Vacation rentals with a pool in Litchfield County

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.

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.

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.

Litchfield Hills Lakefront Getaway!

YellowBird welcomes guests with luxury vaca vibes + gorgeous water and sunset views on friendly Woodridge Lake, just minutes from Litchfield County’s charming small towns, golf, hikes + ski resorts. -2 hrs NYC, 2.5 hrs Boston, only 10 min from Litchfield village center -Gorgeous & fun all year -Enjoy 150 ft of lakefront, swimming, fishing, parks, golf, hiking, mountain and countryside vistas, foliage, covered bridges, antiquing, vineyards, top restaurants, cultural activities & skiing

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.

The Copake Cabin - A rustic-modern retreat.

A quiet place to get away from it all. Modern log cabin with 3 bedrooms and lots of amenities. A private heated pool, outdoor spaces, wood-burning fireplace and outdoor fire pit. For those working remotely, there is super-fast WiFi and a designated work space. Close to the best of the Hudson Valley and the Berkshires. There is a large lake nearby for boating, swimming, and kayaking in the warmer months. Skiing and sledding in the winter. Columbia County STR Registration #: COP-2025-015

Designers Historic Connecticut Home

This historic home, designed and decorated by a talented artist, features four bedrooms, two bathrooms, and a unique "Glamping" shed. The property boasts a heated Gunite lagoon pool, perfect for relaxing and entertaining. Guests can dine at a ten-person farm table under charming string lights, surrounded by Restoration Hardware teak furnishings. The outdoor lounge area on the stone patio offers a cozy retreat, complete with an old-fashioned wood and rope swing hanging from an Elm tree.

Litchfield Luxury Home w/Heated Pool

Escape to this fully renovated 4BR, 2.5BA estate on 12 private acres with sweeping views of Litchfield’s hills. Enjoy a heated pool (seasonal @ $50 per day upcharge), private gym, and walking trails. Inside, relax in beautifully furnished spaces with hardwood floors and New England charm. Just 3 miles from downtown Litchfield’s shops, dining, and hiking. Whether you’re sipping coffee while watching the sunrise or relaxing at sunset by the pool, the views are breathtaking year-round.

Farm Stay with Horses & Pool | Mountaintop Views

Come sleep above the horses at Bloombury Hill Farm. With stunning mountaintop views, this immaculate 2 BR apartment is spacious and boasts over 2000 square feet. Bask in the sunshine at the pool (open Memorial Day through Labor Day from 11a-5pm.) Close to thriving West Hartford Center with loads of restaurants and shopping. Hiking trails, local breweries and wineries, and farm stands are all located close by. All the ingredients for a magical weekend getaway.

Lake House close to Skiing & Indoor Hot Tub

Sleepy Hollow is a small community with lots to offer inside . This home offers so much entertainment you won't even have to leave the driveway . From a pool table, and video games to outside on a luxurious lawn overlooking this private lake. Sit down have a fire , cookout and watch the sun go down. Hunter and Windham mountain are both approx 40 minutes. Hudson is a skip away at 20-25 minutes putting you right on Main Street where all the action is.

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

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.