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Vacation rentals with a pool in Stockbridge

Find and book unique homes with a pool on Airbnb

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Stockbridge rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Superhost
A tranquil saltwater pool is framed by a smooth stone deck, surrounded by lush greenery and mature trees. The soft glow of the sunset reflects off the water, creating a serene atmosphere overlooking the Hudson River.
Home in Stuyvesant
4.94 out of 5 average rating, 72 reviews

Red House on the Hudson

Top guest favorite
Aerial view of the Catskills lake-front house surrounded by greenery, showcasing the serene lake and lush forested area. The property features a large driveway, with the house positioned near the water's edge. Tranquil lake views extend into the distance.
Home in Athens
4.93 out of 5 average rating, 153 reviews

Private lakefront home, hot tub & resort amenities

Superhost
A serene gunite pool is framed by lush greenery, offering a peaceful escape. Surrounding lounge chairs provide ample seating for relaxation. Float toys rest gently on the water's surface, inviting leisure and enjoyment in the natural surroundings.
Home in Hudson
4.9 out of 5 average rating, 60 reviews

16 Acre Hudson Hideaway and Pool

Guest favorite
The spacious bedroom features a large bed with a geometric patterned duvet and plush pillows. Flanking the bed are two nightstands with lamps. A cozy area rug complements the hardwood floor. Robes are hung on the wall, and a doorway leads to the en suite bathroom.
Home in Saugerties
4.93 out of 5 average rating, 138 reviews

Bluestone Escape - Where everyone is at home.

Guest favorite
The expansive outdoor area includes a heated swimming pool, surrounded by a black wrought-iron fence. Comfortable loungers are positioned nearby, with a covered seating area visible in the background. Fall foliage adds a colorful backdrop to the property.
Home in Hillsdale
4.93 out of 5 average rating, 27 reviews

Hillsdale Escape | Pool, Hot Tub, Game Room

Guest favorite
An inviting in-ground heated swimming pool is surrounded by a spacious stone patio, featuring six lounge chairs and a circular dining table with four chairs. A large umbrella provides shade, and a red barn is visible in the background, framed by greenery.
Home in Saugerties
4.94 out of 5 average rating, 155 reviews

5BR close to Village | Diamond Mills | HITS | Pool

Guest favorite
A large country estate is presented, featuring an orange exterior surrounded by lush greenery. The home includes a spacious front entryway with steps leading to double doors, while an expansive driveway and two-car garage are visible on the right.
Home in East Chatham
4.89 out of 5 average rating, 36 reviews

10 Acre Country Estate with Pool, Hot Tub & Views!

Superhost
Home in Kingston
4.85 out of 5 average rating, 107 reviews

Hudson River views with pool and hot tub

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Condo rentals with a pool

An outdoor swimming pool is framed by lounge chairs and umbrellas, with a surrounding fence for privacy. Lush greenery and a distant building are visible in the background, under a clear blue sky with scattered clouds creating a serene setting.
Condo in Hancock
4.89 out of 5 average rating, 9 reviews

Condo Resort at Jiminy Peak Ski Mountain's Base

Guest favorite
A spacious living area features an arrangement of dark leather seating and a wooden dining table. Natural light streams through sliding glass doors that open to a balcony. A stone fireplace adds character, while decorative plants and artwork enhance the inviting ambiance.
Condo in Hancock
4.95 out of 5 average rating, 61 reviews

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

A comfortable living room is presented with two sofas adorned with festive cushions. A coffee table is centered on a cozy area rug, while a television sits atop a media console. Large windows framed by dark curtains allow natural light to fill the space.
Condo in Hancock
4.89 out of 5 average rating, 35 reviews

Unique - Country suite @ Jiminy Peak

Guest favorite
A comfortable living area is presented with a plaid chair and a sofa, complemented by a coffee table. Natural light fills the space through a large window with elegant drapery. A flat-screen television is positioned nearby, enhancing the relaxation setting.
Condo in Hancock
4.88 out of 5 average rating, 32 reviews

