Holiday rentals with a pool in Lenox

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Lenox

Total holiday rentals
Explore 40 holiday rentals in Lenox
Nightly prices starting at
Lenox holiday rentals start at ₹14,416 per night before taxes and fees
Verified guest reviews
Over 410 verified reviews to help you choose
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
40 of Lenox holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Lenox rentals
4.7 Average rating
Lenox stays receive an average rating of 4.7 out of 5 from guests

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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Top guest favourite

A clear view of a fenced swimming pool is surrounded by lush greenery and trees. A stone pathway leads to the pool area, with well-maintained flower beds in the foreground. Seating options are available near the pool for relaxation.

Cottage in Averill Park

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.

ValueLocationBack garden

4.95 out of 5 average rating, 171 reviews

Superhost

A spacious outdoor area is surrounded by vibrant planters filled with blooming flowers. Comfortable seating is arranged around a fire pit, with a green umbrella providing shade. A pink flamingo float is set nearby, alongside a wooden hot tub and a stock tank plunge pool.

Home in Hudson

Hudson getaway w/ hot tub+ plunge pool on 20 acres

Escape to Falls Road – a private mid-century country home nestled on the edge of 20 acres of preserved woodlands. Our home has been thoughtfully updated, featuring an array of resort quality amenities as well as a wood-burning fireplace, soaking tub, outdoor shower, projector & a 4ft deep cedar hot tub to unwind in. The yard includes a stock tank plunge pool, deck, grill, and fire pit. Located just over 2 hours from NYC/Boston and only 8 miles from Hudson center. Minutes to hiking, golf, & more!

ValueFamilyNearby

4.94 out of 5 average rating, 198 reviews

Top guest favourite

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

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.

LocationValueLaundry

4.96 out of 5 average rating, 398 reviews

Top guest favourite

The exterior view of the guest house is framed by a large tree, showcasing the red brick barn-style structure. Outdoor seating areas are visible, along with a shaded patio featuring a red umbrella. The surrounding lawn is well-kept, leading to fenced paddocks in the background.

Farm stay in Red Hook

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.

FamilyLocationLayout

4.98 out of 5 average rating, 179 reviews

Guest favourite

A comfortable living room features a large sectional sofa and a wooden coffee table. A reclining chair is positioned nearby, while a flat-screen TV is mounted on the wall. Natural light enters through glass doors, which open to the outdoor area. Soft colors and warm tones create a cozy ambiance.

Home in Lee

Berkshire Vacation Home in Lee

Our spacious home is situated in a secluded neighborhood in Lee, MA (Berkshire County) and has 5 bedrooms & 2.5 baths. There is a fully equipped open concept kitchen/dining room and 2 living rooms with TVs and gas fireplaces. There is central air/heat, and a sun room that leads out to a deck overlooking our in-ground pool. Tanglewood, Antimony brewery, Balderdash winery, Hilltop Orchards, Laurel Lake, Highlawn Farm, outlets, golf, and Lenox & Stockbridge are all within a 20 minute drive.

LocationFamilyAccuracy

4.93 out of 5 average rating, 106 reviews

Top guest favourite

A modern log cabin sits beneath a clear sky, featuring a spacious deck supported by sturdy beams. The exterior shows natural wood tones, surrounded by lush greenery and trees. A manicured lawn leads to a gravel driveway, providing access to the property.

Cabin in Craryville

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

LocationFamilyShared spaces

5.0 out of 5 average rating, 114 reviews

Guest favourite

A spacious living area features a large sectional sofa with dark cushions, complemented by a wooden chair with patterned fabric. A modern ceiling fan hangs above, and a sleek fireplace is positioned nearby. Large windows invite natural light, providing a view of the greenery outside.

Home in Hudson

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

LocationFamilyTV

4.92 out of 5 average rating, 268 reviews

Guest favourite

A spacious backyard features a heated in-ground pool surrounded by patio pavers. Chaise lounges are set up for relaxation, with a shaded pergola offering seating. Lush greenery and trees provide a serene backdrop, enhancing the private outdoor space.

Home in Lenox

Lenox Grand Colonial with Pool by Evergreen Home

Evergreen Home Vacation Rentals invites you to this spacious 4-bedroom home on a quiet cul-de-sac beneath October Mountain. The picturesque backyard features a private heated in-ground pool and abuts a 10-acre “meditation meadow” for year-round peace. Located just 10 minutes from Lenox and Tanglewood, and 7 minutes to Bousquet Mountain, you are steps away from shops and dining. Enjoy a centrally located retreat perfect for the whole family. Experience the best of the Berkshires today!

FamilyLocationBack garden

4.98 out of 5 average rating, 49 reviews

Top guest favourite

An aerial view captures the spacious villa surrounded by vibrant autumn foliage and rolling hills. The property features a pool nestled among trees, with expansive lawns and a gravel driveway leading up to the home, offering a serene retreat in nature.

Villa in Pownal

Vermont Vacation Villa—Grapevine Getaway

Nestled in the stunning natural beauty of Vermont, this striking villa offers the perfect escape from the hustle and bustle of everyday life. Surrounded by rolling hills, and picturesque countryside, this home is a paradise. Whether exploring the area's cultural institutions, immersing yourself in the natural beauty of Vermont, or relaxing and unwinding with family and friends, this vacation home is the perfect retreat. Experience the magic of this beautiful area for yourself!

FamilyLocationComfort

4.95 out of 5 average rating, 100 reviews

Guest favourite

Home in Hudson

Hudson River Sunset Getaway

With sunset views of the Hudson River and Catskill Mountains you can relax poolside during the summer months or enjoy the changing fall colors next to a cozy back yard bonfire in the fall. Located only 5 mins to downtown Hudson where you’ll find ample dining, drinking & shopping opportunities. Or head out to explore the Catskill Mountain Range only 30 mins away for the best hiking and skiing in the area. Sunset House is the perfect place for families or a couples getaway!

FamilyLocationCleanliness

4.92 out of 5 average rating, 112 reviews

Top guest favourite

A lush, green lawn gently slopes toward a small pond, framed by trees on either side. The natural foliage provides shade and privacy, while a stone is visible among the undergrowth. The area is serene, inviting reflection and connection with nature.

Flat in Otis

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

ValueLocationGrill

4.96 out of 5 average rating, 134 reviews

Guest favourite

The exterior shows a modern home embraced by lush greenery. A wooden deck with a railing wraps around the entrance, complemented by well-maintained landscaping featuring shrubs and plants. Trees provide a natural backdrop, enhancing the tranquil rural setting.

Home in Pittsfield

Berkshire Getaway Ranch 3 acres + saltwater pool

Escape to the Berkshires in my cozy home sitting on 3 acres of land with in-ground saltwater pool. Enjoy the private, rural feel at this property with picturesque sunsets on the hills beyond. Under 5 min to Onota & Pontoosuc lakes, 15 min to Jiminy Peak & Bousquet ski resorts & a short drive to Lenox/Williamstown/North Adams. Light a fire in the living room & enjoy the ambiance of the vaulted wood ceilings & large picture windows framing views of the bucolic hills.

ValueLocationPets

4.93 out of 5 average rating, 109 reviews