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Canaan Vacation Rentals

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In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

Vacation Rentals in Canaan

Exterior
Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very Good, (984)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
United States
Sandhya
The price is ￥22,860
￥25,534 total
includes taxes & fees
Nov 11 - Nov 12
Jiminy Peak Mountain Resort
Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2129)
"Clean and great pool and hot tub facilities "
United States
Alyce
The price is ￥14,074
￥17,403 total
includes taxes & fees
Nov 12 - Nov 13
Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas, sun loungers
The Ponds at Foxhollow

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
The Ponds at Foxhollow
Balcony
Micosta Leisure Inn

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (130)
"It's a beautiful little place with a wonderful owner. Rooms are clean and a good price"
United States
Gail
The price is ￥18,102
￥20,274 total
includes taxes & fees
Nov 21 - Nov 22
Micosta Leisure Inn
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

Lanesborough
9.6 out of 10, Exceptional, (67)
"Very cute! Perfect place for a weekend in the Berkshires"
United States
Melissa P.
The price is ￥20,712
￥31,852 total
includes taxes & fees
Nov 17 - Nov 18
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Property grounds
All the comforts of home

All the comforts of home

Hudson
9.2 out of 10, Wonderful, (27)
"Peaceful, friendly, clean, wish I had more time to explore and hope to return one day! Thank you!!"
United States
Barbara V.
The price is ￥16,293
￥21,686 total
includes taxes & fees
Nov 11 - Nov 12
All the comforts of home
Property grounds
All comforts of home

All comforts of home

Hudson
9.8 out of 10, Exceptional, (50)
"Very quaint and convenient to everything around. Gardens were beautiful and area was quiet."
United States
Catherine H.
The price is ￥15,051
￥20,292 total
includes taxes & fees
Nov 11 - Nov 12
All comforts of home
Exterior
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Hinsdale
9.8 out of 10, Exceptional, (33)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Hancock
10.0 out of 10, Exceptional, (4)
"This is my favorite unit of all the units I have stayed in! The pirate stuff was so cool and we could see our kids ski from the inside! The owner is so easy to communicate with. We love having the ability to cook and spread out while we are in the unit. We aaaaargh definitely going to stay here again!"
United States
Stephanie K.
The price is ￥16,109
￥35,988 total
includes taxes & fees
Nov 12 - Nov 13
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (14)
"Clean and quiet, nicely decorated! "
United States
Robert
The price is ￥19,791
￥53,296 total
includes taxes & fees
Nov 11 - Nov 12
UNIQUE - 1BR Country Condo @ Jiminy Peak
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel

Stephentown
10.0 out of 10, Exceptional, (3)
"Our stay exceeded our expectations! The property is beautiful with a cute patio and modern furnishings/appliances. It had a homey and clean vibe and Dillon was nice enough to provide snacks, oatmeal, coffee, creamer, toothbrushes, etc. Everything we could need! We brought our two dogs and they seemed right at home and love going on walks through the fall leaves. Would definitely recommend for those with dogs, small children, or just traveling on their own!"
United States
Anja H.
The price is ￥16,416
￥34,839 total
includes taxes & fees
Nov 11 - Nov 12
Berkshires Apartment at the Stephentown Hotel
Exterior
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Hancock
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is ￥16,109
￥35,988 total
includes taxes & fees
Nov 12 - Nov 13
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
1 bedroom, iron/ironing board, WiFi, bed sheets
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi

Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi

Hancock
10.0 out of 10, Exceptional, (1)
"Great!"
United States
Susan M.
The price is ￥16,109
￥35,988 total
includes taxes & fees
Nov 12 - Nov 13
Ski On Off Disney Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshi
Exterior detail
Bright Boho Apt in 18th c Berkshire Farmhouse

Bright Boho Apt in 18th c Berkshire Farmhouse

Lanesborough
9.0 out of 10, Wonderful, (22)
"Very nice. Attending a wedding in the area and really needed a place to get dressed and return to sleep. This fit the bill perfectly. Clean and comfortable we enjoyed our visit. Need to come back and visit the many sites in the area."
United States
Margaret K.
The price is ￥22,246
￥33,737 total
includes taxes & fees
Nov 11 - Nov 12
Bright Boho Apt in 18th c Berkshire Farmhouse
Exterior detail
Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake
10.0 out of 10, Exceptional, (13)
"We LOVED our stay! Cabins were spotless and the main building was just great! Waking up to a picture window behind us with all the fall colors in their glory was such a highlight. "
United States
Barb W.
The price is ￥19,178
￥28,099 total
includes taxes & fees
Nov 11 - Nov 12
Taborton Harvest Boulder Pines Cabin in the woods
Dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is ￥20,712
￥37,188 total
includes taxes & fees
Nov 13 - Nov 14
Sweet Cozy Victorian in Housatonic. Close to everything.
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
9.0 out of 10, Wonderful, (19)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is ￥23,320
￥60,313 total
includes taxes & fees
Dec 2 - Dec 3
Historic Berkshires Home Near Tanglewood, Trails & Wineries
2 bedrooms, iron/ironing board, free WiFi, bed sheets
A stunning, modern Lodge with rustic charm at June Farms!

A stunning, modern Lodge with rustic charm at June Farms!

West Sand Lake
10.0 out of 10, Exceptional, (4)
"Our stay at The Lodge at June Farms was amazing! Every little detail and more was thought of in the cabin!! It feels so welcoming and lots of memories were made!! We loved being able to walk down to the farm and see the animals. It’s winter and off season at the farm but I would love to come back when more is happening!!"
United States
Amie o.
The price is ￥62,135
￥111,885 total
includes taxes & fees
Nov 11 - Nov 12
A stunning, modern Lodge with rustic charm at June Farms!
Fridge, microwave, oven, stovetop
Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat

New Lebanon
9.6 out of 10, Exceptional, (22)
"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"
United States
Patty W.
The price is ￥26,235
￥64,093 total
includes taxes & fees
Nov 11 - Nov 12
Near Tanglewood: Historic Summer Retreat
Exterior
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock
9.4 out of 10, Exceptional, (16)
"We absolutely enjoyed this pleasant apartment. Its within the walking distance from the ski lifts which was perfect for all of us including 5 year old kid. "
United States
Janja
The price is ￥16,109
￥35,988 total
includes taxes & fees
Nov 12 - Nov 13
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
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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Top Canaan Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We came here because it was off season, great price, and it had an indoor pool. "
Monica 3-night trip
Posted 4 hours ago
Vacation Village in the Berkshires

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
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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?

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!: This vacation home rental outside of Canaan offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a fridge, a stovetop, and a coffee maker, so you can cook with friends or family. You can relax into your vacation with a garden and foosball.

How many vacation rentals are there in Canaan?

Choose from 13 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.