Stockbridge Hotels with Swimming Pool

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Check availability on Stockbridge Hotels with Swimming Pools

Tonight
30 Jul - 31 Jul
Tomorrow
31 Jul - 1 Aug
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Top Stockbridge Hotels with Swimming Pools

The Red Lion Inn
Relax by the serene pool surrounded by lounge chairs and umbrellas.

The Red Lion Inn

3.5 star property
8.8 out of 10, Excellent, (1012)
"The Res Lion Inn is a New England classic. "
The price is RM817
RM1,102 total
includes taxes & fees
25 Aug - 26 Aug
The Red Lion Inn
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Enjoy a serene garden retreat with a lawn, pool, and lush greenery.

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 star property
9.2 out of 10, Wonderful, (105)
"Great breakfast, friendly helpful staff, pretty yard, good location "
The price is RM1,660
RM2,008 total
includes taxes & fees
12 Aug - 13 Aug
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Blackberry River Inn
Relax by the pool surrounded by lush greenery and comfortable lounge seating.

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (120)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is RM704
RM810 total
includes taxes & fees
4 Aug - 5 Aug
Blackberry River Inn
The Old Inn On The Green
Relax in a serene bedroom with a large bed, window, and comfortable chair.

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (87)
"Beautiful room and property. Perfect weekend getaway!"
The price is RM1,227
RM1,481 total
includes taxes & fees
12 Aug - 13 Aug
The Old Inn On The Green
Sunset Inn
Enjoy a refreshing swim in our pool surrounded by a tiled edge.

Sunset Inn

2.0 star property
7.6 out of 10, Good, (396)
"No frills but it was a great stay!"
The price is RM466
RM520 total
includes taxes & fees
18 Aug - 19 Aug
Sunset Inn
Devonfield Inn B&B
Enjoy a romantic meal for two on this serene patio, surrounded by lush greenery and a beautiful view.

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Swim laps in a serene, well-lit pool surrounded by a simple, functional design.

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

3.5 star property
9.0 out of 10, Wonderful, (682)
"Had a great time"
The price is RM541
RM663 total
includes taxes & fees
6 Aug - 7 Aug
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (4)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is RM673
RM752 total
includes taxes & fees
31 Jul - 1 Aug
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Relax by the pool surrounded by lounge chairs and sunbeds, with views of the surrounding area and greenery.

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is RM872
RM974 total
includes taxes & fees
17 Aug - 18 Aug
Hilton Garden Inn Lenox Pittsfield
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.

Top Stockbridge Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"We were delighted with the quality of the room and the quality of the breakfast offered. The staff was friendly and accommodating. Will definitely recommend The Yankee Inn to friends and will plan to stay there again when we visit Tanglewood. "
Laura 1-night trip
Posted 20 hours ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

What's it like visiting Stockbridge?
If taking it easy by the pool is your idea of the perfect getaway, you may want to explore historic Stockbridge, which offers 5 places to stay with pools. While you're visiting, you can explore sights such as Naumkeag and National Shrine of the Divine Mercy, and then relax and unwind poolside at one of the accommodation options in Stockbridge that guests like for their pools.
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 a health club, an indoor pool and complimentary high-speed (wired) Internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Provides 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli.
How many hotels with pools are there in Stockbridge?
Expedia has 5 hotels in Stockbridge for your poolside break.
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.