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Find Romantic Hotels in Canaan, NY

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Check availability on Canaan Romantic Hotels

Tonight
Dec 5 - Dec 6
Tomorrow
Dec 6 - Dec 7
This weekend
Dec 5 - Dec 7
Next weekend
Dec 12 - Dec 14

Top Canaan Romantic Hotels

Exterior
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 stay!"
United States
Ann
The price is NT$2,794
NT$3,122 total
includes taxes & fees
Dec 11 - Dec 12
The Yankee, Trademark Collection by Wyndham
Restaurant
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, (979)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is NT$2,875
NT$3,211 total
includes taxes & fees
Dec 12 - Dec 13
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Outdoor pool, sun loungers
The Red Lion Inn

The Red Lion Inn

3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1000)
"I love the ambience - historic and comfortable and excellent food. "
United States
Nancy
The price is NT$4,040
NT$5,912 total
includes taxes & fees
Jan 4 - 2026/1/5
The Red Lion Inn
Interior
Berkshires Untold

Berkshires Untold

3.5 star property
Lenox
9.0 out of 10, Wonderful, (806)
"We had a nice room and the food was delicious. Great place to stay. "
United States
Vincent
The price is NT$3,433
NT$3,835 total
includes taxes & fees
Dec 7 - Dec 8
Berkshires Untold
Front of property
Gedney Farm

Gedney Farm

3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (132)
"We loved our stay at Gedney. Michael was a sweetheart, and the grounds are GORGEOUS. We loved our room with fireplace - the whole setting is just country and updated/old. For anyone who loves farms and barns and rustic, this is for you. Can't wait to return."
United States
Lynda
The price is NT$5,808
NT$6,371 total
includes taxes & fees
Dec 7 - Dec 8
Gedney Farm
Exterior
Harbour House Inn

Harbour House Inn

3.5 star property
Cheshire
9.4 out of 10, Exceptional, (53)
"We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! "
United States
Lorie
The price is NT$8,212
NT$8,680 total
includes taxes & fees
Dec 8 - Dec 9
Harbour House Inn
Miscellaneous
1896 House Country Inn & Motels

1896 House Country Inn & Motels

2.5 star property
Williamstown
6.6 out of 10, (448)
"The price is good. It's a classic motel from the '50's, but gets the job done."
United States
edson
1896 House Country Inn & Motels
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
"I enjoyed the holiday inn. I enjoyed the staff made me fell at home. I enjoyed the comfortable atmosphere and the room was nice and clean. I enjoyed the breakfast very much. The staff was very friendly. "
Brendan 1-night trip
Posted 1 day ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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Frequently asked questions

Searching for romantic hotels in Canaan?
If you and your partner need a romantic escape, we've got just the ticket. If you'd like to explore some of the area's notable sights, you might make a stop by Queechy Lake, Hollow FIelds Reserve, or Hand Hollow State Forest. If you'd like to stay close to a particular destination, you can sort by neighborhood and proximity to top sights, so you'll be able to see everything on your list.
When is the best time of year for a romantic getaway to Canaan?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Canaan: 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.
What is there to do in Canaan?
There's nothing better than wandering around a new destination with your sweetheart, so consider checking out all there is to see and do in Canaan. You might think about stopping by Queechy Lake, Hollow FIelds Reserve, or Hand Hollow State Forest while you're seeing the sights.
What's the best way to get to Canaan and around town during my romantic getaway?
These transportation options in Canaan might help your romantic trip go off without a hitch: To get to Canaan, you can fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is the closest major airport, located 8 mi (12.9 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.