Old Chatham vacation rentals

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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.

Vacation rentals with weekly discounts - Old Chatham

Showing deals for:Mar 27 - Apr 3

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

Interior
10 out of 10, Exceptional, (12 reviews)
Exceptional
(12 reviews)

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

Richmond

18% off
Price is $335
$2,342 for 7 nights
All fees included
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

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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:

  • Bousquet Ski Area (14.5 mi / 23.4 km)
  • Kennedy Park (15.2 mi / 24.4 km)
  • Jiminy Peak Mountain Resort (15.9 mi / 25.6 km)
  • Wyndhurst Golf & Club (16.5 mi / 26.6 km)
  • Pineridge Cross Country Ski Center (17.9 mi / 28.8 km)
  • Catamount Ski Area (19.4 mi / 31.3 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)
  • Stockbridge Bowl (14.4 mi / 23.2 km)
  • Berkshire Botanical Garden (15.1 mi / 24.2 km)
  • Kennedy Park (15.2 mi / 24.4 km)
  • The Mount (16 mi / 25.7 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 when booking a vacation rental?
When considering a vacation rental in Old Chatham, New York, the area around the charming village center is an excellent choice. This quaint neighborhood offers a picturesque backdrop with its historic homes and lush landscapes, making it a delightful spot for relaxation. Additionally, you'll find easy access to local attractions such as the Old Chatham Sheepherding Company, where visitors can enjoy farm tours and sheepdog demonstrations. The nearby Chatham Brewing is also a popular destination, known for its craft beers and inclusive setting.

Another appealing area to explore is near the beautiful waterfront along the banks of the Kinderhook Creek. This scenic setting provides a tranquil ambiance and offers opportunities for outdoor activities, such as fishing and kayaking. The tranquil surroundings are great for those looking to unwind while still being close to the heart of the community.

In terms of vacation rentals, Old Chatham features a variety of properties, with many charming options available for visitors. Whether you're seeking a cozy cottage or a spacious farmhouse, you're likely to find accommodations that suit your needs in this lovely area.
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 areas for renting a beach house in Old Chatham?
For renting a beach house in Old Chatham, New York, travelers should explore the nearby areas surrounding the beautiful lakes and rivers that characterize the region. While Old Chatham itself is not directly on the coast, properties around the picturesque Kinderhook Lake and the adjacent areas provide lovely waterfront accommodations.

Many of these vacation rentals offer amenities such as private docks, outdoor patios with stunning views, and spacious living areas that are great for gatherings. Travelers can expect fully equipped kitchens, which allow for home-cooked meals after a day of enjoying water activities like kayaking or fishing.

Additionally, the nearby town of Chatham features charming historic homes and cozy cabins that have been updated to include modern comforts while retaining their rustic charm. Some properties may include access to local parks, hiking trails, and picnic areas, enhancing the overall experience with opportunities for outdoor exploration.

For those looking to enjoy a more relaxed atmosphere, the scenic beauty of the surrounding countryside, with its rolling hills and lush greenery, offers a tranquil backdrop for a beach house retreat.
Where are the best Old Chatham ski resort rentals?
For ski resort rentals near Old Chatham, travelers should consider the nearby area of Catamount Ski Area, located just a short drive away in the town of Hillsdale. This ski resort offers a variety of accommodations in the surrounding region, particularly in towns like Chatham and Great Barrington. Here, visitors can find cozy cabins and charming cottages that cater to both families and groups.

Many of these properties feature amenities such as wood-burning stoves or fireplaces, ideal for warming up after a day on the slopes. Additionally, you'll often find fully equipped kitchens, allowing for convenient meal preparation, along with comfortable living areas designed for relaxation. Some rentals may even offer outdoor spaces, great for enjoying the scenic winter landscape.

In Great Barrington, the vibrant downtown area provides a selection of shops and restaurants, enhancing the overall experience for travelers. The proximity to both the ski slopes and local attractions means guests can enjoy a mix of outdoor activities and cultural experiences.
What is the most popular type of vacation rental accomodation in Old Chatham?
In Old Chatham, vacation houses and cottages are the most popular types of accommodations, with several options available in the area. These properties are often situated in serene, rural settings, providing a peaceful retreat for visitors. Travelers can expect amenities such as fully equipped kitchens, cozy living areas, and outdoor spaces like decks or gardens for enjoying the picturesque surroundings. Many rentals are designed to accommodate families or groups, making them ideal for those looking to unwind and explore the local charm of the Hudson Valley.
Are there any family house rentals in Old Chatham?
In Old Chatham, New York, there are several family-friendly house rentals available, making it a lovely destination for families looking to enjoy the countryside. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where children can play and explore.

