Old Chatham vacation rentals

We found 206 vacation rentals — enter your dates for availability

Discover a selection of 7 homes and other vacation rentals in Old Chatham that are perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation homes have the best amenities for spending time at your vacation home, which might include a pool and a washer and dryer. You'll be able to choose a rental that has what everyone needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Old Chatham

Why visit Old Chatham

  • Charming Scenic Beauty: Old Chatham boasts breathtaking landscapes perfect for romantic getaways and outdoor adventures.
  • Historic Exploration: Discover historic houses and cultural sites that reflect the rich heritage of the area.
  • Family-Friendly Activities: Enjoy serene lakes and nature reserves, ideal for family outings and nature lovers.
  • Nearby Attractions: Venture into the neighboring town of Chatham for additional exploration and enjoyment.
  • Cozy Accommodations: Experience unique vacation rentals, from charming cottages to private homes near local farms.

Popular types of accommodation in Old Chatham

If you're exploring Old Chatham for your next getaway, you'll find a variety of popular vacation rental options, including private homes, cozy condos, and charming cottages. Dive into the local experience by staying near a sheep dairy farm, and enjoy the reviews of nearby hotels to help you make the best choice. Whether you're looking for new properties or established favorites, Old Chatham has something for every traveler.

  • Houses: The top choice for visitors in Old Chatham, offering ample space and comfort for families and groups.
  • Condos: A popular option for vacationers, providing modern amenities and often stunning views.
  • Cottages: Charming and cozy, these rentals are perfect for a quaint getaway in the countryside.
  • Apartments: Conveniently located, they offer a home-like feel in the heart of the community.
  • Cabins: Ideal for nature lovers, these rustic retreats provide a serene escape.**

Top attractions in and around Old Chatham

Old Chatham, New York, offers a charming getaway perfect for outdoor enthusiasts and couples seeking scenic beauty. Visitors can explore historic houses, serene lakes, and nature reserves that cater to those interested in culture and family experiences. Nearby attractions include the town of Chatham, which provides additional opportunities for exploration and enjoyment. Whether you’re looking for relaxation or adventure, Old Chatham has something for everyone.

  • Kinderhook Lake: A picturesque lake located 5 miles from Old Chatham, Kinderhook Lake offers a serene beach atmosphere perfect for relaxation, outdoor activities, and romantic getaways, surrounded by stunning natural scenery.
  • Shaker Museum and Library: Situated in Old Chatham, this museum provides a fascinating glimpse into Shaker culture, showcasing their unique craftsmanship, beliefs, and lifestyle through engaging exhibits and historical artifacts.
  • Martin Van Buren National Historic Site: Located 9 miles from Old Chatham, this site celebrates the life of the eighth U.S. president, offering visitors a rich cultural experience through guided tours and preserved historical buildings.

Things to do recommended for couples

Experience romance in Old Chatham with a concert at Tanglewood Music Center, located 14 miles away, or enjoy skiing at Jiminy Peak Mountain Resort, 16 miles away. For a cozy afternoon, visit Furnace Brook Winery at Hilltop Orchards, just 10 miles away, for wine tasting amidst beautiful scenery.

Things to do recommended for families

Families visiting Old Chatham can relax at Kennedy Park and Mosher Park, both offering serene recreational areas just a short drive away. For thrill-seekers, the Alpine Super Slide provides an exciting amusement ride nearby, ensuring a memorable day for all ages.

Things to do recommended for groups

Enjoy a night of culture and entertainment at the Mac-Haydn Theatre, just 6 miles away. For adventure seekers, the Berkshire Retreat Center offers exciting activities 8 miles from Old Chatham. Don’t forget to visit Zema's Nursery, a charming store located 11 miles away, perfect for unique finds.

