Vacation rentals with a pool in Lenox

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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

A clear blue swimming pool is surrounded by a concrete deck, with lush greenery and tall trees visible in the background. The pool's water shimmers under the sunlight, reflecting the blue sky and scattered clouds.

Guesthouse in Lenox

4.92 out of 5 average rating, 393 reviews

Restored 1735 Granary I King Bed + Views & Pool

Restored 1735 granary on a peaceful Berkshires farmhouse compound. With 15-ft vaulted ceilings, original wide-plank floors, and mountain views, this design-forward retreat blends rustic charm with modern ease. Features a king bedroom, eat-in kitchen, and bathroom with soaking tub + standing shower. Centrally located in the Berkshires and just minutes to Lenox and Tanglewood. A quiet, light-filled space perfect for couples, creatives, and anyone seeking rest, reflection, and connection to nature.

Guest favorite

A circular pool is set within a grassy area, surrounded by lush greenery. A shaded picnic area features a large table beneath a white umbrella. Colorful inflatables are visible on the water's surface, adding a playful touch to the serene outdoor setting.

Bungalow in Easthampton

4.93 out of 5 average rating, 519 reviews

The Creation Station

Welcome to The Creation Station. I am your host John. The Creation Station was built with love and care by me with my friends and family. Amenities? Update! We just installed an 8 person hot tub! Plus our pool, jacuzzi tub, projector, giant deck and a stage with sound system, drums amps and karaoke input. The most unique amenity though is The Enchanted Forest. A lit trail surrounding the property. Fun for kids of all ages! Please let me know how I can make your stay amazing. See you soon! John

Guest favorite

A stock tank plunge pool is surrounded by a wooden deck and gravel, featuring a pink flamingo float. A lounge chair rests nearby, inviting relaxation in the natural setting of greenery.

Home in Hudson

4.96 out of 5 average rating, 162 reviews

Hudson Getaway w/ Hot Tub + Fireplace 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!

Top guest favorite

A refreshing swimming pool is surrounded by lush greenery and trees, with a hammock hanging nearby. A patio area features an umbrella and outdoor seating, complementing the serene, private backyard setting of the guest suite.

Guest suite in Hudson

4.99 out of 5 average rating, 103 reviews

Le Soleil Suite - Fire pit, Views 10 Min To Hudson

A charming one-bedroom suite in a rural neighborhood 10 minutes by car from downtown Hudson. Your rental is a private, independent unit next to the main house. It has a full kitchen, bathroom, electric fireplace and a private backyard with a grill, firepit and pool (June to Sept.). If we are around, we give you privacy. Watch sunset over the Catskills from the living room. 1 Br with queen bed, 1 pullout sofa, 1 fold-out twin upon request. Close to Hudson, hiking, skiing, Olana and Art Omi.

Top guest favorite

The exterior of a modern cabin is displayed, featuring large glass windows and a sleek black facade. A heated pool is visible with a smooth blue surface. Several lounge chairs are arranged around the pool, enhancing the outdoor relaxation space.

Cabin in Red Hook

4.96 out of 5 average rating, 362 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October 26, 2025. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. 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.

Guest favorite

The seasonal saltwater pool presents a clear blue surface, bordered by a wooden deck. A cozy cabana is visible in the background, framed by trees. Potted plants enhance the serene atmosphere, contributing to the inviting outdoor space.

Home in Taghkanic

5 out of 5 average rating, 100 reviews

Sunbeam Lodge: Pool+Hot Tub, 50 Acres, ‘70s Oasis

Our peaceful, skylit, 3-bed 2-bath lodge is a totally private woodland paradise on a quiet country lane. Part secluded retreat, part rustic resort, part '70s-style cottage, it's only 2 hours from NYC & 20 minutes from Hudson. Unwind in 50 acres of untouched forest & grounds, a seasonal saltwater pool & cabana bar, a Finnish sauna & 7-person hot tub (open year-round), an open chef's kitchen & living room, & a sunny deck overlooking endless natural splendor. See more @sunbeamlodge on Instagram.

