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.

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.

Mountaintop Nirvana: Lake, Hot Tub, Pool Table

3 minutes to Ski Sundown. Unwind above tranquil waters, marinate in the pool, bundle beneath the blanket as the crackling fire radiates warmth, savor freshly roasted coffee perched on the mountain, unify with nature or imbibe libations with friends, this property affords serenity for all. After hitting the slopes at Ski Sundown, you can soak in the hot tub and enjoy billiards. The summer affords fishing, hiking, golfing, tubing or boating, leaving you rested and restored.

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.

3 Bed/2.5 Bath with Indoor Pool

Nestled at the edge of the Sharon Wildlife Area this 3 bedroom 2.5 bath home has an indoor pool and outdoor fire pit. The natural landscaping provides an enchanting outdoor space to explore with a seasonal brook that winds through the property on its way to the Housatonic River. The location feels rural while remaining close to destinations like Lime Rock Race Track, Mohawk Ski Mountain, Metro North Wassaic Station and the Hotchkiss School.

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.

Northwest Connecticut Vacation House in Goshen

Our cozy home welcoming guests with vacation vibes on a private, friendly Woodridge Lake, just minutes from Litchfield County's most charming small towns and ski resorts. Only 2 hours from NYC, 2.5 hours from Boston and 10 min from Litchfield village green. You'll discover the lake is exceptionally well-cared for and has a great energy but without the crowds since there is no public boat launch and no jet skis allowed.