A river surrounded by autumn-colored trees and a forested hill.

Find Hotels with a Pool in Stockbridge, MA

Check availability on Stockbridge Hotels with a Pool

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Oct 2 - Oct 3
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Our top choices for Stockbridge hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and a building in the background.
A brick pathway lined with autumn foliage and pumpkins, leading to a white building with a porch decorated with hanging flowers.
A bar with wooden floors and shelves filled with bottles.
A large, multi-story building with a swimming pool, surrounded by dense greenery and trees.

1. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
$196 nightly
$219 total
Nov 2 - Nov 3
Total with taxes and fees
The Red Lion Inn
Indoor pool
A spacious living room with a fireplace, comfortable seating, and large windows.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
A spacious living room with large windows, a fireplace, and a variety of seating options.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
Williamstown
  • Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
$110 nightly
$123 total
Nov 1 - Nov 2
Total with taxes and fees
Vacation Village in the Berkshires
An indoor swimming pool with a high ceiling, multiple windows, and seating areas.
A spacious lobby with a fireplace, seating area, and a bar.
A garden with wooden Adirondack chairs and a stone pathway.
A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$111 nightly
$124 total
Nov 2 - Nov 3
Total with taxes and fees
Berkshire Mountain Lodge
A pool area with a lifeguard chair, a blue plastic bag, and a warning sign.
A living room with a sofa, armchair, coffee table, and a patterned rug.
A hotel room with a large bed, a bathroom with a bathtub, a vanity with a mirror, and a window with curtains.
A building with a porch and multiple windows, surrounded by purple flowers.

4. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
$127 nightly
$142 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Club Vacations Oak 'n Spruce Resort
A well-maintained garden with a swimming pool, surrounded by lush greenery and a white building.
A cozy room with a wooden floor, a dining table with a lamp, a chair, a cabinet, and a window with curtains.
A dining area with tables set for a meal, surrounded by large windows offering a view of trees and a garden.
A two-story house with a brick entrance and a white facade.

5. 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
Stockbridge
  • Seasonal outdoor pool retreat at this colonial b&b invites lounging amid gardens and historic charm.
$405 nightly
$453 total
Nov 1 - Nov 2
Total with taxes and fees
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
A backyard with a swimming pool, surrounded by grass and trees.
Front of property
A modern bathroom with a black marble shower, gold fixtures, and a tiled floor.
A stone fountain surrounded by trees in a park setting.

6. The Inn at Stockbridge

The Inn at Stockbridge
Stockbridge
  • Seasonal outdoor pool beckons for refreshing summer dips at this upscale bed and breakfast in Stockbridge.
$383 nightly
$428 total
Nov 1 - Nov 2
Total with taxes and fees
The Inn at Stockbridge
A swimming pool surrounded by a metal fence, with several lounge chairs and a small table nearby.
A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.
A cozy living room with a fireplace, a blue sofa, a red armchair, and a coffee table with books and a teapot.
A dining table set with a vase of flowers, a book, and cutlery.

7. Brook Farm Inn

Brook Farm Inn
Lenox
  • Dive into luxury poolside moments with a seasonal outdoor swimming area, vibrant bar service, and picturesque garden setting.
$209 nightly
$237 total
Nov 2 - Nov 3
Total with taxes and fees
Brook Farm Inn
A swimming pool with lounge chairs, surrounded by trees and a small building.
A dining area with a table set for two, a view of a green landscape through large windows, and outdoor seating with a view.
A large, two-story house with a well-maintained lawn and a fence.
A spacious living room with a fireplace, a dining area with a table and chairs, and large windows offering a view of the outdoors.

8. Devonfield Inn B&B

Devonfield Inn B&B
Lee
  • Escape to an elegant countryside retreat with an inviting outdoor pool, premium spa services, and made-to-order gourmet breakfast.
$369 nightly
$412 total
Nov 2 - Nov 3
Total with taxes and fees
Devonfield Inn B&B
A poolside area with lounge chairs and a pool.
A wooden cabin with a staircase leading to a deck, surrounded by trees and a gravel path.
A wooden deck with a dog silhouette against a backdrop of autumn foliage.
A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

9. Prospect Berkshires

Prospect Berkshires
Egremont
  • Berkshire mountain retreat features outdoor pool, sauna, and complimentary bicycles.
$375 nightly
$419 total
Nov 2 - Nov 3
Total with taxes and fees
Prospect Berkshires
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A modern cafe with a counter, seating area, and large windows.
A hotel room with a bed, a desk, a chair, a TV, and a wardrobe.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.

10. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Pittsfield
  • Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
$99 nightly
$111 total
Nov 1 - Nov 2
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
View all properties

Choose what matters most at hotels with a pool in Stockbridge

Breakfast included
Hot tub
4 stars
Spa
5 stars

Top Stockbridge Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great place great price!"
James 1-night trip
Posted 19 hours ago
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

8/10 Good
"Room was nice but did not have the view I was hoping for. Another hotel property is mostly blocking views from Yankee Inn looking West; the direction rooms with balcony’s face. The location near"
Theresa 2-night trip
Posted 19 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"I typically do not reserve in motel with parking in front of each space due to security, I was mistaken at this facility. Pleasant neighborhood and the building was situated well off the main street."
Peter 1-night trip
Posted 4 days ago
Quality Inn Great Barrington

Frequently asked questions

What are the best hotels in Stockbridge with outdoor pools?
The Red Lion Inn is a charming 3.5-star hotel that offers an inviting outdoor pool, great for families looking to unwind after a day of adventure in the beautiful Berkshires. Guests rave about the comfortable and quiet rooms, as well as the excellent food and friendly service provided by the staff. Plus, its prime location in a historic district means you're just a stone's throw away from local attractions, including nearby ski areas for winter sports enthusiasts.For a more intimate experience, consider The Stockbridge Country Inn, rated 4.5 stars by travellers. This delightful bed and breakfast not only features an outdoor pool but also provides complimentary full and continental breakfasts, ensuring a great start to your day. With its proximity to the Norman Rockwell Museum and picturesque mountain views, it's an ideal spot for families seeking both relaxation and cultural enrichment. Guests particularly appreciate the peaceful atmosphere and the opportunity for mountain biking right on-site.
How much does a hotel with outdoor pool in Stockbridge cost?
Enjoy staying in a hotel in Stockbridge with an outdoor pool. You can find a great deal from $106 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Is it cheaper to book flights and a Stockbridge hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Stockbridge for you.

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