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Vacation rentals with a pool in Stockbridge

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Stockbridge

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

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Cabin in Stephentown

4.84 out of 5 average rating, 237 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.

Aug 10 – 17

G$56,125 GYD per night

Bungalow in Easthampton

4.92 out of 5 average rating, 430 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 – 26

G$38,639 GYD 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 4 – 11

G$44,961 GYD per night

Condo in Windham

4.89 out of 5 average rating, 132 reviews

Cozy Mountain hideaway Windham, Hunter

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Jul 3 – 10

G$21,808 GYD per night

Home in Hudson

4.93 out of 5 average rating, 227 reviews

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

Sep 13 – 20

G$120,248 GYD per night

Home in Woodstock

4.98 out of 5 average rating, 100 reviews

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Jan 31 – Feb 7

G$170,079 GYD per night

Guesthouse in Stanfordville

4.92 out of 5 average rating, 164 reviews

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.

Sep 1 – 8

G$24,569 GYD 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!

Jul 6 – 13

G$144,109 GYD 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.

Aug 2 – 9

G$30,914 GYD per night

Guesthouse in Lenox

4.95 out of 5 average rating, 282 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 4 – 11

G$32,435 GYD per night

Barn in Hillsdale

4.97 out of 5 average rating, 117 reviews

Hudson Valley Hilltop Barn

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & on a 15-acre hilltop with views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking and tons of games. Perfect for winter sledding right on our hill. 100 acres of untouched nature around property. Near great shops & restaurants in Hudson & Great Barrington. *Pets must get written approval*

Sep 23 – 30

G$227,998 GYD 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.

May 6 – 13

G$65,826 GYD per night

Vacation rentals for every style

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Popular amenities for Stockbridge rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Saugerties

5.0 out of 5 average rating, 132 reviews

Upstate Modern Scandinavian Barn in the Catskills

Oct 27 – Nov 3

G$143,703 GYD per night

Home in Woodstock

4.91 out of 5 average rating, 209 reviews

Japanese Teahouse & Onsen, outside shower, tennis

Dec 29 – Jan 5

G$50,249 GYD per night

Home in Cottekill

4.95 out of 5 average rating, 242 reviews

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

Aug 30 – Sep 6

G$104,697 GYD per night

Home in Rhinebeck

4.96 out of 5 average rating, 164 reviews

On The Hill in Rhinebeck

Dec 20 – 27

G$119,581 GYD per night

Home in Richmond

4.96 out of 5 average rating, 23 reviews

Escape to The Berkshires w/Pool by Evergreen Home

May 13 – 20

G$135,617 GYD per night

Home in Lee

4.98 out of 5 average rating, 62 reviews

Berkshire Vacation Home in Lee (Pool Opens in May)

Jun 3 – 10

G$79,281 GYD per night

Home in Great Barrington

5.0 out of 5 average rating, 52 reviews

Stunning luxury home with pool

Sep 28 – Oct 5

G$162,320 GYD per night

Home in Stockbridge

4.85 out of 5 average rating, 62 reviews

*February/March Special*"Too Good" AKA 2 Goodrich

Feb 11 – 18

G$108,181 GYD per night

Condo rentals with a pool

Condo in Windham

4.74 out of 5 average rating, 243 reviews

Summer getaway w/Pool & Tennis Court

Aug 28 – Sep 4

G$25,698 GYD per night

Condo in Hancock

4.83 out of 5 average rating, 131 reviews

Cozy Condo @ Jiminy Peak

May 30 – Jun 6

G$33,720 GYD per night

Condo in Hancock

4.9 out of 5 average rating, 51 reviews

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

Dec 9 – 16

G$30,063 GYD per night

Condo in Hancock

4.95 out of 5 average rating, 19 reviews

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

Oct 12 – 19

G$67,294 GYD per night

Condo in Windham

4.95 out of 5 average rating, 22 reviews

Lovely stylish 2-bedroom condo with community pool

May 28 – Jun 4

G$23,228 GYD 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 3 – 10

G$43,974 GYD per night

Condo in Hancock

4.9 out of 5 average rating, 21 reviews

All-season Berkshires ski resort condo - Sitzmark

Oct 8 – 15

G$44,648 GYD per night

Condo in Hancock

4.93 out of 5 average rating, 15 reviews

Large one bedroom, two full bath, full kitchen

Oct 15 – 22

G$35,495 GYD per night

Quick stats about vacation rentals with a pool in Stockbridge

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
300 reviews
Nightly prices starting at
G$22,999 GYD before taxes and fees

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