Vacation rentals in Canaan

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Top-rated vacation rentals in Canaan

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Home in Canaan
Country Cottage
Quiet, peaceful cottage nestled on country road w/pond & stream. Located minutes from all season activites; lakes, concerts, theatre, horseracing, VT, MA, skiing, hiking,botanical garden, Tanglewood, Mass Moca, Mt. Greylock & more. Visit local Shaker round barn or simply barbeque on deck & enjoy the woods, flowers, wildlife & nature. Cottage has fully equipped kitchen. Local village has convenience store & Restaurants. Large grocery stores 15-20 mi Vehicle is vital for exploring the area.
Nov 6 – 13
$135 per night
5.0 out of 5 average rating, 131 reviews
Guest favorite
Tiny home in Chatham
Tiny House on 70 Private Acres in Hudson Valley
Welcome to "The Tiny" at The Hemptons in Upstate New York! The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Although we'd encourage you to check out many the local eateries (see below)! The bathroom is full size and likely bigger than the one in your first NYC apartment.
Jul 31 – Aug 7
$133 per night
4.99 out of 5 average rating, 176 reviews
Guest favorite
Farm stay in New Lebanon
Barn Stay at Shadowbrook Farm
Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. Farm tours are also available with a reservation. Instagram: @shadowbrook_farm
Aug 18 – 25
$182 per night
4.95 out of 5 average rating, 183 reviews

Popular amenities for Canaan vacation rentals

Other great vacation rentals in Canaan

Guest favorite
Home in Chatham
2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
Aug 22 – 29
$102 per night
4.9 out of 5 average rating, 143 reviews
Guest favorite
Cottage in Kinderhook
The Cottage on Sylvester Street
Jun 17 – 24
$124 per night
4.98 out of 5 average rating, 167 reviews
Guest favorite
Apartment in Copake Falls
Modern Copake Falls Getaway - 8 Mins to Catamount
Aug 29 – Sep 5
$92 per night
4.93 out of 5 average rating, 247 reviews
Guest favorite
Guest suite in Richmond
Ski/Private Ranch/Kid friendly/Pet Friendly/Horses
May 24 – 31
$171 per night
4.92 out of 5 average rating, 171 reviews
Guest favorite
Apartment in Canaan
Mountain View Getaway
Jan 10 – 17
$91 per night
5.0 out of 5 average rating, 81 reviews
Guest favorite
Home in Canaan
Private Retreat! Hot Tub, Pool Table & Movie Room
Aug 29 – Sep 5
$352 per night
5.0 out of 5 average rating, 8 reviews
Guest favorite
Home in Canaan
Secluded Mountain Top Lake View in Canaan, NY
May 13 – 20
$296 per night
5.0 out of 5 average rating, 17 reviews
Guest favorite
Home in Canaan
NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
Dec 31 – Jan 7
$257 per night
5.0 out of 5 average rating, 15 reviews
Guest favorite
Home in Canaan
Crossings Cottage
Oct 31 – Nov 7
$280 per night
4.95 out of 5 average rating, 20 reviews
Guest favorite
Farm stay in Canaan
Spacious farmhouse, beach access & private trails
Jun 12 – 19
$771 per night
5.0 out of 5 average rating, 21 reviews
Guest favorite
Farm stay in Pittsfield
Private 2nd-floor studio on a working produce farm
Jun 5 – 12
$106 per night
4.99 out of 5 average rating, 101 reviews
Guest favorite
Home in Canaan
Berkshire Lake House, gunite pool, Chef's Kitchen
Oct 12 – 19
$800 per night
4.99 out of 5 average rating, 68 reviews

Quick stats about vacation rentals in Canaan

Total rentals

10 properties

Local attractions

United States Postal Service, Sandy Klempner Antiques & Interiors, and Stoddard Field

Popular amenities

Gym, BBQ grill, and Laptop-friendly workspace

Wifi availability

10 properties include access to wifi

Total number of reviews

360 reviews

Nightly prices starting at

$40 before taxes and fees

Frequently Asked Questions

  • Do bed and breakfast rentals in Canaan have wireless internet?

    Absolutely! We offer over 10 bed and breakfast rentals with wireless internet in Canaan. Enjoy a tailored experience with all the comforts you desire.

  • Do bed and breakfast rentals in Canaan have air conditioning?

    Absolutely! We offer over 10 bed and breakfast rentals with air conditioning in Canaan. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in bed and breakfast rentals in Canaan?

    Experience the best of Canaan with our bed and breakfast rentals, starting at about $140 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for Bed And Breakfast Rentals in Canaan?

    Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with wireless internet, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Columbia County
  5. Canaan