East Chatham holiday homes

We found 454 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other holiday rentals in East Chatham that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and garden. Whatever you're looking for, you'll be able to choose a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – East Chatham

Showing deals for:20 Nov - 27 Nov

Walnut dining table seats ten
Patio accessible from dining/kitchen
Front Door entrance
Double height, open kitchen and dining perfect for large vacation meals
Exceptional
(47 reviews)

Designer Home with Panoramic Views near Hudson

Ghent

7% off
NZ$7,127
for 7 nights, 1 home
NZ$1,018 per night
includes taxes & fees
Designer Home with Panoramic Views near Hudson
Property grounds
Terrace/patio
Screened in porch
Queen bedroom
Exceptional
(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
NZ$4,849
for 7 nights, 1 home
NZ$693 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Living area
Private kitchen
Exterior
Property grounds
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
NZ$9,519
for 7 nights, 1 home
NZ$1,360 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Outdoor dining
Kitchen with counter seating for 4- door on the right to garage
View from entry into living room- perfect spot for relaxing!
Property grounds
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
NZ$6,802
for 7 nights, 1 home
NZ$972 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Interior
Living area
Interior
Exterior detail
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$7,576
for 7 nights, 1 home
NZ$1,082 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
Unwind and cherish moments together in the inviting warmth of the cozy living room.
Add a touch of warmth and charm to your dining experience!
Exceptional
(7 reviews)

Idyllic Retreat; Hot Tub/Sauna by Evergreen Home

Great Barrington

11% off
NZ$9,742
for 7 nights, 1 home
NZ$1,392 per night
includes taxes & fees
Idyllic Retreat; Hot Tub/Sauna by Evergreen Home
Dining
Interior
Exterior
Property grounds
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,654
for 7 nights, 1 cabin
NZ$665 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
View from the lawn by the water
view from the 2nd bedroom
View of the lower deck from the sunroom
Open plan dining area with water views and access to the sunroom
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
NZ$8,324
for 7 nights, 1 home
NZ$1,189 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Living area
Interior
Room
Interior
Exceptional
(40 reviews)

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

Stephentown

8% off
NZ$2,881
for 7 nights, 1 home
NZ$412 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.
Private kitchen
Living area
Terrace/patio
Living area
Exceptional
(8 reviews)

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

Chatham

8% off
NZ$6,586
for 7 nights, 1 home
NZ$941 per night
includes taxes & fees
Modern Log Chalet - 10 acres, views, and a pond!
Front Gardens
Living Room
Back Porch
Kitchen
Exceptional
(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

South Lee

8% off
NZ$5,376
for 7 nights, 1 home
NZ$768 per night
includes taxes & fees
Secluded Family Home in Serene Stockbridge Woods
Great room river view
River view from window
Alfresco dining
dining area
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
NZ$4,265
for 7 nights, 1 home
NZ$609 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Living room
Property grounds
Living room
Exterior
Exceptional
(10 reviews)

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

Chatham

8% off
NZ$2,902
for 7 nights, 1 home
NZ$415 per night
includes taxes & fees
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Kitchen
Interior
Kitchen
Interior
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,603
for 7 nights, 1 home
NZ$943 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Exterior
Interior
Room
Exterior
Exceptional
(5 reviews)

Chatham Cozy Country Retreat

Chatham

8% off
NZ$2,366
for 7 nights, 1 apartment
NZ$338 per night
includes taxes & fees
Chatham Cozy Country Retreat
Dining
Private kitchen
Custom Chef's Kitchen with high end appliances from Bertazzoni and Fisher & Paykel
Gorgeous open concept living room
Exceptional
(11 reviews)

The Penthouse, Downtown Lenox by Evergreen Home

Lenox

11% off
NZ$8,007
for 7 nights, 1 apartment
NZ$1,144 per night
includes taxes & fees
The Penthouse, Downtown Lenox by Evergreen Home
  • 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

Choose a holiday rental for your East Chatham getaway

Learn about the unique charm of East Chatham with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around East Chatham

