Old Chatham vacation rentals

We found 204 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.

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Find out more about Old Chatham

Why visit Old Chatham

  • Outdoor Adventures: Enjoy a variety of outdoor activities in scenic reserves and serene lakes, perfect for nature lovers.
  • Historic Exploration: Discover the rich history of the Town of Chatham and its early settlements.
  • Local Agriculture: Visit Thompson Farm for a hands-on experience of local farming and fresh produce.
  • Family-Friendly Atmosphere: Old Chatham offers a welcoming environment suitable for families, couples, and solo travelers.
  • Comfortable Accommodations: Choose from charming vacation homes, cozy condos, and delightful cottages for a relaxing stay.

Popular types of accommodation in Old Chatham

If you're wondering about the best accommodation options in Old Chatham, you've come to the right place. Our most popular choices include charming Houses, cozy Condos, and delightful Cottages. Whether you’re looking for a spacious living room, a well-equipped kitchen area, or hotel-like amenities, you’ll find it all in Old Chatham. Enjoy the perfect blend of comfort and convenience for your getaway.

  • Houses: These spacious and comfortable homes are the top choice for travelers seeking a relaxing getaway in Old Chatham, perfect for families or groups.
  • Condos: Modern and convenient, condos offer great amenities and are ideal for couples or solo travelers wanting a cozy stay.
  • Cottages: Charming and quaint, cottages provide a peaceful retreat surrounded by nature, perfect for a romantic escape.
  • Apartments: Offering a home-like feel, apartments are great for those looking for flexibility and proximity to local attractions.
  • Cabins: Rustic and inviting, cabins are popular among nature lovers wanting a unique outdoor experience.**

Top attractions near Old Chatham

Old Chatham is the perfect destination for outdoor enthusiasts, couples, and families alike, offering a blend of history and nature. Visitors can explore historic houses, scenic reserves, and serene lakes, providing a rich cultural and outdoor experience. Whether you're seeking a romantic getaway or a fun family trip, Old Chatham’s attractions cater to a variety of interests, ensuring a memorable vacation for everyone.

  • National Shrine of the Divine Mercy: A serene spiritual sanctuary located 17 miles from Old Chatham, this shrine offers a peaceful atmosphere for reflection and prayer, embodying a rich cultural vibe that draws visitors seeking solace and inspiration.
  • Norman Rockwell Museum: Situated 16 miles away, this museum showcases the iconic works of American illustrator Norman Rockwell, providing an engaging cultural experience through its extensive collection and exhibitions that celebrate American life and storytelling.
  • Hudson River: Just 17 miles from Old Chatham, the Hudson River offers stunning natural scenery and outdoor activities, perfect for kayaking, hiking, or simply enjoying the breathtaking views along its banks.

Things to do recommended for couples

Old Chatham offers a charming escape for couples. Explore scenic hiking trails, enjoy a cozy picnic at a local park, or indulge in a wine tasting at nearby vineyards. Don't forget to unwind with a couples' massage at a cozy spa for the perfect romantic getaway.

Things to do recommended for families

Families visiting Old Chatham can explore the beautiful landscapes at the nearby Chatham Fish and Game Club, enjoy hands-on activities at local farms, and take part in seasonal festivals that offer fun games and crafts for kids. It's a perfect spot for creating lasting memories together.

Things to do recommended for groups

Groups visiting Old Chatham can enjoy a guided tour of local farms, participate in wine tastings at nearby vineyards, and explore the scenic landscapes on group hikes. Don’t miss the chance to experience the charming art galleries and unique shops in the area.

*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

When planning your trip, whether you're traveling with a group, enjoying time with family, bringing along pets, or seeking extended stays, be sure to use the right filters to prioritize your needs. Here are some helpful booking tips for using Vrbo.

  • Traveling to Old Chatham with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Old Chatham with young kids: Traveling with little ones can be a bit daunting. It's important to prioritize their comfort and safety, along with ensuring access to suitable amenities like a private pool. Additionally, think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Old Chatham: For many families, a vacation isn’t truly fulfilling without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties offer amenities like feeding bowls and beds, ensuring that both you and your beloved pet feel comfortable and at home.
  • Planning for a long term stay visiting Old Chatham: If you're in search of vacation rentals offering 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 rental options. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Old Chatham

Discover the charm of Old Chatham, New York, where outdoor adventures and romantic getaways await. Explore the nearby Town of Chatham, rich in history with its earliest settlements, and visit the scenic Thompson Farm for a taste of local agriculture. This family-friendly area offers a welcoming atmosphere and budget-friendly options, making it perfect for travelers seeking both relaxation and exploration.

  • East Chatham: Located a mere 3 miles from Old Chatham, East Chatham offers a thrilling escape for adventure seekers and outdoor enthusiasts. Known for its proximity to stunning ski resorts and scenic ski fields, this city invites visitors to embrace winter sports and alpine activities. Beyond skiing, nature lovers can explore picturesque lakes and majestic mountains. A highlight is the historic college university, which adds a cultural touch to the area. Whether you're hitting the slopes or hiking through breathtaking landscapes, East Chatham promises a memorable experience.
  • Malden Bridge: Just 2 miles from Old Chatham, Malden Bridge is a charming city that caters to families and couples alike. This delightful locale is known for its vibrant arts scene, featuring theaters and music concerts that entertain visitors year-round. The surrounding nature, including tranquil lakes and lush parks, provides a perfect backdrop for outdoor activities or a romantic stroll. With a variety of golf courses nearby, Malden Bridge serves as a fantastic destination for leisure and recreation, making it a wonderful spot for all types of travelers.
  • North Chatham: Situated 4 miles away from Old Chatham, North Chatham is a cultural gem that promises outdoor adventures for families and culture enthusiasts. The city is home to beautiful urban parks and serene beaches, offering plenty of space for outdoor fun and relaxation. Visitors can enjoy local theaters and educational venues that enhance the cultural experience. With its focus on family-friendly activities, North Chatham is a great destination for those looking to create lasting memories while exploring the beauty of the Hudson Valley.

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 LowSlightly Low
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 HighSlightly High
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 SunnyAverageAverage
November39.2°F (4.0°C)Light RainMostly SunnyModerately LowAverage
December31.1°F (-0.5°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is a breeze

Are you hoping to save on your next adventure? Being flexible with your travel dates can lead to better prices, as they often fluctuate. Additionally, consider booking a longer stay to take advantage of substantial savings. To discover a Vrbo property that aligns with your budget, utilize our filters to sort by price, location, and the type of vacation rental you're interested in.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board is a fantastic tool that allows you to plan new trips, pick up right where you left off, and easily manage all your travel arrangements. You can find the properties you've saved and booked categorized under Potential, Upcoming, or Current Trips. To start using 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)
  • 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)
  • Furnace Brook Winery at Hilltop Orchards (9.6 mi / 15.4 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)
  • Art Omi International Arts Center - Fields Sculpture Park (9.1 mi / 14.7 km)
  • Mull Island (11.4 mi / 18.3 km)
  • Stockbridge Bowl (14.4 mi / 23.2 km)
  • Berkshire Botanical Garden (15.1 mi / 24.2 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.

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