Vacation rentals with a pool in Pittsfield

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Pittsfield

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Averill Park

4.95 out of 5 average rating, 136 reviews

Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, fire-pit, and a short walk to the lake. Enjoy a relaxing stay at our home exploring the lake and local eateries, or a fun family getaway at the pool. Just a short drive to your winter fun at Jiminy Peak for skiing, or Saratoga during track Season. Minutes to the Crooked Lake House for your wedding stays. Don't forget your four legged family members, while you're snowshoeing, or swimming at the lake. With WIFI and A/C you can tele-work, while sitting pool side this summer.

Superhost

Tiny home in Ghent

4.95 out of 5 average rating, 131 reviews

Country Getaway Tiny House in Woods w/Pool/Sauna.

Tiny Small House - 600 Sq ft. of new living space on 30 private acres with walkable trains in Beautiful Columbia County. Secluded privacy surrounded by nature. House has everything you need and sleeps 4 with two twin loft beds. Enjoy the pool and renovated barn pool house. In the Winter stay warm by the wood stove. Enjoy the 6 person sauna year round. Restaurants close by or stay in and enjoy the property. Located 9 miles from Hudson and 3 miles from Chatham and Kinderhook. Near OMI Arts Center.

Guest favorite

Home in Colonie

4.97 out of 5 average rating, 36 reviews

Adorable house with pool

Beautiful neighborhood home on a quiet dead-end street! and minutes to from airport. Restaurants, groceries store and the regional mall all within minutes!!! This wonderful spacious and family-friendly house offers you: - 3 Bedrooms with comfortable beds! - 2 full Bathrooms - Fully stocked Kitchen along with a dining area - washer and dryer - private in-ground salt water pool - Outdoor patio *Note the pool is open between Memorial Day until Labor Day, under responsibility of the guest.

Superhost

Home in Egremont

5 out of 5 average rating, 4 reviews

Exquisite family friendly home with heated pool!

Stone Hill is an immaculate property with big views! Amenities include: 3+ bedrooms, 3 full baths, sleeps 9 max. High speed internet/wifi, central AC, lovely gas fireplace, all stainless Bosch appliances and a gas range, heated pool with several areas of outdoor furniture, propane BBQ grill, sun deck, 3-season sunny screened porch/sunroom, 2-car garage, gym, ping-pong table, washer/dryer, portable crib, high chair and more! Pet friendly for non-shedding hypoallergenic pets only with pet fee.

Guest favorite

Home in Hudson

4.93 out of 5 average rating, 243 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

Top guest favorite

Cabin in Red Hook

4.96 out of 5 average rating, 348 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Top guest favorite

Townhouse in Hudson

4.95 out of 5 average rating, 209 reviews

Palazzo Hudson: Luxury Home with Pool, Spa, Sauna

Welcome to Palazzo Hudson! The only private vacation home in the town of Hudson with a chef's kitchen, seasonal in-ground pool, deluxe sauna, cedar hot tub & a separate poolhouse library lounge. A home for all seasons, you'll experience inspiration and relaxation from the warm, light-filled rooms, curated art, books, music, luxury spa features, and outdoor deck, patios, and gardens. A quick stroll to the restaurants, bars, cafes, and shops of Warren Street and the Upper Depot District.

Superhost

Cabin in Valatie

4.9 out of 5 average rating, 40 reviews

Private Cabin in the Woods w/ Hot Tub near Hudson

This spacious cabin-style home is surrounded by towering trees. It's perfect for escaping from your worries and enjoying nature at its finest. Venture out to Hudson, NY, where you can find many great restaurants and bars, or explore Hudson Valley's best hiking trails, and scenic views just minutes away. Whether you're looking to unplug from technology or work on your next great novel or chill with the family, this place has everything you need to get away from it all.

Top guest favorite

Home in Athens

4.97 out of 5 average rating, 70 reviews

Lake House with Game Room

Relax with the whole family at this peaceful place. As a guest you'll have access to our Sleepy Hollow Lake community beach area, pools and playgrounds, and pickle-ball, tennis and basketball courts. Athens hosts a gourmet bakery, restaurants and an award-winning brewery. Drive 7 miles to explore historic Catskill, 12 to hip Hudson and for year-round sports enthusiasts - only 30 to Windham and Hunter Mountains. Game room with pool table, shuffleboard and bowling!

Guest favorite

Cottage in Rhinebeck

4.88 out of 5 average rating, 180 reviews

Secluded peaceful loft in barn by woods

La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we use a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

Top guest favorite

Chalet in Craryville

5 out of 5 average rating, 13 reviews

Lockwood Lodge Mountaintop

Welcome to our slice of paradise in the Hudson Valley! Enjoy a secluded hilltop home with beautiful mountain and valley views, surrounded by 18 acres of woods. The open floor plan is perfect for cooking or relaxing in front of the fire, and enjoy grilling and the pool when the weather is right. The location is minutes from Hillsdale, and a 15-20 minute drive from Hudson and Great Barrington, with amazing restaurants and activities for every season.

Guest favorite

Home in Ghent

4.88 out of 5 average rating, 313 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Escape to our recently renovated guest house on a 12-acre property, 15min from Hudson. Take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.

