
Holiday rentals with a pool in Lee
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Lee
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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

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!

4Br Mountain Brook House on 130 acres w/ trails
Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

Le Soleil Suite - Cozy Mountain 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.

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.

1880s balconied luxury pad, best downtown location
Bright, newly renovated, luxuriously furnished, tree-lined flat a few steps from Northampton's vibrant downtown. Sliding glass doors open to a lovely balcony overlooking trees and roofs. Open floor plan, eat-in butcher-block kitchen, dishwasher, living room with movie projector, home theater system, queen pullout sofa. Spacious queen bedroom with 42" HDTV, private study nook. Access to yard areas with outdoor dining table, heated 36-ft pool, play gym. Basement washer/dryer. Off-street parking.

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.

Cozy Vermont Antique Sugar House with Fireplace
Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

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.

A luxurious farm hideaway in the treetops
Want to get away to your own private hideaway, overlooking rolling hills and a pastoral farm? The space is small but luxurious, with a well-equipped kitchen, a comfortable bed with high-end 100% cotton linens, lots of soft throw blankets, real leather furnishings, and a marble-tiled bathroom. The views from the deck are stunning. Plenty of hiking spots, fine dining, and cultural sites nearby. Or just lounge by the pool (Memorial Day through Labor Day)

Cozy Stay – King Bed, Soaking Tub & Fire Pit
Cozy winter reset in Clifton Park—perfectly located for easy trips to Saratoga Springs, Albany, Troy, and Schenectady. Sink into a plush king bed, unwind in the soaking tub, and end the day by the fire pit under string lights. Whether you’re here for a quiet getaway, work trip, or a longer stay, you’ll have comfort, privacy, and the space to truly relax. Outdoor movie screen: “available weather-permitting” + two 65" TV indoors for winter nights.

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.
Popular amenities for Lee rentals with a pool
House rentals with a pool

Luxury Berkshire Retreat, Pool+Hot Tub, Sleeps 18

Bluestone Escape - Where everyone is at home.

Red Rock Summit: Pool | Privacy + Views | Sauna

Historic 1850s Berkshires Retreat "The Bell House"

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

Hudson River views with pool and hot tub

Hollywood Bungalow in the Berkshires #C0191633410

Contemporary, Warm & Cozy Home mins to Saratoga
Apartment rentals with a pool

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

Mount Snow Ski Chalet

Slopes N Seasons | Trailside Condo at Mount Snow

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

Mt Snow Ski In/Out at Seasons

Walk to Mt. Snow-Spa-Summer Pool

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

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck
Other holiday rentals with a pool

Ski-InSki-Out Loft Lift&MT.Views

Berkshire Mountain House

The Catamount Ski Haus with Pool & Hot Tub

Jiminy Peak Ski Loft with Hot Tub

The Pool Cottage at Narrow Valley Estate

$5,500/mo Special * Private Berkshire Escape*

Sweet Dreams Retreat

NE Historical Mansion-pets and pet lovers welcome
When is the best time to visit Lee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 133 | € 136 | € 170 | € 151 | € 166 | € 252 | € 222 | € 222 | € 167 | € 170 | € 200 | € 222 |
| Avg. temp | -3°C | -1°C | 3°C | 10°C | 16°C | 20°C | 24°C | 23°C | 18°C | 12°C | 6°C | 0°C |
Quick stats about holiday rentals with a pool in Lee

Total holiday rentals
Explore 90 holiday rentals in Lee

Nightly prices starting at
Lee holiday rentals start at € 34 per night before taxes and fees

Verified guest reviews
Over 1,500 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
90 of Lee holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Lee rentals

4.9 Average rating
Lee stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with pools Berkshire County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Catamount Mountain Ski Resort
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Zoom Flume
- Bushnell Park
- Mount Snow Ski Resort
- Norman Rockwell Museum
- Bousquet Mountain Ski Area
- Bright Nights at Forest Park
- Taconic State Park
- Mohawk Mountain Ski Area
- Wintonbury Hills Golf Course
- Butternut Ski Area and Tubing Center
- Talcott Mountain State Park
- Mount Sugarloaf State Reservation
- Beartown State Forest
- Hartford Golf Club
- Mount Tom State Reservation
- Albany Center Gallery




