Vacation rentals with a pool in Washington

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

Looking for privacy, seclusion, and direct access to Sleeping Giant State Park right from your back yard? Then look no further! Entire Mid Century home centrally located to many great attractions and colleges. Featuring an open floor plan characterized by large glass windows and open space featuring simplicity and an integration with nature. Access to I-91 or Rt15 are both about 1 mile away, with Yale University and Downtown New Haven about a 20 minute drive. Farmington Canal bike trail-.5 miles

Family · Value · Hot tub

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. 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.

Value · Family · Comfort

Private Estate w/Pool, Hot Tub+Sauna nr Rhinebeck

Perched at the top of a hill on 20 private acres, this upscale, modern log home serves as an ideal home base to discover the picturesque Hudson Valley. The Hammock Hill House offers guests upscale features such as heated gunite pool, Sonos speakers, and a gourmet kitchen complete with Wolf and Miele appliances. A lower level lounge promises hours of fun with a full-size pool table, darts, and classic board games. Either the hot tub or the firepit are a perfect end to a busy day of exploration.

Value · Location · Cleanliness

Magic Red Barn with Heated Salt Pool (opened now)

Escape to magic, just one hour from NYC. No car really necessary. Immerse yourself in nature’s wonderland: wildflowers, scenic trails, and vibrant local farmers’ markets. Unwind in a heated saltwater pool (summer) and cedar soaking tub (winter). Sleep in a stunning renovated loft — 1,000 sq ft of luxury in a private barn. Ideal for family or friends: 1 king, 2 queens, and a toddler bed. Full kitchen with oven, microwave, and half fridge. Fiber optic Wi-Fi. Privacy guaranteed: no other guests.

Value · Family · Pool

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Named one of "The 10 Best Remote AirBnBs for an Escape From Reality" according to the author of 'Leave the World Behind' First Floor Open Space includes a fully equipped Kitchen (Viking Range, Dishwasher, Washer, Dryer, FridgeFreezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Decorative Fireplace, Smart TV & Cable Second floor has 2 Bedrooms: One with a King bed overlooking the paddocks One with 2 Queen beds and a Desk overlooking the pool One bathroom with shower.

Family · Location · Amenities

Country retreat on 4 private acres

Relaxation is offered in all parts of our bright and comfortable home, sitting on 4 acres of mature gardens and woodlands. Try the screened porch for evening dining, morning coffee on the sunny deck or rest poolside in the secret garden. Gardens bursting full of color, paths winding along ancient stone walls and woods full of bird life make this a peaceful retreat. Near East Hamlet Preserve, Lake Waramaug beach and Kent restaurants and shopping. 25 mins to nearest train station into NYC.

Family · Location · Wifi

Upstate Getaway btw Rhinebeck+Hudson

Our home is located on an unpaved, private road in a quiet area and features an in-ground, heated, saltwater pool open between Memorial Day and Late September. In 2026, the pool will be available for bookings 5/22 - 9/18. A quiet and private getaway in the Hudson Valley and convenient to many popular activities. NOTE: For bookings during pool season, guests will be asked to review and agree to the safety rules relating to the pool.

Family · Location · Outdoor spaces

1 Bed Pond Cottage w/ pool/hot tub/sauna access

Adorable & cozy cottage sits on the pondside corner of our 25 acre property. Deck is great for BBQ and stargazing at night. Enjoy fire pit on the beach for s’mores. Pool not heated but hot tub can be heated. Sauna in gazebo. Enjoy the canoe and fish in our private pond (carp & bass) Lots of hiking trails nearby and great restaurants. 20 mins. from Harlem-Valley Wingdale train station. Car is highly recommended as taxi service is limited.

Location · Value · Amenities

Classic Red Barn with game room and gym

Enjoy a fun and romantic stay in this classic red barn in the private countryside. The 2-bedroom barn is only available when the main house is unoccupied, so you will have the full run of the beautiful private exterior property. The barn's game room has ping pong, air hockey and foosball tables, and a basketball hoop outside. We also offer a boxing area, weights bench, and fitness mats. In the summer, enjoy the fire pit, grill and pool.

Family · Location · Nearby

Peaceful Light-Filled Guesthouse salt pool/sauna

Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit, or unwind in the pool side sauna. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Location · Family · Walkability

Retreat with Heated Pool, 1 Mile to NYC Train

The pool is open for the 2026 season. Escape to a stunning 4-BR home on 2 acres in Redding, CT (#1 Small Town). Just 90 mins from NYC, this luxurious retreat comfortably fits 8 guests. Enjoy hotel-style amenities, a heated saltwater pool, and a gourmet kitchen. Breathe in fresh country air in a peaceful, park-like setting. Perfect for families, offering a blend of modern comfort and outdoor living.

Location · Value · Wifi

Escape to a Restored New England Antique Milk Barn

A Bucolic antique farm property in the Fairfield County countryside. Welcome to Connecticut country living at its best! Enjoy the gardens from your private patio, take a dip in the pool, read a book surrounded by fall foliage and retire to your very private suite and relax in the soaking tub. Please note the owners reside on the 4 acre property but give guests the utmost privacy.

Location · Family · Pool