Canaan Vacation Rentals from ￥17,365: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Canaan vacation rentals

1. Vacation Village in the Berkshires

Williamstown

Alex

￥18,301 total

includes taxes & fees

Sep 15 - Sep 16

2. Berkshire Mountain Lodge

Pittsfield

Robert

￥17,365 total

includes taxes & fees

Oct 1 - Oct 2

3. Micosta Leisure Inn

Hudson

Andrea

￥20,769 total

includes taxes & fees

Sep 7 - Sep 8

4. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Stephentown

￥86,504 total

includes taxes & fees

Sep 6 - Sep 7

5. Huttopia Berkshires

Williamstown

GEORGINA

￥15,932 total

includes taxes & fees

Oct 5 - Oct 6

View all properties

Find vacation rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Canaan Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Great stay!!"

The Yankee Inn

8/10 Good

"I did have some difficulty finding outlets for my phone and electronics chargers. The only spot was near the bathroom sink, which is not ideal. Breakfast was great; lots of choices and more than I expected. There was a little noise from the upstairs guest, which woke me out of a sound sleep. I didn't realize my room was direct to the outside and in the future, would choose a room inside the main building for security reasons. Convenient location and price was reasonable. I do plan to come back and utilize the amenities more."

Quality Inn Great Barrington

10/10 Excellent

"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"We had a fantastic stay at the Black Swan Inn in Lee, MA. Our room was incredibly clean, comfortable, and featured a beautiful view of the lake. Both check-in and check-out were completely hassle-free .A special shoutout goes to Carrie, the breakfast attendant! The breakfast area was exceptionally clean and well-stocked thanks to her hard work. Carrie was not only helpful, pleasant, and polite, but she also worked tirelessly to ensure all food items were fresh and fully available. Her excellent service truly made our mornings. We highly recommend this inn!"

Find out more about Canaan

Search for holiday rentals in Canaan on Expedia! You can easily find your home rentals, villas, holiday apartments in Canaan using one of the methods below:

View our selection of featured holiday rentals in Canaan
Use the map to find apartments and other holiday homes in the Canaan neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Canaan while they last

Look no further and take a look at our great range of rental properties in Canaan!

Frequently asked questions

Can I find vacation rentals in Canaan?

Yes, there are vacation rentals near popular points of interest in Canaan, or you can select a more secluded option if you want a relaxing place to stay. Canaan is known for its restaurants and coffeehouses. Make sure you have time to check out the shopping and local tours during your trip.

What's the top vacation rental in Canaan?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This vacation home rental outside of Canaan is located near skiing and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

How many vacation rentals are there in Canaan?

Choose from 7 Expedia vacation rentals in Canaan for a memorable vacation.

What’s there to see and do in Canaan?

Queechy Lake and Hollow FIelds Reserve are a couple of lovely local spots to get outside and enjoy nature. Hand Hollow State Forest and Bates Memorial State Park are other places to visit while you're in town.

What’s a vacation rental in Canaan like?

Vacation rentals are private properties you can book for several days or longer in Canaan. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular choice for a family getaway.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Canaan vacation rentals

1. Vacation Village in the Berkshires

2. Berkshire Mountain Lodge

3. Micosta Leisure Inn

4. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

5. Huttopia Berkshires

Find vacation rentals that suit your style

Top Canaan Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

The Yankee Inn

The Red Lion Inn

Berkshire Mountain Lodge

FairBridge Inn Express

Pocketbook Hotel and Bath

Quality Inn Great Barrington

Hotel On North

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Find out more about Canaan

Frequently asked questions

Go further with the Expedia app