Photo by Robin/Loving Life

Find Hotels with a Pool in Canaan, NY

Start date: Check-in selected.
To Date
End date: Check-out

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Canaan Hotels with a Pool

Top Canaan Hotels with a Pool

Meeting facility
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (954)
"Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned."
United States
Stacey
$88 nightly
The price is $99
Nov 21 - Nov 22
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Indoor pool
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (692)
"Solid location, great room, good breakfast. Fair Price. Been 3 different times and look forward to returning again "
United States
Jamie
$102 nightly
The price is $114
Nov 16 - Nov 17
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Indoor pool, seasonal outdoor pool, sun loungers
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Great place. Friendly staff and very well located. Great breakfast options. "
United States
Abiezer
$100 nightly
The price is $112
Dec 7 - Dec 8
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham
Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.6 out of 10, Exceptional, (10)
"Very friendly with dog. No complaints with accommodations "
United States
Lilian
$135 nightly
The price is $151
Nov 20 - Nov 21
Total with taxes and fees
Element Lenox Berkshires
Indoor pool, outdoor pool, pool umbrellas
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2133)
"We came here because it was off season, great price, and it had an indoor pool. "
United States
Monica
$119 nightly
The price is $133
Nov 14 - Nov 15
Total with taxes and fees
Vacation Village in the Berkshires
Seasonal outdoor pool
The Springs Motel

The Springs Motel

2.0 star property
New Ashford
9.2 out of 10, Wonderful, (85)
"Love this place! I’ve stayed here several times. It is sweet and uncomplicated and convenient."
United States
Jennifer
$100 nightly
The price is $110
Nov 24 - Nov 25
Total with taxes and fees
The Springs Motel
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (753)
"Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome. "
United States
Jeff
$120 nightly
The price is $135
Nov 16 - Nov 17
Total with taxes and fees
Berkshire Mountain Lodge
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (821)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Nov 14 - Nov 15
Total with taxes and fees
Howard Johnson by Wyndham Lenox
Indoor pool
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (656)
"Lovely hotel, room was great along with the staff and the grounds where beautiful. Thank you."
United States
Vicki
$111 nightly
The price is $124
Nov 23 - Nov 24
Total with taxes and fees
Hilton Garden Inn Lenox Pittsfield
Indoor pool
Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

3.0 star property
Lenox
9.2 out of 10, Wonderful, (586)
"Fabulous place"
United States
Mary
$118 nightly
The price is $132
Dec 14 - Dec 15
Total with taxes and fees
Courtyard by Marriott Lenox Berkshires
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Canaan Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Good "
Joy 1-night trip
Posted 3 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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. Berkshire Mountain Lodge: Offers free self parking, an indoor pool, and complimentary wireless internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG: Provides a health club, an indoor pool, and complimentary wired internet access. Berkshires Untold: Features 3 restaurants, an outdoor pool, and spa services. The Black Swan Lee - Lenox, an Ascend Collection Hotel: Offers 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.

Explore a world of travel with Expedia