
Holiday rentals with a pool in Lenox
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Lenox
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!

Lakefront Retreat | Kayaks, Paddle Board & Hot tub
Welcome to the newly renovated lakefront vacation house in the Catskills. It is perfect for family & friends looking for a getaway in the Hudson valley and Catskill mountains. Close to ski resorts like Hunter & Windham. This peaceful retreat is located in a beautiful lake community with a large waterfront backyard. You will enjoy: • Gathering around the fire pit by the waterfront with s’mores • Relaxing in the Hot Tub overlooking the lake • Wake up to the beautiful lake view from your bedroom

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.

Modern Upstate Cabin, near Rhinebeck NY
[ 🏊🏽♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. 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.

Luxury Prvt Estate w/Hot Tub+Gameroom nr Rhinebeck
Perched at the top of a hill on 20 private acres, this upscale, modern log home serves as an ideal home base to discover the picturesque Hudson Valley. The Hammock Hill House offers guests upscale features such as heated gunite pool, Sonos speakers, and a gourmet kitchen complete with Wolf and Miele appliances. A lower level lounge promises hours of fun with a full-size pool table, darts, and classic board games. Either the hot tub or the firepit are a perfect end to a busy day of exploration.

Little Farm Stay Catskill
Rustic first floor apartment on quiet, private horse farm. Private entry, suitable for single adult or couple. Great location at the foothills of the Catskill Mountains! 6 miles to HITS Saugerties, minutes from the village of Catskill and just a short ride to historical Woodstock. Enjoy hiking, bike trails and local shopping! Full Kitchen Bedroom: Queen, small single futon Living area: Cable TV & Foosball Table Back patio: seating, grill, hot tub and pool(seasonally) Fire pit Wi-Fi

Casa Luna Country Retreat with Pool, Hudson, NY
CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

Hudson River Sunset Getaway
With sunset views of the Hudson River and Catskill Mountains you can relax poolside during the summer months or enjoy the changing fall colors next to a cozy back yard bonfire in the fall. Located only 5 mins to downtown Hudson where you’ll find ample dining, drinking & shopping opportunities. Or head out to explore the Catskill Mountain Range only 30 mins away for the best hiking and skiing in the area. Sunset House is the perfect place for families or a couples getaway!

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.

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.

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

The 1770 House

Stunningly Designed Luxury Home w/ Pool & Hot Tub

Shaggerties Cozy Catskills Getaway

Adams Farm-"The Little Farmhouse"

Catskill Mountain View Home with Hot Tub

Stunning luxury home with pool

Hudson River views with pool and hot tub

Hollywood Bungalow in the Berkshires #C0191633410
Apartment rentals with a pool

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

Jiminy Peak Apartment

Jiminy Peak Country Inn 1 Bedroom Suite

Peaceful 1BR Condo with Pond View

Crafts Inn in Vermont 1br suite, Saturday check-in

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

Vacation Village in Berkshires 12/28/25-1/4/26

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

Haddock + Cotter - Chic Farmhouse and Barn w/ Pool

Berkshire Mountain House

Great place|2 BD|Kitchen| Pool

Sweet Dreams Retreat

Mountaintop Nirvana: Lake, Hot Tub, Pool Table

Great Place |2 BD|Kitchen| Pool

Welcome to the Blue Cottage in Claverack NY

Hudson River Waterfrt/HITS/Spec Views/Pool/Deck
Quick stats about holiday rentals with a pool in Lenox

Total holiday rentals
Explore 50 holiday rentals in Lenox

Nightly prices starting at
Lenox holiday rentals start at € 85 per night before taxes and fees

Verified guest reviews
Over 1,110 verified reviews to help you choose

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

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
50 of Lenox holiday rentals include wifi access

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

4.7 Average rating
Lenox stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Bed and breakfasts Lenox
- Family-friendly rentals Lenox
- Rentals with lake access Lenox
- Fitness-friendly rentals Lenox
- Flat rentals Lenox
- House rentals Lenox
- Hotel rooms Lenox
- Rentals with a fireplace Lenox
- Rentals with breakfast Lenox
- Rentals with a washing machine and dryer Lenox
- Rentals with a patio Lenox
- Rentals with a firepit Lenox
- Rentals with outdoor seating Lenox
- Pet-friendly rentals Lenox
- Rentals with pools Berkshire County
- Rentals with pools Massachusetts
- Rentals with pools United States
- Hunter Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Windham Mountain
- Butternut Ski Area and Tubing Center
- Thacher State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Kent Falls State Park
- Taconic State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Ski Sundown
- June Farms
- Norman Rockwell Museum
- Opus 40
- Naumkeag
- Berkshire Botanical Garden
- Millbrook Vineyards & Winery
- Hancock Shaker Village





