The Best Hotels with a Pool in Canaan, NY from AED 323 in 2026

Q: What are some hotels with pools in Canaan?

Berkshire Mountain Lodge : Features free self parking, an indoor pool, and complimentary wireless internet access. Vacation Village in the Berkshires : Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. The Yankee Inn : Provides a seasonal outdoor pool, an indoor pool, and buffet. Quality Inn Great Barrington : Hotel, 15-minute walk from National Shrine of the Divine Mercy. Offers 3 restaurants, an outdoor pool, and spa services. Berkshires Untold : Provides buffet, an indoor pool, and free self parking.

Check availability on Canaan Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Canaan hotels with a pool

The Little Lion

Great Barrington

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

AED 361 total

includes taxes & fees

25 Jun - 26 Jun

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.

AED 587 total

includes taxes & fees

7 Jul - 8 Jul

The Red Lion Inn

Stockbridge

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

AED 736 total

includes taxes & fees

1 Jul - 2 Jul

The Springs Motel

New Ashford

Refreshing mountain retreat boasts a sparkling seasonal pool surrounded by lounging areas and firepits.

AED 426 total

includes taxes & fees

24 Jun - 25 Jun

Berkshire Mountain Lodge

Pittsfield

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

AED 658 total

includes taxes & fees

23 Jul - 24 Jul

Howard Johnson by Wyndham Lenox

Lenox

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

AED 406 total

includes taxes & fees

24 Jun - 25 Jun

Berkshire Inn

Pittsfield

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

AED 323 total

includes taxes & fees

25 Jun - 26 Jun

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.

AED 702 total

includes taxes & fees

6 Jul - 7 Jul

View all properties

Choose what matters most at hotels with a pool in Canaan

Breakfast included

4 stars

Top Canaan Hotel Reviews

The Yankee Inn

10/10 Excellent

"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."

The Red Lion Inn

8/10 Good

"I did not stay in the main building but had a room in a separate building on the same block. I quite liked my room away from the inn. It was roomy, quiet, across the street from a church, easy walk to the cafe, and there was a bunny 🐰 eating grass outside each night. I think I will request such a room away from the hubbub when I return. The food at the Red Lion's Inn's 'Widow's' tavern was delicious. Just know the buildings are indeed OLD so if you are seeking great water pressure or modern vibe, this is not your place. Love the history of this place!"

Spark by Hilton West Coxsackie

10/10 Excellent

"The location was very convenient. We had stayed here before but it was totally redone and beautiful. Staff was very friendly. Bed was very comfortable and room was beautiful. My favorite was the farm fresh yogurt machine you could add granola, nuts, cranberries and brown sugar to but had run out. The staff told me they would make more and it was close to 10:00 closing time for the continental breakfast! We would definitely go there again on our trip upstate!!!"

Comfort Inn & Suites East Greenbush - Albany

10/10 Excellent

"Clean and comfortable location for a stop traveling from OH to MA. Did not use the pool but good place for kids to let off energy. I was traveling with a dog and it was an additional $50 dollars. The location was right off the highway and there was a walking path and field to take your dog out safely."

Quality Inn Great Barrington

8/10 Good

"Room was clean and comfy except for the window A/C unit which quit working about an hour after we turned it on. Opened the windows later at night which helped some, but not a perfect temperature. Did not try the morning continental breakfast because we slept in too late and had to be home by a certain time for a gathering."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Had a wonderful stay. Staff is friendly and helpful. Breakfast was great, especially the automatic pancake maker. Had a wonderful dinner from Mint restaurant. The room was very clean and had the most comfortable hotel bed ever. The shower was a gleaming white as if it had never been used. The swan soap dish was a lovely touch. The view of the lake and mountains is spectacular. Would definitely stay here again."

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Find More Hotels near Canaan

Hotels near popular Canaan Attractions

Frequently asked questions

What are some hotels with pools in Canaan?

Berkshire Mountain Lodge: Features free self parking, an indoor pool, and complimentary wireless internet access. Vacation Village in the Berkshires: Condo, 14-minute walk from Jiminy Peak Mountain Resort. Offers a children's pool, an indoor pool, and free self parking. The Yankee Inn: Provides a seasonal outdoor pool, an indoor pool, and buffet. Quality Inn Great Barrington: Hotel, 15-minute walk from National Shrine of the Divine Mercy. Offers 3 restaurants, an outdoor pool, and spa services. Berkshires Untold: Provides 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.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Canaan Hotels with a Pool