We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Vacation 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.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Cabin in Stephentown

4.84 out of 5 average rating, 238 reviews

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

Jun 2 – 9

ﺩ.ﺇ949 per night

Bungalow in Easthampton

4.92 out of 5 average rating, 432 reviews

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

Jul 21 – 28

ﺩ.ﺇ624 per night

Home in Ghent

4.87 out of 5 average rating, 270 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Escape to our recently renovated guest house on a 12-acre property, 15min from of Hudson. Cozy up in front of the wood burning stove as you 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.

Dec 8 – 15

ﺩ.ﺇ807 per night

Guest suite in Great Barrington

5.0 out of 5 average rating, 45 reviews

Sweet 1-bedroom with salt water pool

Welcome to our home in the beautiful Berkshires! Enjoy this clean, private downstairs apartment with your own entrance. We are just 10-min from downtown Great Barrington and in a wonderful location for exploring. Upstairs is my family- a 6 year old boy and medium-sized dog- you will hear us! Sometimes we have friends and family visiting. In the summer you may see us at the pool with them. We’re happy to meet you and also happy to give you space- it’s your call. Wishing you a wonderful trip :-)

Sep 10 – 17

ﺩ.ﺇ535 per night

Condo in Hancock

4.83 out of 5 average rating, 131 reviews

Cozy Condo @ Jiminy Peak

Nestled in the majestic Berkshire mountains, this Cozy Condo is a home away from home! It features 2 bedrooms with closets & dresser space. The master bedroom connects to a full bathroom and has a TV for when it's time to unwind in the comfort of bed! The fully equipped kitchen/dining area opens into a spacious living room. It's the perfect place for evening gatherings with friends or a romantic night in front of the fireplace! Free access to 2 heated pools, hot tubs, sauna & fitness center.

Sep 22 – 29

ﺩ.ﺇ605 per night

Apartment in Great Barrington

5.0 out of 5 average rating, 15 reviews

King Bed | Stylish | Wi-Fi | *2m Ski Resort*

Remodeled Mid-Century Motel, that sits in the heart of the Berkshires. Located in Great Barrington, MA. Just steps from fantastic restaurants, eateries, shops, etc. A very short drive to Butternut Ski Resort. *1.5 miles to Downtown *1.3 miles to Mahaiwe Performing Arts Center *44 miles to Albany International Airport *4.5 miles to Great Barrington Airport *9.9 miles to Tanglewood KEY FEATURES *MCM Design *Plush King Sized Bed high end bed Linens *High Speed Internet *58"Tv with Hulu Live

Sep 12 – 19

ﺩ.ﺇ661 per night

Bungalow in Great Barrington

4.91 out of 5 average rating, 109 reviews

Idyllic Berkshires Getaway

Secluded large ranch in the country on 8 acres with pastoral scenic views, only 7 minutes drive from the center of Great Barrington and Lake Mansfield Beach, 10 minutes to Ski Butternut, 12 minutes to Stockbridge, 20 minutes to Lenox and Tanglewood . Kids playroom and a spectacular jungle gym, perfect for entertaining inside by the fire or outside on the patio with the bbq with beautiful views surrounded by pine trees. Perfect for fall foliage, skiing, spring and summer!

Jun 7 – 14

ﺩ.ﺇ1,943 per night

Guesthouse in Williamstown

4.93 out of 5 average rating, 219 reviews

Perfect Base for Your Berkshire Adventure

Charming private cottage with shared pool use. This newly renovated garden studio features high ceilings, a separate kitchenette with granite counters, mini fridge, microwave, queen sized bed, and rustic Arts & Crafts furniture. Located in a separate outbuilding, the cottage 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.

Jun 16 – 23

ﺩ.ﺇ484 per night

Cottage in Rhinebeck

4.87 out of 5 average rating, 147 reviews

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 used 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!

Jan 28 – Feb 4

ﺩ.ﺇ598 per night

Guesthouse in Lenox

4.95 out of 5 average rating, 284 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.

