East Chatham vacation rentals

We found 457 vacation rentals — enter your dates for availability

Discover a selection of 8 homes and other vacation rentals in East Chatham that are perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll have the amenities you expect and more, which might include parking and a garden. Whatever you're looking for, you'll be able to choose a rental that has what everyone needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - East Chatham

Showing deals for:Feb 27 - Mar 6

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

11% off
Price is $1,134
$7,935 for 7 nights
All fees included
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

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Find out more about East Chatham

Why visit East Chatham

  • Outdoor Adventures: East Chatham is perfect for nature lovers, offering activities like hiking, fishing, and exploring serene lakes.
  • Historic Charm: Visit historic houses that showcase the rich history and culture of the area.
  • Family-Friendly Excursions: The area is ideal for family vacations with various activities catering to all ages.
  • Cozy Accommodations: Enjoy a range of vacation rentals, from cottages to condos, ensuring a comfortable stay.
  • Local Hospitality: Experience the warm welcome of the locals and explore nearby neighborhoods for a true taste of community.

Popular types of accommodation in East Chatham

Discover the charm of East Chatham, NY, with a variety of vacation rentals tailored to your needs. From houses and cozy cottages to modern condos, there's something for everyone. Whether you're searching for rental listings or apartments in Chatham and East Chatham, our platform offers transparency and reassurance in finding the perfect getaway. Start your adventure today and explore the best rentals this picturesque area has to offer.

  • Houses: The top choice for travelers in East Chatham, offering spacious and comfortable stays perfect for families or groups.
  • Condos: A popular option for those seeking modern amenities and convenience, ideal for couples or small families.
  • Cottages: Charming and cozy, cottages provide a quaint escape, perfect for a peaceful retreat.
  • Apartments: A versatile choice for visitors looking for flexibility and a home-like atmosphere during their stay.
  • Cabins: Rustic and inviting, cabins offer a unique experience for nature lovers and those wanting to unwind.**

Top attractions in and around East Chatham

East Chatham, New York, offers a perfect blend of outdoor adventures and romantic getaways, making it an ideal destination for travelers seeking culture and family experiences. Explore historic houses, enjoy the serene lakes, and visit the local library, all of which highlight the charm of this quaint area. Whether you're looking for an adventurous outing or a peaceful retreat, East Chatham has something for everyone.

  • Shaker Museum and Library: Discover the unique culture and history of the Shaker community at this museum located 4 miles from East Chatham. Explore its exhibits showcasing their innovative crafts, spiritual beliefs, and communal living.
  • National Shrine of the Divine Mercy: Situated 14 miles away, this serene shrine offers a peaceful atmosphere for reflection and prayer, surrounded by beautiful grounds that enhance its spiritual ambiance.
  • Meizinger Lake: Enjoy a romantic outdoor getaway at Meizinger Lake, located within East Chatham. With its scenic views and beach, it's perfect for relaxation and recreation.

Things to do recommended for couples

For a romantic getaway in East Chatham, enjoy a concert at Tanglewood Music Center, indulge in wine tasting at Furnace Brook Winery, or hit the slopes together at Jiminy Peak Mountain Resort. Each location offers a unique atmosphere perfect for couples seeking adventure and romance.

Things to do recommended for families

During your family vacation in East Chatham, explore the wellness vibes at Kennedy Park, only 13 miles away. For thrill-seekers, the Alpine Super Slide, 15 miles from town, offers an exhilarating ride. Don't miss Mosher Park, also 15 miles away, perfect for relaxation and recreation.

Things to do recommended for groups

Your group can enjoy a captivating show at the Mac-Haydn Theatre, indulge in local shopping at Charles H. Baldwin & Sons, or embark on an adventure at the Berkshire Retreat Center, all within a short drive from East Chatham for a memorable experience.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in East Chatham

If you're traveling with a group, family, pets, or planning an extended stay, be sure to apply the right filters to meet your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to East Chatham with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to East Chatham with young kids: Traveling with little ones can be demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, thinking about how close you are to family-friendly attractions is wise.
  • Taking your pets with you to East Chatham: For many families, a vacation wouldn’t feel complete without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting East Chatham: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near East Chatham

East Chatham, New York, offers a delightful blend of outdoor adventures and romantic getaways. Nestled in the beautiful eastern portion of the state, this charming area is perfect for family-friendly excursions and budget-friendly trips. Explore nearby cities and neighborhoods to experience the warm hospitality of the locals and the stunning natural landscapes. Whether you're seeking relaxation or adventure, East Chatham and its surroundings have something for everyone.

