Vacation rentals with a pool in Lenox

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lenox

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 Colonie

4.96 out of 5 average rating, 23 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 favorite

Home in Craryville

5 out of 5 average rating, 36 reviews

Poets Hill - Modern poolhouse with magical views.

On a quiet country road discover Poets Hill, a modern 2 BR 1 bath guest house. The home was renovated from the 13-acre property's barn with serenity in mind. Take in magnificent sunset and meadow views through the sun-drenched windows. A wall of glass slides open to an 82-ft heated saltwater gunite pool (Memorial Day-Oct 1) & outdoor kitchen. The beautiful interior is highlighted by a double-height ceiling with natural wood beams, and a kitchen crafted from stone that opens to the living space.

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 Canaan

5 out of 5 average rating, 23 reviews

Cozy Log Cabin Retreat with Pool on 4 Acres

Gather at the log cabin with fireplace and enjoy the private pool (Memorial Day- Sept). Updated with all the essentials like fast WiFi, Roku, open kitchen/dining area, stocked kitchen, grill. Minutes to ski mountains and all Berkshires area attractions. Space for everyone to stretch out outside on 4 acres! Close to everything, but feels like your own wooded retreat. One mile south of MA 15 min to Great Barrington/Big Y 20 min to Ski Butternut 25 min to Catamount Ski 40 min to Tanglewood

Superhost

Home in Hudson

4.9 out of 5 average rating, 31 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 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 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.

Guest favorite

Home in Athens

4.98 out of 5 average rating, 64 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

Home in Ghent

4.88 out of 5 average rating, 300 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.