A lake surrounded by autumn-colored trees reflecting on the water.

Hotels with Swimming Pool in Monterey, Massachusetts

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Check availability on Monterey Hotels with Swimming Pool

Tonight
Aug 20 - Aug 21
Tomorrow
Aug 21 - Aug 22
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Monterey hotels with a pool

1. Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
Great Barrington
  • Relax in this riverside hotel with an indoor heated pool, where ski-day recovery meets year-round aquatic enjoyment.
P7,109
P7,941 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn Express Hotel & Suites Great Barrington by IHG

2. Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort
South Lee
  • Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.
P7,229
P9,283 total
includes taxes & fees
Sep 14 - Sep 15
Holiday Inn Club Vacations Oak 'n Spruce Resort

3. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
P6,951
P7,764 total
includes taxes & fees
Sep 2 - Sep 3
The Little Lion

4. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
P10,282
P14,556 total
includes taxes & fees
Sep 14 - Sep 15
The Red Lion Inn

5. Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Great Barrington
  • Refreshing indoor pool sanctuary near Ski Butternut lets guests swim year-round after mountain adventures.
P12,027
P13,434 total
includes taxes & fees
Aug 25 - Aug 26
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

6. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
P5,505
P6,150 total
includes taxes & fees
Sep 1 - Sep 2
Sunset Inn

7. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
P9,763
P10,905 total
includes taxes & fees
Sep 14 - Sep 15
The Yankee Inn

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
P5,848
P7,913 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge

9. The Old Inn On The Green

The Old Inn On The Green
Great Barrington
  • Dive into summer luxury at this historic inn's outdoor pool surrounded by garden serenity and natural wonders.
P19,699
P23,771 total
includes taxes & fees
Sep 1 - Sep 2
The Old Inn On The Green

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
P4,881
P5,452 total
includes taxes & fees
Aug 31 - Sep 1
Howard Johnson by Wyndham Lenox
View all properties

Choose what matters most at hotels with a pool in Monterey

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Monterey Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"What a wonderful stay! It was an impromptu overnight to the Berkshires and I’m so glad we chose to stay here. Our room was beautiful and clean, with a lovely view of the pond area out back from the balcony. Great bathroom and shower, very clean. Breakfast was yummy with a nice selection. The pools and hot tub were the BEST part. I absolutely will be back because one night was certainly not enough."
Kelly 1-night trip
Posted 9 hours ago
The Yankee Inn
Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"We only stayed a night but the rooms were clean enough and the staff was extremely kind. Would stay here again."
Sisile 1-night trip
Posted 12 hours ago
Quality Inn Great Barrington
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Perfect."
gordon 1-night trip
Posted 19 hours ago
The Red Lion Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"The motel is in a great location. You could walk to everything. The room was clean and comfortable although the air conditioning in the room didn't work very well. The fan ran but it didn't cool the room."
Jen 1-night trip
Posted 1 day ago
Howard Johnson by Wyndham Lenox
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"0nly 1 of 3 elevators was working. It was a 11 story building, and there was a lot of waiting. My room was wonderful, very clean, and with a fabulous view."
Linda 1-night trip
Posted 4 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

What are some accommodations with pools in Monterey?
The Yankee Inn: Offers a seasonal outdoor pool, an indoor pool, and buffet. Berkshire Mountain Lodge: Provides free self parking, an indoor pool, and complimentary wireless internet access. Berkshires Untold: Features buffet, an indoor pool, and complimentary wired internet access. FairBridge Inn Express: Offers 3 restaurants, an outdoor pool, and spa services. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG: Features free self parking, an outdoor pool, and flat-screen televisions.
What is there to see and do in Monterey?
Spend some time experiencing the great outdoors at Lake Garfield and Bidwell House Museum. Discover sights such as Mount Wilcox during your stay.
When is the best time to book a hotel with a pool in Monterey?
Taking into account the local weather in Monterey can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Monterey are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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