Vacation rentals with a pool in Lanesborough

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Top-rated rentals with a pool in Lanesborough

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, 396 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 clear, inviting pool is surrounded by a well-maintained paved area, providing easy access. Lush greenery borders the space, while a secure fence enhances privacy. Sunlight reflects off the water, creating a serene atmosphere ideal for relaxation.

Cottage in Averill Park

4.94 out of 5 average rating, 152 reviews

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.

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, 104 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.

Superhost

A serene saltwater pool is bordered by natural stone paving, with a spacious umbrella providing shade over several lounge chairs. A black metal fence outlines the pool area, enhancing privacy and safety while offering a peaceful view of the surrounding landscape.

Cottage in Hudson

4.82 out of 5 average rating, 114 reviews

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm

1 minute off Warren St - salt water pool and hot sauna respite! No expense spared reviving this Historic 18th century 80 acre estate - heated pool, cedar barrel sauna, heated bathroom floors, original wood finishes, french door patio under stain glass windows from NYC’s iconic Chelsea Hotel. You’ve found the perfect combination of transcendentalist oasis with modernity providing a most comfortable stay. Enjoy a dip, steam, rolling meadows, goat petting, cocktail by fire on your patio!

Guest favorite

A clear swimming pool is surrounded by lounge chairs and an umbrella. Nearby, picnic tables are situated on a grassy area, with trees visible in the background, providing a peaceful setting for relaxation.

Condo in Dover

4.91 out of 5 average rating, 113 reviews

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

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, 102 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

An inviting outdoor space features a sparkling pool surrounded by a spacious deck. Sun loungers are positioned nearby, while majestic mountain views extend in the background. Clear blue skies provide a bright ambiance, enhancing the tranquil setting.

Home in Germantown

4.95 out of 5 average rating, 133 reviews

Hilltop modern with stunning mountain views

Beautiful modern residence with a pool & fireplace in Germantown. Fantastic as a weekend getaway or longer-term rental. In the front, stunning mountain views wrap around the master bedroom, kitchen, living room and deck. Out back, a spacious yard and rolling hills. Grill & eat on the big pool deck, lounge in chaises. Fully equipped kitchen, washer & dryer, and *fast wifi*. Perfect for remote work, and each space has its own desk. Shop, walk, hike, ski: Close to Hudson, Olana & Catskills.

Guest favorite

The pool area is framed by lush greenery, featuring a large in-ground pool with a slide. A colorful inflatable float is seen in the water. A shaded patio table with chairs provides a space for relaxation, alongside a sun umbrella that casts shade over the area.

Home in Williamstown

4.89 out of 5 average rating, 224 reviews

Hollywood Bungalow in the Berkshires #C0191633410

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

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

4.96 out of 5 average rating, 114 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.

Top guest favorite

An outdoor living space is seen, featuring a furnished patio with comfortable seating and a dining area. String lights illuminate the area, while an outdoor movie screen displays a film. The grassy yard extends beyond the patio, creating an inviting atmosphere.

Townhouse in Clifton Park

4.99 out of 5 average rating, 189 reviews

Near Saratoga – King Bed, Tub, Fire Pit & Movies

Family-friendly Clifton Park apartment near Saratoga Springs (20 min), Schenectady (20 min), and Albany (25 min). Enjoy a fire pit, outdoor movie screen, basketball court, private backyard playground, garden, and a dedicated office for remote work. Includes 1 oversized bedroom, full kitchen, soaking tub & shower, fast Wi-Fi, washer/dryer, and a 20' x 55' parking pad for RVs, trailers, or boats. Quiet cul-de-sac, full guest access, and self check-in.

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

4.92 out of 5 average rating, 249 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.

Guest favorite

The serene swimming pond is framed by lush greenery and vibrant flowers. A wooden deck with lounge chairs overlooks the water, while a gentle slope of open lawn leads to the rustic guest house, partially shaded by trees under a clear blue sky.

Home in Ghent

4.89 out of 5 average rating, 330 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Escape to our recently renovated guest house on a 12-acre property, 15min from Hudson. Take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.