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Find Hotels with a Pool in Canaan, NY

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Check availability on Canaan Hotels with a Pool

Top Canaan Hotels with a Pool

Indoor pool
Element Lenox Berkshires

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
The price is ￥20,348
￥22,729 total
includes taxes & fees
Dec 24 - Dec 25
Element Lenox Berkshires
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (65)
"Very clean room, courteous staff. "
United States
Jeffrey
The price is ￥15,096
￥16,862 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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, (983)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is ￥14,302
￥15,975 total
includes taxes & fees
Dec 12 - Dec 13
Holiday Inn & Suites Pittsfield-Berkshires 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, (1008)
"Great stay!"
United States
Ann
The price is ￥13,904
￥15,531 total
includes taxes & fees
Dec 16 - Dec 17
The Yankee, Trademark Collection by Wyndham
Outdoor pool, open 6:00 AM to 10:00 PM, pool umbrellas, sun loungers
Prospect Berkshires

Prospect Berkshires

3.0 star property
Egremont
9.6 out of 10, Exceptional, (15)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ￥40,386
￥50,316 total
includes taxes & fees
Dec 10 - Dec 11
Prospect Berkshires
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (827)
"Staff was very friendly and helpful."
United States
Pamela
The price is ￥12,271
￥13,706 total
includes taxes & fees
Dec 18 - Dec 19
Howard Johnson by Wyndham Lenox
Indoor pool, open 8:00 AM to 10:00 PM, sun loungers
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1000)
"Clean, pleasant staff and good breakfast. "
United States
Edward
The price is ￥17,273
￥19,293 total
includes taxes & fees
Dec 20 - Dec 21
Hampton Inn & Suites Berkshires-Lenox
Indoor pool
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (781)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
Berkshire Mountain Lodge
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, (2168)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
The price is ￥16,150
￥19,744 total
includes taxes & fees
Dec 10 - Dec 11
Vacation Village in the Berkshires
Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
The Little Lion

The Little Lion

3.0 star property
Great Barrington
8.6 out of 10, Excellent, (547)
"The check-in was easy and the room was ready and clean. It was nice having our dogs with us. "
United States
Maria
The price is ￥17,086
￥19,086 total
includes taxes & fees
Jan 5 - Jan 6, 2026
The Little Lion
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.
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Top Canaan Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Clean spacious toom"
Daniel 2-night trip
Posted 2 days ago
Vacation Village in the Berkshires

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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: Offers buffet, an indoor pool, and free self parking. Comfort Inn & Suites East Greenbush - Albany: Features 3 restaurants, an outdoor pool, and spa services.
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.