Vacation rentals with a pool in Litchfield County

Find and book unique homes with a pool on Airbnb

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Popular amenities for Litchfield County rentals with a pool

House rentals with a pool

Superhost
An expansive outdoor area is captured, featuring a 50ft rectangular pool surrounded by well-maintained grass. A charming pool house with a sloped roof sits at the far end, framed by lush greenery and trees, creating a serene and tranquil setting.
Home in Goshen
4.93 out of 5 average rating, 28 reviews

Beautiful Country Farmhouse w/ Pool

MariaRating, 5 stars5 months ago
This is a beautiful, cozy and tasteful home. We loved the contrast between the original 300 year old farm beautifully maintained and renovated and the newer rooms. Kitchen was great and the fireplace worked wonderfully. Wifi and office space were perfect to get a few hours of work done. Had a great week skiing in nearby Mohawk and visiting Litchfield and Bantam. It was useful to inquire about the lay out and steep stairs. Daire was super responsive and helpful throughout our stay. We had a wonderful time. Thanks for sharing your home!
Superhost
A saltwater pool features a vibrant blue surface and is surrounded by a spacious terrace. Sun loungers are positioned along the poolside, and a fenced area provides safety. Lush greenery creates a serene backdrop, enhancing the outdoor space for relaxation.
Home in Woodbury
4.95 out of 5 average rating, 19 reviews

2 homes in one (in-law design) w/salt water pool

ChristineRating, 5 stars8 months ago
Julie is an outstanding host! This house is perfect for any getaway. It was clean, spacious, well equipped, comfortable, and STUNNING outdoor area with a gorgeous pool. This is 3 FULL baths and 1/2 bath!! Two kitchens! Two family rooms! You had space! It made you want to relax! The kitchen was well stocked with any utensil or appliance you would need. It was private. You could really escape and get away. Woodbury and the surrounding towns were jampacked with things to do. There were many places to choose from to eat. Such a variety from steak, seafood, pizza, and American fare pubs and other specialty restaurants. Lots of variety/antique shops, flea market, wine/liquor stores, convenience stores. Just a short drive into Southbury you find more shops, antiques, restaurants, bigger, grocery store, etc. We also drove to a few other neighboring towns. All under 45 minutes. Friendly people! We had a wonderful time! Price is fabulous, house/outdoor area is A+ value! Thank you Julie!!
Guest favorite
A modern pool area is featured, surrounded by a wooden deck and lush greenery. Large windows of the nearby house provide views overlooking the pool. A lounge chair is positioned on the deck, inviting relaxation by the water's edge.
Home in Rhinebeck
4.93 out of 5 average rating, 58 reviews

Chic Modern Farmhouse in Rhinebeck with pool

SharonRating, 5 stars1 month ago
We loved our stay. The house has a lovely open floor plan with lots of light streaming in. The renovations are very recent and everything is spotless and gleaming. The king-sized bed in the master bedroom is extremely comfortable and the wraparound deck would be delightful when the weather is warm and sunny. The setting is peaceful and the location is ideal, midway between Rhinebeck and Red Hook villages, with easy access to everything those towns have to offer. We would happily return to this lovely house.
Guest favorite
Home in Pine Plains
5 out of 5 average rating, 40 reviews

Stunningly Designed Luxury Home w/ Pool & Hot Tub

NaomiRating, 5 stars2 weeks ago
We had an amazing relaxing weekend. The beds are comfy, pool heated, quiet serene area. All around perfect weekend getaway. The house was clean and had everything we could have possibly needed.
Guest favorite
An aerial view captures a serene retreat surrounded by lush greenery and trees, with a tranquil lake visible nearby. The property includes a swimming pool, emphasizing the natural beauty of the landscape. The expansive scene offers a sense of peace and connection to nature.
Home in Holmes
4.91 out of 5 average rating, 11 reviews

Enchanted Escape | POOL, LAKE, Concierge Services

AnxhelaRating, 5 stars1 week ago
We had such a great experience staying at this Airbnb. The house was beautiful, super clean, and the view was just perfect honestly even better than the photos. What really made our stay stand out though was the host, Sunny. He was amazing so helpful, kind, and incredibly thoughtful. As a Muslim family, we really appreciated how respectful and considerate he was. He made sure we had our privacy and went out of his way to make everything as easy and comfortable as possible for us. It honestly felt like staying at a friend’s place. We’d definitely come back and highly recommend this spot to anyone looking for a peaceful, welcoming place to stay.
Superhost
A private fenced in-ground pool is surrounded by a lush green lawn and a white picket fence. Poolside, a colorful umbrella provides shade over a dining table. Sun loungers and a pool cover are visible, with the house in the background adding to the serene outdoor setting.
Home in Wolcott
5 out of 5 average rating, 3 reviews

Amazing Oasis Private Pool, BBQ, Pool Table.

