Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

East Canaan Vacations

Pack those stellar shades. We have East Canaan vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to East Canaan – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with East Canaan vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to East Canaan

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great East Canaan vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows East Canaan well.

East Canaan Flight + Hotel packages

Top Hotel Deals

See all 77 Hotels in East Canaan
The Red Lion Inn

The Red Lion Inn

30 Main Street, Stockbridge
4.0 out of 5.0

This family-friendly Stockbridge hotel is located in the historical district, within a 15-minute walk of Mission House, Berkshire Theatre Festival, and Naumkeag. ...

$136

$136
Days Inn - Torrington

Days Inn - Torrington

492 East Main St, Torrington
2.0 out of 5.0

Situated in Torrington, this motel is within 1 mi (2 km) of Hotchkiss-Fyler House Museum, Warner Theater, and KidsPlay Museum. Connecticut Valley Winery is 3 ...

$68

$68
Days Inn Great Barrington

Days Inn Great Barrington

372 Main Street, Great Barrington
2.5 out of 5.0

Situated in Great Barrington, this motel is within 1 mi (2 km) of Mahaiwe Performing Arts Center and Lake Mansfield Park. W.E.B. Du Bois Boyhood Homesite is ...

$79

$79
Litchfield Inn BW Premier Collection

Litchfield Inn BW Premier Collection

432 Bantam Rd, Litchfield
4.5 out of 5.0

Situated in a rural location, this romantic inn is within 1 mi (2 km) of Livingston Ripley Waterfowl Conservancy and White Memorial Conservation Center. Litchfield ...

$105

$105
Rodeway Inn & Suites

Rodeway Inn & Suites

395 Winsted Rd, Torrington
3.0 out of 5.0

Situated in the historical district, this hotel is within 2 mi (3 km) of Hotchkiss-Fyler House Museum, Warner Theater, and KidsPlay Museum. Connecticut Valley ...

$75

$75
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

249 Stockbridge Rd, Great Barrington
3.0 out of 5.0

This family-friendly Great Barrington hotel is located in the mountains, within 2 mi (3 km) of Mahaiwe Performing Arts Center and Lake Mansfield Park. Ski Butternut ...

Monument Mountain Motel

Monument Mountain Motel

247 Stockbridge Rd, Great Barrington
3.0 out of 5.0

Situated in Great Barrington, this motel is within 3 mi (5 km) of Mahaiwe Performing Arts Center, Lake Mansfield Park, and Ski Butternut. W.E.B. Du Bois Boyhood ...

The Inn at Stockbridge

The Inn at Stockbridge

30 East Street, Stockbridge
4.5 out of 5.0

Situated in Stockbridge, this bed & breakfast is within 3 mi (5 km) of Berkshire Theatre Festival, Mission House, and Naumkeag. National Shrine of the Divine ...

Holiday Inn Club Vacations Oak n' Spruce Resort

Holiday Inn Club Vacations Oak n' Spruce Resort

190 Meadow Street, South Lee
4.0 out of 5.0

This aparthotel is in South Lee. Local attractions also include Berkshire Theatre Festival and Greenock Country Club.

Interlaken Inn & Resort

Interlaken Inn & Resort

74 Interlaken Road, Lakeville
3.5 out of 5.0

Situated on a lake, this hotel is close to Holley-Williams House Museum and Scoville Memorial Library. Area attractions also include Lime Rock Park and Great ...

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.