Jiminy Peak Apartment

An outdoor heated pool is surrounded by a concrete patio, with lounge chairs positioned nearby. Lush green hills and trees are visible in the background, alongside ski slopes. The pool area is partially shaded by an overhanging roof, allowing for a relaxing atmosphere.
Condo in Hancock
4.6 out of 5 average rating, 154 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

Superhost
A lush green lawn frames a serene pond, reflecting the surrounding landscape. The two-story condo units are visible in the background, showcasing a harmonious blend with the natural setting. Towering trees provide a calming backdrop, enhancing the peaceful atmosphere of the area.
Condo in Lenox
4.7 out of 5 average rating, 10 reviews

Peaceful 1BR Condo with Pond View

Superhost
Icicles hang from a structure in the foreground, with a view of snow-covered ski slopes illuminated by soft lights in the distance. The landscape is blanketed in fresh snow, creating a serene winter atmosphere.
Condo in Hancock
5 out of 5 average rating, 4 reviews

Wyndham Bentley Brook

Guest favorite
A living area features a beige sofa with cushions, positioned beside a dark wood coffee table. Natural light enters through a large window with tan drapes, offering a view of grassy landscaping. A simple lamp stands next to the sofa, enhancing the cozy ambiance.
Condo in Hancock
4.9 out of 5 average rating, 71 reviews

Jiminy Peak Country Inn - ski in/out condo MT view

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Other vacation rentals with a pool

Guest favorite
A well-lit bedroom features a spacious bed adorned with neutral bedding, complemented by a patterned throw. A television is mounted on the wall, and a warm lamp sits beside the bed. A cozy chair and a potted plant add a touch of comfort to the space.
Apartment in Pittsfield
4.83 out of 5 average rating, 6 reviews

Berkshire Victorian Studio - Long Terms Welcome

Top guest favorite
A three-story building is set amidst a grassy area with scattered rocks. A small pond reflects the clear sky and nearby greenery, enhancing the serene landscape that surrounds the resort.
Hotel room in Lee
5 out of 5 average rating, 5 reviews

Beautiful place|2 BD|Kitchen| Pool

Superhost
Home in Lee
4.83 out of 5 average rating, 35 reviews

* Private Berkshire Escape* Monthly Pricing Avail

Guest favorite
Two glasses of red wine are placed beside a lit candle on a window sill. A plate filled with green grapes and assorted chocolates sits in the foreground. Outside, a vibrant garden of yellow flowers and greenery is visible through the window.
Apartment in Sandisfield
4.96 out of 5 average rating, 53 reviews

Sweet Dreams Retreat

Guest favorite
A pool area features a partially enclosed space with large, open doors. A small shed is visible next to the pool, which reflects the blue sky. Comfortable seating in a cozy nook provides a relaxing atmosphere surrounded by greenery.
Home in Hudson
4.96 out of 5 average rating, 27 reviews

Heated Pool| Fire pit | Fall Escape

Guest favorite
The charming blue exterior of the house is framed by lush greenery and mature trees. A gravel pathway leads to the front door, while a well-maintained lawn offers a spacious and inviting setting. Windows reflect the soft natural light filtering through the surrounding foliage.
Cottage in Hudson
4.96 out of 5 average rating, 24 reviews

Welcome to the Blue Cottage in Claverack NY

Guest favorite
A tranquil scene is captured at sunset, showcasing a newly renovated inground pool. The clear water reflects the golden sunlight, surrounded by lush greenery. A protective fence encloses the pool area, offering a serene view of the landscape and mountains in the background.
Home in Cheshire
4.94 out of 5 average rating, 85 reviews

Berkshire County modern home + pool

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

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Quick stats about vacation rentals with a pool in Stockbridge

  • Total rentals

    20 properties

  • Nightly prices starting at

    R1,943 ZAR before taxes and fees

  • Total number of reviews

    250 reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

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