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

Find Hotels with a Pool in Monterey, MA

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Check availability on Monterey Hotels with a Pool

Tonight
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Monterey hotels with a pool

Room
Pool
Exterior
Exterior

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.
￥19,741
￥22,051 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Grand Villa, 3 Bedrooms
Grand Villa, 3 Bedrooms
Pool
Exterior

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.
￥18,626
￥23,917 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Club Vacations Oak 'n Spruce Resort
Pool
Exterior
Breakfast meal
Lobby

3. 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.
￥25,575
￥28,567 total
includes taxes & fees
Sep 7 - Sep 8
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior
Exterior
Room, 2 Double Beds | Pet-friendly
Front of property

4. The Little Lion

The Little Lion
Great Barrington
  • Dive into the dreamy outdoor pool oasis near ski mountains and nature trails in The Berkshires.
￥17,910
￥20,005 total
includes taxes & fees
Sep 1 - Sep 2
The Little Lion
Outdoor pool
Bar (on property)
Exterior
Property grounds

5. The Red Lion Inn

The Red Lion Inn
Stockbridge
  • Escape to a historic haven with outdoor pool and loungers where relaxation flows freely.
￥23,572
￥34,240 total
includes taxes & fees
Sep 8 - Sep 9
The Red Lion Inn
Outdoor pool
View from room
Superior Room, 1 King Bed, Jetted Tub | Jetted tub
Deluxe Room, 1 King Bed, Fireplace | Bathroom

6. The Yankee Inn

The Yankee Inn
Lenox
  • Serene mountain hideaway offers sparkling pool oasis with both indoor and seasonal outdoor swimming.
￥24,209
￥27,041 total
includes taxes & fees
Sep 27 - Sep 28
The Yankee Inn
Pool
Deep soaking bathtub
Interior
Pool

7. Sunset Inn

Sunset Inn
Lee
  • Splash into a seasonal outdoor pool near Tanglewood Music Center, offering a sunny retreat in a peaceful location.
￥15,475
￥17,286 total
includes taxes & fees
Sep 1 - Sep 2
Sunset Inn
Pool
Lobby
Property entrance
Exterior

8. Berkshire Mountain Lodge

Berkshire Mountain Lodge
Pittsfield
  • Serene indoor pool sanctuary complements mountain adventures with sun loungers and rejuvenating hot tub experiences.
￥15,060
￥20,380 total
includes taxes & fees
Aug 31 - Sep 1
Berkshire Mountain Lodge
Restaurant
Thayer House, Room 201, 1 King bed, Jetted tub | Living area
Front of property
Interior

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.
￥50,755
￥61,246 total
includes taxes & fees
Sep 1 - Sep 2
The Old Inn On The Green
Exterior
Exterior
Gazebo
Bathroom

10. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
Lenox
  • Summertime splashes await at this refreshing outdoor pool oasis in Lenox.
￥12,577
￥14,048 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
"Charming hotel with a wonderful breakfast and two lovely pools, plus a nature walk to a lake. The staff were great, really nice and helpful."
Anne 1-night trip
Posted 5 hours ago
The Yankee Inn
The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The room was very nice, super clean. Sitting on the porch is what we love most. Food was good, drinks a bit pricey..but when you're on vacation it hardly matters. The pool was nice, the hot tub too. A pleasant stay in a historic inn. It's the berkshires so its beautiful"
wayne 2-night trip
Posted 7 hours ago
The Red Lion Inn
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

8/10 Good
"Room was clean and comfortable. Always nice to have a frig and microwave."
Maureen 1-night trip
Posted 5 days ago
Howard Johnson by Wyndham Lenox

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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