
Vacation rentals with a pool in Lee
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Top-rated rentals with a pool in Lee
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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.

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.

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.

The Coach House | Modern 2BR Loft + Views & Pool
Restored coach barn with 25-ft cedar ceilings, skylights, and mountain views—part of House on Golden Hill, a historic Lenox farmhouse compound. This airy 2BR + loft retreat blends rustic charm with modern ease. Enjoy a full kitchen, cozy living space, and outdoor area. Set beside a stream with seasonal pool access, it’s perfect for families, couples, or creative escapes. Centrally located and just minutes to downtown Lenox, Tanglewood, and trails—your Berkshires base for rest and inspiration.

Eco Cottage in the Woods
The cottage is light and airy, surrounded by forest. You may see birds and deer from the bedroom or living room. The queen bed is divided from the living room by a bookcase wall. There is a sofa bed in the living room which faces a patio overlooking the woods. We have a 16x36 unheated gunite pool, professionally maintained. The cottage works well for a couple or a couple with children. 2 night minimum required. Pets welcome. Pet owners passing through may stay 1 night.

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.

Country Getaway Tiny House in Woods w/Pool/Sauna.
Tiny House - 600 Sq ft. of living space on 30 private acres with walkable trails in beautiful Columbia County. Secluded privacy and surrounded by nature. House is fully equipped, sleeps 4 with queen bed and twin loft beds. Enjoy the pool, barn pool house and 4 person sauna. In the winter stay warm by the wood stove. Restaurants close by or stay in and enjoy the property. Located 8 miles from Hudson, 3 miles from Chatham and Kinderhook. Near OMI Arts Center. Adults only.

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.

Secluded peaceful loft in barn by woods
La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we use a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

Near Saratoga – King Bed, Tub, Fire Pit & Movies
Escape to this family-friendly Clifton Park retreat—just 20 mins to Saratoga Springs and 25 to Albany. Perfect for fall getaways with a fire pit, outdoor movie screen, private playground, basketball court, and garden. Features a king bedroom, home office, full kitchen, fast Wi-Fi, soaking tub, and 20' x 55' parking for RVs or boats. Relax in the crisp autumn air, enjoy backyard movie nights, and stay productive or cozy in a quiet, peaceful neighborhood.

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)

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

Berkshires Oasis Retreat: Art Meets Nature

Shaggerties - fun cozy catskill mountain getaway

Hudson Valley & Catskill Mountain Views • Hot Tub

Red Rock Summit: Mtn Escape w/ Pool, Sauna + Views

Mountain Blossom Retreat by Evergreen Home

Hilltop: Panoramic Views w/ Pool near Catamount

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

Casa Luna Country Retreat with Pool, Hudson, NY
Condo rentals with a pool

Condo Resort at Jiminy Peak Ski Mountain's Base

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

Unique - Country suite @ Jiminy Peak

Jiminy Peak Country Inn 1 Bedroom Suite

Peaceful 1BR Condo with Pond View

Wyndham Bentley Brook

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

Ski-in/Ski-Out on Jiminy Peak
Other vacation rentals with a pool

Stunning horse farm apt, hot tub

Peaceful, Low Toxin Haven

Cozy Ski Retreat

Artsy Ski Loft with Hot Tub near MassMoca

Sweet Dreams Retreat

Hudson River Sunset Getaway

Trackside Guesthouse w/ Pool

Rustic Cabin with Wood Fireplace
When is the best time to visit Lee?
Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
---|---|---|---|---|---|---|---|---|---|---|---|---|
Avg. price | R2,719 ZAR | R2,788 ZAR | R3,468 ZAR | R3,085 ZAR | R3,398 ZAR | R5,158 ZAR | R4,793 ZAR | R4,758 ZAR | R4,374 ZAR | R4,183 ZAR | R4,095 ZAR | R4,531 ZAR |
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 vacation rentals with a pool in Lee
Total vacation rentals
Explore 90 vacation rentals in Lee
Nightly prices starting at
Lee vacation rentals start at R697 ZAR per night before taxes and fees
Verified guest reviews
Over 1,500 verified reviews to help you choose
Family-friendly vacation rentals
70 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wi-Fi availability
90 of Lee vacation rentals include wi-fi 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
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- Six Flags New England
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Kent Falls State Park
- Mount Greylock Ski Club
- Zoom Flume
- Catamount Mountain Ski Resort
- Bushnell Park
- Norman Rockwell Museum
- Taconic State Park
- Wintonbury Hills Golf Course
- Hartford Golf Club
- Mount Tom State Reservation
- Bright Nights at Forest Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Opus 40
- Beartown State Forest
- Talcott Mountain State Park
- Albany Center Gallery