  • Lenox: Located 13 miles from East Chatham, Lenox is a vibrant city known for its entertainment scene and romantic ambiance. This charming destination attracts visitors with its rich cultural offerings, including music concerts and theatrical performances. Adventure seekers will appreciate the nearby ski areas in the winter months. The stunning landscapes feature picturesque lakes and majestic mountains, providing perfect backdrops for outdoor lovers. Additionally, Lenox hosts various events at its conference venues, making it a hub for gatherings and celebrations.
  • Old Chatham: Only 3 miles from East Chatham, Old Chatham is an idyllic small town renowned for its outdoor experiences and scenic beauty. Nature enthusiasts can enjoy various recreational activities, from skiing in the winter to exploring the local lakes and mountain trails. The town is also home to cultural attractions such as theaters and concert venues, ensuring a lively atmosphere year-round. The historic charm of Old Chatham, adorned with beautiful landscapes, makes it a perfect romantic getaway for couples looking to unwind in a serene setting.
  • Canaan: Situated 4 miles from East Chatham, Canaan is an outdoor adventure paradise that caters to thrill-seekers and nature lovers alike. With its proximity to ski fields and resorts, this city is a favorite for winter sports enthusiasts. The surrounding natural beauty, including lakes and mountains, provides ample opportunities for hiking, fishing, and enjoying the great outdoors. Canaan also features the nearby national state park, offering visitors a chance to immerse themselves in stunning landscapes and diverse wildlife, making it an exciting stop for those seeking adventure.

Best time to go to East Chatham

If you're planning a trip to East Chatham, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in June to July and September, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.4°F (-4.2°C)Light RainMostly CloudySlightly LowAverage
February26.2°F (-3.2°C)Light RainMostly CloudyAverageAverage
March34.2°F (1.2°C)Light RainMostly CloudyAverageSlightly Low
April45.7°F (7.6°C)Light RainMostly CloudyAverageSlightly Low
May57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
June65.3°F (18.5°C)Light RainMostly SunnySlightly HighAverage
July71.6°F (22.0°C)Light RainMostly SunnySlightly HighSlightly High
August69.6°F (20.9°C)Light RainMostly SunnyAverageSlightly High
September62.6°F (17.0°C)Light RainMostly SunnySlightly HighAverage
October51.4°F (10.8°C)Light RainMostly SunnyAverageSlightly Low
November39.2°F (4.0°C)Light RainMostly SunnySlightly LowAverage
December31.1°F (-0.5°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to save money on your upcoming trip? Being flexible with your travel dates can help, as prices can vary significantly. Additionally, booking a longer stay often leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your reservation. Being the planner has its perks. When you join our travel rewards program, One Key, you can immediately access member discounts and earn OneKeyCash on eligible bookings. Sign up now and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, continue from where you last stopped, or manage your travel arrangements. You’ll see your saved or booked properties organized into categories like Potential, Upcoming, and Current Trips. To begin using Trip Boards, simply head over to: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your East Chatham getaway

Learn about the unique charm of East Chatham with a stay in a private vacation home. You'll find plenty to explore during your stay in the area. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Activities and attractions in and around East Chatham

Are you searching for top things to see and do in the city? Venture out of your cozy vacation rental and check out everything that makes East Chatham a fun spot to vacation. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Hudson Chatham Winery (9.1 mi / 14.6 km)

Exploring the natural landscape of East Chatham

Whether you're looking for adventure or just want to appreciate the scenery, East Chatham 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 center:

  • Queechy Lake (5.7 mi / 9.1 km)
  • Kinderhook Lake (7.3 mi / 11.8 km)
  • Lenox Mountain (11.2 mi / 18 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)

Transportation 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 center. If you can't find a flight that works for your travel itinerary, you could book a flight to 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 vacation rental?
When considering a vacation rental in East Chatham, New York, the area surrounding the quaint village center is an excellent choice. This neighborhood offers a charming small-town vibe and easy access to local amenities, making it a convenient base for your stay. With a variety of properties available, ranging from cozy cottages to larger homes, you'll find options that cater to different group sizes and preferences.

