinos & Beaches

Sherri Watson Rating, 5 stars4 weeks ago
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!!
Superhost
The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.
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 favorite
An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars3 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 favorite
A serene pool area features a clear blue in-ground pool surrounded by lounge chairs with red cushions. A vibrant hibiscus flower adds a splash of color, and a slide is visible for added fun. The area is enclosed for safety.
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!
Guest favorite
A serene swimming pool is surrounded by well-maintained greenery, with lounge chairs placed along the deck. Large blue umbrellas provide shade, enhancing the outdoor space suitable for relaxation. A stone wall borders the area, adding a natural touch.
Home in Woodstock
4.94 out of 5 average rating, 238 reviews

Cedar Ridge: House or House+Apartment

HilaryRating, 5 stars1 month ago
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!
Guest favorite
Home in Stonington
4.99 out of 5 average rating, 107 reviews

4BR Private Indoor Heated Pool - Lux Mystic Home

JoshRating, 5 stars2 days ago
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, there’s a great playground just a short walk away. We would definitely stay here again!
Guest favorite
The exterior of a single-story home is presented, featuring a manicured lawn and a symmetrical facade. Solar panels are installed on the roof. Large windows are visible, providing natural light to the interior. A path leads to the front door, flanked by neatly trimmed shrubs.
Home in Montville
4.93 out of 5 average rating, 163 reviews

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

KacieRating, 5 stars2 weeks ago
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!
Guest favorite
Home in Litchfield
4.93 out of 5 average rating, 189 reviews

Stunning Views, Bucolic Bliss in 1790s Farmhouse

ThomasRating, 5 stars2 weeks ago
Only complaint would be the noise from road during the morning commute

Weekly house rentals

Guest favorite
A spacious living area features a red sectional sofa and a small round coffee table with a plant centerpiece. The open layout connects to a well-lit kitchen in the background, visible through a doorway, blending comfort and functionality.
Home in Manchester
4.9 out of 5 average rating, 42 reviews

Charming Cape Home, Close to All

ThayerRating, 5 stars6 days ago
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.
Guest favorite
A spacious living area features a red sectional sofa facing large windows that allow natural light to fill the room. Exposed wooden beams add character to the ceiling, and a cozy fireplace is situated against a dark accent wall, complementing the warm wooden flooring.
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!
Top guest favorite
A comfortable living area features a brown leather sofa and two accent chairs positioned around a round coffee table. Light-colored curtains frame large windows, allowing natural light to fill the space. A decorative rug adds warmth, while framed artwork enhances the walls.
Home in West Hartford
5 out of 5 average rating, 15 reviews

West Hartford Center Gem 2!

DavidRating, 5 stars1 day ago
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 😆 and the bathrooms were immaculate. And being right across the police station made our kids feel so safe.
Top guest favorite
An outdoor deck features a large table surrounded by several comfortable chairs. A gas fire pit is centrally located on the table, and a grill is positioned nearby. Lush greenery can be seen in the background, enhancing the outdoor space.
Home in West Hartford
5 out of 5 average rating, 73 reviews

Prime West Hartford Center Location: Historic Gem

RomanRating, 5 stars2 weeks 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 favorite
A multi-story wooden house is set against a backdrop of lush green trees. Colorful flowering bushes, primarily in shades of pink, enhance the natural landscape, while a glass solarium extends from one side of the house, showcasing outdoor living space.
Home in New Hartford
4.96 out of 5 average rating, 69 reviews

Private Woodland Sanctuary—3 mins to a lake beach!

EmilyRating, 5 stars2 weeks 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.
Superhost
A single-story home is framed by vibrant autumn foliage, with a well-maintained front yard covered in fallen leaves. The house features a welcoming entrance with a set of stairs, and large windows that allow natural light to fill the interior.
Home in Ellington
4.8 out of 5 average rating, 66 reviews

Cheerful 3 bedroom home with large back yard

Olga MariaRating, 5 stars4 days ago
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.
Superhost
A living area features a navy sofa paired with wooden chairs around a circular table. A stone fireplace creates a focal point, with a clock affixed above. The kitchen is visible in the background, showcasing stainless steel appliances and wooden cabinetry.
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 favorite
A dining area features a glass table surrounded by several brown chairs. Placed on the table are circular placemats and a decorative centerpiece. A serene beach scene is displayed on the wall, while light blue curtains frame the window, allowing natural light to fill the space.
Home in South Windsor
4.95 out of 5 average rating, 22 reviews

5 Bd 2.5 Bth Home Away From Home

KristinaRating, 5 stars4 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

Top guest favorite
The exterior of a two-story waterfront home is shown, featuring a modern design with blue siding. A spacious deck is visible above a landscaped area with carefully arranged plants and gravel, while a driveway leads to the front of the house, surrounded by greenery.
Home in Rocky Hill
4.96 out of 5 average rating, 26 reviews

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

TanyiaRating, 5 stars5 days ago
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.
Guest favorite
The dining area features a wooden table surrounded by sleek chairs, illuminated by a modern chandelier. A decorative circular placemat sits at the center of the table. Nearby windows allow natural light to fill the space, highlighting the neutral wall colors and fireplace.
Home in Hartford
4.91 out of 5 average rating, 76 reviews

Renovated & Modern Victorian in Historic West End

AmandaRating, 5 stars3 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!
Top guest favorite
The outdoor patio is illuminated, featuring a large hot tub and a dining area with a table and chairs. Surrounding the space are twinkling string lights, adding a cozy ambiance. A grill and lush greenery complete the inviting exterior setting of the home.
Home in Plymouth
4.98 out of 5 average rating, 42 reviews

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

ChristopherRating, 5 stars1 day ago
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
Top guest favorite
The spacious living area features a large sectional sofa with plush cushions, arranged around a minimalist coffee table. A flat-screen TV is mounted on the wall above a stylish console. Natural light streams in through multiple windows, which are framed with light-colored treatments.
Home in Newington
5 out of 5 average rating, 41 reviews

Urban Luxury in Central CT w/ free RV parking

DonnaRating, 5 stars2 weeks ago
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 “Flying Monkeys” 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!
Superhost
A cozy living area features a stone fireplace with candles, complemented by a modern flat-screen TV mounted above it. A plush armchair provides seating, while windows invite natural light, showcasing a peaceful outdoor view. A small bookshelf holds various books.
Home in Manchester
4.91 out of 5 average rating, 45 reviews

4BR House- Central Location

PhilRating, 5 stars1 month ago
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.
Guest favorite
The open concept living space features a small dining table with two stools, complemented by a well-equipped kitchen showcasing light wooden cabinetry, a black stove, and modern appliances. A wall-mounted television and a round clock add functional touches to the bright, welcoming environment.
Home in West Hartford
5 out of 5 average rating, 36 reviews

The little house that could!

MaggieRating, 5 stars5 months ago
I had a great time here in the space, it felt very comfortable and safe.
Superhost
A covered patio features a wooden deck with comfortable seating, including two orange chairs and a wooden table. A grill is positioned nearby under the pergola, which is adorned with greenery. Bright blue skies create a vibrant backdrop.
Home in Enfield
4.78 out of 5 average rating, 32 reviews

RiverView Oasis

AnnRating, 5 stars1 day ago
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.
Guest favorite
The historic red brick farmhouse is nestled among a field of vibrant yellow dandelions. A grassy area surrounds the house, which features multiple windows and a central door. Trees stand in the background, complementing the serene rural setting.
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.

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

Destinations to explore