Find Hotels with an Outdoor Pool in Pittsfield, MA

Start date: Check-in selected.
To Date
End date: Check-out
  • Upfront pricing

    Our total price for your stay includes taxes and fees
  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
  • Be picky

    Search almost a million properties worldwide

Check availability on Pittsfield Hotels with an Outdoor Pool

Top Pittsfield Hotels with an Outdoor Pool

Berkshire Inn

2.0 star property
Pittsfield
7.8 out of 10, Good, (838)
"This property has a mid century motel look from the street but the rooms have been recently upgraded and are fully modern inside. A great value and comfortable place to stay"
United States
Phillip
$75 nightly
The price is $84
Nov 24 - Nov 25
Total with taxes and fees
Berkshire Inn

The Springs Motel

2.0 star property
New Ashford
9.2 out of 10, Wonderful, (85)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
$103 nightly
The price is $114
Nov 15 - Nov 16
Total with taxes and fees
The Springs Motel

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1001)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
$99 nightly
The price is $111
Dec 15 - Dec 16
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (822)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Nov 16 - Nov 17
Total with taxes and fees
Howard Johnson by Wyndham Lenox

Maple Terrace Motel

2.5 star property
Williamstown
9.6 out of 10, Exceptional, (583)
"Pool, fire pit, grounds and staff were great!"
United States
Kristy
$99 nightly
The price is $111
Nov 17 - Nov 18
Total with taxes and fees
Maple Terrace Motel

Willows Motel Williamstown

2.0 star property
Williamstown
9.0 out of 10, Wonderful, (983)
"The room is very nice. This is the best free breakfast I've ever seen at a hotel. I would definitely stay here again."
United States
Ellen
$85 nightly
The price is $95
Dec 1 - Dec 2
Total with taxes and fees
Willows Motel Williamstown

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very Good, (984)
"We didn't spend much time there, but it was nice, comfortable, clean and quiet. It was close to the things we had planned to do."
United States
Philip
$149 nightly
The price is $166
Nov 15 - Nov 16
Total with taxes and fees
Jiminy Peak Mountain Resort

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (409)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
$86 nightly
The price is $97
Dec 2 - Dec 3
Total with taxes and fees
Sunset Inn

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (133)
"Perfect location "
United States
krystle
$136 nightly
The price is $152
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow

Prospect Berkshires

3.0 star property
Egremont
9.4 out of 10, Exceptional, (13)
"Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway "
United States
Andy
$250 nightly
The price is $280
Nov 17 - Nov 18
Total with taxes and fees
Prospect Berkshires
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.

Find out more about Pittsfield

Discover top Pittsfield attractions

Pittsfield, Massachusetts, offers a tranquil escape with a range of activities that cater to relaxed vacations. Begin your exploration at the beautiful Pittsfield State Forest, where you can hike scenic trails that wind through lush forests and showcase stunning views of the Berkshires. After a day of outdoor adventure, unwind at the Berkshire Museum, which features an eclectic mix of art, history, and science exhibits, perfect for families looking to spark curiosity in their children. The serene Bousquet Ski Area is not just for winter sports; during the warmer months, it transforms into a scenic spot for hiking and offers a lovely picnic area for a peaceful family day out. Don't miss the renowned Barrington Stage Company, where you can enjoy high-quality live performances in an intimate setting, providing a cultural touch to your relaxing getaway. Finally, exploring the vibrant downtown area reveals charming local shops and delightful eateries where you can savor the flavors of the region. For an ideal stay, consider booking one of the hotels near the downtown area, which often feature inviting pools perfect for unwinding after a day of exploration. These accommodations typically offer family-friendly amenities, attentive service, and the convenience of being close to key attractions, ensuring you feel pampered throughout your stay.

Find the best hotels with an outdoor pool in Pittsfield

For travelers seeking refreshing outdoor experiences in Pittsfield, these hotels offer delightful outdoor pool options perfect for unwinding and enjoying the sunshine.

Hilton Garden Inn Lenox Pittsfield

  • Why it's great for poolside lounging: The Hilton Garden Inn Lenox Pittsfield is an ideal retreat for travelers who appreciate outdoor leisure, showcasing a review rating of 9.2. Guests can enjoy the inviting outdoor pool, perfect for relaxation after a day of exploring the beautiful Berkshire region. Additionally, the hotel features an indoor pool, providing year-round swimming options that cater to all preferences.
  • Other amenities: Alongside its pool amenities, guests can benefit from a range of features including free daily breakfast, a fitness center for active travelers, and convenient self-parking. The hotel also offers spacious suites with kitchen facilities, making it ideal for longer stays. With a terrace to enjoy the fresh air and a grocery store nearby, guests have everything they need for a comfortable and enjoyable visit.
  • Nearby attractions: Pleasant Valley Wilderness Sanctuary - 1.51 miles, Herman Melville's Arrowhead - 1.94 miles, Bousquet Ski Area - 1.38 miles

Berkshire Mountain Lodge

  • Why it's great for poolside lounging: The Berkshire Mountain Lodge provides an excellent option for travelers who enjoy outdoor leisure with its outdoor pool featuring sun loungers, complemented by a strong review rating of 9.0. The lodge's inviting atmosphere and beautiful surroundings make it a perfect spot for relaxation and rejuvenation after a day of adventure in the mountains.
  • Other amenities: In addition to the outdoor pool, guests can indulge in the indoor pool and hot tub for a truly luxurious experience. The hotel also features convenient amenities such as free self-parking, a game room, and nearby golf opportunities. For those seeking outdoor activities, ski rentals and snow tubing are easily accessible, ensuring that all guests have a variety of recreational options.
  • Nearby attractions: Pleasant Valley Wilderness Sanctuary - 2.12 miles, Herman Melville's Arrowhead - 2.23 miles, Bousquet Ski Area - 1.29 miles

Berkshire Inn

  • Why it's great for poolside lounging: The Berkshire Inn is a budget-friendly choice for travelers who appreciate simplicity and convenience, featuring a strong review rating of 7.8. While it does not have an outdoor pool, the inn offers a comfortable atmosphere with essential amenities for a pleasant stay, ensuring guests can enjoy their time in Pittsfield without breaking the bank.
  • Other amenities: Guests will find daily housekeeping services, free self-parking, and air conditioning for added comfort. The hotel is conveniently located near outdoor activities such as skiing and golfing, making it an excellent base for those looking to explore the natural beauty of the area.
  • Nearby attractions: Colonial Theater - 0.6 miles, Berkshire Athenaeum - 0.75 miles, Berkshire Museum - 0.57 miles

Top Pittsfield Hotel Reviews

Explore a world of travel with Expedia