East Chatham holiday lettings

We found 454 holiday rentals — enter your dates for availability

Discover a selection of 8 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:13 Feb - 20 Feb

Image gallery for Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Pool
10 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Ghent, NY

10% off
Price is £6,796
for 7 nights, 1 home
£971 per night
includes taxes & fees
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

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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)
  • Art Omi International Arts Center - Fields Sculpture Park (9.1 mi / 14.6 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 a holiday rental in East Chatham, New York, the area surrounding the picturesque East Chatham village centre is an excellent choice. This charming neighbourhood offers a delightful blend of rural beauty and convenient access to local attractions. Staying here allows you to enjoy the serenity of the countryside while being close to the vibrant local community.

One of the standout attractions nearby is the historic Chatham Town Park, which provides lovely walking trails and picnic areas, great for a leisurely afternoon. Additionally, the region is known for its scenic landscapes and outdoor activities, with opportunities for hiking and exploring the surrounding natural beauty.
How much does it cost to rent a holiday home in East Chatham?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in East Chatham to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for East Chatham holiday house rentals?
You can find great discounts on house rentals in East Chatham on Vrbo, 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.
Where are the best East Chatham ski resort rentals?
For ski resort rentals near East Chatham, New York, travellers should consider the nearby areas of Catamount Ski Area and Jiminy Peak. Catamount, located just a short drive away, offers a variety of rental options in the town of Hillsdale, which is known for its picturesque landscapes and quaint charm. Here, visitors can find rustic cabins and modern chalets featuring amenities such as wood-burning stoves, fully equipped kitchens, and spacious living areas that are superb for relaxing after a day on the slopes.

Further afield, in the direction of Jiminy Peak, which is a bit more of a drive but offers a larger ski area, the town of Hancock provides additional rental opportunities. Accommodations in this area often include ski-in/ski-out lodges and condos, equipped with amenities like hot tubs, fitness centres, and communal game rooms. Many properties also have easy access to local dining options and shops, enhancing the overall experience.
What is the most popular type of holiday rental accomodation in East Chatham?
In East Chatham, holiday houses are among the most popular rental options, with several available throughout the area. These properties typically provide spacious interiors, multiple bedrooms, and fully equipped kitchens, making them suitable for families or groups. Many also feature outdoor spaces, such as gardens or patios, superb for enjoying the serene surroundings. Additionally, there are several cabins and cottages that offer a rustic charm, often located in more secluded spots, which can enhance the getaway experience. Apartments are also available, providing a more compact and convenient option for travellers looking to explore the local area.
Are there any family house rentals in East Chatham?
In East Chatham, there are several family-friendly house rentals available, making it a lovely spot for a family getaway. This charming area features properties with ample living space, full kitchens for preparing meals, and inviting outdoor areas great for children to play and explore. Many homes also come equipped with amenities such as Wi-Fi and comfortable furnishings to ensure a pleasant stay.
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 or hot tubs. This charming area, set amidst the picturesque landscapes of the Hudson Valley, offers a tranquil escape for travellers. Many of these properties come equipped with private outdoor pools, hot tubs, and spacious decks, making them ideal for relaxation and entertaining.
Can I find long-stay holiday rentals in East Chatham?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in East Chatham?
In East Chatham, there are several pet-friendly house rentals available, great for travellers looking to enjoy a relaxing getaway with their furry companions. Many of these properties come equipped with amenities such as spacious gardens, outdoor seating areas, and fully fitted kitchens, allowing for a comfortable stay while providing a cozy feel.
Are there any remote work holiday rentals in East Chatham?
In East Chatham, New York, there are several remote work-friendly holiday rentals available, with around 11 options to choose from. This charming area, located amidst the scenic beauty of the Berkshires, provides a peaceful environment for those looking to blend work and leisure. Many of the properties come equipped with essential amenities such as high-speed Wi-Fi, dedicated workspaces complete with desks and comfortable chairs, and even computer monitors in some cases, catering specifically to remote professionals. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any East Chatham holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
What are popular rental amenities in East Chatham?
In East Chatham, popular rental amenities typically include kitchens, allowing guests to prepare their own meals during their stay. Many properties also feature patios, providing outdoor spaces to relax and enjoy the surrounding scenery. A common highlight among rentals is the mountain view, which adds to the tranquil atmosphere of the area. Additionally, amenities such as stovetops and cookware, dishware, and utensils are often offered, ensuring that guests have everything they need for a comfortable self-catering experience.
When is the best time to visit East Chatham for a holiday rental?
July is the most popular time to visit East Chatham, New York, when summer reaches its peak and the area buzzes with energy. During the months of June to August, visitors flock to the region to enjoy a variety of outdoor activities, from hiking the scenic trails to discovering local art galleries and enjoying the vibrant farmers' markets. This is a prime time for those who appreciate a lively atmosphere and the chance to mingle with fellow travellers.

In July, you can expect comfortable temperatures, typically ranging from the mid to high 20s Celsius, superb for exploring the charming surroundings. The lush greenery and picturesque scenery provide a beautiful backdrop for outdoor adventures, while the local events and festivals add to the delightful experience.

For those looking for a more budget-friendly option, consider planning your visit in December. During this time, this month offers a unique charm with picturesque winter landscapes and a chance to experience the tranquillity of East Chatham without the summer crowds.
How early should I book a East Chatham holiday rental?
Book your East Chatham holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my East Chatham home rental booking on Vrbo?
To find East Chatham holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the East Chatham holiday rental prices shown on Vrbo?
Vrbo 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.

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