Vacation rentals with a pool in Litchfield

4.93 out of 5 average rating, 318 reviews

A stone pathway leads to a sparkling pool surrounded by lush greenery. Flowering plants in pots frame the pool area, while lounge chairs and a shaded umbrella provide seating options. Tall trees offer privacy, creating a serene outdoor retreat.

Guesthouse in Southbury

Charming Guest Cottage with Modern Amenities

CarolineRating, 5 stars3 months ago

John’s place was the perfect respite for our multi-day stay! The clean and cozy space is perfectly situated close to trails and parks for our Australian shepherd, but only a short drive to all the shopping you’d need (e. g. ShopRite for groceries and necessities). We thoroughly enjoyed our stay and know you will too!

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!

4.97 out of 5 average rating, 200 reviews

The outdoor area features a large in-ground pool surrounded by a fence, with lounge chairs and shaded umbrellas. A spacious wooden deck is visible, along with seating and a small shed. The lush greenery of the backyard complements the serene setting.

Home in Monroe

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars2 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!

4.9 out of 5 average rating, 49 reviews

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.

Home in Litchfield

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, 23 reviews

A large outdoor saltwater pool is visible, surrounded by a paved area. Lush greenery and trees are present in the background, complemented by a blue sky. A fence encloses the pool area, providing privacy and safety.

Vacation home in Holmes

The Dahlia Villa within Westerhall Gardens

GlenRating, 5 stars6 months ago

This is an exceptional property in every way, and provided an amazing weekend getaway for us. The design sense, amenities and attention to detail are all exquisite, inside and out. The cabin itself is lovely, somehow both modern and rustic, and the grounds with pond, landscaping and art pieces make for a lovely setting (including for dog walks). The location provides a great central hub, including hiking at Wonder Lake State Park literally 5 minutes away. We also went antiquing in Newburgh and shopping/dining in Cold Spring, both 20-30 minutes away. Lisa and Billy are considerate and friendly hosts, making clear they are available but not at all intrusive. We highly recommend this location.

4.98 out of 5 average rating, 121 reviews

A spacious outdoor pool area is outlined by a brick patio, featuring a clear blue swimming pool and shaded seating under a pergola. Lush greenery surrounds the space, while a large building and trees are visible in the background, contributing to a serene atmosphere.

Barn in Bloomfield

Mountaintop Horse Farm with Pool

JanetRating, 5 stars1 week ago

Our stay at the Mountaintop Horse Farm was idyllic. Our apartment was immaculately clean, tastefully furnished, and so very comfortable. We loved living above the horses, so well cared for and handsome. We felt we were on a working horse farm, though our apartment was near luxurious. One early evenng, we were on the covered balcony outside our apartment. A light rain had stopped, the sun came out and a lovely rainbow spread across the sky. Julianne & Frank were excellent hosts. Julianne welcomed us and gave us a brief tour of the area. Both Julianne & Frank were responsive, approachable, and seemed to enjoy our questions about the farm. When we are in the area, we will definitely book a return stay at Mountaintop Farm.

4.96 out of 5 average rating, 48 reviews

A private heated pool area is surrounded by a spacious patio, featuring lounge chairs and a shaded table. The red two-story cabin is visible in the background, with large windows and step access to the pool area. Lush greenery completes the inviting outdoor space.

Home in Stanfordville

Charming lakeside cabin with private heated pool

JustinRating, 5 stars7 months ago

My family and I stayed for a long weekend and were so glad that we did! It’s a beautiful cabin, with all the things you need. Kitchen is stocked with essentials, enough bathrooms, beds are super comfortable, hooks to actually hang things like towels, jackets… but we loved the outdoors even more! We walked to the lake, spent way too many hours in the pool, grilled, lounged, made s’mores by the fire pit and watched the beautiful stars at night. Couldn’t ask for more. Paula and her lovely family are SO welcoming it’s crazy. 😂. Hope to be back next summer!

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

4.99 out of 5 average rating, 84 reviews

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.

Home in Litchfield

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.

4.98 out of 5 average rating, 233 reviews

A swimming pool is set in a lush green yard, surrounded by trees and flowering plants. Comfortable lounge chairs are positioned nearby, while a large rock adds a natural element to the pool area. The property's main house stands in the background, completing the inviting scene.

Barn in Bethel

Escape to a Restored New England Antique Milk Barn

StaceyRating, 5 stars1 week ago

We had an amazing stay at Sally’s place in Bethel! My fiancé and I visited CT for the first time to celebrate my birthday and go to a convention nearby. This cottage was perfect for the two of us. The host was very responsive and accommodating as well! The cottage was in pristine condition, the house manual was very easy to follow, the recommendations were great, the scenery was out of a movie, and my favorite part was the hot tub in our restroom which was perfect after a long day! We had a great time and would love to come back again! Thanks for your hospitality Sally! ☺️

Vacation rentals for every style

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Popular amenities for Litchfield rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 18 reviews

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

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

ChristineRating, 5 stars7 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!!

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

4.95 out of 5 average rating, 21 reviews

A serene outdoor area features a sparkling blue pool surrounded by lush greenery. A charming gazebo stands nearby, offering shaded seating. A decorative lion statue is positioned in the foreground, adding an elegant touch to the tranquil scene.

Home in New Milford

Spacious and relaxing New Milford 5br home w pool!

ElizabethRating, 5 stars4 months ago

Jarret was extremely helpful and friendly. The house was exactly what we needed. I will definitely come back and stay here next time I’m in town.

4.67 out of 5 average rating, 3 reviews

A clear blue private pool is framed by a stone patio, with lounge chairs positioned along the edges. Lush greenery surrounds the area, enhancing the outdoor ambiance. A shaded umbrella is visible at one end, offering a cool retreat under the sun.

Home in Carmel Hamlet

Stone Cottage

LauraRating, 5 stars3 months ago

The stone cottage was the perfect getaway for our New Years trip! The space is cozy and well appointed, and the host was thoughtful and accommodating when we ended up arriving in town earlier than anticipated. We would love to come back and stay in the summer to sit by the pool in such private and peaceful surroundings.

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.

4.94 out of 5 average rating, 31 reviews

A serene backyard scene is presented, featuring a sparkling pool surrounded by gray lounge chairs. Lush green trees create a privacy barrier in the background, while a garden area and fencing add to the charm of the outdoor space.

Home in North Salem

North Salem Home with Pool & Great Yard

DanielleRating, 5 stars6 months ago

This was a lovely home. Very easy getting inside. Everything was exactly as listed, pictured and described. We felt so cozy and welcomed by Susan. The house had everything you could possibly need to make your stay easy and convenient and was very clean. I had a few questions during our visit and Susan was extremely responsive and so kind. I highly recommend this home. The beds were very comfortable. Showers were very nice and had great water pressure and nice hot water. We truly felt at home and we're beyond satisfied. I highly recommend this home for anyone need of an Airbnb in the area. Lovely home and property.

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.