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

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

Pittsfield

Indoor pool sanctuary in the Berkshires offers extended hours and a hot tub to soothe tired muscles.

NT$6,546 total

includes taxes & fees

Aug 9 - Aug 10

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$6,798 total

includes taxes & fees

Jul 15 - Jul 16

Berkshire Travel Lodge

Austerlitz

Splash into sunny days at this motel's refreshing outdoor pool, complete with terrace views and garden surroundings.

NT$2,433 total

includes taxes & fees

Jul 26 - Jul 27

Sunset Inn

Lee

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

NT$3,955 total

includes taxes & fees

Jul 22 - Jul 23

Howard Johnson by Wyndham Lenox

Lenox

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

NT$3,560 total

includes taxes & fees

Jul 26 - Jul 27

Berkshire Inn

Pittsfield

Experience seasonal poolside bliss at this central motel with comfortable modern rooms and helpful staff for a relaxing getaway.

NT$3,236 total

includes taxes & fees

Jul 27 - Jul 28

Deep-tissue massages, Swedish massages, facials, 5 treatment rooms

Pocketbook Hotel and Bath

Hudson

NT$9,610 total

includes taxes & fees

Jul 15 - Jul 16

Little Cat Lodge

Copake Falls

Soak up mountain charm at the seasonal pool where forest meets relaxation at this renovated lodge.

NT$7,952 total

includes taxes & fees

Aug 12 - Aug 13

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Choose what matters most at hotels with a pool in Canaan

Breakfast included

4 stars

Top Canaan Hotel Reviews

Quality Inn Great Barrington

10/10 Excellent

"Comfortable rooms within walking distance to Great Barrington."

Comfort Inn & Suites East Greenbush - Albany

8/10 Good

"Room was spacious and clean. The lobby and common areas were also spacious and comfortable. All the seating areas in the lobby with the sun coming in was a nice place to spend a few minutes in the morning. Breakfast was good, enough to get us through the day. We didn’t have time to use the amenities, but they looked nice. Overall, would definitely recommend a stay there."

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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Our top choices for Canaan hotels with a pool