Find Hotels with an Outdoor Pool in Great Barrington, MA

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Top Great Barrington Hotels with an Outdoor Pool

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
$250 nightly
The price is $280
Dec 10 - Dec 11
Total with taxes and fees
Prospect Berkshires

The Little Lion

3.0 star property
Great Barrington
8.6 out of 10, Excellent, (547)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
$110 nightly
The price is $123
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Little Lion

The Old Inn On The Green

4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90)
"Beautiful Inn and outstanding chef"
United States
Catherine
$336 nightly
The price is $368
Dec 10 - Dec 11
Total with taxes and fees
The Old Inn On The Green

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1008)
"Great stay!"
United States
Ann
$89 nightly
The price is $100
Dec 16 - Dec 17
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

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 10 - Dec 11
Total with taxes and fees
Howard Johnson by Wyndham Lenox

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1001)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
$183 nightly
The price is $205
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Red Lion Inn

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, (797)
"Place was great!"
United States
Benjamin
$131 nightly
The price is $147
Dec 11 - Dec 12
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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 10 - Dec 11
Total with taxes and fees
Little Cat Lodge

Berkshire Inn

2.0 star property
Pittsfield
7.8 out of 10, Good, (840)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
$82 nightly
The price is $92
Dec 15 - Dec 16
Total with taxes and fees
Berkshire Inn

Blackberry River Inn

3.0 star property
Norfolk
9.4 out of 10, Exceptional, (163)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
$164 nightly
The price is $189
Dec 10 - Dec 11
Total with taxes and fees
Blackberry River Inn
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 Great Barrington

Discover top Great Barrington attractions

Great Barrington, Massachusetts, is a charming town that offers a blend of relaxation and adventure for families seeking a tranquil getaway. Start your day with a visit to the picturesque Lake Mansfield, where you can enjoy a leisurely stroll or a picnic by the water, surrounded by breathtaking mountain views. For a bit of culture, explore the Norman Rockwell Museum, showcasing the beloved artist's iconic works, which can be a delightful educational experience for both adults and children. If you're in the mood for some outdoor fun, the nearby Catamount Ski Area offers year-round activities, from skiing in the winter to zip-lining and mountain biking in the summer, perfect for adventurous families. Don’t miss a visit to Main Street, lined with charming shops and local eateries, where you can savor farm-to-table cuisine and artisanal ice cream. For accommodations, the area surrounding Lake Mansfield features hotels with pools, providing a perfect retreat after a day of exploring. Enjoy the serene atmosphere while unwinding by the pool, and take advantage of the attentive service that ensures you feel pampered throughout your stay.

Find the best hotels with an outdoor pool in Great Barrington

For travelers looking to unwind by the water in Great Barrington, these hotels offer refreshing outdoor pool experiences alongside comfortable accommodations. Enjoy the perfect blend of relaxation and adventure.

The Old Inn On The Green

  • Why it's great for poolside lounging: Although The Old Inn On The Green does not feature an outdoor pool, its charm and luxurious amenities make it a delightful option for travelers seeking a unique experience. With a remarkable review rating of 9.2, this upscale inn offers a cozy atmosphere with features like a deep soaking bathtub and fireplace in many rooms, perfect for relaxation after a day of exploring.
  • Other amenities: Guests can indulge in complimentary breakfast and enjoy beautiful outdoor spaces including a terrace and garden. The inn also provides convenient self-parking and daily housekeeping services. While it's near ski areas, the focus here is on providing a peaceful, romantic setting with premium bedding and a friendly atmosphere.
  • Nearby attractions: Questing - 2.54 miles, Dry Hill - 2.77 miles, New Marlborough Town Hall - 3.34 miles

Top Great Barrington Hotel Reviews

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