
Find Hotels with a Pool in Pittsfield, MA
- Upfront pricingOur total price for your stay includes taxes and fees
- Treat yourselfSave 10% or more on over 100,000 hotels worldwide with Member PricesLearn about One Key
- Be pickySearch almost a million properties worldwide
Check availability on Pittsfield Hotels with a Pool
Tonight
Sep 7 - Sep 8Tomorrow
Sep 8 - Sep 9This weekend
Sep 11 - Sep 13Next weekend
Sep 18 - Sep 20Our top choices for Pittsfield hotels with a pool




1. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
$113 nightly
$126 total
Oct 1 - Oct 2
Total with taxes and fees




2. Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
- Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
$118 nightly
$132 total
Sep 13 - Sep 14
Total with taxes and fees




3. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
- Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
$127 nightly
$141 total
Sep 10 - Sep 11
Total with taxes and fees




4. Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox PittsfieldPittsfield
- Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
$146 nightly
$163 total
Sep 10 - Sep 11
Total with taxes and fees




5. Berkshire Inn
Berkshire InnPittsfield
- Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
$84 nightly
$94 total
Oct 7 - Oct 8
Total with taxes and fees




6. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
$113 nightly
$126 total
Sep 9 - Sep 10
Total with taxes and fees




7. Hampton Inn & Suites Berkshires-Lenox
Hampton Inn & Suites Berkshires-LenoxLenox
- Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
$122 nightly
$136 total
Sep 30 - Oct 1
Total with taxes and fees




8. Howard Johnson by Wyndham Lenox
Howard Johnson by Wyndham LenoxLenox
- Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
$78 nightly
$87 total
Sep 13 - Sep 14
Total with taxes and fees
View all properties
Top Pittsfield Hotel Reviews
Berkshire Inn
8/10 Good
"was looking for a cheap 1 night stay. dated hotel from the outside, but rooms had been updated. clean. would stay again."
The Yankee Inn
10/10 Excellent
"On an overpriced holiday weekend in the Berkshires, Yankee Inn was a great balance of price and amenities. The indoor pool was nicer than most, and the hot tub was great. Outdoor pool was a bit oddly placed between the parking lot and the main road, but nice as well. Both very clean. Room was spacious and clean, beds were comfortable, though I think they were doubles rather than queens. The included breakfast was on the very good end of standard - the fruit was fresh and delicious, there were both eggs and waffles, plus cereal, yogurt, bacon/sausage. Meh on the pastries, and the coffee was terribly watery. My true only gripe is that there was truly not a single place to hang wet bathing suits that didn't result in them dripping all over the floor. Had we been on the 2nd floor, we would have had an outside railing, but on the first floor there was none. With 4 people using the pool and hot tub, it was an annoyance. Overall, great place for a quick stay."
Hotel Downstreet, an Ascend Collection Hotel
8/10 Good
"Nice and conveniently located"
Comfort Inn & Suites East Greenbush - Albany
10/10 Excellent
"The hotel was clean, quiet, and conveniently located."
Holiday Inn & Suites Pittsfield-Berkshires by IHG
8/10 Good
"Staff was helpful. Location close to Tanglewood. Bed and pillows were awesome. One elevator was not working so that was inconvenient"
Frequently asked questions
Explore a world of travel with Expedia
- Luxury Hotels in Pittsfield
- Motels in Pittsfield
- Hotels with Room Service in The Berkshires
- Hotels with Free Wifi in Springfield
- Motels in Berkshire County
- Hotels with Room Service in Springfield
- Springfield Hotels
- Quiet Resorts & in Springfield
- Hotels with Laundry Facilities in Pittsfield
- Fishing Resorts & in Western Massachusetts
- Hotels with Laundry Facilities in The Berkshires
- Pet-Friendly Hotels in Pittsfield
- Hotels with Hot Tubs in Pittsfield
- North Adams Hotels
- Beach Hotels in Pittsfield
- 4 Star Hotels in Pittsfield
- Extended Stay Hotels in The Berkshires
- Quiet Resorts & in The Berkshires
- Golf Hotels in Springfield
- Resorts & Hotels with Spas in Pittsfield
- Hotels with Kitchenettes in Western Massachusetts
- Historic Hotels in Pittsfield
- Guest Houses in Pittsfield
- Hotels with Tennis Courts in Springfield
- Hotels near Jiminy Peak Mountain Resort
- Hotels with an Indoor Pool in Pittsfield
- Apartments in Pittsfield
- Hotels with Fireplaces in Pittsfield
- B&B in Pittsfield
- Hotels with a View in Springfield
- Boutique Hotels in Lenox
- Lee Hotels
- Ski Hotels in Springfield
- Hotels with Connecting Rooms in Pittsfield
- Hotels with Free Breakfast in Springfield
- Oceanfront Hotels in Springfield
- Pittsfield Hotels
- Hotels with Balconies in Pittsfield
- Green Hotels in The Berkshires
- Hotels with a Lazy River in The Berkshires
- 3 Star Hotels in Pittsfield
- Stockbridge Hotels
- Hotels with Bars in Western Massachusetts
- Lenox Hotels
- Beach Hotels in The Berkshires
- Hotels with Restaurants in Pittsfield
- Winery Hotels in Pittsfield
- Hotels with Bars in The Berkshires
- Hotels with Room Service in Western Massachusetts
- Gay friendly Hotels in Pittsfield
- Hotels with Childcare in The Berkshires
- Hotels with an Outdoor Pool in Pittsfield
- All-Inclusive Resorts in Springfield
- Hotels on the Lake in Pittsfield
- Hotels with Kitchenettes in Pittsfield
- Hotels on the Lake in Springfield
- Hotel Wedding Venues Hotels in West Springfield
- Extended Stay Hotels in Pittsfield
- Hotels & Resorts for Couples in Western Massachusetts
- Hotels with a Gym in The Berkshires
- Cheap Hotels in Pittsfield
- Hotels with Restaurants in West Springfield
- Hotels with a Pool in The Berkshires
- Resorts & Hotels with Spas in Lenox
- Hotels with Bars in Pittsfield
- Great Barrington Hotels
- Hotels with smoking rooms in Pittsfield
- Hotels near Tanglewood Music Center
- Hotel Wedding Venues Hotels in Pittsfield
- Hotels with Free Breakfast in The Berkshires
- Hotels & Resorts for Couples in Springfield
- Hotels with Laundry Facilities in Springfield
- Resorts in Pittsfield
- Cheap Hotels in Lenox
- Romantic Hotels in Pittsfield
- Family Hotels in Pittsfield
- Ski Hotels in Pittsfield
- Boutique Hotels in Pittsfield
- Hotels with Early Check-in in Western Massachusetts
- Hotels with Free Breakfast in Pittsfield
- Cabin Rentals in Pittsfield
- Enterprise Rental Cars in Pittsfield
- Budget Rental Cars in Pittsfield
- Van Car Rentals in Pittsfield
- Avis Rental Cars in Pittsfield
- Hertz Rental Cars in Pittsfield
- Thrifty Car Rental Rental Cars in Pittsfield
- Car rental Pittsfield
- National Car Rental Rental Cars in Pittsfield
- Alamo Rent A Car Rental Cars in Pittsfield







