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Monterey Hotel Guide - Hotels with Pool in Monterey, Massachusetts

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Check availability on Monterey Hotels with Pool

Our top choices for Monterey hotels with a pool

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 €133
includes taxes & fees
19 Jan - 20 Jan
Element Lenox 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, (718 reviews)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is €94
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Hotel & Suites Great Barrington by IHG
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, (1,001 reviews)
"Everything was great! "
Canada
Daphne
The price is €97
includes taxes & fees
19 Jan - 20 Jan
The Yankee, Trademark Collection by Wyndham
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (1,004 reviews)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is €94
includes taxes & fees
23 Jan - 24 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 €125
includes taxes & fees
14 Jan - 15 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Indoor pool, open 8:00 AM to 10:00 PM, pool loungers
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,001 reviews)
"Very comfortable beds! "
United States
Gerald
The price is €107
includes taxes & fees
25 Jan - 26 Jan
Hampton Inn & Suites Berkshires-Lenox
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 €106
includes taxes & fees
12 Jan - 13 Jan
The Little Lion
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 €232
includes taxes & fees
13 Jan - 14 Jan
Prospect Berkshires
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (810 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is €114
includes taxes & fees
1 Feb - 2 Feb
Berkshire Mountain Lodge
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828 reviews)
"Staff was very friendly and helpful."
United States
Pamela
The price is €76
includes taxes & fees
12 Jan - 13 Jan
Howard Johnson by Wyndham Lenox
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.
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Top Monterey Hotel Reviews

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Perfectly Clean. Great Service. Beautiful Place!"
Joseph 1-night trip
Posted 3 days ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

What are some accommodation options with pools in Monterey?
Holiday Inn & Suites Pittsfield-Berkshires by IHG: Features a health club, an indoor pool and complimentary high-speed (wired) Internet access. The Yankee, Trademark Collection by Wyndham: 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: Offers 3 restaurants, an outdoor pool and spa services. The Red Lion Inn: Features 2 indoor swimming pools, 2 outdoor swimming pools and a snack bar/deli.
What is there to see and do in Monterey?
Make a point to visit attractions such as Iroquis Waterfront and Berkshire Botanical Garden. Discover sights such as Bidwell House Museum during your stay.
When is the best time to book a hotel with a pool in Monterey?
Taking the local weather in Monterey 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 Monterey are January, March, February and November, with each month seeing an average of 18 cm of snowfall.