*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 Old Chatham

If you're planning a trip with friends, family, pets, or need accommodations for an extended stay, be sure to use the appropriate filters to prioritize your needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Old Chatham with a group: Think about how many bedrooms you'll require, as well as any additional features you might want, like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily narrow down your options on Vrbo to find exactly what you need and more.
  • Traveling to Old Chatham with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Old Chatham: For many families, a getaway isn’t truly enjoyable without their furry companion by their side. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer amenities like food bowls and beds to ensure that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Old Chatham: If you’re seeking vacation rentals with discounts for month-long stays, 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 options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Old Chatham

Old Chatham, New York, is a charming destination perfect for outdoor enthusiasts and romantics alike. Nestled in Columbia County, it offers breathtaking scenery and a family-friendly atmosphere. Explore nearby towns for delightful excursions, and enjoy the warmth of friendly locals. Whether you're seeking a budget-friendly getaway or a business retreat, Old Chatham and its surroundings promise a memorable experience steeped in natural beauty and community spirit.

  • East Chatham: Located a mere 3 miles from Old Chatham, East Chatham is a charming city that invites visitors seeking outdoor adventures and romantic getaways. The surrounding natural beauty offers a plethora of activities, from skiing in the winter to exploring the nearby national state park during warmer months. Travelers can indulge in local theater and music concerts, enhancing their cultural experience. Highlights include picturesque lakes and majestic mountains, perfect for hiking or simply enjoying a peaceful day outdoors.
  • Malden Bridge: Just 2 miles from Old Chatham, Malden Bridge is a delightful city known for its stunning scenery and romantic ambiance. The area is ideal for those who appreciate the outdoors, with opportunities to attend music concerts and theater performances throughout the year. Nature enthusiasts will find nearby waterfalls and serene lakes, offering breathtaking views and great spots for photography. Whether you're looking to relax or explore, Malden Bridge provides a perfect backdrop for a memorable vacation.
  • North Chatham: Situated 4 miles from Old Chatham, North Chatham is a quaint city that captivates visitors with its scenic landscapes and outdoor pursuits. Known for its educational venues and vibrant cultural scene, North Chatham is an excellent choice for those interested in music and theater. The area features beautiful lakes, impressive monuments, and intriguing caves, making it a wonderful spot for exploration and adventure. Whether you're hiking, picnicking, or simply soaking in the views, North Chatham promises a fulfilling experience.

Best time to go to Old Chatham

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.6°F (-4.1°C)Light RainMostly CloudyModerately 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 SunnyModerately HighAverage
July71.6°F (22.0°C)Light RainMostly SunnyModerately HighSlightly High
August69.6°F (20.9°C)Light RainMostly SunnyModerately HighSlightly High
September62.6°F (17.0°C)Light RainMostly SunnyAverageAverage
October51.4°F (10.8°C)Light RainMostly SunnyAverageSlightly Low
November39.2°F (4.0°C)Light RainMostly SunnyModerately LowAverage
December31.1°F (-0.5°C)Light RainMostly CloudyModerately LowSlightly High

Booking with Vrbo is simple

Looking to save money on your next vacation? Consider being flexible with your travel dates, as prices can change significantly. Also, booking an extended stay can often lead to substantial savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to narrow down your search by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you'll gain immediate access to member savings and the ability to earn and redeem OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform where you can easily create new trips, resume planning from where you last stopped, or manage your existing travel plans. You’ll see your saved or booked properties organized into sections for Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Old Chatham getaway

Enjoy the museums and other features of Old Chatham. You'll find plenty to explore during your stay in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Old Chatham

Do you want to find things to do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Old Chatham a fun spot to vacation. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • Furnace Brook Winery at Hilltop Orchards (9.6 mi / 15.4 km)
  • Bousquet Ski Area (14.5 mi / 23.4 km)
  • Jiminy Peak Mountain Resort (15.9 mi / 25.6 km)
  • Wyndhurst Golf & Club (16.5 mi / 26.6 km)
  • Catamount Ski Area (19.4 mi / 31.3 km)
  • Hudson Chatham Winery (9.8 mi / 15.8 km)

