The Best Monterey Hotels with Pools from $88 - Hotels with indoor pools in Monterey, MA

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

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Our top choices for Monterey hotels with a pool

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1. 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.

$128 nightly

$143 total

Sep 13 - Sep 14

Total with taxes and fees

2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers

Grand Villa, 3 Bedrooms | Iron/ironing board, cribs (free), WiFi, bed sheets

2. Holiday Inn Club Vacations Oak 'n Spruce Resort

South Lee

Float in mountain serenity at four incredible pools offering a perfect family-friendly oasis.

$135 nightly

$150 total

Sep 3 - Sep 4

Total with taxes and fees

Room, 1 Queen Bed, Mobility Accessible | Bathroom | Shower, free toiletries, hair dryer, towels

3. The Little Lion

Great Barrington

Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.

$111 nightly

$124 total

Sep 2 - Sep 3

Total with taxes and fees

4. The Red Lion Inn

Stockbridge

Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.

$218 nightly

$243 total

Sep 14 - Sep 15

Total with taxes and fees

5. 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.

$195 nightly

$217 total

Aug 24 - Aug 25

Total with taxes and fees

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

Superior Room, 1 King Bed, Jetted Tub | Jetted tub

Deluxe Room, 1 King Bed, Fireplace | Bathroom | Shower, free toiletries, hair dryer, towels

6. The Yankee Inn

Lenox

Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.

$158 nightly

$176 total

Sep 14 - Sep 15

Total with taxes and fees

Basic Double Room | Blackout drapes, iron/ironing board (on request), WiFi (free)

7. Sunset Inn

Lee

Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.

$99 nightly

$111 total

Sep 1 - Sep 2

Total with taxes and fees

8. Berkshire Mountain Lodge

Pittsfield

Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.

$125 nightly

$139 total

Aug 31 - Sep 1

Total with taxes and fees

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Choose what matters most at hotels with a pool in Monterey

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Top Monterey Hotel Reviews

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."

The Red Lion Inn

8/10 Good

"Maintenance problems in room. Property made up for it."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Lovely location on Laurel lake. Our balcony was directly over looking the lake. A wonderful spot for morning coffee and a book. Dogs are welcome! Well behaved, of course. A short drive to Lenox, Tanglewood and Stockbridge. Always coming back!"

The Yankee Inn

8/10 Good

"The stay was very good however the rooms are dated though well maintained. I felt the price was very high for the accommodations. I had expected more for the price ($350) but it was their peak season and they need to price accordingly. Certainly this Inn did not offer the feel or quality level of even a Holiday Inn or Hampton Inn. That being said it was very clean, the staff was very friendly and the breakfast was good."

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."

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: Features buffet, an indoor pool, and complimentary wired internet access. Berkshires Untold: Offers 3 restaurants, an outdoor pool, and spa services. FairBridge Inn Express: 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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Check availability on Monterey Hotels with a Pool

Our top choices for Monterey hotels with a pool

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