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

Find Hotels with an Outdoor Pool in Stockbridge, MA

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Check availability on Stockbridge Hotels with an Outdoor Pool

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A covered porch with wicker furniture and hanging flower baskets.

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 5 - Nov 6
Total with taxes and fees
The Red Lion Inn
A two-story house with a brick entrance and a white facade.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.

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
A hallway with wooden bookshelves, a door, and a bedroom with a bed and floral wallpaper.
Exterior
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 living room with a sofa, armchair, coffee table, and a patterned rug.
A café with a display case, a frozen food section, and a marketplace sign.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.

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 26 - Oct 27
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 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.
A sign for The Little Lion Inn with a lion emblem, indicating a themed establishment.
A hotel room with two beds, a nightstand with a lamp, and a framed picture 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 hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
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.

6. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$106 nightly
$118 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 hotel room with two beds, a chair, and a bedside table with a phone.
A standard rectangular bathtub with a single faucet, tiled walls, and a geometric patterned floor.
A swimming pool with a fenced area, lounge chairs, and a warning sign.

7. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
$92 nightly
$103 total
Oct 26 - Oct 27
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 multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A hotel room with a dining area, a sofa, a coffee station, and a TV mounted 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 dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
A bedroom with a large bed, a fireplace, a bathtub, and a window with a view of greenery.
A house with a fire pit in the yard, outdoor seating, and a large window overlooking the yard.

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
Lobby sitting area
Front of property
Lobby sitting area

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 18 - Oct 19
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
"Clean room. Special thank you to the cleaning and breakfast staff. Great balcony view. We will come back again."
Christopher 2-night trip
Posted 13 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"good location, friendly helpful staff"
Scott Patterson 6-night trip
Posted 13 hours ago
Quality Inn Great Barrington
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We had a wonderful family stay at Vacation Village in the Berkshires! We traveled with our children and their grandmothers, and it was such a special opportunity to make memories together. Our accommodation felt like two apartments in one, with plenty of space for everyone. We loved the layout and the beautiful views, especially with the fall colors surrounding us. It was lovely to enjoy the scenery right where we were staying. The location was a great base for exploring the Berkshires, and we felt we got excellent value for the price. This trip was very special for our family, and we would love to come back. Highly recommend it for a family getaway!"
Viviane 2-night trip
Posted 1 day ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Our room was nice and clean. The suite is perfect. Can fix a cup of tea or a meal, everything you need just bring your food. A restaurant on site if you don't want to cook. Bed was comfortable with crisp white linens."
Anna 2-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort

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