Landoll's Mohican Castle, Christmas lights.

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Check availability on Stockbridge Hotels with Pool

Our top choices for Stockbridge hotels with a pool

Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,011 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is 3.980.038 ₫
5.621.814 ₫ total
includes taxes & fees
1 Jul - 2 Jul
The Red Lion Inn
Seasonal outdoor pool, open 9:00 AM to 6:00 PM, pool loungers

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
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (111 reviews)
  • cleanliness
    Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
The price is 8.682.811 ₫
10.503.683 ₫ total
includes taxes & fees
6 Jul - 7 Jul
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is 3.348.286 ₫
3.739.972 ₫ total
includes taxes & fees
21 Jun - 22 Jun
The Yankee Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (569 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is 2.316.424 ₫
2.587.446 ₫ total
includes taxes & fees
21 Jun - 22 Jun
The Little Lion
Indoor pool

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (773 reviews)
  • cleanliness
    Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
The price is 3.790.512 ₫
4.234.002 ₫ total
includes taxes & fees
22 Jun - 23 Jun
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool, open 8:00 AM to 10:00 PM, pool 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.
The price is 3.853.161 ₫
4.303.981 ₫ total
includes taxes & fees
25 Jun - 26 Jun
Hampton Inn & Suites Berkshires-Lenox
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (987 reviews)
  • cleanliness
    Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is 3.694.262 ₫
4.714.547 ₫ total
includes taxes & fees
19 Jul - 20 Jul
Berkshire Mountain Lodge
Seasonal outdoor pool

The Springs Motel

The Springs Motel
2.0 star property
New Ashford
9.4 out of 10, Exceptional, (102 reviews)
  • cleanliness
    Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.
The price is 3.139.018 ₫
3.443.503 ₫ total
includes taxes & fees
23 Jun - 24 Jun
The Springs Motel
2 indoor pools, 2 outdoor pools, pool umbrellas, pool loungers

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.2 out of 10, Wonderful, (910 reviews)
  • cleanliness
    Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
The price is 3.174.554 ₫
4.060.592 ₫ total
includes taxes & fees
21 Jun - 22 Jun
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,398 reviews)
  • cleanliness
    Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is 3.393.503 ₫
4.079.305 ₫ total
includes taxes & fees
22 Jun - 23 Jun
Vacation Village in the 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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Choose what matters most at hotels with a pool in Stockbridge

Breakfast included
Hot tub

Top Stockbridge Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Had a wonderful stay. Staff is friendly and helpful. Breakfast was great, especially the automatic pancake maker. Had a wonderful dinner from Mint restaurant. The room was very clean and had the most comfortable hotel bed ever. The shower was a gleaming white as if it had never been used. The swan soap dish was a lovely touch. The view of the lake and mountains is spectacular. Would definitely stay here again."
Danielle 3-night trip
Posted 12 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

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 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Stockbridge are January, March, February and November, with each month seeing an average of 18 cm of snowfall.