Vacation rentals with a pool in Litchfield County

5 out of 5 average rating, 6 reviews

An infinity pool is framed by lush greenery and expansive views of the landscape. Two black lounge chairs and a small table are positioned nearby on a stone terrace, inviting relaxation by the water’s edge under a partly cloudy sky.

Home in Washington

Zoom In Lux 5*Washington "Calhoun 4BR" PoshPadsCT

AllisonRating, 5 stars9 months ago

Stephen was very accommodating as we had a reservation canceled last minute. Accommodations were beautiful. Scenic views. Infinity pool was amazing. Very comfortable. Washington is a great town with nice restaurants and shops. We would definitely stay at one of Stephen’s properties again.

5 out of 5 average rating, 47 reviews

Home in Warren

Moody Pond House: Weekend Country Escape

ShivaniRating, 5 stars1 month ago

Jessica and her husband were truly such lovely hosts, and have a beautiful home. Ahead of our stay, they sent us a great package of local restaurants and things to do, going above and beyond to even offer to connect us to local hospitality in the area. We had a few questions about how to use Uber in the area and Jessica & Adrian were very responsive. The house itself is exactly as pictured-- very stylish, relaxing, clean, great light, modern appliances and everything you'd need as a guest. Very easy to access the home, which can be a hurdle with other vacation homes. We visited as a group of 4 and really felt the home was perfect for a couples getaway weekend. I'd definitely recommend this home to others looking for an idyllic, inspiring weekend away and really appreciate the kindness of this family as hosts!

4.85 out of 5 average rating, 108 reviews

A clear blue pool is surrounded by a stone patio, featuring colorful floatation devices in the water. A diving board extends over the edge, while lounge seating and cabana beds are visible in the background. The pool area is enclosed by a white fence.

Apartment in Burlington

Charming apartment with breathtaking view!

RebeccaRating, 5 stars7 months ago

Stayed here for 2 nights with a couple friends. Perfect spot for a quick getaway. Backyard and pool area was exactly what we were looking for with lots of space to lounge and relax. Lots of entertainment if you wanted to just hang inside as well. As some of the other reviewers noted, you can definitely hear the hosts move around upstairs. Didn't impact us too much except for Saturday morning. Was a little difficult to sleep in b/c of the noise.

4.92 out of 5 average rating, 146 reviews

A serene outdoor pool area is surrounded by lush greenery and mature trees. Several lounge chairs are positioned around the pool, along with a dining set. A stone patio borders the pool, creating a spacious area for relaxation and enjoyment of the natural scenery.

Apartment in Kent

Loft 22

RachelleRating, 5 stars5 months ago

The place is beautifully located in the middle of the woods and is easy to find. It is important to note that the room is located in the attic of the garage. It is very clean and extremely well-equipped. Guests should know that the bathroom is not on the same level as the bedroom. A perfect place to stay for 3 people for a short visit. Thank you!

A serene swimming pool is visible in a sunlit pool deck area surrounded by lush greenery. Multiple lounge chairs are positioned around the deck, inviting relaxation. A kayak rests alongside the pool, adding a hint of outdoor adventure.

4.9 out of 5 average rating, 49 reviews

Woodland Country Retreat-Pool+FirePit-nearWineries

Sarah & SteveRating, 5 stars5 months ago

Jean was extremely friendly to let us book a last-minute stay at this home the day prior. The home is in a good location and has a nice layout, although we were only three people and did not use all of the house. One thing to note is that the heat was restricted to 70° and 72° depending on the thermostat and my elderly parents from Florida were extremely cold the entire weekend, wearing jackets and warm hats the round the clock even inside during their visit. Sadly for our group, the foliage of Fall had all disappeared save for one tree. Also, the pool was not available so we cannot comment on this. All in all, a lovely home, but definitely priced quite high, considering.

5 out of 5 average rating, 17 reviews

A view from the deck reveals a landscaped yard surrounded by trees, featuring an in-ground pool. Two lounge chairs are positioned near the water's edge, while flower beds add color to the lush greenery. Sunlight filters through the foliage, creating a serene atmosphere.

Home in Roxbury

Bright Mid-Century Modern Retreat-90 min from NYC

SidRating, 5 stars2 months ago

My family and I had a wonderful weekend at the house. The house is beautiful and was extremely clean when we arrived. Luiz kindly left a sled for my kids to use in the yard. There is plenty of outdoor space and the yard has a good deal of privacy. There are two bedrooms and a den/office with a TV. The kitchen has everything we needed. Luiz was very easy to communicate with.

4.96 out of 5 average rating, 28 reviews

The outdoor area features a tranquil private pool set against a backdrop of lush greenery and autumn foliage. A wooden fence encloses the space, with expansive views of rolling hills and trees, creating a serene and inviting atmosphere.