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What guests are saying

Lenox Grand Colonial with Pool by Evergreen Home

4.97 out of 5 average rating, 35 reviews2 months ago

The host, Evergreen, and the owner, Craig, were very responsive and a pleasure to communicate with. The house was perfect for our two families with kids with an extra room to make it an office for eventual work calls. It is conveniently located near Bousquet Mountain and Lenox. It was well-stocked with everything we needed, including plenty of wood for the fireplace. We also appreciated the lovely towels. Don’t miss a walk through the meditation meadow behind the property—even in winter, it’s a serene experience. We hope to have the chance to return in the future!

Home in Lenox

What guests are saying

5-BR Villa with Pool and Dog Friendly!

4.89 out of 5 average rating, 47 reviews6 months ago

The villa is exactly as promised. It’s on a hill overlooking the Hudson with great views and outdoor space. It’s dog friendly with a fenced in yard, a wonderful feature for dogs and people. We were there for a family wedding so did not make full use of the outdoor spaces, but the pool and fire pit are very inviting. The bedrooms were comfortable and we enjoyed lounging in the living room with tv football games. The location is a short walk from downtown Coxsackie for coffee and treats. You should know that access to front door is up about 12 or so steps but there was a railing if anyone has mobility issues. We would return if we were to come back to the area. Lakpa is super responsive.

Villa in Coxsackie

What guests are saying

Saltwater Pool 2 Bed Cottage@HudsonClearCreekFarm

5 out of 5 average rating, 3 reviews8 months ago

We (aunt + adult niece) really enjoyed our long weekend at Todd’s Airbnb. Having separate, adjacent cottages with our own beds & baths was ideal. The beds were very comfortable & the baths supplied with plenty of towels, including for the pool, & amenities. Having an afternoon dip in the pool on hot August afternoons was a real bonus. The cottages were very quiet, with no audible traffic noise. The location felt like it was in the country, but close enough to Hudson that take-away from its good restaurants was still hot after dashing into town to pick it up. Hudson itself lived up to its billing of good restaurants and shopping—antiques, home goods, & clothes, in particular. Todd is an excellent communicator & was clearly willing to go the extra mile to meet our needs & ensure a good stay. A special shout out to the goats, chickens, & Hemingway the cat are also in order—the best medicine for lowering blood pressure. We highly recommend Todd’s place for a relaxing getaway.

Apartment in Hudson

What guests are saying

The Catamount Ski Haus w. Pool/Hot Tub

5 out of 5 average rating, 29 reviews4 days ago

We loved this beautifully decorated home. When we arrived the wood-burning stove and hot tub were already on! It was a very welcoming environment and very close to great barrington, MA and Hudson, NY. We would love to come back and spend either a winter or summer holiday here.

Home in Egremont

What guests are saying

Modern 4 season lakefront rental

5 out of 5 average rating, 20 reviews6 months ago

An amazing house for a family stay in the Catskills area. Antonia has designed a beautiful home, with so many unique retro nods and details. The basement is an awesome additional space for everyone to hang out in. The backyard set up is also great- with easy access to the hot tub and a few steps to the lake. 15 min drive to great restaurants and things to do-Loved our stay here!

Home in Athens

What guests are saying

Berkshire Mountain home views, pool, Queechy Lake

4.98 out of 5 average rating, 59 reviews2 months ago

The house was very spacious, the kids ranging from 6-10 loved the games, especially cue ball and fuzz ball. The adults loved the fact there was a lower half where the kids can watch movies and play, while the adults did grown up chatting in the living space. A memorable ski weekend that everyone enjoyed to the fulliest and sad it went so fast. We look forward returning one day in the spring or summer to see a different aspect of the area. Thank you!

Home in New Lebanon

What guests are saying

The Copake Cabin - A rustic-modern retreat.

5 out of 5 average rating, 86 reviews2 months ago

The location is amazing with the beautiful surroundings, the Catamount ski resort is in 10 minutes drive, we had a blast tubing there with my 4yo. The house was spacious and clean, easy to find and get in. Communication with Austin was perfect, he's a very helpful host.

Cabin in Craryville

What guests are saying

10 Acre Country Estate with Pool, Hot Tub & Views!

4.9 out of 5 average rating, 20 reviews1 month ago

We loved staying here with our family. It worked out perfectly having our daughter’s family on the one side of the house so if the baby cried it wouldn’t wake anyone up. A pack and play was also provided by Justin so we had a place for the baby downstairs as well. The house was roomy and comfortable for everyone. The hot tub wasn’t working right away but they let us know and had it fixed so we were able to use it during our trip. We would definitely stay here again and try it in warmer weather so we could use the pool as well. Thank you for a wonderful place to stay

Home in East Chatham

What guests are saying

Hilltop: Panoramic Views w/ Pool near Catamount

4.9 out of 5 average rating, 29 reviews4 months ago

We had the most wonderful stay. Having traveled from Rhode Island for an escape from the holidays we had actually rented a hotel in Germantown initially. Without going into too much detail the hotel was not up to our standards. After one night there we began looking into alternatives. we found Hilltop and it looked perfect. Quickly, we were able to secure a booking for the remainder of our trip. Very responsive interaction throughout booking. It proved to be a peaceful oasis for the remainder of our trip and was a very memorable experience. The modern aesthetic was fantastic and we appreciated the architectural thoughtfulness which went into the design. It even snowed during our stay at the higher elevation the property is situated on. We were already planning a return visit to experience the surroundings in the summer. Thank you for sharing your place with us!

Home in Hillsdale

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