Best Resorts in East Canaan

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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21
In one month
Jan 2 - Jan 4
In two months
Jan 30 - Feb 1

Resorts in East Canaan

No exact matches found, but these alternatives could be just right

Recommended hotels in East Canaan

Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
$105 nightly
The price is $121
Dec 8 - Dec 9
Total with taxes and fees
Locust Tree Bed and Breakfast LLC
Exterior
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, (703)
"We stay here every year and it never disappoints "
United States
Elizabeth
$102 nightly
The price is $114
Dec 15 - Dec 16
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Desk, free cribs/infant beds, rollaway beds, free WiFi
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

2.0 star property
Torrington
7.4 out of 10, Good, (1002)
"Clean comfortable room,great parking and local shopping "
United States
Julie
$84 nightly
The price is $97
Dec 10 - Dec 11
Total with taxes and fees
Days Inn by Wyndham Torrington
Lobby
Quality Inn

Quality Inn

2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1000)
"Clean room, nice location "
United States
Devron
$76 nightly
The price is $85
Dec 21 - Dec 22
Total with taxes and fees
Quality Inn
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (803)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
$67 nightly
The price is $74
Dec 8 - Dec 9
Total with taxes and fees
Monument Mountain Motel
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
$190 nightly
The price is $213
Jan 5 - Jan 6, 2026
Total with taxes and fees
The Red Lion Inn
In-room safe, desk, free cribs/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
7.6 out of 10, Good, (562)
"The staff were very friendly and accommodating "
United States
Tom
$75 nightly
The price is $84
Dec 8 - Dec 9
Total with taxes and fees
Travelodge by Wyndham Great Barrington 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
$110 nightly
The price is $123
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Little Lion
Double Room | Egyptian cotton sheets, premium bedding, memory foam beds, desk
The Brooks Motel

The Brooks Motel

2.0 star property
Hillsdale
7.4 out of 10, Good, (118)
"Yes everything was perfect, just had a little trouble getting the WIFI for the TV set up! "
United States
Zenovia
$102 nightly
The price is $115
Dec 14 - Dec 15
Total with taxes and fees
The Brooks Motel
Egyptian cotton sheets, premium bedding, down comforters, minibar
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
$247 nightly
The price is $276
Jan 7 - Jan 8, 2026
Total with taxes and fees
Prospect Berkshires
Dinner served, American cuisine
the Alander

the Alander

2.5 star property
Copake
9.0 out of 10, Wonderful, (187)
"The Alander has such a fun story, and was a great stay. We were just passing through for the night and it had everything we could need! It reminded me of Rosebud Motel group from Schitts Creek ;) if you know you know! Will definitely be staying again!"
United States
Jenna
$140 nightly
The price is $157
Dec 9 - Dec 10
Total with taxes and fees
the Alander
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (757)
"Clean room, very courteous staff "
United States
Thomas
$127 nightly
The price is $142
Dec 14 - Dec 15
Total with taxes and fees
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Standard Room, 1 King Bed | Desk, iron/ironing board, free cribs/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

2.0 star property
Lee
6.4 out of 10, (649)
"Great place. , good staff "
United States
ketul
$63 nightly
The price is $70
Dec 21 - Dec 22
Total with taxes and fees
Econo Lodge Lee - Great Barrington
Lobby
Quality Inn

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1000)
"Clean room and good breakfast "
United States
Kelly
$91 nightly
The price is $101
Dec 28 - Dec 29
Total with taxes and fees
Quality Inn
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
South Lee
9.0 out of 10, Wonderful, (795)
"Place was great!"
United States
Benjamin
$152 nightly
The price is $169
Dec 8 - Dec 9
Total with taxes and fees
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Terrace/patio
The Abner Hotel

The Abner Hotel

3.0 star property
Litchfield Historic District
9.2 out of 10, Wonderful, (45)
"Spacious room and friendly staff "
United States
Frank
$217 nightly
The price is $250
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Abner Hotel
Seasonal outdoor pool
Sunset Inn

Sunset Inn

2.0 star property
Lee
7.6 out of 10, Good, (410)
"Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose "
United States
Kimberly
$90 nightly
The price is $101
Dec 8 - Dec 9
Total with taxes and fees
Sunset Inn
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Private kitchen | Mini-fridge, microwave, electric kettle
East Rock Inn

East Rock Inn

2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (36)
"We had a great stay at East Rock Inn! Newly remodeled, clean room, comfortable bed, easy access to town. I will definitely stay there again."
United States
Laura
$134 nightly
The price is $150
Jan 5 - Jan 6, 2026
Total with taxes and fees
East Rock Inn
Exterior
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Cozy 3 Flr Private 1 Bdrm Apt Tree Line View

Torrington
9.6 out of 10, Exceptional, (4)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
$298 nightly
The price is $342
Dec 8 - Dec 9
Total with taxes and fees
Cozy 3 Flr Private 1 Bdrm Apt Tree Line View
Seasonal outdoor pool
Little Cat Lodge

Little Cat Lodge

2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (66)
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "
United States
kim
$169 nightly
The price is $189
Dec 8 - Dec 9
Total with taxes and fees
Little Cat Lodge
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top East Canaan Hotel Reviews

the Alander

the Alander

10/10 Excellent
"Always a fun stay"
Richard 1-night trip
Posted 1 day ago
the Alander

Find out more about East Canaan

East Canaan Resorts information

Number of reviews
10,095
Accommodation
2 Resorts
Lowest Price
$70
Highest Price
$342

Frequently asked questions

What is East Canaan like for a resort vacation?
Longing for a relaxing escape? Indulge in the comforts and luxuries of a resort, where you can find everything you want for your vacation from tasty dining options to activities and shopping. Browse the resorts in the area and discover the one that's best for you, whether you picture yourself sipping drinks by a sprawling pool or hitting the golf course for an afternoon game.
What's a favorite resort for my stay in East Canaan?
Here's our top-rated resort near East Canaan: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 18.4 mi (29.6 km) from East Canaan. Features a sauna, a fitness center, and a terrace.
What can I do in East Canaan?
Beckley Furnace Industrial Park and Land of Nod Vineyard and Winery are a few of the interesting sights to visit. Other attractions in the area include Haystack Mountain State Park and Infinity Music Hall and Bistro.
What's the weather like in East Canaan?
The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in East Canaan are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around East Canaan?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 28.8 mi (46.3 km) away from the city center. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 29.5 mi (47.6 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia