Compare Canann Village Historic District Cottage Rentals

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Featured Cottages in Canann Village Historic District

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!

New Marlborough MA
Guests staying at this cottage enjoy a gym, laundry facilities, and local meal delivery service. Other amenities at this family-friendly cottage include barbecue grills and a garden.
Kitchen
Washer
The Blue Elm - A Historic Berkshire Cottage

The Blue Elm - A Historic Berkshire Cottage

Sheffield MA
This cottage is a smoke-free cottage.
Kitchen
Free WiFi
Idillic summer getaway in Litchfield Hills, CT.

Idillic summer getaway in Litchfield Hills, CT.

Sharon CT
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Waterfront Cottage 10 Min From Great Barrington

Waterfront Cottage 10 Min From Great Barrington

New Marlborough MA
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
The Cottage at Highland Lake, year-round, waterfront with a boat dock

The Cottage at Highland Lake, year-round, waterfront with a boat dock

Winsted CT
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Free WiFi
Ashley Falls Home w/ Fire Pit: Hike & Ski!

Ashley Falls Home w/ Fire Pit: Hike & Ski!

3 out of 5
Ashley Falls MA
Guests staying at this cottage enjoy free WiFi in public areas and an arcade/game room. If you plan to drive, free parking is available.
Kitchen
Parking included
Private Island - Largest Fresh Water Reservoir in Mass

Private Island - Largest Fresh Water Reservoir in Mass

Otis MA
Guests staying at this cottage can enjoy a gym, barbecue grills, and a garden.
Kitchen
Pet friendly
Summer Lake Cottage, private beach, Berkshire Hills, small village

Summer Lake Cottage, private beach, Berkshire Hills, small village

Lakeville CT
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Pool & Private Acreage: Luxe Hudson Valley Home

Pool & Private Acreage: Luxe Hudson Valley Home

3 out of 5
Pine Plains NY
Guests staying at this cottage enjoy an outdoor pool, free WiFi in public areas, and barbecue grills. If you drive, take advantage of free parking. This smoke-free cottage also has a garden.
Pool
Kitchen
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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.

Hotel Options in Canann Village Historic District

    The Red Lion Inn

    The Red Lion Inn

    30 Main Street Stockbridge MA
    $180 nightly
    The price is $202 total per night from Jan 14 to Jan 15
    $202 total
    Jan 14 - Jan 15, 2026
    Total with taxes and fees
    8.6/10 Excellent! (1,000 reviews)
    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

    190 Meadow Street South Lee MA
    $139 nightly
    The price is $155 total per night from Dec 21 to Dec 22
    $155 total
    Dec 21 - Dec 22
    Total with taxes and fees
    9/10 Wonderful! (804 reviews)
    Quality Inn Great Barrington

    Quality Inn Great Barrington

    372 Main Street Great Barrington MA
    $76 nightly
    The price is $85 total per night from Jan 4 to Jan 5
    $85 total
    Jan 4 - Jan 5, 2026
    Total with taxes and fees
    8.4/10 Very Good! (1,003 reviews)

Cottages

Book a cottage in Canann Village Historic District
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Canann Village Historic District. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Canann Village Historic District better.

Cottage apartments in Canann Village Historic District range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Canann Village Historic District
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Canann Village Historic District and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Canann Village Historic District cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Canann Village Historic District. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Canann Village Historic District Cottages essential information

Accommodation
67 Cottages
Lowest Price
$85
Highest Price
$202
Popular accommodation
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly! , The Blue Elm - A Historic Berkshire Cottage, Idillic summer getaway in Litchfield Hills, CT., Waterfront Cottage 10 Min From Great Barrington, The Cottage at Highland Lake, year-round, waterfront with a boat dock , Ashley Falls Home w/ Fire Pit: Hike & Ski!, Private Island - Largest Fresh Water Reservoir in Mass, Summer Lake Cottage, private beach, Berkshire Hills, small village, Pool & Private Acreage: Luxe Hudson Valley Home