MarisaRating, 5 stars1 week ago
This house was perfect for my family to stay for the weekend so we could attend a family wedding. Wish the weather was nicer so we could have enjoyed the pool on our down time. But house was perfect!! Soo cute and Glenda responded very fast. She was so helpful! I would highly recommend this place to anyone and everyone!!
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!
Superhost
A spacious dining area features a large wooden table accompanied by a bench, illuminated by a modern chandelier. Expansive windows provide captivating views of the surrounding landscape and lake, allowing natural light to fill the room. A minimalist decor complements the inviting atmosphere.
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!

Condo rentals with a pool

A well-maintained exterior features a spacious patio area, bordered by manicured flower beds and shrubs. The multi-panel front doors provide an inviting entrance, while the grey shingle siding complements the home's architecture. Bright sunlight enhances the natural colors of the outdoor space.
Condo in Westbrook

Watersedge resort time share Westbrook ct

AbbieRating, 5 stars48 months ago
Andrew’s place was awesome. Just steps to a beautiful pool and the ocean! Couldn’t have asked for a better place.
A balcony offers a view of the surrounding landscape under a bright sun. The sky features a mix of clouds and blue, while a wooden railing surrounds the space. Below, other buildings and trees are visible, creating a sense of tranquility.
Condo in Danbury
4.72 out of 5 average rating, 18 reviews

Quaint spacious unit, A+ location

EmilyRating, 5 stars2 weeks ago
Will was pleasant, easy to reach for quick fixes and very communicative! He answered any questions we had and was incredibly helpful with locating the apartment as the map location was a little off. The apartment was beautiful, well decorated and clean! We stayed for 16 days and had little to no issues. I am confident anyone else would find this place to be worth the price!
Superhost
A spacious living area features large glass doors leading to a balcony, allowing natural light to fill the space. Two comfortable sofas in neutral tones are arranged around a coffee table, complemented by a simple area rug. A decorative plant adds a touch of greenery to the setting.
Condo in Hartford
3.75 out of 5 average rating, 4 reviews

Beautiful 2 bedrooms/ 2 bath Condo

BrentRating, 5 stars116 months ago
Sheryl was great. I was in town for a conference and my schedule got thrown off by traffic on 95. She was very understanding and flexible with making my arrival time work. Once we met to get keys and a quick tour of the place she remained a phone call away but otherwise left us to enjoy the space. The other inhabitants of the place were very laid back and nice - that being said I was so busy with a conference that I was barely around. Not the Ritz but a HUGE savings over staying at any hotel downtown even if it's not right downtown. Splurge on some cabs and you are still saving money.
Superhost
A clean and inviting bedroom features a spacious bed with neutral bedding, accent pillows, and soft bedside lighting. Built-in shelves are displayed with decorative items, and a window allows natural light to brighten the area, complemented by light curtains.
Condo in Farmington
4.81 out of 5 average rating, 53 reviews

Farmington -NEWLY UPDATED NEAR UCONN HC and WEHA

DenisRating, 5 stars6 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!
A stylish living room features a dark accent wall with a large TV displaying floral imagery. A low, wooden sideboard adds texture, complemented by decorative items. A cozy, light-coloured couch is paired with a patterned area rug, creating an inviting atmosphere.
Condo in Wallingford
New place to stay

Cozy and charming retreat in quiet area of Wlfd.

JoeRating, 5 stars2 weeks ago
Cristina's home was great for our stay! She was extremely helpful even before we checked in, providing clear instructions on where to park and the location of the entrance. She even left out some toys for our son to play with during our time there. It's small space, but what we needed and exactly as described in the listing. We would absolutely stay here again, when we come back to the area!
An outdoor view of a lively resort features a large swimming pool surrounded by sun loungers, with families enjoying the water. Nearby, tennis courts are visible, and a mini-golf course is positioned in the foreground, blending seamlessly with the natural landscape.
Condo in Lee
4.79 out of 5 average rating, 33 reviews

Holiday Inn Club/ Oak and Spruce, Berkshires

StaceyRating, 5 stars9 months ago
This was a perfect place to stay with my kids for a weekend at Tanglewood. We used the Lions Gate parking at Tanglewood and got back to the place in 15 min! Easy

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