Hotels with Swimming Pools in Great Barrington

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Great Barrington Hotels with Swimming Pools

Our top choices for Great Barrington hotels with a pool

Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, pool loungers
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18 reviews)
"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
The price is S$332
includes taxes & fees
10 Feb - 11 Feb
Prospect Berkshires
Indoor pool
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (719 reviews)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is S$154
includes taxes & fees
26 Jan - 27 Jan
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (761 reviews)
"Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again."
United States
Dinh
The price is S$205
includes taxes & fees
29 Jan - 30 Jan
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior
The Little Lion

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548 reviews)
"Perfect for pets "
United States
Maria
The price is S$158
includes taxes & fees
14 Jan - 15 Jan
The Little Lion
Exterior
Charming 6 Bdrm Countryside Stay

Charming 6 Bdrm Countryside Stay

Charming 6 Bdrm Countryside Stay
3.0 star property
Great Barrington
The price is S$3,318
includes taxes & fees
7 Feb - 8 Feb
Charming 6 Bdrm Countryside Stay
Breakfast, lunch, dinner served; American cuisine
The Old Inn On The Green

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is S$473
includes taxes & fees
14 Jan - 15 Jan
The Old Inn On The Green
Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (16 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is S$200
includes taxes & fees
20 Jan - 21 Jan
Element Lenox Berkshires
Indoor pool, seasonal outdoor pool, pool loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Everything was great! "
Canada
Daphne
The price is S$145
includes taxes & fees
21 Jan - 22 Jan
The Yankee, Trademark Collection by Wyndham
2 indoor pools, 2 outdoor pools, pool umbrellas, pool loungers
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

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

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, (818 reviews)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is S$187
includes taxes & fees
20 Jan - 21 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (73 reviews)
"Very clean and friendly staff that go above and beyond for their guests even in a snow storm! "
United States
Kira
The price is S$176
includes taxes & fees
1 Feb - 2 Feb
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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 properties

Top Great Barrington Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Everything was great! "
Daphne 2-night trip
Posted 5 days ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

What are some accommodation options with pools in Great Barrington?
Prospect Berkshires: Features a sauna, an outdoor pool and spa services. Holiday Inn Express Hotel & Suites Great Barrington by IHG: Offers buffet, an indoor pool and complimentary high-speed (wired) Internet access. The Little Lion: Features full, an indoor pool and complimentary high-speed (wired) Internet access. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires: Provides a health club, an indoor pool and complimentary high-speed (wired) Internet access. Quality Inn Great Barrington: Features a seasonal outdoor pool, an indoor pool and buffet.
What is there to see and do in Great Barrington?
Surround yourself with nature at Housatonic River Walk and Housatonic River. During your stay, visit sights such as Mahaiwe Performing Arts Center, Ski Butternut and Monument Mountain. Travellers love Great Barrington for its array of dining options.
When is the best time to book a hotel with a pool in Great Barrington?
Taking the local weather in Great Barrington into account can help you maximise your time at the pool during your trip. The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Great Barrington are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

Explore a world of travel with Expedia