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 19 - Oct 20
Tomorrow
Oct 20 - Oct 21
This weekend
Oct 23 - Oct 25
Next weekend
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 covered porch with wicker furniture and hanging flower baskets.
A bar with wooden floors and shelves filled with bottles.
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 17 - Nov 18
Total with taxes and fees
The Red Lion Inn
A two-story house with a brick entrance and a white facade.
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
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 4 - Nov 5
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.
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 living room with a television, sofa, coffee table, and two lamps.
A building with a porch and multiple windows, surrounded by purple flowers.
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 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 hotel room with two beds, a nightstand with a lamp, and a framed picture on the wall.
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.

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 20 - Oct 21
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 swimming pool with a surrounding deck, a stone wall, and a building in the background.
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 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 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.
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 multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
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 hotel room with a dining area, a sofa, a coffee station, and a TV mounted on the wall.

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 20 - Oct 21
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 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.

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
Exterior
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 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

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"The suite was clean with full kitchen. There are a lot of fun activities within the property. We felt safe during our entire stay."
Renette 2-night trip
Posted 1 hour ago
Jiminy Peak Mountain Resort
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great location! Quiet safe and comfortable surroundings. Indoor pool and out door hot tub was a plus. Room was perfect with kitchenette and gas fireplace."
Christopher 2-night trip
Posted 2 hours ago
Vacation Village in the Berkshires
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"-"
Serena 1-night trip
Posted 10 hours ago
Quality Inn Great Barrington
The Yankee Inn

The Yankee Inn

8/10 Good
"Lovely, super clean unit with nice furnishings, however, the dining chair cushions need a good cleaning as the dirt could be seen. There also was candy/gum stuck to one of the cushions and another cushion was completely loose from the chair. There was mention of a "two-burner hotplate" in the description, but the photos showed a two-burner electric stove top. What actually is there is a two-burner infared hotplate. Instructions on how to use it is posted on the wall above the sink, not on the wall above the hotplate. Unfortunately, we were assigned an end unit in Building #13, which is currently being renovated. There was a family occupying the unit above us. The children ran up and down the stair and allowed the outside door to slam each and every time until late in the evening. No noise during quiet hours though. :o)"
Julio 1-night trip
Posted 11 hours ago
The Yankee Inn

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