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 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Stockbridge hotels with an outdoor pool

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
$198 nightly
$222 total
Nov 4 - Nov 5
Total with taxes and fees
The Red Lion Inn

2. 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

3. 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.
$376 nightly
$420 total
Nov 1 - Nov 2
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

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 12 - Oct 13
Total with taxes and fees
Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

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

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

7. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
$86 nightly
$96 total
Oct 26 - Oct 27
Total with taxes and fees
Sunset Inn

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 7 - Oct 8
Total with taxes and fees
Howard Johnson by Wyndham Lenox

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

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.
$67 nightly
$76 total
Oct 7 - Oct 8
Total with taxes and fees
Berkshire Travel Lodge
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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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Love the fireplace in our room! The amenities always make this place worth the money, and the views to top it all off!!"
Jennifer 1-night trip
Posted 18 hours ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Beautiful location plenty of activities and very convenient having the country store on site! Also the onsite restaurant was amazing!"
Jeffrey 1-night trip
Posted 23 hours ago
Jiminy Peak Mountain Resort
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"The staff was very pleasant and helpful. Breakfast was good. They had delicious and fresh muffins. Parking was right outside our door."
Leslie 2-night trip
Posted 1 day ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great staff, heated bathroom floors."
Ellen 3-night trip
Posted 1 day ago
The Red Lion Inn

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