Hotels with Swimming Pool in West Stockbridge, Massachusetts

  • 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 Swimming Pool

Our top choices for West Stockbridge hotels with a pool

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
"Helpful and friendly staff, clean room, great pool amd jaccuzzi."
United States
Zina
The price is P5,478
P6,119 total
includes taxes & fees
May 18 - May 19
The Yankee Inn
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (932 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
"Spacious, clean, and the pool was warm and perfect for family swimming"
United States
Danielle
The price is P5,387
P7,389 total
includes taxes & fees
May 24 - May 25
Berkshire Mountain Lodge
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (93 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
"Clean rooms, friendly staff, pool was very clean"
United States
Camille
The price is P7,240
P8,087 total
includes taxes & fees
May 19 - May 20
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
"The pool and hot tube were open, maybe bring a swimsuit if you are up for a soak in the hot tub on a cold snowy day or night."
United States
Judith Pauline
The price is P9,616
P13,485 total
includes taxes & fees
May 27 - May 28
The Red Lion Inn
Indoor pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
  • cleanliness
    Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
"The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
The price is P9,764
P10,906 total
includes taxes & fees
May 28 - May 29
Element Lenox Berkshires
Seasonal outdoor pool

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (96 reviews)
  • cleanliness
    Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
"The pool is well maintained and cleaned."
United States
Geraldine
The price is P6,655
P7,301 total
includes taxes & fees
May 27 - May 28
The Springs Motel
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (559 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
"we loved using the pool at the beautiful Red Lion"
United States
Lisa
The price is P5,834
P6,516 total
includes taxes & fees
Jun 11 - Jun 12
The Little Lion
Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (177 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
"Pool was perfect."
United States
Diane
The price is P9,561
P10,995 total
includes taxes & fees
May 17 - May 18
Blackberry River Inn
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (853 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
"Plenty of parking and nice pool."
United States
Dan
The price is P4,851
P5,419 total
includes taxes & fees
May 17 - May 18
Howard Johnson by Wyndham Lenox
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
"Nice pool and gym facility."
United States
Melanie
The price is P7,320
P8,176 total
includes taxes & fees
May 25 - May 26
Hampton Inn & Suites Berkshires-Lenox
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

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

Breakfast included
4 stars

Top West Stockbridge Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Great place to stay on our road trip."
Susan 1-night trip
Posted 16 hours ago
Hampton Inn & Suites Berkshires-Lenox

Frequently asked questions

What are some accommodations with pools in West Stockbridge?
Shaker Mill Inn: Provides free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Offers a children's pool, an indoor pool, and free self parking. Berkshires Untold: Features 3 restaurants, an outdoor pool, and spa services. Vacation Village in the Berkshires: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. The Red Lion Inn: Features buffet, an indoor pool, and complimentary wired internet access.
What is there to see and do in West Stockbridge?
Make a point to visit attractions like Stockbridge Bowl and Charles H. Baldwin & Sons. During your stay, check out sights such as Hotchkiss Mobile Studio, 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 into account the local weather in West Stockbridge is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in West Stockbridge are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

Explore a world of travel with Expedia