The Best Hotels with an Indoor Pool in The Berkshires, MA from ₩104,793 in 2026

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Our top choices for The Berkshires hotels with an indoor pool

Two Adirondack chairs facing a river with a forested hill in the background.

1. The Yankee Inn

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

₩193,680 total

includes taxes & fees

Nov 20 - Nov 21

A Holiday Inn Express & Suites building with a clear entrance, a covered parking area, and a stone facade.

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.

₩126,577 total

includes taxes & fees

Dec 7 - Dec 8

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

3. 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.

₩191,558 total

includes taxes & fees

Nov 15 - Nov 16

4. Berkshire Mountain Lodge

Pittsfield

Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.

₩147,555 total

includes taxes & fees

Dec 6 - Dec 7

A Fairfield by Marriott hotel with a covered entrance, multiple stories, and a well-maintained lawn.

5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.

₩244,996 total

includes taxes & fees

Nov 15 - Nov 16

A spacious hotel lobby with multiple seating areas, large windows, and a television.

6. Hampton Inn & Suites Berkshires-Lenox

Lenox

Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.

₩167,219 total

includes taxes & fees

Nov 15 - Nov 16

A tranquil stream with rocks and trees, a building with balconies and a red railing, and a clear sky.

7. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.

₩205,119 total

includes taxes & fees

Nov 11 - Nov 12

A hotel patio with outdoor seating and a fire pit.

8. Hilton Garden Inn Lenox Pittsfield

Pittsfield

Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.

₩180,983 total

includes taxes & fees

Nov 15 - Nov 16

9. Vacation Village in the Berkshires

Williamstown

Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.

₩137,501 total

includes taxes & fees

Nov 10 - Nov 11

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

10. Element by Marriott Lenox Berkshires

Lenox

Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.

₩205,879 total

includes taxes & fees

Nov 15 - Nov 16

View all properties

Top The Berkshires Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

10/10 Excellent

We were greeted by extremely friendly staff. Check in and check out was seamless. Room was very nice and immaculate. We especially liked the bathroom design - didn't have to trip over the toilet to get in the shower as in most hotels! Free breakfast was the usual fare, but in a very pleasant and uncrowded room. Appreciated the free US News and NY Times Beautiful indoor pool - wish we'd brought our bathing suits!

Anonymous traveler

A large, historic building with a covered porch and outdoor seating area.

Simsbury 1820 House

Simsbury Center

10/10 Excellent

Warren

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

t

The Yankee Inn

Lenox

10/10 Excellent

We had a fantastic stay at the Yankee! Our adjoining rooms were clean, large and comfortable. We loved that the rooms had a fireplace and balcony! All the amenities were appreciated. The breakfast had so many offerings, including fresh fruit and two kinds of eggs. The front desk staff (especially George) were professional, helpful and friendly. This was our first stay at the Yankee, but it won't be the last!

Colleen

Courtyard by Marriott Lenox Berkshires

Lenox

10/10 Excellent

Alyssa

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

South Lee

10/10 Excellent

I love this place and have stayed here before. Even with the precautions for COVID-19, my kids and I still had a great time. The check-in was smooth and safe. The room was clean and sanitized. In fact, we had to "break the seal" on the door to enter and the seal was evidence of the cleaning that was done. Of course, the arcade and movie theatre were closed, but that was no surprise. The pools were open and reservations required to ensure everyone could be safe and still have fun. Lots of...

David

Berkshire Mountain Lodge

Pittsfield

10/10 Excellent

Elliott

A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

Hotel Downstreet, an Ascend Collection Hotel

North Adams

10/10 Excellent

Ann

Vacation Village in the Berkshires

Williamstown

10/10 Excellent

Anonymous traveler

A fire feature with a metal frame and a brick wall in the background.

Fairfield Inn & Suites by Marriott Williamstown

Williamstown

10/10 Excellent

Diane

A hotel with a covered entrance, stone facade, and arched windows.

Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

10/10 Excellent

Jenny

A large indoor swimming pool with multiple levels of balconies, surrounded by tables and chairs.

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

10/10 Excellent

Gipsy

An indoor swimming pool with clear water, metal railings, and lounge chairs.

Hampton Inn Bennington

Bennington

10/10 Excellent

Andrrw

Find out more about The Berkshires

Discover top The Berkshires attractions

The Berkshires offer a serene escape, perfect for families seeking relaxation with plenty of activities. Nature lovers can explore the stunning landscapes at Tanglewood, where summer concerts blend beautifully with the serene surroundings. Kids will love the interactive exhibits at the Berkshire Museum, showcasing local wildlife and art that inspire curiosity. For a taste of history, visit the Norman Rockwell Museum, which captures the charm of Americana through its iconic artworks. Outdoor enthusiasts can embark on gentle hikes in the picturesque Mount Greylock State Reservation, where the views from the summit are simply breathtaking. After a day of adventures, unwind at charming hotels in Lenox or Stockbridge, where many accommodations feature inviting pools, perfect for a refreshing dip after your explorations. Enjoy family-friendly amenities and attentive service that cater to your every need, ensuring a pampered experience as you soak in the beauty of this tranquil region.

Find Hotels with an Indoor Pool in The Berkshires, MA

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for The Berkshires hotels with an indoor pool

1. The Yankee Inn

2. Holiday Inn Express Hotel & Suites Great Barrington by IHG

3. Courtyard by Marriott Lenox Berkshires

4. Berkshire Mountain Lodge

5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

6. Hampton Inn & Suites Berkshires-Lenox

7. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

8. Hilton Garden Inn Lenox Pittsfield

9. Vacation Village in the Berkshires

10. Element by Marriott Lenox Berkshires

Top The Berkshires Hotel Reviews

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

10/10 Excellent

Find out more about The Berkshires

Discover top The Berkshires attractions