Exploring the natural features in Old Chatham

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Old Chatham is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • Kinderhook Lake (4.9 mi / 7.8 km)
  • Queechy Lake (7.9 mi / 12.7 km)
  • Berkshire Botanical Garden (15.1 mi / 24.2 km)
  • The Mount (16 mi / 25.7 km)
  • Sleepy Hollow Lake (16 mi / 25.8 km)
  • Naumkeag Museum (16.3 mi / 26.3 km)

Transportation options to and around Old Chatham

Fly into Hudson, NY (HCC-Columbia County), the closest airport, located 12.7 mi (20.4 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is 13.9 mi (22.3 km) away.

Frequently asked questions

What is the best area to stay in Old Chatham, New York, United States of America when booking a vacation rental?
When looking to book a vacation rental in Old Chatham, New York, the area surrounding the quaint village center is an excellent choice. This charming locale offers a peaceful atmosphere, superb for a relaxing getaway. You'll find a variety of properties, from cozy cottages to more spacious homes, suiting different preferences and group sizes.

One of the top attractions nearby is the picturesque Chatham Town Park, where visitors can enjoy beautiful walking trails and a serene pond, ideal for a leisurely stroll or a picnic. Additionally, the area is home to the renowned Old Chatham Country Store, where you can discover local goods and artisanal products, making it a delightful stop for visitors.
How much does it cost to rent a vacation home in Old Chatham?
Prices for vacation rentals in Old 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 Old 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 Old Chatham vacation house rentals?
You can find great discounts on house rentals in Old 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 Old Chatham ski resort rentals?
For ski resort rentals near Old Chatham, travelers should consider the nearby area of Windham, which is approximately a 30-minute drive away. Windham Mountain is a well-known ski destination that offers a variety of accommodations, including cozy cabins and modern condos. Many of these properties feature amenities such as wood-burning fireplaces, ski storage, and fully equipped kitchens, great for families or groups looking to unwind after a day on the slopes.

In addition to Windham, the town of Hunter, also close to Old Chatham, provides another excellent option for ski rentals. Here, visitors can find charming lodges and vacation homes that often include hot tubs, game rooms, and outdoor spaces for enjoying the mountain views. The Hunter Mountain Ski Resort offers a range of slopes suitable for all skiing levels, and many nearby rentals provide easy access to the ski lifts.

Both Windham and Hunter boast a variety of local dining options and shops, adding to the convenience for travelers. For those looking to explore beyond skiing, the surrounding Catskill Mountains offer hiking trails and stunning scenery, with accommodations often featuring outdoor decks or patios to take in the natural beauty.
What is the most popular type of vacation rental accomodation in Old Chatham?
In Old Chatham, vacation houses and cottages are the most popular rental options, with several of each type available throughout the area. These accommodations typically feature cozy interiors with fully equipped kitchens, comfortable living spaces, and outdoor areas for enjoying the tranquil surroundings. Travelers can expect a cozy feel, superb for unwinding after exploring the local charm of this picturesque town.
Are there any family house rentals in Old Chatham?
In Old Chatham, New York, there are several family-friendly house rentals available, providing a charming retreat in the Hudson Valley. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely. Visitors can expect amenities such as Wi-Fi, air conditioning, and comfortable furnishings, ensuring a cozy atmosphere for everyone.

