Vacation rentals with a pool in Litchfield County

5 out of 5 average rating, 48 reviews

Home in Warren

Moody Pond House: Weekend Country Escape

AliceRating, 5 stars2 weeks ago

Jessica and Adrian were such wonderful hosts! Incredibly responsive, friendly, and helpful. We truly felt welcomed. Home was beautiful and the location was also beautiful and peaceful. It’s clear a lot of thought, work, and love went into this home

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.

Superhost

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 stars6 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 stars1 week 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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What guests are saying

Long Meadow Manor- Heated Pool, near Apple Picking

4.86 out of 5 average rating, 35 reviews6 months ago

Fantastic stay! The house was absolutely beautiful, plenty of space and very kid friendly. Scott & Jennifer were excellent hosts, replied quickly and were extremely friendly and helpful. They went above and beyond to make sure our family had a wonderful weekend.

Home in Bethlehem

What guests are saying

A Little Slice of Paradise II

5 out of 5 average rating, 13 reviews8 months ago

Darilyn and Dermot were exquisite hosts and the space was superb — spotless, thoughtful touches, absolutely everything our family of 4 could need. It’s a beautiful property in a beautiful area with such lovely hosts - hard to imagine not coming back here. Would highly recommend for anyone looking for some peaceful time away. Simply lovely, a wonderful experience all around.

Guest suite in Cornwall

What guests are saying

Cozy Lakefront Retreat | New Backyard & Hot Tub

5 out of 5 average rating, 13 reviews6 days ago

Our family of five loved staying at Yoka and Val's place. The location is very quiet with a peaceful pond across the street. The house itself is very clean and comfortable with everything you need - towels, soap, shampoo, conditioner, coffee and spices - easily available. The beds were also very comfortable. The best part, of course, was the private hot tub in the back yard. It was set in a canopy for extra privacy and wind protection. We loved it. We would definitely stay here again if in the area.

Cottage in Plymouth

What guests are saying

Hidden Serenity at TuKasa - Pool & Billiards

4.97 out of 5 average rating, 31 reviews1 month ago

I recently had the pleasure of staying at Tukasa and overall, it was an excellent experience. The space was beautifully decorated, clean, and well-equipped with most things we needed for a comfortable stay. The host was incredibly welcoming and responsive, with any issue that we had. The game room and bar area was a great bonus. The location was perfect, with easy access to local stores and restaurants, which made our trip even more enjoyable. Overall, I would highly recommend this place for anyone looking for a cozy getaway. However, the apartment is attached to the main home (basement apartment) and I did notice that conversations and foot traffic were audible at times, which might be a concern for light sleepers or those working remotely. Despite this, I would still consider staying here again due to the fantastic amenities and the overall quality of the experience. Just be prepared for a little bit of noise since you are on the lower level!

Guest suite in Watertown

What guests are saying

Tranquil Luxury Retreat + Saltwater Pool

5 out of 5 average rating, 3 reviews51 months ago

Beautiful, relaxing home near Kent. We stayed during a snow storm and it was wonderful to watch the snow fall through the huge windows in front of a fire! My toddler loved running around the big main room. The house is very modern, clean and well stocked. It is close to town and nearby parks, which we are excited to come back and explore further. Jana was very responsive and helpful.

Home in Kent

What guests are saying

A luxurious farm hideaway in the treetops

4.99 out of 5 average rating, 79 reviews1 month ago

I had a wonderful stay at this Airbnb! The host was so responsive and friendly, thanks to her instructions I had no issues finding the Airbnb. The space itself was gorgeous, private, and had great amenities (my favorite being the pool table!). Will definitely be staying here again.

Farm stay in Canaan

What guests are saying

Contemporary Dream Home

4.85 out of 5 average rating, 27 reviews6 months ago

An Awesome last minute find in the area! The Place was very private and secluded, and the bonus was the pool and jacuzzi, which was used daily! House was roomy and large, everyone enjoyed their time there, sadly too short! Will definitely use again when in the area, which we are on a frequent basis! Many thanks Kapllan for great hosting and comms, much appreciated indeed!

Home in Sherman

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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

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.

Superhost

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!

4.96 out of 5 average rating, 25 reviews

A serene pool area is framed by lush greenery, with lounge chairs arranged around the water. Umbrellas provide shade for relaxation, while flower pots add a touch of color to the natural setting. The pool reflects the surrounding trees, creating a calm atmosphere.

Home in Kent

Country retreat on 4 private acres

SamanthaRating, 5 stars1 month ago

We had a great trip at Monica and Hugo’s house!

Superhost

An above ground pool is surrounded by a wooden deck, shaded by leafy trees. Clear blue water reflects sunlight, creating a refreshing atmosphere. A yellow rubber duck floats on the surface, adding a playful touch to the tranquil outdoor setting.

Home in Warren

4.73 out of 5 average rating, 75 reviews

Tranquil Country Escape with NEW pool/hot tub

KeithRating, 5 stars7 months ago

Jennifer was a great host and easily communicated before and during our stay. This property was great for some R&R in the pool and especially the hot tub!! Short ride to many hiking trails and some wineries added to the weekend. We made big meals at the house each night but there are some towns nearby with dinner options. If you are looking for a relaxing weekend getaway with family or friends Jennifer's place is the spot!