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Compare 480 Vacation Homes in Canaan with updated reviews, rates, and availability.

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"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...
The price is AED 437
AED 570 total
includes taxes & fees
4 Jun - 5 Jun
Deluxe Queen Room with 2 Queen Beds

Home w/ Fire Pit, Near Downtown Hudson + Skiing!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Lovely time; great property with comfortable furniture!!"
Home w/ Fire Pit, Near Downtown Hudson + Skiing!

Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

10.0 out of 10, Exceptional, (2)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.

10.0 out of 10, Exceptional, (19)
"We stayed here for skiing over a holiday weekend. The place was *very* clean and Tara was very responsive to helping with the only issue we had (which was weather related and not related to the house). The house is well outfitted and they also left a few basics for us in the kitchen which was a nice touch."
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

10.0 out of 10, Exceptional, (51)
"Great spot on the lake. Super quiet and relaxing."
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (10)
"Lots of cozy relaxation by the fire and fun meals at the spacious dinning table. We had plenty of room to spread out and enjoy ourselves. "
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House

Charming 3-bedroom house in the Catskills-Sleepy Hollow Lake community

10.0 out of 10, Exceptional, (3)
"Comfortable, clean , easy. "
Charming 3-bedroom house in the Catskills-Sleepy Hollow Lake community

Yacca House NEW Serene Retreat in Canaan

Yacca House NEW Serene Retreat in Canaan

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

10.0 out of 10, Exceptional, (20)
"The property was close to town and very cozy, clean & comfortable. Would highly recommend attention to the details was impressive."
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"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"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Stay Lakeside This Summer!

9.8 out of 10, Exceptional, (70)
"Perfect location for a peaceful, scenic vacation."
Stay Lakeside This Summer!

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (13)
"The house was perfect for our group of couples and young kids. Large bedrooms and beautiful property "
Quintessential 6-BR Berkshires Lodge

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (56)
"Perfect location and accommodation for my family. The home was as described. I would recommend it. The property owner was easy to work with. "
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Berkshire Lake at the Pillow, and EV!

9.4 out of 10, Exceptional, (15)
"Comfortable and relaxing spot. Really pretty lake. Fun stuff for paddling around the lake."
Berkshire Lake at the Pillow, and EV!

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

10.0 out of 10, Exceptional, (11)
"Very comfortable, clean home with all the amenities. We really enjoyed our stay in the beautiful area. Big yard for outdoor fun. Close to many attractions."
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

4 Mi to Great Barrington: Berkshires Retreat!

4 Mi to Great Barrington: Berkshires Retreat!

Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

10.0 out of 10, Exceptional, (2)
"We had a large family group, 10 people, for graduation weekend. This property was an easy drive from Albany—we had plenty of space in a nice, secluded area. We will definitely keep this property in mind for future events. "
Secluded w/ Deck Views, Hot Tub, & Ping Pong | Hudson in the Berks by AvantStay

Cozy log cabin in Lake Community.

10.0 out of 10, Exceptional, (19)
"It was quiet, cozy, spacious and clean!! So very inviting and we did not want to leave!!"
Cozy log cabin in Lake Community.

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

10.0 out of 10, Exceptional, (11)
"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"
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
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.
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