Vacation rentals with a pool in New Milford

4.95 out of 5 average rating, 177 reviews

A spacious pool area is framed by well-maintained greenery and flowering plants. Two large umbrellas provide shade over lounge chairs beside a sparkling pool, with expansive coastal views and a serene landscape of grasses and trees beyond.

Cottage in Guilford

Luxury cottage by the sea with hot tub and pool

Jennifer And JonRating, 5 stars3 months ago

We loved this airbnb and stayed for 3 weeks. It sits right on the edge of the marsh with an extraordinary view. We greatly enjoyed how a short walk away is Chaffinch Island, which is a gorgeous park full of tides pools and hackberry trees. The space was clean and comfortable and Mary was a fantastic host. You can see a lighthouse on an island 3 miles out sea from all the rooms, even the main bed.

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.

4.9 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 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.

4.96 out of 5 average rating, 348 reviews

The exterior of a modern cabin is displayed, featuring large glass windows and a sleek black facade. A heated pool is visible with a smooth blue surface. Several lounge chairs are arranged around the pool, enhancing the outdoor relaxation space.

Cabin in Red Hook

Modern Upstate Cabin, near Rhinebeck NY

RichRating, 5 stars6 days ago

Tina’s place is fabulous. The modern decor and architecture is beautiful. The location is peaceful and the fenced in yard was amazing; our dog loved roaming around and exploring. The outdoor space is great for grilling and sitting around the fire pit. We especially loved the kitchen. It is fully appointed and the kitchen island is incredible for prep and serving. The washer dryer combo was an excellent touch and we were able to do a couple of quick washes so that everything was clean and ready to unpack at home. Saving the best for last; the soaker tub in the master bedroom is luxurious and relaxing. Thank you, Tina. We can’t wait to visit again soon.

5 out of 5 average rating, 5 reviews

A central living space features a spiral staircase and high cathedral ceilings supported by wooden beams. Light streams through large windows, illuminating a mix of white sofas and chairs positioned on a natural fiber rug. The open layout connects to the kitchen area in the background.

Home in Stanfordville

The Round House w/ Heated Pool

JonathanRating, 5 stars5 months ago

An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.

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.

4.95 out of 5 average rating, 167 reviews

A serene salt-water pool reflects the surrounding greenery and blue sky. The natural stone edge frames the pool, while two lounge chairs are positioned nearby, creating a peaceful outdoor retreat.

Home in Cold Spring

Cozy, Modern Retreat in the Woods of Cold Spring

ChristopherRating, 5 stars1 month ago

We had a peaceful and relaxing stay at Shawna’s beautiful Cold Spring country-style home. We were in town for a family gathering and accommodations, cleanliness and Shawn’s communication were five star. We absolutely recommend the house and Shawna as a host for you to stay with!

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!

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Popular amenities for New Milford rentals with a pool

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Pool

Free parking on premises

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House rentals with a pool

5 out of 5 average rating, 12 reviews

The exterior view showcases a red house surrounded by a large green lawn and mature trees. Autumn colors are displayed in the foliage, with blue skies and clouds above. Several vehicles are parked near the house, which features multiple sections connected by landscaped areas.

Home in Saugerties

The House on the Hill

NicolasRating, 5 stars9 months ago

Gorgeous house in the heart of Saugerties. The house is located on a quiet street among nature and right next to the water. It is full of old world charm and extremely spacious with a fantastic garden and a very large pool. We were two families (9 total) so we put the whole house to great use. The 5 bedrooms allowed everyone to have their own space. Multiple living rooms and a nice porch were great features The kitchen is well stocked and was put to good use! Claudia and Paul were super reactive to any questions or query. Saugerties is very close (5 min drive) and Woodstock is only a 15 min drive away. Highly recommend for families or group getaway!

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

4.98 out of 5 average rating, 160 reviews

An outdoor deck surrounds a circular swimming pool, complemented by a patio table and chairs. Several lounge chairs are arranged near the pool, and a large umbrella offers shade. Lush greenery borders the space, creating a private and serene environment.

Home in Saugerties

Spacious Staycation near HITS & the Hudson

McKennaRating, 5 stars6 months ago

My group loved our stay at Alan and Cara’s place for the Sheep & Wool festival. Great space for a large group; we especially loved how comfortable the living room couches were and how there was space for everyone there to gather. The place was immaculately clean. We’d love to come back again!

5 out of 5 average rating, 133 reviews

An inviting outdoor area features a heated pool surrounded by a spacious patio. Comfortable lounge chairs are neatly arranged on the side, with umbrellas providing shade. Lush greenery and trees create a serene backdrop, enhancing the tranquil setting of the Pool House.

Home in Cheshire

Pool House

EllenRating, 5 stars2 weeks ago

Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.

4.98 out of 5 average rating, 58 reviews

An in-ground pool surrounded by a stone patio is visible, with clear blue water reflecting the sky. Green trees and shrubs are present in the background, enhancing the natural setting. Two lounge chairs are positioned nearby for relaxation.

Home in Germantown

Columbia County Farmhouse with Pool

CarolineRating, 5 stars3 weeks ago

Beautiful house with lots of beds and spaces to hang out. We had a lovely time here visiting the Hudson Valley in the early spring. Would certainly come back!

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!

4.67 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.