Are you hoping to discover attractions to visit while you're in the area? Venture out of your cosy holiday rental and check out everything that makes East Chatham a one-of-a-kind holiday spot. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Furnace Brook Winery at Hilltop Orchards (7.3 mi / 11.7 km)
  • Bousquet Ski Area (12.5 mi / 20.2 km)
  • Wyndhurst Golf & Club (14 mi / 22.5 km)
  • Jiminy Peak Mountain Resort (15.5 mi / 25 km)
  • Catamount Ski Area (17.1 mi / 27.5 km)
  • Ski Butternut (18.9 mi / 30.5 km)

Exploring the natural landscape of East Chatham

Whether you're an active traveller or just want to take in the scenery, East Chatham is a great place to get out in nature. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Queechy Lake (5.7 mi / 9.1 km)
  • Kinderhook Lake (7.3 mi / 11.8 km)
  • Stockbridge Bowl (11.8 mi / 19 km)
  • Berkshire Botanical Garden (12.3 mi / 19.8 km)
  • The Mount (13.4 mi / 21.6 km)
  • Naumkeag Museum (13.6 mi / 21.9 km)

Transport options to and around East Chatham

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 12 mi (19.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Hudson, NY (HCC-Columbia County), which is 12.5 mi (20.1 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in East Chatham?
The most sought-after types of holiday homes in East Chatham are houses. Searching for something different? Bookabach has plenty of options to match our guests' needs, so you'll see holiday properties in all shapes and sizes, and for all budgets. The ideal fit is ready and waiting for you — find yours today.
How much does it cost to rent a holiday home in East Chatham?
Several factors influence how much you'll pay for a holiday home in East Chatham, including the type of property, season and length of stay. Still, all of our holiday homes have something in common — incredible value. Simply enter your travel dates to find your ideal fit.
How much does it cost to rent a beach house in East Chatham?
The average price for a holiday home close to the beach in East Chatham depends on when you're visiting the area and the size and type of property you're searching for. Find prices easily and quickly on Bookabach by entering your preferred travel dates. Then use the handy filters to choose the number of bedrooms and amenities important to you, such as WiFi, air conditioning and a pool.
Are there pet-friendly holiday homes in East Chatham?
With six properties that welcome four-legged guests, your furry best friend can join in the fun on your East Chatham holiday. Use the filter tool to search our pet-friendly holiday homes and find a pad that'll set tails wagging on Bookabach.
Can I rent a house with a pool in East Chatham?
Mark the "pool" box in our filter tool and you'll find two houses with private pools in East Chatham on Bookabach. Morning swim, afternoon splash or midnight soak? Leisure time is your call when your holiday property boasts a swimming pool.
What are popular home amenities in East Chatham?
A garden, a sauna and a fireplace top the list of most popular home amenities in East Chatham. Whether you're planning to travel on your own, with your better half or a group of family members, Bookabach will help you find a holiday home that suits your style with all the options you need.
Are there large group holiday homes in East Chatham?
With two properties that can host 10 or more people in East Chatham, there's no need to hold back on your invites. From extended family holidays to special events like Christmas or New Year's Eve parties, Bookabach can help you find a large group home to match the occasion.
Are there holiday homes in East Chatham that welcome kids?
East Chatham has six family-friendly holiday homes to pick from. And booking a stay that welcomes kids is a breeze with our "Properties good for families" filter. Besides having the whole place to yourselves, you'll have access to perks and amenities like multiple bedrooms, kitchens and yards.
What are the top attractions for families in East Chatham?
You'll find lots of exciting things to see and do with the family in East Chatham, such as:
  • Shaker Museum and Library
  • Kinderhook Lake
  • Mount Lebanon Shaker Village
Are there holiday homes with WiFi in East Chatham?
Choose from four holiday homes with WiFi in East Chatham. If you'd like to disconnect from daily life on your escape, but still want to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in East Chatham?
You can choose from five Bookabach holiday homes with air conditioning in East Chatham offering that cooling breeze and extra touch of comfort. Simply enter your chosen travel dates and then make use of our filter tool to help you locate properties with air conditioning.
How old do you have to be to rent a holiday home in East Chatham?
We recommend you check with the East Chatham holiday home you're looking at on Bookabach as the minimum age varies. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in East Chatham for?
It's really down to the East Chatham property. To view all available options offering extended stays, just enter your travel dates and number of guests into the Bookabach search page. You can look forward to having the whole place to yourself, as well as amenities such as a fully-equipped kitchen, air conditioning and an outdoor space to play in. Keep an eye out for any long-term stays that offer discounted weekly or monthly prices.