Vacation rentals with a pool in Windham County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Windham County rentals with a pool

House rentals with a pool

Superhost
Home in Tolland
4.85 out of 5 average rating, 47 reviews

Peaceful Estate Getaway

JodyRating, 5 stars1 month ago
The house was perfect for the weekend with family and friends. We were celebrating graduation for our daughter and 2 other friends. Vijay was great about letting us gather at his place to celebrate the graduates. He was very responsive when I reached out to him about questions that I had. I would highly recommend this house. There was plenty of space for our gathering, lots of beds, kitchen was great and the yard was perfect.
Top guest favorite
Home in East Lyme
5 out of 5 average rating, 28 reviews

Niantic Getaway w/ Pool, Spa & Many Activities

RoseRating, 5 stars5 days ago
We loved the home and yard. Beautiful is the best description with so many seating options. The house is bright and inviting. The hosts have done a great job decorating and providing so many amenities not even listed. I would recommend this beautiful home to anyone wanting a place to relax and enjoy what is there.
Top guest favorite
Home in Hampton
5 out of 5 average rating, 28 reviews

Connecticut Country Escape

BrookeRating, 5 stars1 week ago
What a GEM of a place!!!! Book this house you will not regret it for a second!!!! First the house is so spacious and easily fit our two families on our weekend getaway and it was perfect!! The fish pond was perfect for our kids entertainment they stayed down there for hours fishing, we did have one rainy day and still managed to get some playing on the porch inbetween the rain storms. Porch is huge with a beautiful table for eating outside. I loved the entertainment room in the lower level we were still able to play games and the husbands played pool, they have a great restaurant style booth seating down there which is perfect for kiddos to eat or do crafts! Absolutely loved the layout of this home. Every room was big with big closets too! Easily could’ve fit a pack n play in each one. This house was built to perfection and to house some amazing memories and that’s just what we got some beautiful memories and a weekend of fun!!! Absolutely will be back!!! Great hosts!!!
Top guest favorite
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars1 month 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
Home in Stonington
4.97 out of 5 average rating, 228 reviews

Perfect New England Getaway has a pool/ hot tub

DestinyRating, 5 stars1 day ago
Had booked a girls getaway at Tracy and Patrick’s place and it was perfect, even with gloomy weather! The house perfectly matches all pictures and descriptions and has everything you’ll need and more for the perfect relaxing and fun getaway! We even got a cute surprise visit from their furry friends which is always loved!! There are also shops and beaches a short drive away, we just didn’t happen to go visit because we were enjoying our cozy time at the home. Thank you again Tracy and Patrick:) we would totally recommend and want to come back!
Guest favorite
Home in Brimfield
4.88 out of 5 average rating, 73 reviews

Luxury Home * Pool * Fireplace

DanaRating, 5 stars4 months ago
We had a very nice stay for a family wedding. Sharing the house with two combined families in January and the house was great for this. There are rooms with 3-4 beds in each so if you are looking for bedroom privacy then this house probably isn’t it. That said, we are all family so was fun to bunk up! The area is beautiful and there r a great set of trails right at the end of the road for hiking, walking cross country skiiing etc. Overall, a great stay and Kimberly was very communicative with everything
Superhost
Home in Lebanon
4.61 out of 5 average rating, 18 reviews

Casa Rio Rosa: A Secluded & Spacious Retreat

LisaRating, 5 stars3 months ago
Our stay was exactly what we needed during a difficult time. The property was just as described, and it provided all the comforts of home. It was a peaceful and welcoming space, which helped our family feel at ease while we were in town for a funeral. The amenities were perfect, and everything was well-equipped for our needs. We truly appreciated the thoughtfulness of the host and how comfortable the space made us feel during this challenging time. Highly recommend for anyone in need of a cozy and convenient place to stay.
Guest favorite
Home in East Marion
4.96 out of 5 average rating, 112 reviews

Quiet, Upscale Retreat by the Beach with NEW Pool

JoanneRating, 5 stars2 months ago
We had a lovely stay at Eric's home. The home exceeded our expectations and we felt right at home. The decor was warm and inviting. Everything you could possibly need was in the stunning, modern kitchen. The beds were all comfortable and we slept very well. The property was very peaceful. We enjoyed seeing deer, turkeys and hawks each day. The fixtures in the home were modern, clean and high-end. It was great being so close to Greenport with it's wonderful restaurants and shops. We can't wait to return.

Condo rentals with a pool

Superhost
Condo in Norwich
4.84 out of 5 average rating, 151 reviews

Villa Flora @ Norwich Inn & Spa

ChristianRating, 5 stars1 month ago
Our stay was peaceful located in a great place , the home its self was perfect if we come back next year we will book this place again
Guest favorite
Condo in Norwich
4.85 out of 5 average rating, 27 reviews

Near Casino-KING Bed-Heated Pool/Jacuzzi/Sauna-Spa

ShainaRating, 5 stars2 weeks ago
We had a wonderful weekend at this property. The condo was clean, cozy, and close to tons of great activities. The pre-arrival instructions were super helpful, check-in was seamless, and access to the clubhouse was an added bonus. Highly recommend!
Superhost
Condo in Farmington
4.81 out of 5 average rating, 53 reviews

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

DenisRating, 5 stars7 months ago
Felt right at home, check in was very easy, beautiful place, very friendly enjoyed his place thinking to coming back again my business send me to Connecticut! Thank you!
Guest favorite
Condo in Norwich
4.97 out of 5 average rating, 31 reviews

Cozy French style Villa-3 Bed-Casino-Pools-Jacuzzi

MatthewRating, 5 stars5 days ago
My friends and I had an amazing time at Natalie's vila. It was so beautiful and accommodating. Our host was responsive and helpful. You will love staying here!
Guest favorite
Condo in Norwich
4.94 out of 5 average rating, 32 reviews

Cozy Vacation Villa 5 minutes from Mohegan

WilliamRating, 5 stars4 weeks ago
The stay was very peaceful, friendly neighbors. The scenery was great, Desiree was there for any concerns we had, and with timely response. I would anyone that want a pleasurable stay while in Norwich, this is the place to be. Thanks again, for a wonderful stay. William & Potreen
Superhost
Condo in Old Saybrook
4.89 out of 5 average rating, 74 reviews

Seashore getaway - CT shoreline

RussellRating, 5 stars2 weeks ago
Lisa and I enjoyed our stay at Laurens place. Felt right at home. Very clean, open space. We had the best time and did not want to leave. We will be back for sure.
Guest favorite
Condo in Norwich
4.89 out of 5 average rating, 18 reviews

Newly Renovated Villa with King Bed at Norwich Spa

JillianRating, 5 stars2 weeks ago
Would definitely stay here again! No complaints
Top guest favorite
Condo in Norwich
4.98 out of 5 average rating, 184 reviews

Peaceful Oasis steps from Mohegan Sun

EleanorRating, 5 starstoday
We absolutely loved our stay here. The house was comfortable and clean. The amenities are perfect. It is such a perfect place to stay. Christina was very helpful, kind, personable and always quick to reply. Would definitely recommend staying here.

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