Find Hotels with a Pool in Pittsfield, MA from CA $140
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Pittsfield Hotels with a Pool
Our top choices for Pittsfield hotels with a pool
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
8.0 out of 10, Very good, (1,001 reviews)
- Splash into year-round relaxation at this hotel's indoor pool, steps from vibrant city adventures.
The price is CA $182
CA $203 total
includes taxes & fees
Jul 21 - Jul 22
9.2 out of 10, Wonderful, (1,000 reviews)
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is CA $215
CA $240 total
includes taxes & fees
Jul 19 - Jul 20
7.8 out of 10, Good, (880 reviews)
- Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is CA $126
CA $141 total
includes taxes & fees
Jul 19 - Jul 20
9.2 out of 10, Wonderful, (695 reviews)
- Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.
The price is CA $296
CA $330 total
includes taxes & fees
Jul 19 - Jul 20
9.0 out of 10, Wonderful, (1,007 reviews)
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
The price is CA $188
CA $241 total
includes taxes & fees
Aug 16 - Aug 17
9.2 out of 10, Wonderful, (1,001 reviews)
- Splash into art deco luxury at this indoor pool sanctuary, where relaxation meets mountain adventure.
The price is CA $296
CA $331 total
includes taxes & fees
Aug 16 - Aug 17
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHGPittsfield
9.4 out of 10, Exceptional, (137 reviews)
- Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is CA $233
CA $260 total
includes taxes & fees
Jul 22 - Jul 23
8.8 out of 10, Excellent, (2,451 reviews)
- Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
The price is CA $205
CA $245 total
includes taxes & fees
Jul 20 - Jul 21
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.
Top Pittsfield Hotel Reviews
Vacation Village in the Berkshires
10/10 Excellent
Frequently asked questions
Explore a world of travel with Expedia
- Cheap Hotels in Amherst
- Hotels near Tanglewood Music Center
- Hotels with Hot Tubs in Greenfield
- B&B in Lee
- Hotels near National Shrine of the Divine Mercy
- Hancock Hotels
- Apartments in Cheshire
- Hotels near The Clark Art Institute
- Hotels with Kitchenettes in Western Massachusetts
- Lanesborough Hotels
- Lenox Hotels
- Family Hotels in The Berkshires
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- North Adams Hotels
- Waterpark Hotels in Springfield
- Historic 1804 house in N Becket Village in the Berkshires
- Pet-Friendly Hotels in Sheffield
- Cheap Hotels in The Berkshires
- 3 Star Hotels in Pittsfield
- Williamstown Hotels
- The Whitlock
- Pittsfield Hotels
- Cabin Rentals in Savoy
- Hotels with Hot Tubs in Western Massachusetts
- Pet-Friendly Hotels in Western Massachusetts
- Washington Hotels
- Villas in Beartown State Forest
- Lee Hotels
- Hotels near Frelinghuysen Morris House and Studio
- Plainfield Hotels
- Country Houses in Alford
- Resorts in Lenox
- Chestnut Lodge
- One Bedroom Luxury Cottage at Blantyre
- Becket Hotels
- Luxury Hotels in The Berkshires
- Cheap Hotels in Lenox
- Historic Rectory Retreat in Stockbridge – Getaway for 8
- Oceanfront Hotels in Western Massachusetts
- B&B in Adams
- Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak
- Spa Hotels in Northampton
- Cheap Hotels in Springfield
- Holiday Inn Express & Suites Pittsfield
- Hotels near Lee Premium Outlets
- Cheap Hotels in Sandisfield
- Hotels with an Indoor Pool in Western Massachusetts
- Stockbridge Hotels
- Chalets in Becket
- Cottages in The Berkshires
- Luxury Hotels in Berkshire County
- The Red Door B&B
- Cheap Hotels in Lee
- Pet-Friendly Hotels in The Berkshires
- Pet-Friendly Hotels in Springfield
- Cheap Hotels in Holyoke
- Great Barrington Hotels
- Pet-Friendly Hotels in Amherst
- Pet-Friendly Hotels in Pittsfield
- Hotels with a Lazy River in Western Massachusetts
- Hotels with a Pool in Western Massachusetts
- Pet-Friendly Hotels in Stockbridge
- Pet-Friendly Hotels in North Adams
- West Stockbridge Hotels
- Lgbt Friendly Hotels in Cheshire
- Casino Hotels in Springfield
- Luxury Hotels in Springfield
- Flights from Windsor
- Flights from Becket
- Flights from Ithaca (ITH) to Pittsfield (PSF)
- Flights from Toronto (YYZ) to Pittsfield (PSF)
- Flights to West Stockbridge
- Flights from Plattsburgh (PBG) to Pittsfield (PSF)
- Flights to Pittsfield
- Flights to Lenox
- Flights from Lenox
- Flights from Boston (BOS) to Pittsfield (PSF)
- Flights to Williamstown
- Flights to Stockbridge
- Flights from Phoenix (PHX) to Pittsfield (PSF)
- Flights from Dalton
- Flights from Seattle (SEA) to Pittsfield (PSF)