Visitors will appreciate the serene environment, with amenities like Wi-Fi and air conditioning ensuring a comfortable stay. The area is surrounded by beautiful landscapes great for outdoor activities such as hiking and picnicking. Additionally, nearby attractions include charming local farms and scenic parks, providing plenty of opportunities for family outings and creating lasting memories.
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, making it an appealing option for travelers seeking relaxation and leisure. This charming rural area in New York offers a picturesque setting, surrounded by beautiful landscapes that are superb for outdoor activities. Many of the rentals include amenities such as private swimming pools, hot tubs, spacious patios for outdoor dining, and fully equipped kitchens, ideal for enjoying meals with family or friends after a day of exploration. Additionally, the properties often provide a tranquil atmosphere, allowing guests to unwind in a serene environment.
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, there are several pet-friendly house rentals available, offering a cozy and welcoming atmosphere for travelers with furry companions. Many of these vacation homes feature amenities such as spacious backyards, allowing pets to roam freely, and fully equipped kitchens for convenient meal preparation. The interiors often include comfortable living spaces, multiple bedrooms, and some properties even have additional touches like fireplaces or outdoor seating areas for relaxation.

The surrounding area offers picturesque landscapes, making it an ideal destination for nature lovers and pet owners alike. Nearby parks, hiking trails, and open fields provide plenty of opportunities for outdoor activities with pets, ensuring that both guests and their four-legged friends can enjoy the beauty of the Hudson Valley.
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. Travelers can expect properties equipped with amenities like Wi-Fi, dedicated desks, and comfortable office chairs, making it easy to maintain productivity while enjoying a peaceful retreat. Many rentals also feature additional comforts such as spacious living areas, full kitchens, and outdoor spaces for relaxation after work hours. The surrounding area offers a serene environment with beautiful landscapes, great for unwinding after a day of work. 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, popular vacation rental amenities include WiFi, kitchens equipped with modern appliances such as a kitchen island and a blender, and many rentals also feature private pools.
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 vibrant summer months, specifically from June to August. This peak season attracts travelers seeking a mix of relaxation and adventure, with July standing out as the most popular month. Visitors can take part in outdoor activities like hiking and cycling, all while enjoying the warm, pleasant temperatures that typically range from the mid-60s to upper 80s Fahrenheit.

During these months, the lush greenery of the surrounding countryside enhances your outdoor experiences, making it an ideal time for exploring the scenic beauty of the Hudson Valley. Whether you're wandering through the charming local shops, attending summer festivals, or savoring farm-to-table dining, there's no shortage of activities to enjoy.

For those looking for a more budget-friendly option, November presents a wonderful alternative. While this month signals the end of the peak tourist season, it offers a quieter atmosphere great for restful retreats and scenic drives through the fall foliage. The crisp air and colorful landscapes create a serene backdrop for leisurely exploration.

Ultimately, the ideal time to book a vacation rental in Old Chatham depends on your preferences. If you thrive on the energy of summer activities and social events, the peak season will suit you greatly. However, for a tranquil getaway where you can appreciate nature's beauty at a more leisurely pace, consider visiting in November.
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?
In Old Chatham, visitors can enjoy a quaint rural atmosphere with several attractions that highlight the region's charm. The Old Chatham Country Store is a popular spot for local goods and homemade treats, offering a taste of the community's spirit. The surrounding countryside is great for outdoor enthusiasts, with opportunities for hiking and enjoying nature in the nearby Taconic State Park, which features trails and scenic views.

Art lovers can explore the work of local artisans at various galleries throughout the area, while the historic architecture of the town provides a picturesque backdrop for leisurely walks. Additionally, the Old Chatham Sheepherding Company offers great experiences, such as sheepdog demonstrations and farm tours, showcasing the agricultural heritage of the region.
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.

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