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Vacation rentals with a pool in Lee

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Lee rentals with a pool

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a pool

Superhost
An in-ground pool is surrounded by lush greenery, with landscaped grasses and trees in the background. Lounge chairs are positioned nearby, and lanterns add a touch of ambiance around the pool's perimeter, enhancing the tranquil outdoor setting.
Home in Old Chatham
4.94 out of 5 average rating, 34 reviews

Haddock + Cotter - Chic Farmhouse and Barn w/ Pool

Guest favorite
A fenced outdoor area features a serene pool surrounded by lush greenery, with a gazebo nearby. A decorative sculpture adds an artistic touch, and several outdoor chairs provide spaces for relaxation. A pathway leads to the pool area, enhancing accessibility.
Home in Otis
4.93 out of 5 average rating, 14 reviews

Berkshires Oasis Retreat: Art Meets Nature

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
4.95 out of 5 average rating, 149 reviews

Private lakefront home, hot tub & resort amenities

Top guest favorite
Home in Catskill
4.98 out of 5 average rating, 61 reviews

Hudson Valley & Catskill Mountain Views • Hot Tub

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, 324 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Superhost
Home in Kingston
4.85 out of 5 average rating, 106 reviews

Hudson River views with pool and hot tub

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, 223 reviews

Hollywood Bungalow in the Berkshires #C0191633410

Guest favorite
An outdoor patio area is showcased, featuring a sparkling pool surrounded by a faux stone deck. Comfortable wooden lounge chairs and a coffee table are positioned near the pool, with a hot tub visible in the background. Lush green hills stretch into the distance under a clear blue sky.
Home in Catskill
4.92 out of 5 average rating, 125 reviews

Pool*Hot Tub*Pirate Ship*Fire Pit*Luxury Farmhouse

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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
4.88 out of 5 average rating, 34 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, 153 reviews

Jiminy Peak Country Inn 1 Bedroom Suite

An inviting indoor pool area is surrounded by large windows that provide a view of the outdoors. Lounge chairs line the poolside, and natural light fills the space, highlighting the tiled flooring and gently rippling water.
Condo in Hancock
5 out of 5 average rating, 3 reviews

Ski Jiminy Peak - 1BD

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 spacious living area features a large pool table with a vibrant red felt surface. A round dining table with four yellow chairs is positioned in front of a bright window. A cozy sofa and an armchair offer comfortable seating, complemented by artistic decor and wooden flooring.
Barn in Pine Plains
4.95 out of 5 average rating, 19 reviews

Stunning horse farm apt, hot tub

Top guest favorite
Villa in Stockbridge
4.94 out of 5 average rating, 50 reviews

Historic Stockbridge Villa on 25 acres sleeps 16

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
4.92 out of 5 average rating, 26 reviews

Hillsdale Escape | Pool, Hot Tub, Game Room

Top guest favorite
The private heated pool is surrounded by a green lawn and wooden fence. Lounge chairs are positioned nearby for relaxation. A log cabin is visible in the background, complemented by trees and natural scenery.
Cabin in Craryville
5 out of 5 average rating, 95 reviews

The Copake Cabin - A rustic-modern retreat.

Guest favorite
An outdoor scene features a clear blue sky above a heated saltwater pool set within a spacious green yard. Surrounding trees provide a natural backdrop, and a small shed is visible next to the pool, which is enclosed by a wooden fence.
Home in New Lebanon
4.98 out of 5 average rating, 66 reviews

Berkshire Mountain home views, pool, Queechy Lake

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

Top guest favorite
A large, inviting pool is framed by lounge chairs, offering ample seating for relaxation. The pool reflects the cloudy sky and surrounds are well-maintained. The house is visible in the background, featuring a bank of windows that overlooks the serene lake landscape beyond.
Home in Pittsfield
4.97 out of 5 average rating, 59 reviews

Berkshire Lakefront Home W/Pool-100%Renovated

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, 35 reviews

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

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Quick stats about vacation rentals with a pool in Lee

  • Total rentals

    80 properties

  • Nightly prices starting at

    G$25,064 GYD before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    60 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

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