Staying near the village center allows you to explore the beautiful Chatham area and enjoy attractions like the nearby East Chatham Historic District, where you can admire picturesque architecture and learn about the local history. Additionally, the nearby Ooms Conservation Area provides lovely trails for hiking and birdwatching, great for those looking to immerse themselves in nature.

Another appealing option is to consider properties near the scenic lakes and parks in the region. This area not only offers stunning views but also proximity to recreational activities like fishing and kayaking. Here, you can relax and unwind in a serene environment while still being close to the vibrant local culture and attractions.
How much does it cost to rent a vacation home in East Chatham?
Prices for vacation 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 vacation 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 areas for renting a beach house in East Chatham?
For renting a beach house in East Chatham, New York, the nearby area of Chatham offers beautiful coastal experiences. The picturesque beaches along the Cape Cod Bay are a short drive away, particularly in the town of Chatham, which features charming beach homes with stunning ocean views. Many of these properties come equipped with amenities such as outdoor decks, spacious living areas, and direct access to the beach, making them ideal for families or groups looking to enjoy a seaside getaway.

Additionally, the surrounding neighborhoods near the Chatham Lighthouse Beach provide options for vacation rentals that often include spacious yards and outdoor grilling areas, great for summer barbecues after a day in the sun. The area is also known for its quaint downtown, where travelers can explore local shops, restaurants, and art galleries, adding a vibrant community feel to the beach retreat.

For those who enjoy outdoor activities, the nearby Monomoy National Wildlife Refuge offers opportunities for kayaking, birdwatching, and hiking, with rentals often featuring easy access to these natural attractions.
Where are the best East Chatham ski resort rentals?
For ski resort rentals near East Chatham, travelers should look towards nearby ski areas like Catamount Ski Area, located just a short drive away in Hillsdale, Massachusetts. This area offers a selection of cozy lodges and vacation homes that cater to families and groups looking to hit the slopes. Many of these properties feature essential amenities such as fully equipped kitchens, comfortable living spaces with fireplaces, and easy access to outdoor activities.

In the town of Chatham itself, visitors can find charming inns and bed-and-breakfasts that provide a warm, homey atmosphere, often with breakfast included. These accommodations typically offer amenities such as cozy common areas, private bathrooms, and some even have access to hot tubs or outdoor seating areas, great for relaxing after a day of skiing.

For those willing to venture a bit further, the towns of Great Barrington and Pittsfield also provide additional rental options. Here, travelers can find cabins or mountain lodges that often come with modern conveniences like Wi-Fi, outdoor fire pits, and expansive decks with scenic views of the surrounding landscapes. These rentals allow for quick access to not just skiing but also hiking and other winter sports, making it an excellent base for outdoor enthusiasts.
What is the most popular type of vacation rental accomodation in East Chatham?
In East Chatham, vacation houses are a popular choice, with several available throughout the area. These houses typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups seeking a comfortable home base. Many also include outdoor spaces like decks or gardens, great for enjoying the serene surroundings. Additionally, there are several cottages and cabins that offer a cozy, rustic charm. These rentals often come with unique amenities such as fireplaces and proximity to local hiking trails and nature spots.
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 traveling with children. This charming area offers a mix of spacious homes located amid the scenic beauty of the Hudson Valley. Many properties boast amenities like large living rooms, fully equipped kitchens for family meals, and outdoor areas that are great for kids to play or for family gatherings.

Visitors will appreciate the proximity to local attractions such as the picturesque Chatham Village, where they can explore boutique shops and enjoy local dining.
Can I rent a vacation home with a pool or hot tub in East Chatham?
In East Chatham, there are several vacation homes available for rent that feature pools and hot tubs, making it a great choice for travelers seeking relaxation and leisure. This picturesque area in upstate New York offers a tranquil setting surrounded by beautiful landscapes, great for a peaceful getaway.

