A nighttime view of a residential area with houses adorned with holiday lights.

Stockbridge Hotels with Swimming Pool

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Stockbridge Hotels with Swimming Pools

Tonight
21 Sept - 22 Sept
Tomorrow
22 Sept - 23 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Stockbridge hotels with a 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.
RM643
RM921 total
includes taxes & fees
30 Sept - 1 Oct
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.
RM1,738
RM2,038 total
includes taxes & fees
22 Sept - 23 Sept
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.
RM2,108
RM2,550 total
includes taxes & fees
12 Oct - 13 Oct
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
RM478
RM613 total
includes taxes & fees
27 Sept - 28 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort

5. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
RM473
RM529 total
includes taxes & fees
22 Sept - 23 Sept
The Yankee Inn

6. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
  • Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
RM506
RM565 total
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express Hotel & Suites Great Barrington by IHG

7. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
RM422
RM472 total
includes taxes & fees
18 Oct - 19 Oct
The Little Lion

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
RM325
RM454 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge

9. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness centre.
RM577
RM645 total
includes taxes & fees
27 Sept - 28 Sept
Courtyard by Marriott Lenox Berkshires

10. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
RM512
RM572 total
includes taxes & fees
28 Sept - 29 Sept
Hampton Inn & Suites Berkshires-Lenox
View all properties

Choose what matters most at hotels with a pool in Stockbridge

Breakfast included
Hot tub
4 stars
Spa
5 stars

Top Stockbridge Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"The room was spacious, clean and comfortable. I will definitely stay there again."
William 2-night trip
Posted 1 hour ago
The Yankee Inn
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Even in the off season it was beautiful."
Karen 1-night trip
Posted 7 hours ago
Jiminy Peak Mountain Resort
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"This is a wonderful, historic inn. Check out the Red Lion Den for music. We heard a terrific local group. We ate in the Tavern and the food was tasty. This is not a luxurious place. It dates back to the 1700s. But it is really charming. My friends and I stayed in a suite in an out building. We had a low-ceiled living room downstairs, which was a. great place to talk and catch up. The bedroom situation was a little funky because the bathroom was right next to the bed in one of two sleeping areas upstairs and the door really squeaked when it opened and closed. But that was about our only complaint. I'd be delighted to return."
Gerald 1-night trip
Posted 7 hours ago
The Red Lion Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Excelente A+, lo recomiendo"
Erick 1-night trip
Posted 1 day ago
Vacation Village in the Berkshires
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

10/10 Excellent
"Good"
Kauan 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lenox

Frequently asked questions

What are some accommodation options with pools in Stockbridge?
The Red Lion Inn: Features 3 restaurants, an outdoor pool and spa services. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: Offers full, a seasonal outdoor pool and free self parking. Vacation Village in the Berkshires: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool and free self parking. Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. Quality Inn Great Barrington: Provides a seasonal outdoor pool, an indoor pool and buffet.
What is there to see and do in Stockbridge?
Make a point to visit attractions such as Naumkeag Museum and Berkshire Botanical Garden. During your stay, visit sights such as National Shrine of the Divine Mercy, Norman Rockwell Museum and Stockbridge Bowl. The bars and historic landmarks are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Stockbridge?
Taking the local weather in Stockbridge into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 19Β°C, while the coldest months are January and February, with an average of -3Β°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

Explore a world of travel with Expedia