Photo by Robin/Loving Life

Canaan holiday homes

We found 528 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in Canaan that are perfect for your trip. Whether you're going on holiday with family or friends, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a pool. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Canaan

Showing deals for:13 Nov - 20 Nov

Dining room with butcher block table
Terrace/patio
Queen bedroom
Property grounds
Exceptional
(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
NZ$4,651
for 7 nights, 1 home
NZ$664 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Dining
Private kitchen
Property grounds
Interior
Exceptional
(5 reviews)

Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak

Williamstown

20% off
NZ$3,554
for 7 nights, 1 room
NZ$508 per night
includes taxes & fees
Dog Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak
Reading nook with natural lighting
Fully screened porch!
Front Staircase
Dining Room w/ Doors to Screened Porch Dining Area
Exceptional
(7 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

12% off
NZ$6,567
for 7 nights, 1 home
NZ$938 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Interior
Property grounds
Interior
Exterior
Exceptional
(11 reviews)

Mountain View Retreat in Hudson Valley near Berkshire Attractions

Old Chatham

8% off
NZ$3,089
for 7 nights, 1 cottage
NZ$441 per night
includes taxes & fees
Mountain View Retreat in Hudson Valley near Berkshire Attractions
Interior
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$7,300
for 7 nights, 1 home
NZ$1,043 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Welcome Home!
The open-concept living space seamlessly blends the comfort of the living room with the functionality of the kitchen, all adorned by a double sided
Add a touch of warmth and charm to your dining experience!
Unwind and cherish moments together in the inviting warmth of the cozy living room.
Exceptional
(6 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
NZ$9,385
for 7 nights, 1 home
NZ$1,341 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Workstation with a view!
view from the 2nd bedroom
View from the lawn by the water
View of the lower deck from the sunroom
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
NZ$8,370
for 7 nights, 1 home
NZ$1,196 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Property grounds
Interior
Dining
Exterior
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,680
for 7 nights, 1 cabin
NZ$669 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Room
Interior
Living area
Exterior
Exceptional
(40 reviews)

A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.

Stephentown

7% off
NZ$2,957
for 7 nights, 1 home
NZ$422 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.
Country Inn heated pool & outdoor hot tub is open all year.  Towels are provided
Spring at Jiminy Peak 2019
Interior
Night skiing view from living room
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

12% off
NZ$9,611
for 7 nights, 1 home
NZ$1,373 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Front Gardens
Living Room
Kitchen
Property grounds
Exceptional
(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

South Lee

8% off
NZ$5,406
for 7 nights, 1 home
NZ$772 per night
includes taxes & fees
Secluded Family Home in Serene Stockbridge Woods
Living area
Living area
Private kitchen
Terrace/patio
Exceptional
(8 reviews)

Modern Log Chalet - 10 acres, views, and a pond!

Chatham

7% off
NZ$5,111
for 7 nights, 1 home
NZ$730 per night
includes taxes & fees
Modern Log Chalet - 10 acres, views, and a pond!
Blue House side entry from driveway
River view from window
Great room river view
dining area
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
NZ$4,289
for 7 nights, 1 home
NZ$613 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Beautiful, Spacious Living Room with high ceilings and floor to ceiling windows!
Create your special memories in our Bellavista Barn!
Beautiful Large In-Ground Heated Pool! Complete Privacy!
Enjoy Breakfast at kitchen table overlooking the pool & patios!
Exceptional
(98 reviews)

Incredible Estate: Pool, Pond, Gym, Arcade, Trails & more: Perfect Summer Vacate

Old Chatham

8% off
NZ$21,210
for 7 nights, 1 home
NZ$3,030 per night
includes taxes & fees
Incredible Estate: Pool, Pond, Gym, Arcade, Trails & more: Perfect Summer Vacate
Living room
Property grounds
Coming up the path from down by the creek
Living room
Exceptional
(10 reviews)

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

8% off
NZ$2,963
for 7 nights, 1 home
NZ$423 per night
includes taxes & fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Kitchen
Interior
Property grounds
Interior
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,640
for 7 nights, 1 home
NZ$949 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Main Level Living Area
The Deck at Christiansen's Tavern
Outdoor Pool near The Country Store
Outdoor dining
Exceptional
(24 reviews)

Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak

Hancock

8% off
NZ$8,927
for 7 nights, 1 home
NZ$1,275 per night
includes taxes & fees
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
Exterior
BBQ dinner not included :)
Interior
Interior
Exceptional
(10 reviews)

Family Fun in The Berkshires at Beautiful Hygge House

Richmond

8% off
NZ$6,278
for 7 nights, 1 home
NZ$897 per night
includes taxes & fees
Family Fun in The Berkshires at Beautiful Hygge House
Dining
Living area
Room
Property grounds
Exceptional
(40 reviews)

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Craryville

7% off
NZ$2,361
for 7 nights, 1 home
NZ$337 per night
includes taxes & fees
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior
Interior
Exterior
Interior
Exceptional
(5 reviews)

Chatham Cozy Country Retreat

Chatham

8% off
NZ$2,324
for 7 nights, 1 apartment
NZ$332 per night
includes taxes & fees
Chatham Cozy Country Retreat
another view of kitchen
new backyard table
another view of same bedroom as well as makeup table
Beaver Pond Pool/clubhouse
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Lanesborough

