Canaan Vacation Rentals from ￥17,009: Search Short-Term Rentals

Q: What's the top vacation rental in Canaan?

Deluxe Queen Room with 2 Queen Beds : This vacation home rental outside of Canaan is equipped with an outdoor pool, air-conditioning, and WiFi to help you feel comfortable during your stay.

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Vacation Rentals in Canaan

"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...

￥22,571 total

includes taxes & fees

Jun 23 - Jun 24

"We had a wonderful time at the cabin by the lake. Beautiful views in the Morning!! Loved it."

"Great house in the woods. We were there for a spotting event so didn't spend a lot of time at the house. There were great walks around there"

"We had a wonderful stay. The cabin was clean and comfortable! "

"Great location near town and on a pretty lake. Owners easy to deal with and very responsive. Our family had a great trip to the Berkshires!"

"We had a great experience hiking the AT & enjoying the Berkshires and surrounding area. The home had everything we needed, was nicely decorated, and well stocked with all things from cookware to linens. Plenty of spaces in the home to gather as a group or family or separate for privacy. House is very convenient to Sheffield & Barrington where you’ll find plenty of restaurants & shopping. Brooks was great to quickly address any questions we had about the house or the area. Great home!"

"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "

"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"

"Another excellent experience stay at this house!"

"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."

"Property was very clean and had all amenities that we needed. It was perfect for a cozy winter getaway weekend. Would definitely stay there again! "

"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"

"Great location. "

"Had a lovely time at this lake house. The lake access was a plus and the house was well stocked with water accessories and food items. Otis is a short distance from Lee and Lenox providing easy Berkshire access. Having a garage to park the car in was also nice. The only downside is the relatively poor condition of the driveway / shared road the house is on. The neighborhood is made up of single lane dirt roads that have suffered from some wet weather. All in all would definitely recommend."

"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "

￥116,839 total

includes taxes & fees

Jun 23 - Jun 24

"The host was great and the property had everything we wanted and more. We will be back."

"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."

￥53,102 total

includes taxes & fees

Jun 24 - Jun 25

"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "

Smart TV, fireplace, table tennis, stereo

"Overall it was a great location for a relaxing girls trip. The hot tub and sunroom were great places to hang out. The pictures were very accurate of the house. We did have some issues with cleanliness and pests that we were not expecting. We would recommend it for a relaxing lakefront thing stay."

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

Sign in

Sign up, it's free

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!

Recent reviews of Canaan properties

Holiday Inn Express Hotel & Suites Great Barrington by IHG

5/5 Excellent

"Pleasant lobby, good breakfast, helpful staff, large room with frig."

A verified traveler stayed at Holiday Inn Express Hotel & Suites Great Barrington by IHG

Posted 23 hours ago

5/5 Excellent

"Beautiful, beautiful hotel and outstanding customer service and attention to detail. Not only was my room designed impeccably and clean, but there were free waters, snacks and freshly baked cookies available upon arrival. Their breakfast was outstanding (and free) and they had coffee, beverages and snacks available at all times of day - something almost all other hotels will charge you for. This is hospitality and going the extra mile to make customers happy. Love, love, loved my stay, thank you!"

A verified traveler stayed at The Litchfield Inn

Posted 4 days ago

Explore a world of travel with Expedia

All accommodation types in Canaan

Resorts in Canaan

Frequently asked questions

Are there vacation rentals in Canaan?

Yes, there are vacation rentals close to the most popular local attractions in Canaan, or you can select a more secluded option if you're looking for a relaxing stay. Canaan is known for its restaurants and coffeehouses.

What's the top vacation rental in Canaan?

Deluxe Queen Room with 2 Queen Beds: This vacation home rental outside of Canaan is equipped with an outdoor pool, air-conditioning, and WiFi to help you feel comfortable during your stay.

How many vacation rentals are there in Canaan?

Expedia has 5 vacation rentals for your stay in Canaan.

What’s there to see and do in Canaan?

Housatonic River and Eddy Field are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Connecticut Railroad Historical Museum and C H Pease Museum.

What’s a vacation rental in Canaan like?

Vacation rentals are private properties you can stay in for a long or short time in Canaan. Vacation rentals offer amenities such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for families.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Canaan Vacation Rentals

Check prices for these dates

Vacation Rentals in Canaan

Deluxe Queen Room with 2 Queen Beds

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

Beautiful retreat in a lake community to the enjoy the summer season.

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

Stay Lakeside This Summer!

4 Mi to Great Barrington: Berkshires Retreat!

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Large Barn styled vacation home that fits groups with space to spare.

Spectacular views and close to Great Barrington.

Peace and quiet on the lake

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Berkshire Lake at the Pillow, and EV!

Guesthouse Cabin vacation rentals in Berkshire County

Lakefront Summer Spectacular in New England Just 2 Hours From NYC

Exclusive Estate, Heated Yearround Outdoor Pool

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

Quintessential 6-BR Berkshires Lodge

Immaculate waterfront home nestled in the Litchfield hills w/ tons of...

Find out more about Canaan

Recent reviews of Canaan properties

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Quality Inn

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

The Red Lion Inn

Quality Inn

The Litchfield Inn

The Little Lion

Days Inn by Wyndham Torrington

Americas Best Value Inn Torrington CT

Explore a world of travel with Expedia

Frequently asked questions