A waterfall cascading over rocks in a forested area.

Find Hotels with a Pool in Hinsdale, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Hinsdale Hotels with a Pool

Tonight
Oct 15 - Oct 16
Tomorrow
Oct 16 - Oct 17
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Hinsdale hotels with a pool

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".

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
₩115,190
₩158,686 total
includes taxes & fees
Nov 9 - Nov 10
Berkshire Mountain Lodge
A swimming pool with a surrounding deck, a stone wall, and a building in the background.
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.
A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

2. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
₩142,438
₩159,103 total
includes taxes & fees
Nov 1 - Nov 2
The Yankee Inn
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A covered outdoor area with stone pillars and a view of a road and green hills.

3. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
Lenox
  • Dive into year-round aquatic relaxation at this Berkshires retreat with a sparkling indoor pool and modern fitness center.
₩168,650
₩188,382 total
includes taxes & fees
Nov 1 - Nov 2
Courtyard by Marriott Lenox Berkshires
A large indoor swimming pool with clear water, surrounded by tiled walls and a tiled floor.
A gym with exercise equipment including treadmills, a stationary bike, and free weights.
A modern bathroom with a wooden vanity, a toilet, and two framed pictures on the wall.
A spacious hotel lobby with multiple seating areas, large windows, and a television.

4. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
Lenox
  • Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
₩147,222
₩164,447 total
includes taxes & fees
Nov 8 - Nov 9
Hampton Inn & Suites Berkshires-Lenox
An indoor swimming pool with clear water, tiled floors, and a blue wall.
A reception area with a modern design, including a reception desk, a Holiday Inn Express sign, and a refrigerator stocked with beverages.
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.

5. 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.
₩132,922
₩148,473 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A modern kitchen with a marble countertop, stainless steel appliances, and a variety of food items displayed on the counter.
A hotel patio with outdoor seating and a fire pit.
A spacious living room with a large sofa, a coffee table, and a fireplace.

6. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield
  • Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
₩171,698
₩191,784 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Lenox Pittsfield
A hot tub with a tiled floor and a metal ladder.
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.
A hotel room with a large bed, a desk with a lamp, a television, and a view of the city.
Room

7. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pittsfield
  • Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
₩138,293
₩154,474 total
includes taxes & fees
Nov 13 - Nov 14
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool
A spacious living room with large windows, a fireplace, and a variety of seating options.
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
An outdoor patio area with tables and chairs, green umbrellas, and a building with large windows.

8. 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.
₩107,871
₩135,221 total
includes taxes & fees
Nov 11 - Nov 12
Vacation Village in the Berkshires
A swimming pool with a white fence, a flag, and a view of a town with houses and a hill in the background.
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.
A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.
A gazebo with a metal roof and wooden benches, surrounded by a white fence and lush greenery.

9. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
₩106,069
₩118,480 total
includes taxes & fees
Oct 26 - Oct 27
Howard Johnson by Wyndham Lenox
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A fenced outdoor area with a pool, lounge chairs, and umbrellas.
A motel with a parking lot, a swimming pool, and outdoor seating.
A bathroom with a bathtub, toilet, and shower.

10. Berkshire Inn

Berkshire Inn
Pittsfield
  • Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
₩115,454
₩128,962 total
includes taxes & fees
Oct 20 - Oct 21
Berkshire Inn
View all properties

Choose what matters most at hotels with a pool in Hinsdale

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Hinsdale Hotel Reviews

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"Sitting around the fire pit after a long day of leaf peeping was glorious..."
Steve 2-night trip
Posted 6 hours ago
Courtyard by Marriott Lenox Berkshires
The Yankee Inn

The Yankee Inn

10/10 Excellent
"Clean room. Special thank you to the cleaning and breakfast staff. Great balcony view. We will come back again."
Christopher 2-night trip
Posted 12 hours ago
The Yankee Inn
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We had a wonderful family stay at Vacation Village in the Berkshires! We traveled with our children and their grandmothers, and it was such a special opportunity to make memories together. Our accommodation felt like two apartments in one, with plenty of space for everyone. We loved the layout and the beautiful views, especially with the fall colors surrounding us. It was lovely to enjoy the scenery right where we were staying. The location was a great base for exploring the Berkshires, and we felt we got excellent value for the price. This trip was very special for our family, and we would love to come back. Highly recommend it for a family getaway!"
Viviane 2-night trip
Posted 1 day ago
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

10/10 Excellent
"Our room was nice and clean. The suite is perfect. Can fix a cup of tea or a meal, everything you need just bring your food. A restaurant on site if you don't want to cook. Bed was comfortable with crisp white linens."
Anna 2-night trip
Posted 4 days ago
Jiminy Peak Mountain Resort

Frequently asked questions

What are some accommodations with pools in Hinsdale?
Vacation Village in the Berkshires: Aparthotel, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. Berkshire Mountain Lodge: Provides free self parking, an indoor pool, and complimentary wireless internet access. Quality Inn Great Barrington: Offers a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn: Offers daily, an indoor pool, and free self parking. Berkshires Untold: Provides 3 restaurants, an outdoor pool, and spa services.
What is there to see and do in Hinsdale?
The picturesque setting of Ashmere Lake showcases the area's natural beauty. Discover sights such as Bas Ridge Golf Course during your stay.
When is the best time to book a hotel with a pool in Hinsdale?
Taking into account the local weather in Hinsdale 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 Hinsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

Explore a world of travel with Expedia