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Stockbridge Hotel Guide - Hotels with Pool in Stockbridge, Massachusetts

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Check availability on Stockbridge Hotels with Pool

Top Stockbridge Hotels with Pool

Outdoor pool, pool loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
  • Outdoor pool
  • Pool loungers
8.8 out of 10, Excellent, (1002)
Sparkling waters invite refreshment at the outdoor pool, complemented by a rejuvenating hot tub that remains open year-round. Beyond aquatic pleasures, this historic hotel enchants with excellent dining, tasteful accommodation, and friendly service.
The price is €183
includes taxes & fees
16 Nov - 17 Nov
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
  • Pool loungers
9.2 out of 10, Wonderful, (110)
Seasonal swimming awaits at this luxury bed & breakfast, where summer days unfold between pool loungers and excellent breakfasts. Adventure seekers can enjoy kayaking, mountain biking, and horseback riding before returning to individually furnished rooms.
The price is €399
includes taxes & fees
27 Nov - 28 Nov
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
  • Indoor pool
9.6 out of 10, Exceptional, (9)
Swimming enthusiasts appreciate the serene indoor pool that provides year-round aquatic enjoyment regardless of weather. After energising laps, guests gather at the outdoor firepit or enjoy a complimentary manager's reception before retreating to individually furnished rooms.
The price is €130
includes taxes & fees
16 Nov - 17 Nov
Element Lenox Berkshires
Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
  • Indoor pool
8.0 out of 10, Very good, (947)
Swimmers splash in the pristine indoor pool from 7 AM to 9 PM, complemented by an on-site health club for complete wellness. Hiking trails and skiing opportunities nearby make this centrally located hotel an ideal family-friendly retreat.
The price is €95
includes taxes & fees
21 Nov - 22 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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
  • Indoor pool
8.8 out of 10, Excellent, (692)
Splash into the warm, pristine indoor pool after exploring nearby hiking trails or skiing at Butternut. Modern rooms with premium bedding await, while a complimentary breakfast buffet energises adventures in Great Barrington's vibrant surroundings.
The price is €103
includes taxes & fees
30 Nov - 1 Dec
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool, seasonal outdoor pool, pool loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
  • Indoor pool
  • Pool loungers
  • Hot tub
9.2 out of 10, Wonderful, (1002)
Shimmering waters beckon at dual pool options, where indoor relaxation meets seasonal outdoor splendour. After exploring nearby Bousquet Ski Area, guests unwind in the rejuvenating hot tub while mountain vistas provide a stunning backdrop for aquatic serenity.
The price is €98
includes taxes & fees
18 Nov - 19 Nov
The Yankee, Trademark Collection by Wyndham
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
  • 2 outdoor pools
  • 2 indoor pools
  • Poolside bar
  • Pool loungers
9.0 out of 10, Wonderful, (781)
Swimming enthusiasts rejoice at this four-pool paradise nestled in the Berkshires. Families appreciate the well-maintained waters complemented by sun loungers, umbrellas, and refreshing poolside drinks, creating memorable mountain getaways year-round.
The price is €141
includes taxes & fees
12 Nov - 13 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
  • Indoor pool
9.2 out of 10, Wonderful, (656)
Sparkling waters await in the pristine indoor swimming pool, complemented by a modern fitness centre for complete rejuvenation. Nearby Tanglewood Music Centre offers cultural enrichment, while Jae's Asian Fusion restaurant provides delicious dining options.
The price is €107
includes taxes & fees
16 Nov - 17 Nov
Hilton Garden Inn Lenox Pittsfield
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
  • Indoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (1004)
Splash into holiday mode at the indoor pool where comfortable loungers await after exhilarating outdoor adventures. This art deco haven balances active pursuits with relaxation, offering fitness facilities and a delicious free breakfast buffet to fuel Berkshire explorations.
The price is €107
includes taxes & fees
16 Nov - 17 Nov
Hampton Inn & Suites Berkshires-Lenox
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
  • Outdoor pool
  • Indoor pool
  • Pool loungers
  • Hot tub
8.6 out of 10, Excellent, (132)
Swimmers glide through crystal waters at indoor and outdoor pools surrounded by serene Berkshire landscapes. Beyond aquatic pleasures, this resort boasts tennis courts, a sauna, and spacious accommodation with cosy fireplaces and full kitchens.
The Ponds at Foxhollow
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 Stockbridge Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"The hotel is very nice and updated. The hotel room smelled wonderful. Parking was kinda a pain. The parking garage was being used. Maybe they are redoing it. So you had to park in a parking lot around the corner which was a pain. But I would definitely stay here again "
Robert 2-night trip
Posted 5 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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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. Tanglewood Suites: Provides full, a seasonal outdoor pool and free self parking. The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool and free self parking. Vacation Village in the Berkshires: Offers free self parking, an indoor pool and complimentary wireless Internet access. Berkshire Mountain Lodge: Features a health club, an indoor pool and complimentary high-speed (wired) Internet access.
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 Housatonic River. 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.