Find Hotels with a Pool in Pittsfield, MA
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Pittsfield Hotels with a Pool
Tonight
Tomorrow
This weekend
Next weekend
Compare Pittsfield Hotels with a Pool room rates, reviews, and availability. Most hotels are fully refundable.

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
8.0 out of 10, Very Good, (749)
The price is SAR 413
SAR 461 total
includes taxes & fees
22 Mar - 23 Mar

Berkshire Inn
Berkshire Inn
7.8 out of 10, Good, (764)
The price is SAR 323
SAR 360 total
includes taxes & fees
12 Mar - 13 Mar

Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
9.2 out of 10, Wonderful, (629)
The price is SAR 490
SAR 548 total
includes taxes & fees
16 Mar - 17 Mar
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
Find out more about Pittsfield
Recent reviews of Pittsfield hotels
Recent reviews of Pittsfield hotels

Vacation Village in the Berkshires
5/5 Excellent
"It was very nice. Had a kitchen and 2 tvs!"
A verified traveler stayed at Vacation Village in the Berkshires
Posted 4 days ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Find More Hotels near Pittsfield
More Hotel Options in Pittsfield
- Adventure Hotels in Pittsfield
- Boutique Hotels in Pittsfield
- Business Hotels in Pittsfield
- Cheap Hotels in Pittsfield
- Family Hotels in Pittsfield
- Golf Hotels in Pittsfield
- Historic Hotels in Pittsfield
- Hotel Wedding Venues in Pittsfield
- Hotel with a Concierge in Pittsfield
- Hotels with Bars in Pittsfield
- Hotels with Free Parking in Pittsfield
- Hotels with Hot Tubs in Pittsfield
- Hotels with WiFi in Pittsfield
- Hotels with an Indoor Pool in Pittsfield
- Hotels with smoking rooms in Pittsfield
- Luxury Hotels in Pittsfield
- Pet-friendly Hotels in Pittsfield
- Resorts & Hotels with Spas in Pittsfield
- Romantic Hotels in Pittsfield
- Shopping Hotels in Pittsfield
- Ski Hotels in Pittsfield
- Winery Hotels in Pittsfield
More Accommodation Types in Pittsfield
- Vacation Homes in Massachusetts
- Apartments in Massachusetts
- Cottages in Massachusetts
- Condo Rentals in Massachusetts
- B&B in Massachusetts
- Motels in Massachusetts
- Guest Houses in Massachusetts
- Resorts in Massachusetts
- Aparthotels in Massachusetts
- Cabin Rentals in Massachusetts
- Farmstay in Massachusetts
- Inns in Massachusetts
- Villas in Massachusetts
- Houseboats in Massachusetts
- Lodges in Massachusetts
- Hostels in Massachusetts
- Chalets in Massachusetts
- Condo Resorts in Massachusetts
- Holiday Park Resorts in Massachusetts
- RV Parks in Massachusetts
- Residences in Massachusetts
Hotels near popular Pittsfield Attractions
- Hotels near Bousquet Ski Area
- Hotels near Hancock Shaker Village
- Hotels near Colonial Theater
- Hotels near Berkshire Museum
- Hotels near Barrington Stage Company
- Hotels near Herman Melville's Arrowhead
- Hotels near Berkshire Athenaeum
- Hotels near Guido's Marketplace
- Hotels near Canoe Meadows Wildlife Sanctuary
- Hotels near Arrowhead Museum
Pittsfield Hotels by Star Rating
Explore more hotels
- Vacation Village in the Berkshires
- Life House Berkshires
- The Yankee, Trademark Collection by Wyndham
- The Williams Inn
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- The Red Lion Inn
- Hotel Downstreet, Ascend Hotel Collection
- The Black Swan Lee - Lenox, Ascend Hotel Collection
- Comfort Inn & Suites East Greenbush - Albany
- Holiday Inn Express Hotel & Suites Great Barrington by IHG
- Quality Inn
- The Constance, The Whitlock, & The Dewey By The Lenox Collection
- Fairfield Inn & Suites by Marriott Williamstown
- Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
- The Cornell Inn, Lenox
- Courtyard by Marriott Lenox Berkshires
- Hampton Inn & Suites Berkshires-Lenox
- The Porches Inn at Mass MoCA
- Quality Inn
- The Little Lion