Vacation rentals with a pool in Great Barrington

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Great Barrington

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, 131 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.

Guest favorite

Home in Saugerties

4.94 out of 5 average rating, 64 reviews

Perfect Family Retreat•Pool•Playground•nr HITS

This stylish, 3-bed, 2-bath home has a plethora of amenities that will keep the kids occupied for hours, including: seasonal heated pool with waterslide & child safety fence, tree house, beach volleyball crt, swing set, large back yard w newly built FIREPIT area. The back acre of the property offers another grassy expanse & leads to a creek. Inside a huge kids play area. Close to Saugerties, W/Stock & 15 mins to HITS - lots of parking. Relax with the whole family at this peaceful place to stay.

Guest favorite

Townhouse in Hudson

4.95 out of 5 average rating, 201 reviews

Palazzo Hudson: Luxury Pool, Hot Tub, and 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 & the Blue Library-Lounge Barn. A home for all seasons, you'll experience inspiration and relaxation in the warm and whimsical spaces of our unique light-filled home's art, books, music, luxury spa features, outdoor patios, deck, and gardens. A quick stroll to restaurants, bars, cafes, and shops of Warren Street and the Upper Depot District.

Guest favorite

Home in Saugerties

4.94 out of 5 average rating, 18 reviews

The Woods | Luxury, Hot Tub, Fire pit, Pool

New home ! Check our hundreds super host reviews. Sit back and relax in this new built calm, stylish space. Sitting on 8 acres of woods property complete with gorgeous views. This 3,000 sq ft 1-story peaceful escape has everything you need to relax. Sleeps up to 10, 4 bedrooms, 3 full baths, TV room, floating fireplace, pool, hot tub, fire pit, dining areas, luxury kitchen, tons of natural light, yoga area, back and front patios and multiple areas to unwind. Perfect for families and friends.

Guest favorite

Home in Hudson

4.93 out of 5 average rating, 242 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

Superhost

Home in Egremont

5 out of 5 average rating, 4 reviews

Beautiful 3 bedroom with sunny heated pool!

Immaculate, with Mountain Views, Heated pool, Home Gym, Screened Porch, Sun Decks, and Sleeps up to 9! Amenities include : 3+ bedrooms, 3 full baths (main floor sleep space with ensuite bathroom) grill, fiber internet, central AC, outdoor seating, garage, ping-pong, washer/dryer, mats, weights and a peloton bike (bring your shoes). Family-friendly with portable crib, baby bath. and high chair! Only hypoallergenic, non-shedding pet breeds are permitted due to owners sensitivities.

Superhost

Cabin in Ruby

4.91 out of 5 average rating, 106 reviews

Enchanting Upstate Cabin w Pool, Firepit

Welcome to our family-friendly haven in the heart of the beautiful Hudson Valley, just 10 minutes from Kingston, Saugerties, and Woodstock. Less than 2 hours from New York, our retreat offers an idyllic escape surrounded by enchanting forest views. Great for large groups, and year round stays with a heated pool and air conditioning in summer months. Just 40 mins away from skiing Hunter. Listing pics by @dirtandglass and @heypamcakes See more snapshots @theserenityhomes on IG.

Superhost

Cabin in Valatie

4.97 out of 5 average rating, 31 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.

Superhost

Home in Stanfordville

5 out of 5 average rating, 4 reviews

The Round House w/ Heated Pool

Make some memories at this unique and family-friendly estate. Private & secluded on over 20 acres with heated inground pool this spacious 4 bed, 2 full baths, plus den with sleeping sofa has plenty of space for all. Park-like grounds featuring open fields, picturesque stonewalls overlooking beautiful, heated pool and expansive stone patio where you can entertain or just relax and enjoy nature. Inside, discover effortless living in this fun yet chic, modern design.

Guest favorite

Home in Ghent

4.88 out of 5 average rating, 302 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.

Guest favorite

Home in Pittsfield

4.98 out of 5 average rating, 50 reviews

Berkshire Lakefront Home W/Pool-100%Renovated

On beautiful Lake Pontoosuc in The Berkshires, you can enjoy this brand new construction complete with pool! This home has been entirely renovated from top to bottom! Every room has a king sized bed! 2 bedrooms are on the main floor complete with en-suite baths. Gorgeous views from every room! Conveniently located near Lenox, Williamstown, North Adams and West Stockbridge. Motorboat lake with rentals available! Kayaks supplied!

Guest favorite

Home in Stanfordville

4.96 out of 5 average rating, 48 reviews

Charming lakeside cabin with private heated pool

This lakeside retreat an ideal family getaway. Complete with private heated pool and patio area and just up the driveway from beautiful Hunns Lake. The space has a rustic cabin feel, with an open two-story windowed dining area, beautiful wood paneling and quaint spiral staircase up to the main bedrooms. The unit is a private apartment adjoining the main house. The rental unit has its own driveway, entrance and secluded pool area.