Hotels with Pool & Resorts in The Berkshires
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on The Berkshires Hotels with Pool
Tonight
11 Aug - 12 AugTomorrow
12 Aug - 13 AugThis weekend
14 Aug - 16 AugNext weekend
21 Aug - 23 AugOur top choices for The Berkshires hotels with a pool
1. The Yankee Inn
The Yankee InnLenox
- Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
NZ$313
includes taxes & fees
7 Sept - 8 Sept
2. The Red Lion Inn
The Red Lion InnStockbridge
- Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
NZ$382
includes taxes & fees
9 Sept - 10 Sept
3. Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
- Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
NZ$236
includes taxes & fees
8 Sept - 9 Sept
4. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
- Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating spa pool experiences.
NZ$217
includes taxes & fees
31 Aug - 1 Sept
5. Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
- Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
NZ$233
includes taxes & fees
9 Sept - 10 Sept
NZ$440
includes taxes & fees
31 Aug - 1 Sept
7. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
- Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.
NZ$202
includes taxes & fees
2 Sept - 3 Sept
8. 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 spa pool to soothe tired muscles.
NZ$241
includes taxes & fees
8 Sept - 9 Sept
View all properties
Hotels with pools and free breakfast in The Berkshires
Holiday Inn Club Vacations Oak 'n Spruce Resort
Holiday Inn Club Vacations Oak 'n Spruce ResortSouth Lee
NZ$236
includes taxes & fees
8 Sept - 9 Sept
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHGGreat Barrington
NZ$233
includes taxes & fees
9 Sept - 10 Sept
NZ$278
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/BerkshiresGreat Barrington
NZ$369
includes taxes & fees
31 Aug - 1 Sept
NZ$264
includes taxes & fees
9 Sept - 10 Sept
NZ$353
includes taxes & fees
19 Aug - 20 Aug
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHGPittsfield
NZ$241
includes taxes & fees
26 Aug - 27 Aug
NZ$150
includes taxes & fees
1 Sept - 2 Sept
NZ$313
includes taxes & fees
10 Sept - 11 Sept
4-star hotels with pools in The Berkshires
NZ$739
includes taxes & fees
3 Sept - 4 Sept
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and ChesterwoodStockbridge
NZ$678
includes taxes & fees
7 Sept - 8 Sept
NZ$654
includes taxes & fees
1 Sept - 2 Sept
NZ$786
includes taxes & fees
7 Sept - 8 Sept
NZ$416
includes taxes & fees
10 Sept - 11 Sept
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.
View all propertiesTop The Berkshires Hotel Reviews
Vacation Village in the Berkshires
8/10 Good
"Beautiful location and pricey, but less expensive than most places in the area. It is spacious with a kitchen that we did not use, the rooms are very dated. You can hear through the walls very well. Didn’t use pool because it was so crowded."
The Red Lion Inn
10/10 Excellent
"This is an old inn. It’s elegant, fun and very comfortable. Lots of dark, antique furniture and communal card games. The staff is friendly and some have been there many years. Many of the guests return year after year. If that’s what you’re looking for, you will love it. I do. If you are looking for sleek and spotless, you are best suited elsewhere."
The Yankee Inn
8/10 Good
"The room was clean. Linens in good shape. Good access to lots of activities nearby. Breakfast can be crowded. Go early."
Jiminy Peak Mountain Resort
10/10 Excellent
"Quiet and serene. Great weekend escape!"
Holiday Inn & Suites Pittsfield-Berkshires by IHG
10/10 Excellent
"Hotel is currently under renovation which impacted parking and only 1 elevator available. Hotel staff, cleanliness and location excellent."
Howard Johnson by Wyndham Lenox
10/10 Excellent
"Parking"
Explore a world of travel with Expedia
- Lgbt Welcoming Hotels in Northampton
- Cheap Hotels in Northampton
- Luxury Hotels in Hampshire County
- Lgbt Welcoming Hotels in Lee
- Beach Hotels in Lee
- Pet Friendly Hotels in North Adams
- Luxury Hotels in North Adams
- Cheap Hotels in Lenox
- Luxury Hotels in The Berkshires
- Golf Hotels in The Berkshires
- Spa Hotels in Adams
- Hotels with Pool in Sheffield
- Lgbt Welcoming Hotels in Hadley
- Cheap Hotels in West Springfield
- Resort in Hinsdale
- B&B in Great Barrington
- Resort in The Berkshires
- Cabin Rentals in The Berkshires
- B&B in The Berkshires
- Apartments in Southwick
- B&B in Western Massachusetts
- Country House in Western Massachusetts
- Apartments in Westfield
- Cottages in Mill River
- Motels in Becket
- Condo Rentals in Otis
- Resort in Granville
- Apartments in Granville
- B&B in Granville
- Cottages in Lenox
- B&B in Lenox
- Cottages in Southfield
- Accor Hotels in Russell
- Lenox Hotels
- Great Barrington Hotels
- Stockbridge Hotels
- Peru Hotels
- Washington Hotels
- Becket Hotels
- Hotels near Berkshire Museum
- Hotels near Magnolia Bluffs Casino
- Chesterfield Hotels
- Chester Hotels
- Mount Washington Hotels
- Blandford Hotels
- Hotels near Tanglewood Music Center
- Pittsfield Hotels
- Hotels near Walter J. Koladza
- Sheffield Hotels
- Granville Hotels
- Hotels near Lake Mansfield Park
- New Marlborough Hotels
- South Egremont Hotels
- Russell Hotels
- Alford Hotels
- Tyringham Hotels
- Richmond Hotels
- Lee Hotels
- Huntington Hotels
- Monterey Hotels
- Otis Hotels
- Dalton Hotels
- Berkshire County Hotels
- West Stockbridge Hotels
- Hotels near Guido's Marketplace
- Westfield Hotels
- Hotels near Ashintully Gardens
- Southampton Hotels
- Southwick Hotels
- Beach Holiday Packages Western Massachusetts
- All inclusive Holiday Packages Western Massachusetts
- Goose Pond Reservation
- Otis Holidays
- Pittsfield Holidays
- Ski Butternut
- National Shrine of the Divine Mercy
- Norman Rockwell Museum
- Visit Western Massachusetts
- Visit The Berkshires
- Visit Great Barrington
- Visit West Stockbridge
- Visit Middlefield
- Visit Tyringham
- Visit Otis