East Chatham holiday homes

We found 453 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:25 Dec - 1 Jan

Open plan dining area with water views and access to the sunroom
view from the 2nd bedroom
View from the lawn by the water
Workstation with a view!
Exceptional
(66 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
NZ$10,172
for 7 nights, 1 home
NZ$1,453 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior
Private kitchen
Terrace/patio
Living area
Exceptional
(10 reviews)

Beautiful House in the Woods: Huge Yard, Hot Tub

Great Barrington

8% off
NZ$14,924
for 7 nights, 1 home
NZ$2,132 per night
includes taxes & fees
Beautiful House in the Woods: Huge Yard, Hot Tub
Dining area and small sitting are with flat screen TV. Stairs to second floor
Property grounds
House 1- Mountain views from this open concept kitchen, dining, sitting room
Welcome!
Exceptional
(7 reviews)

Grand Estate w/ Mountain Views by Evergreen Home

Ghent

11% off
NZ$11,998
for 7 nights, 1 home
NZ$1,714 per night
includes taxes & fees
Grand Estate w/ Mountain Views by Evergreen Home
Interior
Living area
Outdoor dining
Interior
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$8,092
for 7 nights, 1 home
NZ$1,156 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Exterior
Interior
Dining
Living area
Exceptional
(8 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,878
for 7 nights, 1 cabin
NZ$697 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Double height, open kitchen and dining perfect for large vacation meals
Patio accessible from dining/kitchen
Pool
Walnut dining table seats ten
Exceptional
(47 reviews)

Designer Home with Panoramic Views near Hudson

Ghent

6% off
NZ$8,849
for 7 nights, 1 home
NZ$1,264 per night
includes taxes & fees
Designer Home with Panoramic Views near Hudson
Private kitchen
Outdoor dining
Room
Living area
Exceptional
(11 reviews)

Glass Lake Cottage

Averill Park

8% off
NZ$6,306
for 7 nights, 1 home
NZ$901 per night
includes taxes & fees
Glass Lake Cottage
Living area
Interior
Exterior
Room
Exceptional
(43 reviews)

A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.

Stephentown

8% off
NZ$2,990
for 7 nights, 1 home
NZ$427 per night
includes taxes & fees
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Screened in porch
Terrace/patio
Queen bedroom
Property grounds
Exceptional
(103 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

11% off
NZ$5,374
for 7 nights, 1 home
NZ$768 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Blue House side entry from driveway
River view from window
dining area
Alfresco dining
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Housatonic

8% off
NZ$5,202
for 7 nights, 1 home
NZ$743 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Kitchen
Interior
Interior
Kitchen
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,853
for 7 nights, 1 home
NZ$979 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
Exterior
Interior
Interior
Exterior
Exceptional
(6 reviews)

Chatham Cozy Country Retreat

Chatham

8% off
NZ$2,598
for 7 nights, 1 apartment
NZ$371 per night
includes taxes & fees
Chatham Cozy Country Retreat
Living Room, wow!
Dining
Entry and living room
Interior
Exceptional
(17 reviews)

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

Richmond

17% off
NZ$4,414
for 7 nights, 1 apartment
NZ$631 per night
includes taxes & fees
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Room
Private entry is with the parking in the rear of the house.
Our hanging egg chair is the most popular seat in the house #Instagram yourself!
Exterior
Exceptional
(24 reviews)

New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.

Stockbridge

24% off
NZ$3,282
for 7 nights, 1 apartment
NZ$469 per night
includes taxes & fees
New Reno, New Everything! Crisp and Clean 2 Bedroom in Stockbridge Center.
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$9,464
for 7 nights, 1 apartment
NZ$1,352 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:

  • 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)
  • Furnace Brook Winery at Hilltop Orchards (7.3 mi / 11.7 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:

  • Kinderhook Lake (7.3 mi / 11.8 km)
  • Lenox Mountain (11.2 mi / 18 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 best area to stay in East Chatham when booking a holiday rental?
When considering the best area to stay in East Chatham, New York, for a holiday rental, the neighbourhood surrounding the village centre is an excellent choice. This area offers a charming blend of rustic charm and modern amenities. You'll find a selection of properties that cater to various preferences, from quaint cottages to more spacious homes, ensuring that there's something for everyone.One of the top attractions nearby is the picturesque Olana State Historic Site, which features stunning views of the Hudson River and beautiful grounds to explore. Additionally, the East Chatham area is not far from the vibrant town of Chatham, where you can enjoy delightful shops, local eateries, and cultural events, making it a superb spot for those looking to immerse themselves in local culture.Furthermore, the surrounding countryside offers plenty of opportunities for outdoor enthusiasts, including hiking trails and scenic drives.
Where are the best East Chatham ski resort rentals?
For ski resort rentals near East Chatham, the closest option is Jiminy Peak, located approximately 30 minutes away in Massachusetts. This family-friendly ski area offers a range of accommodations in nearby towns such as Hancock and Pittsfield. In Hancock, you can find cozy cabins and chalets that typically come with amenities like full kitchens, fireplaces, and outdoor decks, great for relaxing after a day on the slopes.In Pittsfield, you'll discover a mix of modern apartments and historic homes, many of which feature conveniences such as laundry facilities, Wi-Fi, and easy access to local shops and restaurants. These properties often cater to groups and families, providing ample space for everyone to unwind.Additionally, the surrounding Berkshires region is rich in natural beauty and offers plenty of outdoor activities beyond skiing, including hiking and snowshoeing.
What is the most popular type of holiday rental accomodation in East Chatham?
In East Chatham, holiday houses are the most popular type of holiday rental, with several available in the area. These houses typically offer spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also feature outdoor spaces such as patios or gardens, superb for enjoying the serene surroundings. Additionally, cabins and cottages are commonly found, providing a rustic charm and a closer connection to nature, often equipped with cozy living areas and outdoor seating. Apartments are also an option, though less common, offering a more compact stay with essential amenities.
Are there any family house rentals in East Chatham?
In East Chatham, New York, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. This charming area offers spacious homes that often come with ample living space, full kitchens for preparing family meals, and outdoor areas where kids can play and explore. Many properties also feature amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for the whole family.Visitors will find the picturesque countryside surrounding East Chatham superb for outdoor activities. Nearby attractions include the stunning landscapes of the Taconic State Park, which offers hiking trails suitable for all ages. Additionally, the quaint village atmosphere provides opportunities to discover local shops and eateries, enhancing the overall experience.
Can I rent a holiday home with a pool or hot tub in East Chatham?
In East Chatham, there are several holiday homes available for rent that feature pools and hot tubs, making it a lovely option for those seeking relaxation and leisure. This serene area in New York's Hudson Valley offers a picturesque setting, with properties often set amidst lush landscapes and tranquil surroundings. Travellers can expect amenities such as private swimming pools, hot tubs, spacious outdoor patios for entertaining, and fully equipped kitchens ideal for family gatherings.Additionally, many rentals provide comfortable living spaces and easy access to local attractions, including parks and nature trails.
Are there pet-friendly house rentals in East Chatham?
In East Chatham, there are several pet-friendly house rentals available, suiting those travelling with furry companions. Visitors can expect a variety of amenities in these properties, such as spacious backyards, outdoor seating areas, and fully equipped kitchens, providing comfortable accommodations for families or groups.The area is surrounded by scenic landscapes, with opportunities for outdoor activities that are pet-friendly. Nearby, the charming Chatham area offers parks and walking trails where pets are welcome, allowing owners to enjoy nature walks together. Additionally, the local community often features pet-friendly shops and cafes, enhancing the overall experience for visitors with pets.
Are there any remote work holiday rentals in East Chatham?
In East Chatham, there are several remote work-friendly holiday rentals available—approximately 11 in total. This picturesque area in New York offers a serene environment, great for those looking to balance work and relaxation. Many of these properties come equipped with amenities tailored for remote work, such as high-speed Wi-Fi, dedicated desks, and printer access, ensuring you can stay productive during your stay.The charming surroundings provide a peaceful backdrop, with opportunities for outdoor activities like hiking and exploring local parks after work hours. East Chatham also features a welcoming community with quaint shops and dining options nearby, making it an ideal location for both work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in East Chatham?
In East Chatham, popular holiday rental amenities include well-equipped kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature inviting decks or patios, superb for enjoying the fresh air and scenic views of the surrounding countryside. A fireplace is a common amenity, providing a cosy atmosphere, especially in the cooler months. Onsite parking is typically available, making it convenient for guests to explore the area without any hassle.
When is the best time to visit East Chatham for a holiday rental?
The best time to visit East Chatham for a holiday rental is during the peak season from June to August. July is particularly popular, drawing families and outdoor enthusiasts eager to soak up the summer sun while exploring the area's beautiful landscapes. This vibrant time of year is great for hiking, biking, and enjoying lakeside activities, providing plenty of opportunities for adventure and relaxation.During these summer months, temperatures typically range from 20 to 30 degrees Celsius, creating a delightful climate for sightseeing and outdoor pursuits. Whether you're wandering through charming local shops, visiting art galleries, or enjoying picnics in nearby parks, the atmosphere is lively and inviting.If you're looking for a more budget-friendly option, consider planning your visit in December. Although this month is quieter in terms of tourist activity, it offers a unique charm with the peacefulness of winter and the chance to enjoy holiday festivities in the area. The serene landscape, dusted with snow, creates a picturesque setting for a cosy retreat.
What are the top attractions in East Chatham?
In East Chatham, visitors can enjoy a tranquil rural setting with several attractions that highlight the area's natural beauty and cultural heritage. The nearby Chatham Fish and Game Club offers opportunities for outdoor activities like fishing and hiking, superb for nature enthusiasts. Additionally, the picturesque scenery of the surrounding hills and farmlands provides a lovely backdrop for leisurely drives or cycling.Art lovers may appreciate the proximity to the town of Chatham, which features charming shops and galleries showcasing local artists. The historic Chatham Town Hall, with its distinctive architecture, adds a touch of local history to the area. For those seeking a taste of the outdoors, the nearby Olana State Historic Site, the former home of painter Frederic Edwin Church, offers stunning views of the Hudson River Valley and beautiful walking trails.
Are all fees included in the East Chatham holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any East Chatham holiday homes with parking?
Bookabach offers a wide selection of holiday homes in East Chatham with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for East Chatham holiday homes?
You can find great discounts on holiday homes in East Chatham on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my East Chatham holiday home booking on Bookabach?
To find East Chatham holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in East Chatham?
A long-stay holiday home in East Chatham is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a East Chatham holiday home?
Book your East Chatham holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in East Chatham?
Prices for holiday homes in East Chatham vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in East Chatham to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.