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Find Romantic Hotels in Canaan, NY

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Check availability on Canaan Romantic Hotels

Our top choices for Canaan romantic hotels

Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (984)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
The price is AED 340
AED 380 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
The Yankee, Trademark Collection by Wyndham

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 there!! Very friendly staff"
United States
Ann
The price is AED 275
AED 307 total
includes taxes & fees
24 Dec - 25 Dec
The Yankee, Trademark Collection by Wyndham
Outdoor pool, sun loungers
The Red Lion Inn

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 AED 549
AED 777 total
includes taxes & fees
6 Jan - 7 January 2026
The Red Lion Inn
Interior
Berkshires Untold

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (813)
"Easiest check in and out. Great food in dining room. "
United States
William
The price is AED 403
AED 450 total
includes taxes & fees
14 Dec - 15 Dec
Berkshires Untold
Fridge, microwave, oven, stovetop
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!
Lanesborough
9.8 out of 10, Exceptional, (269)
"The cottage was amazing. Hope to be visit again and again. "
United States
Mark M.
The price is AED 496
AED 759 total
includes taxes & fees
12 Dec - 13 Dec
Berkshire Village Carriage House - Super Private!!
Exterior
Harbour House Inn

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 AED 790
AED 835 total
includes taxes & fees
7 Jan - 8 January 2026
Harbour House Inn
Front of property
Gedney Farm

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 AED 681
AED 747 total
includes taxes & fees
18 Dec - 19 Dec
Gedney Farm
Miscellaneous
1896 House Country Inn & Motels

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
Fridge, microwave, oven, stovetop
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very Good, (12)
"Great location and property. thank you"
United States
Christine P.
The price is AED 482
AED 923 total
includes taxes & fees
14 Dec - 15 Dec
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Exterior
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (20)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
The price is AED 386
AED 862 total
includes taxes & fees
15 Dec - 16 Dec
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The best of the best A definite destination and accommodations"
Seth 1-night trip
Posted 3 days ago
The Red Lion Inn

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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.