The Best Hotels with a Pool in Hawley, MA from ₩138,678 in 2026

Q: What are some accommodations with pools in Hawley?

The Yankee Inn : Provides a seasonal outdoor pool, an indoor pool, and buffet. Vacation Village in the Berkshires : Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. Berkshire Mountain Lodge : Offers free self parking, an indoor pool, and complimentary wireless internet access. Red Roof Inn PLUS+ South Deerfield – Amherst : Provides buffet, an indoor pool, and complimentary wired internet access. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG : Hotel, 6-minute walk from Massachusetts Museum of Contemporary Art. Features daily, an indoor pool, and free self parking.

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Our top choices for Hawley hotels with a pool

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

₩217,342 total

includes taxes & fees

Jul 6 - Jul 7

Indoor pool, open 6:00 AM to 10 PM, sun loungers

Hotel Downstreet, an Ascend Collection Hotel

North Adams

Poolside bliss awaits with mountain views in this rejuvenating indoor pool and hot tub retreat.

₩293,879 total

includes taxes & fees

Jul 8 - Jul 9

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers

Maple Terrace Motel

Williamstown

Dive into a heated pool oasis where crystal clear waters beckon at this tranquil Williamstown retreat.

₩221,531 total

includes taxes & fees

Jul 9 - Jul 10

Willows Motel Williamstown

Williamstown

Escape to a poolside oasis with a swim-up bar and the freedom to float from dawn to dusk.

₩138,678 total

includes taxes & fees

Jul 6 - Jul 7

Cozy Corner Motel

Williamstown

Pool paradise awaits with a lazy river and mountain views at this tranquil family-friendly retreat.

₩158,585 total

includes taxes & fees

Jul 19 - Jul 20

Berkshire Mountain Lodge

Pittsfield

Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.

₩262,504 total

includes taxes & fees

Aug 3 - Aug 4

The Nutmeg

Wilmington

Summer river retreats with exclusive seasonal poolside fun from July through September.

₩318,029 total

includes taxes & fees

Jul 15 - Jul 16

The Springs Motel

New Ashford

Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.

₩251,085 total

includes taxes & fees

Jul 5 - Jul 6

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Choose what matters most at hotels with a pool in Hawley

Breakfast included

4 stars

Top Hawley Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good

"Breakfast was great! We were caught off guard by the parking lot renovation but the free valet parking made up for it. Staff was very friendly! "

Vacation Village in the Berkshires

10/10 Excellent

"These types of time sharing places look a bit outdated, but there is value because they have a full kitchen and living room. Better lighting and cleaner hallways could be a plus. Beautiful setting in the mountains. Not too far from Tanglewood and rte 100 in the Green Mountains in Vermont!"