The Best Hotels with a Pool in Canaan, NY from NT$2,433 in 2026

Q: What are some hotels with pools in Canaan?

Vacation Village in the Berkshires : Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. The Yankee Inn : 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. The Red Lion Inn : Features 3 restaurants, an outdoor pool, and spa services. Berkshires Untold : Features buffet, an indoor pool, and free self parking.

A calm lake with reflections of the sky and trees, surrounded by lush greenery and hills.

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Our top choices for Canaan hotels with a pool

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

The Yankee Inn

Lenox

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

NT$6,800 total

includes taxes & fees

Jul 19 - Jul 20

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.

NT$5,541 total

includes taxes & fees

Jul 23 - Jul 24

Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

Williamstown

Family-friendly pools await at this Berkshires condo with indoor, outdoor, and kids' options.

NT$5,613 total

includes taxes & fees

Jul 19 - Jul 20

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.

NT$7,003 total

includes taxes & fees

Aug 10 - Aug 11

Hilton Garden Inn Lenox Pittsfield

Pittsfield

Serene indoor pool sanctuary offers year-round plunge spot at this Lenox-Pittsfield retreat.

NT$7,580 total

includes taxes & fees

Jul 19 - Jul 20

Comfort Inn & Suites East Greenbush - Albany

Castleton-on-Hudson

Dive into refreshing bliss at this East Greenbush hotel's indoor pool, complete with cozy sun loungers for ultimate relaxation.

NT$4,685 total

includes taxes & fees

Jul 26 - Jul 27

The Red Lion Inn

Stockbridge

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

NT$8,039 total

includes taxes & fees

Jul 23 - Jul 24

Howard Johnson by Wyndham Lenox

Lenox

Summertime splashes await at this refreshing outdoor pool oasis in Lenox.

NT$3,559 total

includes taxes & fees

Jul 27 - Jul 28

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Choose what matters most at hotels with a pool in Canaan

Breakfast included

4 stars

Top Canaan Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"absolute fav place!"

Jiminy Peak Mountain Resort

10/10 Excellent

"Everything about our stay was wonderful We made a last-minute decision just to go up for a night and we were able to use several amenities like the chairlift ride for sightseeing. The pool a few times which was at a very comfortable temperature just to get in and relax We were able to use their locker room to take showers before we left to go home on our trip The room was very clean. The bed was comfortable plenty of pillows to choose from. Every staff member we encountered were very accommodating and friendly"

The Black Swan Lee - Lenox, an Ascend Collection Hotel

8/10 Good

"I found the staff very helpful, especially the young man who worked over night. We experienced a slight problem, and he could not have been nicer. He represented the hotel extremely well. Breakfast was uninspiring but generally good. The view from the breakfast room is lovely. The common areas seem a little tired, but the room was very good value - especially as we overlooked the lake. The location is wonderful for Lee, Lenox, Stockbridge, all the cultural centers and the Mass Pike. A beach is adjacent for swimming. We plan to return next year."

Frequently asked questions

What are some hotels with pools in Canaan?

Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Features a children's pool, an indoor pool, and free self parking. The Yankee Inn: 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. The Red Lion Inn: Features 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Features buffet, an indoor pool, and free self parking.

What is there to see and do in Canaan?

The picturesque setting of Queechy Lake showcases the area's natural beauty. During your stay, check out sights such as Hollow FIelds Reserve, Hand Hollow State Forest, and Bates Memorial State Park.

When is the best time to book a hotel with a pool in Canaan?

Taking into account the local weather in Canaan 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 27°F. The snowiest months in Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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