Holiday rentals with a pool in Hancock

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Hancock

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

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Guest favourite

Cottage in Averill Park

4.95 out of 5 average rating, 132 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 favourite

Home in Colonie

4.96 out of 5 average rating, 26 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 Valatie

4.84 out of 5 average rating, 25 reviews

Secluded home w/ pool and hot tub Kinderhook

Come relax in this calm, stylish space. Located at the top of the hill above Kinderhook lake, this house offers a charming escape from the city and is a short drive to both Jimmy Peak Ski Resort and Hudson Town. This 4 bedroom, 5 bed has a fully-equipped kitchen, 10-seater dining room, and a cozy living room with fireplace. The spacious basement includes a gym, a pool table, plus a large TV cinema set up. And outside you can relax around the heated pool, grill, and enjoy a drink on the porch.

Guest favourite

Townhouse in Hudson

4.95 out of 5 average rating, 202 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 & 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.

Superhost

Home in Hudson

4.91 out of 5 average rating, 33 reviews

Wander Hudson Ridge

A one-of-a-kind glass house whose focal point is a magical pool that extends towards views of the Catskills. Nestled in the hills of New York's Hudson Valley, the home spans 25 secluded acres of woods and fields. Featured in the NY Times, this Eastern escape with Californian charm is inspired by Pierre Koenig's iconic Stahl House. Surrounded by floor-to-ceiling glass, two separate bedrooms open right up to the seasonal pool and year-round hot tub. Equipped with fast WiFi and two workstations!

Guest favourite

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 Valatie

4.97 out of 5 average rating, 32 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.

Guest favourite

Home in Athens

4.99 out of 5 average rating, 67 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 favourite

Home in Ghent

4.88 out of 5 average rating, 307 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 favourite

Home in Pittsfield

4.98 out of 5 average rating, 53 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!