Home in Warren

Farm Valley Cottage + 60 ft Pool

AnaRating, 5 stars4 days ago

We can't say enough great things about our stay at this home! Everything was way beyond our expectations, and we had such an amazing time. The house was spotless, spacious, warm, and inviting, beautifully decorated. We loved the delicious eggs from their own chickens, visiting the chickens and the baby chicks, the pond, the great selection of books and music for staying in on rainy days, all made the experience truly special. Communication with Steve and Abe was always easy, friendly, responsive and prompt and they really made us feel incredibly welcome. The caretakers are also very considerate. We truly enjoyed our stay and can't recommend this place enough. Thank you for such an unforgettable experience!

4.94 out of 5 average rating, 32 reviews

A spacious outdoor area is visible, featuring a winding path that leads through a grassy landscape. Trees of varying heights frame the view, capturing seasonal colors with a backdrop of rolling hills under a clear blue sky.

Home in New Milford

Serene Country home 24 mi Mohawk ski area

ConnieRating, 5 stars1 month ago

A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries

5 out of 5 average rating, 38 reviews

A private pool is surrounded by a natural stone wall, with lush greenery and trees in the background. Chaise lounges are positioned near the water's edge, providing a serene space for relaxation. The pool reflects the clear sky, enhancing the calm atmosphere of the estate.

Guesthouse in Cornwall

Charming Guest Cottage with Private Pool

LisaRating, 5 stars6 months ago

Brooke was terrific on communication and very responsive. The cottage is truly lovely and the property is beautiful. This is a very remote location (which we were aware). My daughter and I were exploring the Hudson Valley and while the driving was lovely, it was a bit more driving than I planned for based on location. The cottage is darling and very cozy. Fortunately we picked up some wine, charcuterie, fruit to have that evening as there's not much right in the vicinity. We also arrived before dark on the first night since we weren't familiar with the area. Brooke's directions were perfect. The setting is breathtaking and to be enjoyed in nice weather!

A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.

4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars2 months ago

Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.

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Popular amenities for Litchfield County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.88 out of 5 average rating, 24 reviews

A spacious backyard area is surrounded by lush greenery, featuring a well-maintained lawn. An above-ground pool with a deck is positioned among the trees, creating a private and inviting outdoor space. A few steps lead up to the pool area, adding accessibility.

Home in Millerton

Farmhouse with a view, hot tub, pool, and fire pit

JakeRating, 5 stars5 months ago

Property was good could be a bit cheaper for the value of it . Host is very good at communicating and house was clean . It did the job

5 out of 5 average rating, 6 reviews

A spacious lakefront retreat is depicted, featuring a newly remodeled pool surrounded by a green lawn. Large windows provide expansive views of Candlewood Lake and surrounding trees, while outdoor seating is arranged near the pool for relaxation.

Home in New Milford

Private Dock & Pool - Candlewood Lake

ShariRating, 5 stars1 month ago

The house is well maintained. It has an unreal view of the lake that is so serene. A very quiet area.

A refreshing outdoor pool is framed by neatly arranged landscaping and lush greenery. The clear water reflects sunlight, creating a serene atmosphere. A couple of lounge chairs are positioned nearby on the textured stone patio, providing a relaxing spot for enjoying the surroundings.

5 out of 5 average rating, 10 reviews

Litchfield Family-friendly Country Home

HasmikRating, 5 stars7 months ago

We thoroughly enjoyed our stay at this stunning and tranquil location. Shawn was an exceptional host, and the house was impeccably clean and beautifully decorated. I highly recommend this property for a delightful getaway!

5 out of 5 average rating, 23 reviews

A clear, inviting pool is surrounded by a spacious wood deck, ideal for relaxation. The cabin's exterior is visible in the background, featuring several large windows and a sloped roof. Lush greenery encircles the area, offering a private, wooded setting.

Home in Canaan

Cozy Log Cabin Retreat with Pool on 4 Acres

DanielRating, 5 stars7 months ago

This was a very nice and secluded place located in a very quiet and picturesque part of the state that's a little off the beaten path. We quite enjoyed the large yard and the well equipped kitchen during our stay. The host was very friendly and quick to respond to any inquiries we had during our stay. Would love to stay again during the summer months when the pool is open, it looked like a very nice setup. It's clear that a lot of work has been done to make the place feel comfortable and accommodating.

The image features a glistening swimming pool, bordered by a wooden deck. Lush green grass and trees are seen surrounding the area, with a two-story farmhouse visible in the background. A patio with outdoor seating is located near the pool's edge.

4.65 out of 5 average rating, 23 reviews

Litchfield Modern Farmhouse

AlexanderRating, 5 stars7 months ago

Great place, very comfortable, easy to get in and out of Litchfield; very responsive host and all in all good value!

4.79 out of 5 average rating, 38 reviews

The backyard features a kidney-shaped pool, surrounded by a stone patio. The split-level home has large windows that provide unobstructed views of the outdoor space. Lush greenery enhances the tranquil setting, complemented by a stone wall and an inviting entryway.

Home in New Hartford

Mountain Nirvana above Lake; Pool, Hot Tub, Nature

MadanRating, 5 stars4 days ago

100% recommend this house to anyone looking, I’ve been to a lot of Airbnbs before and this by far was my best one. The home is so big, the listing doesn’t do it justice, the only scary thing was the hill driveway but when you get to the top everything is fine. Thank you guys for hosting us!