Find Hotels with an Outdoor Pool in Western Massachusetts, MA

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Top Western Massachusetts Hotels with an Outdoor Pool

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1003)
"Great stay!"
United States
Ann
$89 nightly
The price is $100
Dec 15 - Dec 16
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
$189 nightly
The price is $212
Dec 18 - Dec 19
Total with taxes and fees
The Red Lion Inn

MGM Springfield

4.0 star property
Metro Center
9.0 out of 10, Wonderful, (1444)
"The room was amazing. Loved the bed amazing"
United States
Akira
$169 nightly
The price is $192
Jan 4 - Jan 5, 2026
Total with taxes and fees
MGM Springfield

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2168)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
$111 nightly
The price is $124
Dec 8 - Dec 9
Total with taxes and fees
Vacation Village in the Berkshires

The Porches Inn at Mass MoCA

3.5 star property
North Adams
9.4 out of 10, Exceptional, (445)
"It is the perfect place to stay!"
United States
Darrell
$181 nightly
The price is $202
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Porches Inn at Mass MoCA

The Springs Motel

2.0 star property
New Ashford
9.2 out of 10, Wonderful, (87)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
$103 nightly
The price is $114
Dec 9 - Dec 10
Total with taxes and fees
The Springs Motel

Little Cat Lodge

2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (66)
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "
United States
kim
$169 nightly
The price is $189
Dec 8 - Dec 9
Total with taxes and fees
Little Cat Lodge

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (827)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Dec 8 - Dec 9
Total with taxes and fees
Howard Johnson by Wyndham Lenox

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
9.0 out of 10, Wonderful, (796)
"Place was great!"
United States
Benjamin
$152 nightly
The price is $169
Dec 8 - Dec 9
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Willows Motel Williamstown

2.0 star property
Williamstown
9.0 out of 10, Wonderful, (992)
"Warm welcome. Great location. Best fresh fruit breakfast ever."
United States
Melissa
$85 nightly
The price is $95
Dec 8 - Dec 9
Total with taxes and fees
Willows Motel Williamstown
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.

Find out more about Western Massachusetts

Discover top Western Massachusetts attractions

Western Massachusetts offers a serene escape for travelers seeking relaxation, with a variety of attractions that cater to families and those looking to unwind. Begin your exploration in the picturesque town of Stockbridge, where you can stroll through the lovely gardens of the Norman Rockwell Museum, showcasing the artist's iconic American illustrations. Just a short drive away, the tranquil landscapes of the Berkshires invite you to hike or bike along the scenic trails of Mount Greylock State Reservation, the highest peak in Massachusetts, offering breathtaking views and a chance to reconnect with nature. For a touch of culture, visit Tanglewood, the summer home of the Boston Symphony Orchestra, where you can enjoy outdoor concerts amidst lush surroundings. Families will love the interactive exhibits at the Springfield Science Museum, which offers a fun and educational experience for children of all ages. After a day of exploration, unwind at one of the region's hotels relaxing pools—consider staying in Lenox, a charming town with several upscale accommodations that feature luxurious amenities and attentive service. Here, you can enjoy a refreshing dip in the pool after a day of adventures, making it the perfect base for your Western Massachusetts getaway.

Top Western Massachusetts Hotel Reviews

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