Find Hotels with a Pool in West Stockbridge, MA

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Check availability on West Stockbridge Hotels with a Pool

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for West Stockbridge hotels with a pool

Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is ￥21,052
￥23,516 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Element Lenox Berkshires
Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ￥14,448
￥16,139 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Yankee, Trademark Collection by Wyndham
Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (998)
"Very clean and timely and efficient and the lady who checked me in named Valerie did an amazing job and was very informative and helpful . "
United States
Dwight
The price is ￥13,754
￥15,363 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

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, (68)
"Extremely impressed by this hotel. The staff was very friendly and professional. The rooms were so comfortable and high quality everything! Check in and check out was easy. Highly recommend!"
United States
Jeanne
The price is ￥18,391
￥20,543 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (795)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is ￥15,389
￥20,673 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Berkshire Mountain Lodge
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
"Staff was very friendly and helpful."
United States
Pamela
The price is ￥12,319
￥13,760 total
includes taxes & fees
Dec 26 - Dec 27
Howard Johnson by Wyndham Lenox
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"Old time charm and hot tub under the stars"
United States
Lori
The price is ￥22,456
￥32,051 total
includes taxes & fees
Jan 14 - Jan 15, 2026
The Red Lion Inn
Indoor pool
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (659)
"The room was very clean with comfortable King bed. We really enjoyed the hot tub."
United States
Christine
The price is ￥19,942
￥22,275 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Hilton Garden Inn Lenox Pittsfield
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is ￥17,153
￥19,160 total
includes taxes & fees
Jan 1 - Jan 2, 2026
The Little Lion
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (16)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ￥45,534
￥56,087 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Prospect Berkshires
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.
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Top West Stockbridge Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"The bed was very comfortable. The staff was helpful and courteous"
Timothy 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

What are some accommodations with pools in West Stockbridge?
Pleasant Valley Motel West Stockbridge: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Provides a children's pool, an indoor pool, and free self parking. Shaker Mill Inn: Features a seasonal outdoor pool, an indoor pool, and buffet. Vacation Village in the Berkshires: Offers a health club, an indoor pool, and complimentary wired internet access. The Yankee, Trademark Collection by Wyndham: Features free self parking, an indoor pool, and complimentary wireless internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: 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 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.