Hotels with Swimming Pool in Monterey, Massachusetts

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Check availability on Monterey Hotels with Swimming Pool

Our top choices for Monterey hotels with a pool

Indoor pool

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is P8,060
P9,003 total
includes taxes & fees
Mar 1 - Mar 2
Element Lenox Berkshires
Indoor pool, seasonal outdoor pool, sun loungers

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,006 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is P5,372
P6,001 total
includes taxes & fees
Mar 1 - Mar 2
The Yankee, Trademark Collection by Wyndham
Exterior

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (833 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is P4,001
P4,469 total
includes taxes & fees
Feb 18 - Feb 19
Howard Johnson by Wyndham Lenox
Indoor pool

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (844 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is P6,610
P8,678 total
includes taxes & fees
Feb 18 - Feb 19
Berkshire Mountain Lodge
Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (168 reviews)
"Courteous welcoming staff, amazing breakfast, and restful stay, highly recommend."
United States
Paulina
The price is P9,028
P10,383 total
includes taxes & fees
Feb 22 - Feb 23
Blackberry River Inn
Indoor pool

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, (734 reviews)
"Great property, very accommodating. "
United States
Shanice
The price is P6,205
P6,930 total
includes taxes & fees
Mar 1 - Mar 2
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (553 reviews)
"Great friendly staff"
United States
Pablo
The price is P6,378
P7,125 total
includes taxes & fees
Feb 18 - Feb 19
The Little Lion
Indoor pool

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,007 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is P5,915
P6,607 total
includes taxes & fees
Mar 7 - Mar 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (843 reviews)
"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
The price is P4,986
P5,570 total
includes taxes & fees
Feb 22 - Feb 23
Berkshire Inn
Property grounds

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,000 reviews)
"As always, our stay at The Red Lion Inn was memorable. Everything was top notch."
United States
Gary
The price is P8,640
P12,241 total
includes taxes & fees
Mar 18 - Mar 19
The Red Lion 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.
View all properties

Choose what matters most at hotels with a pool in Monterey

Breakfast included
4 stars

Top Monterey Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Pool and hot tub are terrific, great breakfast spread, convenient location, super comfortable mattress. Clean."
Emma 1-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

What are some accommodations with pools in Monterey?
Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. The Yankee, Trademark Collection by Wyndham: Provides a seasonal outdoor pool, an indoor pool, and buffet. Berkshires Untold: Offers 2 indoor pools, 2 outdoor pools, and a snack bar/deli. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG: Features a health club, an indoor pool, and complimentary wired internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Provides 3 restaurants, an outdoor pool, and spa services.
What is there to see and do in Monterey?
Spend some time experiencing the great outdoors at Bidwell House Museum. During your stay, check out sights such as Lake Buel, Tyringham Cobble, and Ski Butternut.
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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