Hotels with a Pool in Pittsfield, MA
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Pittsfield Hotels with Pool

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Free Cancellation
$118 nightly
The price is $132 total per night
$132 total
May 17 - May 18
Total with taxes and fees
Guests of Holiday Inn & Suites Pittsfield-Berkshires by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free valet parking. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, luggage storage, and tours or tickets. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly

Berkshire Inn
150 W Housatonic St Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$74 nightly
The price is $83 total per night
$83 total
May 25 - May 26
Total with taxes and fees
Guests of Berkshire Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and a TV in a common area. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. This smoke-free motel also has a picnic area.
Pool
Parking included

Hilton Garden Inn Lenox Pittsfield
1032 South Street Pittsfield MA
Free Cancellation
Reserve now, pay when you stay
$127 nightly
The price is $141 total per night
$141 total
May 17 - May 18
Total with taxes and fees
At Hilton Garden Inn Lenox Pittsfield, guests enjoy an indoor pool, a gym, and free WiFi in public areas. Free parking is available if you drive. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, luggage storage, and securing valuables. Additional amenities include a terrace, laundry facilities, and a convenience store.
Pool
Pet friendly
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.
Pittsfield hotels essential information
Accommodation | 1,374 hotels |
|---|---|
Lowest Price | $83 |
Highest Price | $141 |
Popular hotels | Holiday Inn & Suites Pittsfield-Berkshires by IHG, Berkshire Inn, Hilton Garden Inn Lenox Pittsfield |
Recent Hotels with Pool Reviews

Berkshire Mountain Lodge
3/5 Okay
"When we arrived we were hit with a $150 hold for incidentals but were told we could not get a receipt for it or one at checkout. We pay housekeeping fees yet the room instructions state to remove linens and used towels and place them in the tub before leaving. If i wanted to do housekeeping I'd stay home. Upon removing the pillow cases I saw a pillow stained with yellow streaks and dried blood. I immediately brought it to the front desk. The only thing said was "sorry about that" I was disgusted. The fact that you pay for 2 nights/3 days but cant check in til 4 p.m. and gave to check out at 10 a.m. is a scam. 2 days lost that I paid for. The room itself was nice though the door was very hard to open and close. Just overall disappointed. For the money I will go where you at least get a continental breakast. "
A verified traveler stayed at Berkshire Mountain Lodge
Posted 14 hours ago
More to Explore
More to Explore
- Hotels near Kennedy Park
- Hotels near Hancock Shaker Village
- Cabin Rentals in Berkshire County
- Cottages in Berkshire County
- Country Houses in Berkshire County
- Extended Stay Hotels in Berkshire County
- Arcade Hotels in Berkshire County
- Cheap Hotels in Berkshire County
- Hotels with Airport Transfers in Berkshire County
- Hotels with Pool in Berkshire County
- Hotels with Air Conditioning in Berkshire County
- Hotels with a Gym in Berkshire County
- Hotels with Free Parking in Berkshire County
- Hotels with Kitchenettes in Berkshire County
- Hotels on the Lake in Berkshire County
- Hotels on the River in Berkshire County
- Hotels with Shopping in Berkshire County
- 5 Star Hotels in Dalton
- Cabin Rentals in Dalton
- Dalton Hotels
- Motels in Dalton
- Vacation Homes in Dalton
- Resorts in Dalton
- Adventure Hotels in Massachusetts
- Business Hotels in Massachusetts
- Hotels with WiFi in Massachusetts
- Hotels with Air Conditioning in Massachusetts
- Hotels with Balconies in Massachusetts
- Hotels with Childcare in Massachusetts
- Hotels with Free Airport Shuttle in Massachusetts
- Hotels with Free Parking in Massachusetts
- Hotels with Restaurants in Massachusetts
- Hotels with Tennis Courts in Massachusetts
- Hotels on the River in Massachusetts
- Hotels near Pleasant Valley Wilderness Sanctuary
- Hotels near Canoe Meadows Wildlife Sanctuary
- Hotels near Guido's Marketplace
- Hotels near Crane Museum of Papermaking
- Hotels near Berkshire Museum
- Hotels near Pittsfield Municipal
- Adventure Hotels in Lenox
- Beach Resorts & in Lenox
- Boutique Hotels in Lenox
- Cheap Hotels in Lenox
- Kid Friendly Hotels in Lenox
- Gay Friendly Hotels in Lenox
- Golf Resorts & in Lenox
- Hotels with Pool in Lenox
- Hotels with Balconies in Lenox
- Hotels with Bar in Lenox
- Hotels with Free Breakfast in Lenox
- Hotels with Hot Tubs in Lenox
- Hotels with an Indoor Pool in Lenox
- Pet Friendly Hotels in Lenox
- Romantic Getaways & Hotels in Lenox
- Ski Resorts & in Lenox
- Spa Resorts & in Lenox
- Lenox Hotels
- Hotels near Barrington Stage Company
- Hotels near Berkshire Athenaeum
- Hotels near Skyline Country Club
- Hotels near Herman Melville's Arrowhead
- 4 Star Hotels in Lanesborough
- Farmstay in Lanesborough
- B&B in Lanesborough
- Cabin Rentals in Lanesborough
- Condo Rentals in Lanesborough
- Cottages in Lanesborough
- Guest Houses in Lanesborough
- Hotels with Free Parking in Lanesborough
- Luxury Hotels in Lanesborough
- Ski Resorts & in Lanesborough
- Lanesborough Hotels
- Vacation Homes in Lanesborough
- Hotels near Tanglewood Music Center
- Hotels near Bousquet Ski Area
- Flights to Berkshire County
- Flights from Pittsfield Municipal
- Flights from Pittsburgh (AGC) to Pittsfield (PSF)
- Flights from Oranjestad (AUA) to Pittsfield (PSF)
- Flights from Araguaina (AUX) to Pittsfield (PSF)
- Flights from Biak (BIK) to Pittsfield (PSF)
- Flights from Nashville (BNA) to Pittsfield (PSF)
- Flights from Coimbatore (CJB) to Pittsfield (PSF)
- Flights from Kannur (CNN) to Pittsfield (PSF)
- Flights from Charleville (CTL) to Pittsfield (PSF)
- Flights from East London (ELS) to Pittsfield (PSF)
- Flights from El Aaiun (EUN) to Pittsfield (PSF)
- Flights from Atyrau (GUW) to Pittsfield (PSF)
- Flights from Washington (IAD) to Pittsfield (PSF)
- Flights from Imperatriz (IMP) to Pittsfield (PSF)
- Flights from Manchester (MAN) to Pittsfield (PSF)
- Flights from Chicago (ORD) to Pittsfield (PSF)
- Flights from Puerto Maldonado (PEM) to Pittsfield (PSF)
- Flights from Fort Myers (RSW) to Pittsfield (PSF)
- Flights from Salt Lake City (SLC) to Pittsfield (PSF)
- Flights from Tirana (TIA) to Pittsfield (PSF)
- Flights from Lanesborough