Guest favorite

A serene outdoor area is showcased with lush green grass and a stone pathway leading to a private, fenced pool. Flowering plants and bushes are visible, adding natural beauty to the yard. Trees in the background indicate a tranquil wooded setting.

Guest suite in Richmond

4.95 out of 5 average rating, 41 reviews

Berkshire Mountain Retreat

Studio apartment with private entrance nestled in bucolic Richmond. Located on a quiet mountain road adjacent to miles of hiking and biking trails. Close to 4 ski areas and minutes to Tanglewood, Kripalu, Clark Art Museum, Mass MoCA, Hancock Shaker Village, the Mass Audubon Wildlife Sanctuary and more. A short drive to Lenox, Stockbridge, and Great Barrington where shopping and fine dining await. Your relaxing vacation begins here with an expansive yard, views and in ground pool!

Top guest favorite

The serene backyard features a sparkling blue pool surrounded by vibrant landscaping, including colorful flowers. The house, displaying a modern aesthetic, has large windows and a covered patio that invites natural light, set against a backdrop of lush trees.

Home in Great Barrington

4.99 out of 5 average rating, 75 reviews

Stunning luxury home with pool

Welcome to our weekend home in the Berkshires! We now rent it out when we’re not there, following a top-to-bottom renovation with all new furniture, and hope our guests enjoy it as much as we do. Our home is in Great Barrington, 2.5 hours' drive from NYC, surrounded by trees and parkland (Monument Mountain is next door). Yet it's less than 10-15 minutes' drive to town, shopping, restaurants, skiing, and Tanglewood. Come enjoy the Berkshires with complimentary gourmet coffee!

Guest favorite

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.

Apartment in Otis

4.95 out of 5 average rating, 111 reviews

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.

Guest favorite

A private, heated saltwater pool is set against a backdrop of lush greenery and rolling hills. The pool's clear water reflects the blue sky and fluffy clouds. A black dog stands at the edge, observing the tranquil scene.

Home in Richmond

4.97 out of 5 average rating, 32 reviews

Escape to The Berkshires w/Pool by Evergreen Home

This 4Br home is filled with cheeky pop art, stylish comfortable spaces and all the amenities you need for the ideal Berkshire vacation. This is the perfect spot to hang with friends or bring the whole family. The private, heated saltwater pool is available May- Sept, and nearly everywhere you look are mountain views. Venture out your front door to explore the hiking trails nearby or hop in your car for a 5 minute drive to Richmond Pond;10 minutes to Tanglewood!

Guest favorite

A charming red cabin is nestled among lush green trees, surrounded by moss-covered ground. The exterior features multiple windows, allowing natural light to fill the space. A small shed is visible to the left of the cabin, enhancing the serene woodland setting.

Cabin in Guilford

4.95 out of 5 average rating, 171 reviews

Silver Brook Cabin

Waterfront setting in a relaxing, but convenient, location in southeastern Vermont. Photos and captions do the best job of describing our cabin, adjacent brook, and very nearby Green River with its covered bridge and swimming holes. The cabin is 20 minutes from Brattleboro with its many restaurants, shops, movie theater, and galleries. Not only is the immediate area wonderful for swimming, biking, and hiking, you can also simply relax with a good book or two.

Guest favorite

A serene pool area features a large in-ground pool surrounded by lush greenery. Several lounge chairs, including two green loungers and a round table with chairs, are situated on the patio. A bright red umbrella provides shaded seating, adding to the inviting outdoor space.

Guesthouse in Williamstown

4.93 out of 5 average rating, 245 reviews

Perfect Base for Your Berkshire Adventure

Charming private guesthouse with shared pool use. Newly renovated, the space features high ceilings, queen sized bed, rustic Arts & Crafts furniture, heat/air conditioning, and kitchenette. Located in an outbuilding on the property, the guesthouse is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3 - 5.