The locale is surrounded by beautiful landscapes, making it ideal for outdoor activities like hiking and exploring nearby parks. Families can also enjoy local attractions, including farms and markets that offer fresh produce and artisanal goods.
Can I rent a vacation home with a pool or hot tub in Old Chatham?
In Old Chatham, there are several vacation homes available for rent that feature pools and hot tubs. This charming area in New York offers a picturesque rural setting, making it an excellent choice for travelers seeking relaxation and outdoor activities. Many of these rentals come equipped with amenities such as private swimming pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, great for family gatherings or retreats with friends.
Can I find long-stay vacation rentals in Old Chatham?
A long-stay vacation rental in Old 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 Old Chatham?
In Old Chatham, travelers will find several pet-friendly house rentals that cater to both comfort and convenience. Many of these homes come equipped with amenities such as spacious backyards, fully equipped kitchens, and cozy living spaces, making them ideal for families or groups traveling with pets. The surrounding area is picturesque, characterized by its rolling hills and charming rural landscapes, providing a serene backdrop for your stay.

For outdoor enthusiasts, Old Chatham offers easy access to various parks and nature trails where pets are welcome. Nearby, the Chatham Town Park features walking paths and open spaces for pets to enjoy. Additionally, the area is dotted with local shops and eateries that are pet-friendly, further ideal for travelers with furry companions. See all pet-friendly rentals in Old Chatham.
Are there any remote work vacation rentals in Old Chatham?
In Old Chatham, New York, there are several vacation rentals that cater to remote work needs. These properties typically offer amenities such as dedicated workspaces, including desks and comfortable desk chairs, along with Wi-Fi access to ensure a productive environment. Many accommodations also feature in-room safes for added security of personal items.

The area's peaceful surroundings provide a tranquil setting for working remotely, while still being close to local attractions and the natural beauty of the region. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Old Chatham vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Old 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 Old Chatham?
In Old Chatham, vacation rentals commonly feature a range of amenities that enhance the guest experience. Many properties include fully equipped kitchens, allowing travelers to prepare their own meals and feel at home. A workspace with a desk and chair is also a frequent amenity, suiting those who may need to catch up on work during their stay. Additionally, the presence of a coffee and tea maker is popular, ensuring guests can enjoy their favorite hot beverages at their convenience. Many rentals are also equipped with cozy fireplaces, creating a warm and inviting atmosphere, especially during the cooler months.
When is the best time to visit Old Chatham for a vacation rental?
The best time to visit Old Chatham for a vacation rental is during the peak summer season from June to August, with July being the most popular month. This vibrant period attracts travelers looking to immerse themselves in outdoor activities, enjoy local festivals, and explore the picturesque countryside. Warm temperatures, typically ranging from the low 60s to mid-80s Fahrenheit, create an inclusive setting for hiking, biking, and leisurely strolls through charming streets.

During these months, visitors can take advantage of the lush landscapes and participate in various events, including farmers' markets and art shows, which showcase the local culture and community spirit. The natural beauty of the Hudson Valley is in full bloom, making it an ideal backdrop for outdoor adventures and sightseeing.

For those seeking a more budget-friendly option, consider visiting in November. This month offers a quieter experience, superb for enjoying the tranquil beauty of Old Chatham as the fall colors transition into a serene winter landscape. It's a great time for cozy getaways, where you can relish in the charm of local eateries and quaint shops without the summer crowds.

Ultimately, the choice of when to visit Old Chatham hinges on your preference for lively summer activities or peaceful autumn retreats.
How early should I book a Old Chatham vacation rental?
Book your Old 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 Old Chatham, New York, United States of America?
In Old Chatham, visitors can enjoy a serene rural atmosphere with a range of attractions that highlight the area's natural beauty and local culture. The picturesque landscape is ideal for outdoor enthusiasts, with opportunities for hiking and exploring nearby parks such as the beautiful Chatham Forest and the scenic areas around the Taconic State Park.

The town is also known for its charming historic architecture, with top structures like the Old Chatham Quaker Meeting House, which offers a glimpse into the town's rich history. Art lovers may find interest in local galleries and studios, showcasing works by regional artists.

For those seeking a taste of local flavors, Old Chatham is home to several farms and markets, where visitors can sample fresh produce and artisanal products.
Can I change or cancel my Old Chatham home rental booking on Vrbo?
To find Old 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 Old 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.

More Vacation Ideas