A mountainous landscape with a lake and dense forests.

Search Hotels with Pool in West Stockbridge

  • 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 West Stockbridge Hotels with Pool

Tonight
23 Aug - 24 Aug
Tomorrow
24 Aug - 25 Aug
Next weekend
28 Aug - 30 Aug
In two weeks
4 Sep - 6 Sep

Our top choices for West Stockbridge hotels with a pool

1. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
฿5,162
฿5,766 total
includes taxes & fees
14 Sept - 15 Sept
The Yankee Inn

2. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
฿5,204
฿7,436 total
includes taxes & fees
23 Sept - 24 Sept
The Red Lion Inn

3. 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.
฿3,822
฿4,908 total
includes taxes & fees
31 Aug - 1 Sept
Holiday Inn Club Vacations Oak 'n Spruce Resort

4. 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.
฿3,757
฿4,197 total
includes taxes & fees
20 Sept - 21 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG

5. 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.
฿4,259
฿4,758 total
includes taxes & fees
22 Sept - 23 Sept
Hampton Inn & Suites Berkshires-Lenox

6. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
฿3,090
฿4,182 total
includes taxes & fees
31 Aug - 1 Sept
Berkshire Mountain Lodge

7. 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.
฿2,205
฿2,470 total
includes taxes & fees
25 Aug - 26 Aug
Berkshire Travel Lodge

8. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
฿3,675
฿4,105 total
includes taxes & fees
1 Sept - 2 Sept
The Little Lion

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.
฿5,804
฿6,483 total
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Lenox Berkshires

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
฿2,581
฿2,883 total
includes taxes & fees
31 Aug - 1 Sept
Howard Johnson by Wyndham Lenox
View all properties

Choose what matters most at hotels with a pool in West Stockbridge

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top West Stockbridge Hotel Reviews

The Yankee Inn

The Yankee Inn

8/10 Good
"the room smelled like marijuana and cigarettes at initial arrival. I was in the 2nd bldg. and not able to get fresh coffee in the morning. overall, our stay was well worth it."
Luann 1-night trip
Posted 16 hours ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"Price - quality =awesome"
Anastasia 3-night trip
Posted 17 hours ago
Vacation Village in the Berkshires
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We loved our stay here. It’s not a modern cookie cutter experience. We loved the history and antique nature of the property."
Evan M 1-night trip
Posted 19 hours ago
The Red Lion Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Lenox
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"I had 2 rooms. 1 room (414) did not have a phone, the microwave didn't have power. The other room was fine. We didn't like that there was only 1 elevator working as we had to wait quite a while sometimes to go up or down. We understand that the hotel is undergoing renovations. Overall, we enjoyed our stay."
Frank 2-night trip
Posted 2 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

8/10 Good
"It was good place to stay over night for our plan. Friendly staff and clean room. Deer family are living near by, enjoy viewing them. It’s a old building, but nice quiet place."
Yoko 1-night trip
Posted 12 days ago
Pleasant Valley Motel West Stockbridge

Frequently asked questions

What are some accommodation options with pools in West Stockbridge?
Pleasant Valley Motel West Stockbridge: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Shaker Mill Inn: Offers a seasonal outdoor pool, an indoor pool and buffet. Vacation Village in the Berkshires: Features free self parking, an indoor pool and complimentary wireless Internet access. The Yankee Inn: Features buffet, an indoor pool and complimentary high-speed (wired) Internet access. Berkshire Mountain Lodge: Offers 3 restaurants, an outdoor pool and spa services.
What is there to see and do in West Stockbridge?
Make a point to visit attractions such as Stockbridge Bowl and Hotchkiss Mobile Studio. During your stay, visit sights such as Charles H. Baldwin & Sons, Ebenezer II Gifts and Antiques and Hoffman's Pottery. The gardens and restaurants 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 West Stockbridge?
Taking the local weather in West Stockbridge into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in West 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