Travelers can expect a variety of amenities in these rentals, including private pools for cooling off during warm days, hot tubs for unwinding in the evenings, and spacious outdoor areas for enjoying the fresh air. Many properties also come equipped with fully stocked kitchens, cozy living spaces, and modern conveniences like Wi-Fi and air conditioning.
Can I find long-stay vacation rentals in East Chatham?
A long-stay vacation rental in East Chatham is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in East Chatham?
In East Chatham, travelers can find several pet-friendly house rentals that cater to those looking to enjoy a getaway with their furry companions. Many of these homes are set against a picturesque backdrop of the Hudson Valley, providing a serene environment for relaxation. Expect to find amenities such as spacious backyards, fully equipped kitchens, and cozy living areas that make these rentals ideal for families or groups.

The area is also well-suited for outdoor activities with pets, as there are nearby parks and walking trails, allowing you to explore the beautiful countryside. Additionally, East Chatham is conveniently located near local shops and restaurants, enhancing the overall experience for visitors.
Are there any remote work vacation rentals in East Chatham?
In East Chatham, New York, there are about 11 vacation rentals that cater to remote workers. This picturesque town, located in the heart of the Berkshires, offers a serene environment ideal for productivity. Many of these rentals come equipped with essential amenities for remote work, including desks, ergonomic chairs, high-speed Wi-Fi, and even computer monitors in some properties, ensuring a comfortable workspace during your stay.

The area is surrounded by beautiful landscapes, making it great for breaks or after-work relaxation. Nearby attractions include local parks and hiking trails, which provide excellent opportunities for outdoor activities. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any East Chatham vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in East Chatham with parking available—perfect for families or travelers 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 vacation rental amenities include WiFi, kitchens, patios, and decks, along with stunning mountain views. These features allow travelers to enjoy a comfortable stay while taking in the beautiful surrounding landscape. Rentals typically provide the convenience of cooking facilities, making it easy for guests to prepare their meals while enjoying the outdoors. The patios and decks offer great spaces for relaxation, whether it's sipping coffee in the morning or unwinding at sunset after a day of exploration.
When is the best time to visit East Chatham for a vacation rental?
The best time to visit East Chatham for a vacation rental is during the vibrant peak season from June to August, with July being particularly popular among travelers. This summer period is superb for those seeking outdoor adventures, as the warm weather invites activities such as hiking, biking, and exploring the picturesque landscapes of the Hudson Valley.

During these months, visitors can enjoy comfortable temperatures ranging from the mid-60s to the high 80s Fahrenheit, making it ideal for sightseeing and enjoying the local charm. The area buzzes with energy, offering a range of festivals, farmers' markets, and cultural events that showcase the essence of East Chatham and its surroundings.

For travelers looking for a more budget-friendly option, consider visiting in December. This quieter month offers a unique perspective of East Chatham, with the opportunity to experience the beauty of winter while taking in the serene landscapes and cozy ambiance of local accommodations. The holiday season adds a special touch, with festive decorations and events that create a warm and friendly space.

Ultimately, your choice of when to visit East Chatham will depend on whether you prefer the lively summer season filled with outdoor activities or the peaceful charm of winter's embrace.
How early should I book a East Chatham vacation rental?
Book your East Chatham vacation 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 vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in East Chatham?
In East Chatham, visitors can enjoy a blend of natural beauty and local charm. The area is known for its picturesque landscapes and outdoor activities, particularly in the nearby Catamount State Park, which offers hiking trails and scenic views. The local community has a quaint vibe, with charming shops and cafes that reflect the area's artistic spirit. Additionally, the East Chatham area is close to the tranquil waters of the Kinderhook Lake, providing opportunities for fishing, kayaking, and relaxing by the shore.
Can I change or cancel my East Chatham home rental booking on Vrbo?
To find East Chatham vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the East Chatham vacation 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing 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 favorites, and build the perfect itinerary together.

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