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

Find Hotels with a Pool in Monterey, MA

  • 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 Monterey Hotels with a Pool

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul

Our top choices for Monterey hotels with a pool

Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, sun loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
The price is SAR 478
SAR 533 total
includes taxes & fees
6 Jul - 7 Jul
The Yankee Inn
Desk, laptop workspace, iron/ironing board, free cribs/infant beds

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (576 reviews)
  • cleanliness
    Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
The price is SAR 421
SAR 470 total
includes taxes & fees
5 Jul - 6 Jul
The Little Lion
Seasonal outdoor pool

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (871 reviews)
  • cleanliness
    Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.
The price is SAR 292
SAR 326 total
includes taxes & fees
5 Jul - 6 Jul
Berkshire Inn
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
The price is SAR 664
SAR 909 total
includes taxes & fees
22 Jul - 23 Jul
The Red Lion Inn
Seasonal outdoor pool

Sunset Inn

Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (418 reviews)
  • cleanliness
    Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
The price is SAR 369
SAR 412 total
includes taxes & fees
6 Jul - 7 Jul
Sunset Inn
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (481 reviews)
  • cleanliness
    Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.
The price is SAR 253
SAR 284 total
includes taxes & fees
6 Jul - 7 Jul
Berkshire Travel Lodge
Seasonal outdoor pool

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (91 reviews)
  • cleanliness
    Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.
The price is SAR 571
SAR 640 total
includes taxes & fees
6 Jul - 7 Jul
Little Cat Lodge
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (120 reviews)
  • cleanliness
    Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.
The price is SAR 591
SAR 661 total
includes taxes & fees
8 Jul - 9 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Outdoor pool

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (879 reviews)
  • cleanliness
    Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
The price is SAR 372
SAR 415 total
includes taxes & fees
5 Jul - 6 Jul
Howard Johnson by Wyndham Lenox
Seasonal outdoor pool

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (190 reviews)
  • cleanliness
    Seasonal outdoor pool beckons at historic bed & breakfast with lobby fireplace and garden grounds.
The price is SAR 511
SAR 588 total
includes taxes & fees
6 Jul - 7 Jul
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.
View all properties

Choose what matters most at hotels with a pool in Monterey

Breakfast included
4 stars

Top Monterey Hotel Reviews

Quality Inn Great Barrington

Quality Inn Great Barrington

8/10 Good
"Room was small but fine. The bed was very comfortable. The staff member at the desk Amanda was very pleasant and helpful"
Ann Lauren 1-night trip
Posted 4 hours ago
Quality Inn Great Barrington

Explore a world of travel with Expedia

Frequently asked questions

What are some accommodations with pools in Monterey?
Lakefront Retreat with Stunning Views | Forget-Me-Not by AvantStay: Offers a seasonal outdoor pool, an indoor pool, and buffet. The Yankee Inn: Provides free self parking, an indoor pool, and complimentary wireless internet access. Berkshire Mountain Lodge: Offers 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Features buffet, an indoor pool, and complimentary wired internet access. The Red Lion Inn: Provides 2 indoor pools, 2 outdoor pools, and a snack bar/deli.
What is there to see and do in Monterey?
Spend some time experiencing the great outdoors at Bidwell House Museum and Lake Garfield. During your stay, check out sights such as Ashintully Gardens, Lake Buel, 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.