Canaan Vacation Rentals from ￥16,158: Search Short-Term Rentals

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Vacation Rentals in Canaan

"Clean room, friendly staff, affordable."

￥18,761 total

includes taxes & fees

Sep 29 - Sep 30

"Staff was very nice and helpful. Property was a little bit outdated but very clean and functional. Surroundings are beautiful!!"

￥24,768 total

includes taxes & fees

Oct 19 - Oct 20

"Perfect place for a relaxing getaway! We loved everything! "

￥16,158 total

includes taxes & fees

Sep 28 - Sep 29

Indoor pool, outdoor pool, pool umbrellas, sun loungers

"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"

"Great stay!"

￥21,483 total

includes taxes & fees

Sep 28 - Sep 29

"Such a sweet spot in the woods! Can’t wait to come back."

￥27,035 total

includes taxes & fees

Sep 29 - Sep 30

"Kind and responsive host."

￥69,893 total

includes taxes & fees

Sep 28 - Sep 29

"Loved the property. Perfect for our gathering."

5 bedrooms, iron/ironing board, WiFi, bed sheets

￥90,602 total

includes taxes & fees

Oct 1 - Oct 2

"Amazing Inn. Cozy and everything we needed. "

￥164,003 total

includes taxes & fees

Sep 29 - Sep 30

"Beautiful, spacious house in a great location!"

"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "

"Excellent stay!"

￥119,342 total

includes taxes & fees

Sep 26 - Sep 27

"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."

￥27,257 total

includes taxes & fees

Sep 26 - Sep 27

"Very friendly hosts, great location. "

"Great property. Lots of space and activities for a large group. All amenities are well maintained and the owner was very responsive and helpful. Had a fantastic long weekend! "

"Great value, so much better than all the touristy motels in the area!"

￥30,645 total

includes taxes & fees

Sep 26 - Sep 27

"Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn"

￥50,534 total

includes taxes & fees

Oct 22 - Oct 23

"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "

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Top Canaan Hotel Reviews

The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"It's just a nice place and the staff is very nice "

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent

"Valerie at the front desk and who checked me in was above and beyond in customer service. She checked to see if I had a IGH account—which I did but had forgotten, and reminded me about the points and promotions. This Holiday Inn is a well managed property. Thank you"

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

10/10 Excellent

"We stayed for 5 nights and really enjoyed the surroundings and the drive to the property. The area is peaceful and quiet, with plenty to do for kids, including a mountain hike that even our 2- and 6-year-olds managed well. The grounds are beautiful for photos, very well maintained, and we often saw the crew cleaning and painting the sidewalks. I booked 2 suites, which were a good size for a family of four and offered plenty of space. The only downsides were that check-in felt a bit tedious it took several tries to swipe my card and there was no housekeeping service or follow-up to check on amenities during our stay. A self check-in option would make things smoother. Overall, we loved the quietness, the family-friendly activities, and the clean, well-kept property. With a few improvements in guest service, this could easily be a 5-star experience."

Find out more about Canaan

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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?

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table: This vacation home rental outside of Canaan is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals are there in Canaan?

Choose from 15 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.

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Canaan Vacation Rentals

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Vacation Rentals in Canaan

Cozy cabin in tranquil Canaan NY with WiFi, AC

Cozy cabin in tranquil Canaan NY with WiFi, AC

Vacation Village in the Berkshires

Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

Huttopia Berkshires

Huttopia Berkshires

The Ponds at Foxhollow

The Ponds at Foxhollow

Micosta Leisure Inn

Micosta Leisure Inn

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

The Kemble- Built by a US Secretary of State in Lenox

The Kemble- Built by a US Secretary of State in Lenox

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

Amore Estate - beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

The Lakeshore House

The Lakeshore House

Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Top Canaan Hotel Reviews

The Yankee, Trademark Collection by Wyndham

Find out more about Canaan

Find out more about Canaan

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

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