Sep 6 – 13

ﺩ.ﺇ544 per night

Tiny home in Ghent

4.96 out of 5 average rating, 139 reviews

Country Getaway Tiny House in woods w/Pool/Sauna

New Tiny House living space on 30 private acres with a mile of walkable trails in Beautiful Columbia County near Hudson/Chatham/Kinderhook. House has everything you need with a Queen bed, full bed, and full kitchen. The cozy space is an ideal getaway for relaxing. In the warm months enjoy the large in ground pool and renovated barn pool house. Enjoy the 6 person Sauna year round. ** Pool closed Mid-October - Mid-May, Confirm before booking.

Jul 8 – 15

ﺩ.ﺇ886 per night

Cabin in Red Hook

4.96 out of 5 average rating, 305 reviews

Modern Upstate Cabin, near Rhinebeck NY

🏊🏽‍♂️Heated pool is open. (Will be winterized mid October Welcome to Maitopia. This beautifully designed passive glass and wood modern cabin offers elegant modern details and the warmth that only an upstate energy efficient retreat could. With a soaking egg tub, fires at every turn and a heated pool you will fall in love with the place and the towns nearby.

Sep 22 – 29

ﺩ.ﺇ1,744 per night

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodations and amenities

Popular amenities for Lenox rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Hudson

4.93 out of 5 average rating, 227 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

Sep 13 – 20

ﺩ.ﺇ2,157 per night

Home in Saugerties

5.0 out of 5 average rating, 132 reviews

Upstate Modern Scandinavian Barn in the Catskills

Dec 29 – Jan 5

ﺩ.ﺇ2,577 per night

Home in Cottekill

4.95 out of 5 average rating, 242 reviews

Peace & Privacy - High Falls (hot tub & salt pool)

Oct 2 – 9

ﺩ.ﺇ1,358 per night

Home in Saugerties

4.96 out of 5 average rating, 150 reviews

Lux 1800's renovated farmhouse w/hot tub+pool

Oct 19 – 26

ﺩ.ﺇ4,271 per night

Home in Rhinebeck

4.96 out of 5 average rating, 164 reviews

On The Hill in Rhinebeck

Aug 30 – Sep 6

ﺩ.ﺇ2,448 per night

Home in Lenox

4.96 out of 5 average rating, 24 reviews

Lenox Grand Colonial with Pool by Evergreen Home

Dec 4 – 11

ﺩ.ﺇ1,522 per night

Home in Lee

4.98 out of 5 average rating, 62 reviews

Berkshire Vacation Home in Lee (Pool Opens in May)

Oct 19 – 26

ﺩ.ﺇ1,423 per night

Home in Dalton

4.89 out of 5 average rating, 81 reviews

Private & Stylish Berkshires House for All Seasons

Apr 12 – 19

ﺩ.ﺇ1,633 per night

Condo rentals with a pool

Condo in Hancock

4.9 out of 5 average rating, 51 reviews

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

Sep 21 – 28

ﺩ.ﺇ496 per night

Condo in Hancock

4.95 out of 5 average rating, 19 reviews

Upscale 2 bed/2bath Condo at a Mountain Resort!

Dec 2 – 9

ﺩ.ﺇ1,009 per night

Condo in Hancock

4.9 out of 5 average rating, 21 reviews

All-season Berkshires ski resort condo - Sitzmark

Aug 5 – 12

ﺩ.ﺇ725 per night

Condo in Hancock

4.95 out of 5 average rating, 22 reviews

Jiminy Peak Apartment

May 18 – 25

ﺩ.ﺇ614 per night

Condo in Hancock

4.96 out of 5 average rating, 27 reviews

SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2

May 8 – 15

ﺩ.ﺇ788 per night

Condo in Hancock

4.97 out of 5 average rating, 37 reviews

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

Jan 10 – 17

ﺩ.ﺇ1,985 per night

Condo in Hancock

4.88 out of 5 average rating, 33 reviews

Unique - Country suite @ Jiminy Peak

Mar 10 – 17

ﺩ.ﺇ1,288 per night

Condo in New Ashford

Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8

Dec 6 – 13

ﺩ.ﺇ616 per night

Quick stats about vacation rentals with a pool in Lenox

Total rentals
60 properties
Wifi availability
60 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
710 reviews
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees

Destinations to explore