Vacation rentals with a pool in Berkshire County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Berkshire County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Superhost
Cabin in Stephentown
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.
Apr 1 – 8
$228 per night
4.84 out of 5 average rating, 226 reviews
Guest favorite
Guesthouse in Williamstown
Perfect Base for Your Berkshire Adventure
Fabulous private studio with shared pool use! This newly renovated garden cottage with separate entry 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 gorgeous 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.
Jul 14 – 21
$145 per night
4.93 out of 5 average rating, 219 reviews
Guest favorite
Condo in Hancock
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.
Apr 27 – May 4
$150 per night
4.83 out of 5 average rating, 129 reviews

Popular amenities for Berkshire County rentals with a pool

House rentals with a pool

Guest favorite
Home in Becket
Woodland Haven w/ Heated Pool by Evergreen Home
May 15 – 22
$349 per night
4.88 out of 5 average rating, 17 reviews
Guest favorite
Home in Great Barrington
Newly Remodeled Private Estate-Pool, Tennis Court!
Feb 4 – 11
$925 per night
4.97 out of 5 average rating, 33 reviews
Guest favorite
Home in Great Barrington
Stunning luxury home with fire pit
May 29 – Jun 5
$707 per night
5.0 out of 5 average rating, 53 reviews
Guest favorite
Home in Pittsfield
Berkshire Getaway Ranch 3 acres + saltwater pool
Sep 7 – 14
$274 per night
4.96 out of 5 average rating, 56 reviews
Guest favorite
Home in Cheshire
Berkshire County modern home + pool
Jan 10 – 17
$379 per night
4.94 out of 5 average rating, 50 reviews
Guest favorite
Home in Pittsfield
Stunning Berkshires Retreat, Large and Private
Jan 15 – 22
$615 per night
5.0 out of 5 average rating, 40 reviews
Guest favorite
Home in New Marlborough
Berkshires Colonial Farmhouse
Sep 18 – 25
$800 per night
5.0 out of 5 average rating, 18 reviews
Guest favorite
Home in Egremont
Mountain View Estate Sleeps 18
Apr 4 – 11
$457 per night
4.92 out of 5 average rating, 24 reviews
Guest favorite
Home in Canaan
Berkshire Lake House, gunite pool, Chef's Kitchen
Dec 17 – 24
$700 per night
4.99 out of 5 average rating, 68 reviews
Guest favorite
Home in Pittsfield
Berkshire Lakefront Home W/Pool-100%Renovated
Sep 8 – 15
$800 per night
4.97 out of 5 average rating, 34 reviews
Guest favorite
Home in Lanesborough
6-BR Country Estate 14-Min. to Jiminy Peak
Oct 13 – 20
$899 per night
5.0 out of 5 average rating, 15 reviews
Superhost
Home in Dalton
Private & Stylish Berkshires House for All Seasons
Nov 15 – 22
$378 per night
4.89 out of 5 average rating, 80 reviews

Condo rentals with a pool

Guest favorite
Condo in Hancock
Jiminy Peak Country Inn - ski in/out condo MT view
Apr 26 – May 3
$119 per night
4.9 out of 5 average rating, 48 reviews
Guest favorite
Condo in Hancock
Upscale 2 bed/2bath Condo at a Mountain Resort!
May 1 – 8
$236 per night
4.94 out of 5 average rating, 18 reviews
Guest favorite
Condo in Hancock
Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Apr 24 – May 1
$461 per night
4.97 out of 5 average rating, 34 reviews
Guest favorite
Condo in Hancock
SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1
May 21 – 28
$281 per night
4.93 out of 5 average rating, 57 reviews
Guest favorite
Condo in Hancock
Large one bedroom, two full bath, full kitchen
Oct 29 – Nov 5
$145 per night
4.93 out of 5 average rating, 14 reviews
Guest favorite
Condo in Hancock
All-season Berkshires ski resort condo - Sitzmark
May 10 – 17
$151 per night
4.89 out of 5 average rating, 19 reviews
Guest favorite
Condo in Hancock
Unique - Country suite @ Jiminy Peak
Oct 18 – 25
$198 per night
4.91 out of 5 average rating, 32 reviews
Condo in Hancock
Jiminy Peak Country Inn 1 Bedroom Suite
Jul 18 – 25
$112 per night
4.63 out of 5 average rating, 134 reviews
Condo in Lee
Holiday Inn Club/ Oak and Spruce, Berkshires
Apr 11 – 18
$252 per night
4.74 out of 5 average rating, 27 reviews
Guest favorite
Condo in Hancock
Ski-in/Ski-Out on Jiminy Peak
Jul 28 – Aug 4
$205 per night
4.8 out of 5 average rating, 5 reviews
Condo in Hancock
Bentley Brook Presidents Week & Christmas
Dec 22 – 29
$379 per night
5.0 out of 5 average rating, 3 reviews
Condo in New Ashford
Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8
Nov 5 – 12
$168 per night
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