North Canaan Holiday Rentals

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

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in North Canaan

Our top choices for North Canaan holiday rentals

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

8.8 out of 10, Excellent, (24)
"The cabin was great! Exactly as described and pictured. The kitchen was well stocked with all the basic cooking instruments and utensils. We had a blast and would absolutely come back."
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

9.6 out of 10, Exceptional, (223)
"Great place to get away from it all. Very quiet. Short drive to trailheads and restaurants and all the other hustle and bustle of the Berkshires."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating

Spacious 5-bedroom house in charming Lee with WiFi

The price is NZ$1,047
includes taxes & fees
29 Sept - 30 Sept
Spacious 5-bedroom house in charming Lee with WiFi

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is NZ$1,184
includes taxes & fees
24 Sept - 25 Sept
Guesthouse Cabin vacation rentals in Berkshire County

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (55)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

A Grand property in Historic Stockbridge

10.0 out of 10, Exceptional, (102)
"The Taggart House was a wonderful place to gather with friends and family to celebrate my birthday. The house is beautiful; the rooms are large; kitchen is great; bugs kept us from hanging out in the backyard but the conservatory was light and bright and a perfect spot for cocktails. We loved the proximity to the town of Stockbridge and we would walk back and forth a couple times a day. We had a couple of small issues, and Caitlin was very responsive in answering my questions/concerns. All in...
A Grand property in Historic Stockbridge

Peace and quiet on the lake

9.6 out of 10, Exceptional, (222)
"Comfortable home with amazing view. Enjoyed taking a walk around the lake (1 hour approx). Had an amazing dinner at Dream Away lodge which is 15 minutes away. "
Peace and quiet on the lake

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Everything was great...and beautiful!"
The price is NZ$689
includes taxes & fees
30 Sept - 1 Oct
The Blue Elm - A Historic Berkshire Cottage

Whispering Estate Guest House - A Romantic Countryside Getaway

10.0 out of 10, Exceptional, (3)
"Beautiful property and great location. A true retreat. "
The price is NZ$1,994
includes taxes & fees
25 Sept - 26 Sept
Whispering Estate Guest House - A Romantic Countryside Getaway

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

9.4 out of 10, Exceptional, (82)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

9.8 out of 10, Exceptional, (20)
"We had a wonderful time, the property is lovely and the house is delightful."
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

The Studio mini home away from home in the Berkshires

9.6 out of 10, Exceptional, (29)
"Great place to stay in Berkshires."
The Studio mini home away from home in the Berkshires

Garfield Townhouse in the Berkshires on Main St

10.0 out of 10, Exceptional, (15)
"Great location and comfortable."
Garfield Townhouse in the Berkshires on Main St

The Meadows House @ Otis Ridge w/ 7-person hot tub

9.6 out of 10, Exceptional, (37)
"We had a lovely time. Peaceful and cozy house, great private hot tub"
The Meadows House @ Otis Ridge w/ 7-person hot tub

Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

10.0 out of 10, Exceptional, (2)
"It's a wonderful house, lots of space to visit with family and the bed rooms were confortable and cozy. The host was very helpful and accesible at all times."
Woodland Retreat 4-Bedroom with Hot Tub, Fire Pit, and Woodstove

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (91)
"Enjoyed the property, location and charming house that was well stocked with everything we needed."
Antique Farmhouse Totally Restored

Private Island - Largest Fresh Water Reservoir in Mass

8.8 out of 10, Excellent, (8)
"We had a great time. The owner Bill was a great host."
Private Island - Largest Fresh Water Reservoir in Mass

The Race Mountain House

2.0 star property
9.2 out of 10, Wonderful, (5)
"I spent my 60th birthday with a few friends at Mountain House and it was even better than I dreamed. The comfort and simplicity of the decor along with the mountain views. A must for those who like simple elegance."
The Race Mountain House

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is NZ$668
includes taxes & fees
29 Sept - 30 Sept
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top North Canaan Hotel Reviews

Find out more about North Canaan

Find out more about North Canaan

Everything you need to know about North Canaan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the North Canaan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect North Canaan holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

North Canaan holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in North Canaan. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A North Canaan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of North Canaan holiday rentals we have selected for you start as low as NZ$668 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on North Canaan rentals

At Expedia, we put the best North Canaan holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top North Canaan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream North Canaan holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around North Canaan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in North Canaan?

Yes, there are holiday rentals close to the most popular sights in North Canaan, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that North Canaan has to offer?

Spacious 5-bedroom house in charming Lee with WiFi: This holiday home rental outside of North Canaan offers a fireplace, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a microwave can make your holiday run smoothly.

How many holiday rentals are there in North Canaan?

Choose from 8 Expedia holiday rentals in North Canaan for a memorable holiday.

What can I see and do in North Canaan?

Housatonic River and Lawrence Field are a couple of lovely local spots to get outside and enjoy nature. While here, Campbell Falls State Park and North Canaan Town Hall are other places worth a visit.

What are holiday rentals like in North Canaan?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in North Canaan. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which makes a holiday rental a great option for family trips or small group gatherings.