A river surrounded by autumn-colored trees and a forested hill.

Find Hotels with an Outdoor Pool in Stockbridge, MA

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Stockbridge Hotels with an Outdoor Pool

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Stockbridge hotels with an outdoor pool

A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.
A bar with wooden floors and shelves filled with bottles.
A covered porch with wicker furniture and hanging flower baskets.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
$191 nightly
$214 total
Nov 4 - Nov 5
Total with taxes and fees
The Red Lion Inn
A two-story house with a brick entrance and a white facade.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
A neatly arranged bedroom with a bed, bedside table, and a dresser.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.

2. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Stockbridge
  • Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
$393 nightly
$439 total
Nov 1 - Nov 2
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property
Exterior
A living room with a fireplace, leather sofas, and a dog.
A stone fountain surrounded by trees in a park setting.

3. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
  • Seasonal outdoor pool beckons for refreshing summer dips at this upscale bed and breakfast in Stockbridge.
$383 nightly
$428 total
Nov 1 - Nov 2
Total with taxes and fees
The Inn at Stockbridge
A building with a porch and multiple windows, surrounded by purple flowers.
A Holiday Inn Club Vacations sign for Oak N'Spruce Resort.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A living room with a sofa, armchair, coffee table, and a patterned rug.

4. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
$135 nightly
$150 total
Oct 20 - Oct 21
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires
A large house with a balcony and a grassy yard.
A hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
A two-story building with a gabled roof and a chimney.
A room with a white desk, two floral chairs, a small round table with a plant, a hanging lamp, and two framed artworks on the wall.

5. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
$115 nightly
$128 total
Oct 18 - Oct 19
Total with taxes and fees
The Little Lion
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.
A cozy room with a wooden desk, a chair with a blanket, a fireplace with a fire, a mirror, and a poster on the wall.
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

6. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$101 nightly
$112 total
Nov 1 - Nov 2
Total with taxes and fees
The Yankee Inn
A clear blue swimming pool with a tiled edge and a few lounge chairs along the side.
A swimming pool with a fenced area, lounge chairs, and a warning sign.
A covered corridor with a metal railing, white walls, and a view of a street with parked cars.
A hotel room with two beds, a chair, and a bedside table with a phone.

7. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
$80 nightly
$89 total
Nov 8 - Nov 9
Total with taxes and fees
Sunset Inn
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.
A hotel room with a dining area featuring a table and chairs, a kitchenette with a coffee machine, and a television on the wall.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

8. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
$79 nightly
$88 total
Oct 18 - Oct 19
Total with taxes and fees
Howard Johnson by Wyndham Lenox
A large, two-story house with a well-maintained lawn and a fence.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.

9. Devonfield Inn B&B

Devonfield Inn B&B
Lee
  • Escape to an elegant countryside retreat with an inviting outdoor pool, premium spa services, and made-to-order gourmet breakfast.
$369 nightly
$412 total
Nov 2 - Nov 3
Total with taxes and fees
Devonfield Inn B&B
Outdoor pool
Exterior
Lobby sitting area
Front of property

10. Berkshire Travel Lodge

Berkshire Travel Lodge
Austerlitz
  • Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
$75 nightly
$84 total
Oct 21 - Oct 22
Total with taxes and fees
Berkshire Travel Lodge
View all properties

Find out more about Stockbridge

Discover top Stockbridge attractions

For travelers seeking a serene getaway, Stockbridge, Massachusetts, offers a delightful blend of relaxation and activities. Immerse yourself in the tranquil beauty of the Berkshire Mountains as you stroll through the lush grounds of the Norman Rockwell Museum, where you can explore the iconic artist's works and feel the charm of Americana come alive. Just a short drive away, the picturesque gardens of Naumkeag invite you to unwind among meticulously designed landscapes, perfect for a leisurely afternoon picnic. The nearby Stockbridge Bowl is a lovely spot for a refreshing swim or a peaceful kayak session, offering a chance to soak in nature while enjoying the warm sun. For art enthusiasts, the Berkshire Botanical Garden showcases stunning flora and hosts seasonal events that provide a perfect backdrop for relaxation and inspiration. Finally, the charming downtown area features quaint shops and eateries where you can savor local delicacies. Staying in hotels with pools in the heart of Stockbridge allows you to refresh after a day of exploration, providing a luxurious retreat to unwind and rejuvenate. Imagine enjoying a dip in the pool, followed by a cocktail on the terrace as the sun sets over the mountains, making your stay both comfortable and indulgent.

Find the best hotels with an outdoor pool in Stockbridge

For travelers seeking a refreshing escape with outdoor pool options in Stockbridge, Massachusetts, these two hotels combine comfort and leisure perfectly. Each offers inviting outdoor pools among other amenities to enhance your stay.The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

  • Why it's great for poolside lounging: The Stockbridge Country Inn stands out for travelers looking for a luxurious getaway that includes an inviting outdoor pool. With a remarkable guest review rating of 9.2, this hotel offers a serene pool area equipped with comfortable sun loungers, perfect for soaking up the sun while enjoying the peaceful surroundings. The B&B's delightful atmosphere is further enhanced by its nearby cultural sites like the Norman Rockwell Museum.
  • Other amenities: Beyond the pool, guests can indulge in a complimentary full breakfast each morning, ensuring a delightful start to the day. The inn features an onsite art gallery, terrace, and hiking and biking opportunities right on the premises. Additional amenities include air conditioning, luxury bedding, and a concierge service to help plan excursions. For those interested in golf, nearby courses are available, and the hotel also offers self-parking for added convenience.
  • Nearby attractions: Housatonic River - 0.03 miles, Chesterwood - 0.61 miles, Norman Rockwell Museum - 0.94 miles

The Red Lion Inn

  • Why it's great for poolside lounging: The Red Lion Inn is an excellent choice for travelers who appreciate the charm of outdoor leisure. With a solid guest review rating of 8.8, this hotel features a lovely outdoor pool complemented by sun loungers, providing the perfect spot for relaxation under the sun. Guests can also enjoy the historic ambiance of this inn while taking in the serene surroundings.
  • Other amenities: In addition to the outdoor pool, The Red Lion Inn offers a variety of amenities to enhance guests' experiences. Enjoy 24-hour room service, an onsite spa for rejuvenating treatments, and daily housekeeping. For those seeking adventure, the hotel is situated near skiing, snowboarding, and hiking opportunities, making it ideal for outdoor enthusiasts. Other features include complimentary toiletries, a fireplace in select rooms, and concierge services to assist with local activities.
  • Nearby attractions: Housatonic River - 0.13 miles, Berkshire Theatre Festival - 0.51 miles, Naumkeag Museum - 0.64 miles

Top Stockbridge Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Well run and worth it!Hot tub closed for maintenance."
Vincent 1-night trip
Posted 6 hours ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This place is a must stay! We loved every bit of it and had a best time!!! Def recommend 100%"
Hope 1-night trip
Posted 20 hours ago
The Red Lion Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."
Christopher 3-night trip
Posted 2 days ago
Jiminy Peak Mountain Resort

Explore a world of travel with Expedia