A historic building with classical architecture, a traffic light, and a yellow taxi.

Find Hotels with a Pool in Pittsfield, MA

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Check availability on Pittsfield Hotels with a Pool

Tonight
Oct 26 - Oct 27
Tomorrow
Oct 27 - Oct 28
This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Pittsfield hotels with a pool

Indoor pool
A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.
A spacious living room with a fireplace, comfortable seating, and large windows.
A spacious living room with large windows, a fireplace, and a variety of seating options.

1. 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.
$128 nightly
$143 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, multiple seating areas, and a chandelier.
A garden with wooden Adirondack chairs and a stone pathway.
Exterior

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$115 nightly
$128 total
Nov 24 - Nov 25
Total with taxes and fees
Berkshire Mountain Lodge
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.

3. 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.
$95 nightly
$106 total
Nov 24 - Nov 25
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A large indoor swimming pool with multiple levels of balconies, surrounded by tables and chairs.
A spacious dining area with a long wooden table, multiple chairs, and pendant lighting.
Meeting facility
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

4. 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.
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Pool
A modern living room with a fireplace, flat-screen TV, sofa, chairs, and tables.
Exterior
A spacious hotel lobby with multiple seating areas, large windows, and a television.

5. 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.
$110 nightly
$122 total
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn & Suites Berkshires-Lenox
A large indoor swimming pool with clear blue water, surrounded by white lounge chairs and a few potted plants.
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.
A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.
A reception area with a wooden reception desk, modern pendant lighting, and a vertical garden wall.

6. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
Lenox
  • Modern comforts and year-round indoor pool await at Element Lenox Berkshires near Tanglewood.
$135 nightly
$151 total
Nov 8 - Nov 9
Total with taxes and fees
Element by Marriott Lenox Berkshires
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A bathroom with a bathtub, toilet, and shower.
A hotel room with a TV, desk, chair, lamp, and a bathroom with a sink and mirror.
A motel with a parking lot, a swimming pool, and outdoor seating.

7. Berkshire Inn

Berkshire Inn
Pittsfield
  • Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
$79 nightly
$88 total
Nov 26 - Nov 27
Total with taxes and fees
Berkshire Inn
A large indoor swimming pool with multiple lanes, surrounded by lounge chairs and a glass wall.
A restaurant with multiple dining tables, chairs, and a large Buddha statue centerpiece.
A spacious living room with a large sofa, a coffee table, and a fireplace.
A multi-story hotel with a prominent entrance, a parking lot, and a flagpole.

8. 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.
$119 nightly
$133 total
Nov 15 - Nov 16
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
An indoor swimming pool with clear glass walls, a hot tub area, and a seating area with chairs and tables.
A covered outdoor area with stone pillars and a view of a road and green hills.
A modern restaurant with wooden flooring, bar area, and seating arrangements.
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

9. 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.
$126 nightly
$140 total
Nov 1 - Nov 2
Total with taxes and fees
Courtyard by Marriott Lenox 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 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.
A bathroom with a white sink, mirror, and toilet.

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
$79 nightly
$88 total
Oct 27 - Oct 28
Total with taxes and fees
Howard Johnson by Wyndham Lenox
View all properties

Choose what matters most at hotels with a pool in Pittsfield

Breakfast included
Hot tub
Spa
4 stars
5 stars

Find out more about Pittsfield

Discover top Pittsfield attractions

Pittsfield, a hidden gem in the Berkshires, offers a delightful mix of cultural attractions and outdoor adventures perfect for travelers seeking quality experiences. Begin your exploration at the vibrant downtown area, where charming boutiques and artisanal shops invite leisurely strolls. Just a short drive away, you can immerse yourself in the rich history of the area with a visit to a historic estate, where guided tours reveal fascinating stories of the past. For art enthusiasts, the local galleries showcase impressive works from both emerging and established artists, providing a perfect opportunity to discover unique pieces. If you're looking for outdoor fun, the nearby scenic trails promise breathtaking views and refreshing hikes suitable for families. After a day of adventure, unwind at one of the area’s upscale accommodations, known for their attentive service and luxurious amenities, ensuring that your stay is as memorable as your experiences. With so much to see and do, Pittsfield promises an enjoyable and well-rounded getaway.

Top Pittsfield Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"We love staying at this hotel every fall. It is in an easy access location with plenty of parking and very clean. The staff are very friendly and the breakfast is fantastic. We’ll be back!!"
Patricia 2-night trip
Posted 8 hours ago
Quality Inn Great Barrington
Comfort Inn & Suites East Greenbush - Albany

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent
"Excellent accommodations! Our room was very clean and comfortable. We appreciated the well lit parking lot, quality breakfast foods, and friendly staff. Thank you!"
Nancy 2-night trip
Posted 10 hours ago
Comfort Inn & Suites East Greenbush - Albany
Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Everything was absolutely perfect! Staff was extremely friendly and the property is so clean and inviting. We loved it so much that we extended our stay!"
Angelina 7-night trip
Posted 13 hours ago
Vacation Village in the Berkshires
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good
"After having been away from The Black Swan Inn since the 1980’s, I was happy to see the hotel is being maintained and cared for. The lakeside views are beautiful (even though I had to pay an up charge to get this side upon check in). The room was large. My only wish regarding the bedding, is that the pillows weren’t so hard and stiff. Balconies need a little maintenance. A staff member, “Rocky”, was especially nice to be greeted by in the breakfast room on the morning we left. Thank you."
Stephanie 2-night trip
Posted 14 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

10/10 Excellent
"Great"
Sharath 1-night trip
Posted 2 days ago
Hotel Downstreet, an Ascend Collection Hotel
Berkshire Inn

Berkshire Inn

10/10 Excellent
"Very clean room and apparently the room had been upgraded recently by real craftsmen. Well done. You don't expect this quality from an older motel, but the owners obviously take pride in the property."
Jeff 1-night trip
Posted 6 days ago
Berkshire Inn
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

8/10 Good
"Nice people, ok and clean room. Too much light from around the window shades and all the gizmos (thermostat, TV etc.) to the point of inhibiting sleep."
Graydon 2-night trip
Posted 8 days ago
Hilton Garden Inn Lenox Pittsfield

Frequently asked questions

What are some accommodations with pools in Pittsfield?
Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. FairBridge Inn Express: Provides buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG: Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Hotel On North: Provides a health club, an indoor pool, and free valet parking. Best Western Plus Berkshire Hills Inn & Suites: Features a snack bar/deli, a pool, and complimentary wired internet access.
What is there to see and do in Pittsfield?
Surround yourself with nature at Housatonic River and Onota Lake. During your stay, check out sights such as Berkshire Museum, Colonial Theater, and Bousquet Ski Area. The sporting events and theater scene 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 Pittsfield?
Taking into account the local weather in Pittsfield can help you maximize your time at the pool during your trip. 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 Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to travel around Pittsfield?
Knowing the transportation options in Pittsfield can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station. Pittsfield might not have many public transit options to choose from so consider a car rental to maximize your time.

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