22% off
NZ$6,252
for 7 nights, 1 apartment
NZ$893 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Gorgeous open concept living room
Private kitchen
Quarter & Rift sawn white oak floors
Custom Chef's Kitchen with high end appliances from Bertazzoni and Fisher & Paykel
Exceptional
(11 reviews)

The Penthouse, Downtown Lenox by Evergreen Home

Lenox

11% off
NZ$7,784
for 7 nights, 1 apartment
NZ$1,112 per night
includes taxes & fees
The Penthouse, Downtown Lenox by Evergreen Home
Views from the back of the 16 acres on the property
View from 2nd floor balcony (after leaves have fallen)
Large Smart HDTV with electric fireplace in living room, showing dining room
Smart TV in Downstairs room with view of entrance to house and doors to room
Exceptional
(72 reviews)

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Williamstown

12% off
NZ$4,157
for 7 nights, 1 home
NZ$594 per night
includes taxes & fees
2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

The trendy city of Canaan awaits you

Enjoy the museums and other features of Canaan. Well known for its restaurants, shopping and local tours, this trendy city won't disappoint. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Canaan

Are you looking for top things to see and do while you're in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Canaan has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Bousquet Ski Area (8.5 mi / 13.8 km)
  • Wyndhurst Golf & Club (10.3 mi / 16.6 km)
  • Jiminy Peak Mountain Resort (12.7 mi / 20.4 km)
  • Catamount Ski Area (17 mi / 27.4 km)
  • Ski Butternut (17.1 mi / 27.5 km)
  • Furnace Brook Winery at Hilltop Orchards (3.4 mi / 5.4 km)

Exploring the natural features in Canaan

Whether you're an active traveller or just want to take in the scenery, Canaan is a great spot to appreciate mother nature. Here are some of the area’s most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Queechy Lake (1.7 mi / 2.7 km)
  • Stockbridge Bowl (8.4 mi / 13.5 km)
  • Berkshire Botanical Garden (9.5 mi / 15.3 km)
  • The Mount (9.9 mi / 15.9 km)
  • Naumkeag Museum (10.8 mi / 17.3 km)
  • Kinderhook Lake (11.1 mi / 17.8 km)

Travelling to and around Canaan

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 8 mi (12.9 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Hudson, NY (HCC-Columbia County), which is 15.8 mi (25.4 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Canaan?
The most sought-after types of holiday homes in Canaan are houses. Ready for more choices? Bookabach has a variety of options to match our guests' unique needs, so you'll see properties in all sizes and shapes. The perfect fit is waiting for you — discover yours today.
How much does it cost to rent a holiday home in Canaan?
A range of things affect how much you'll pay for a holiday home in Canaan, such as the season, type of property and length of stay. Still, all of our holiday homes have one thing in common — unbeatable value. Just add your travel dates to find your dream escape.
How much does it cost to rent a beach house in Canaan?
Prices for beach houses in Canaan will vary depending on the type and size of the property and when you're travelling. Simply enter your travel dates into Bookabach and the number of guests to view your holiday home options and prices. From there you can use our filter tool to narrow down your search by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday homes in Canaan?
Pack a travel bag for your canine companion because Canaan has 13 properties that throw open their doors to pets. Let your four-legged friend have fun with the family at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates then check our "Pets allowed" filter box.
Can I rent a house with a pool in Canaan?
Add a whole other level of fun to your getaway by booking your family into one of the three houses with a private pool in Canaan. Use our search filter to find the kind of property you want on Bookabach, and then spend your days splish-splashing around in a swimming pool that's for your use only.
What are popular home amenities in Canaan?
The most popular home amenities people look for in Canaan are a lake view, tennis and nearby museums. Whether you're on a trip with family, buddies or even pets, Bookabach holiday homes come with the best amenities for starting a new adventure with the people you cherish the most.
Are there large group holiday homes in Canaan?
With two properties that can host 10 people or more in Canaan, there's no need to keep anyone off the invite list. From family holidays to events like Christmas and birthday parties, Bookabach will help you find a large group home to suit the occasion.
Are there holiday homes in Canaan that welcome kids?
Canaan has 13 family-friendly holiday homes to choose from. And discovering a stay that welcomes kids is easy with Bookabach's "Properties good for families" filter. On top of having the whole place to yourselves, you'll enjoy access to conveniences and perks such as dining rooms, kitchens and yards.
What are the top attractions for families in Canaan?
Keep your kids busy at these fabulous family-friendly attractions in Canaan:
  • Shaker Museum and Library
  • Mount Lebanon Shaker Village
  • The Mac-Haydn Theatre
Are there holiday homes with WiFi in Canaan?
You can pick from six holiday homes with WiFi in Canaan. If you'd like to disconnect from daily life on your break, but still want to be connected to the internet, these properties are just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Canaan?
Canaan has eight holiday homes where you can spend your days in air-conditioned comfort. To book a property on Bookabach that offers this perk, enter your desired travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Canaan?
You'll have to check with the Canaan holiday property you'd like on Bookabach as the age limit varies. However, typically it's 16, 18 or 21.
How long can I rent a holiday home in Canaan for?
It all depends on the Canaan property. To view all available options offering extended stays, simply enter your dates and guest number into the Bookabach search page. You can enjoy having the entire place to yourself, along with amenities such as air conditioning, a kitchen and an outdoor space where the little ones can play. Be on the lookout for long-term stays that offer weekly or monthly discounts.