Old Chatham vacation rentals

We found 200 vacation rentals — enter your dates for availability

Nestled in the heart of the Hudson Valley, Old Chatham beckons with its charming blend of scenic beauty and rich history. Explore serene lakes and lush reserves, perfect for outdoor adventures, or delve into the town's captivating past. With delightful accommodations ranging from cozy condos to spacious cottages, families and groups can revel in a home-like atmosphere that combines comfort and convenience. Experience the best of this welcoming destination while creating unforgettable memories together.

Holiday rentals with weekly discounts - Old Chatham

Showing deals for:Dec 4 - Dec 11

Welcome!
Property grounds
3 season Sunroom
House 1- Mountain views from this open concept kitchen, dining, sitting room
Exceptional
(6 reviews)

Grand Estate w/ Mountain Views by Evergreen Home

Ghent

12% off
$790
$5,532 for 7 nights
All fees included
Grand Estate w/ Mountain Views by Evergreen Home
Property grounds
Terrace/patio
Game room
Pool
Exceptional
(5 reviews)

Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room

Hillsdale

8% off
$691
$4,839 for 7 nights
All fees included
Hillsdale Retreat Farmhouse with Pool, Firepit, Hot Tub and Game Room
Reading nook with natural lighting
Fully screened porch!
Front Staircase
Dining Room w/ Doors to Screened Porch Dining Area
Exceptional
(7 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

12% off
$402
$2,812 for 7 nights
All fees included
Berkshires Colonial on 2 Acres by Evergreen Home
Room
Interior
Interior
Exterior
Exceptional
(41 reviews)

A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.

Stephentown

9% off
$213
$1,491 for 7 nights
All fees included
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Walnut dining table seats ten
Patio accessible from dining/kitchen
Pool
Double height, open kitchen and dining perfect for large vacation meals
Exceptional
(47 reviews)

Designer Home with Panoramic Views near Hudson

Ghent

9% off
$509
$3,565 for 7 nights
All fees included
Designer Home with Panoramic Views near Hudson
Living room
Property grounds
Coming up the path from down by the creek
Living room
Exceptional
(13 reviews)

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Chatham

9% off
$225
$1,576 for 7 nights
All fees included
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Interior
BBQ dinner not included :)
50 inch TV for family movie night!
Interior
Exceptional
(10 reviews)

Family Fun in The Berkshires at Beautiful Hygge House

Richmond

9% off
$481
$3,364 for 7 nights
All fees included
Family Fun in The Berkshires at Beautiful Hygge House
Interior
Interior
Exterior
Exterior
Exceptional
(5 reviews)

Chatham Cozy Country Retreat

Chatham

8% off
$176
$1,233 for 7 nights
All fees included
Chatham Cozy Country Retreat
Interior
Dining
Living Room, wow!
view into large bathroom
Exceptional
(17 reviews)

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

Richmond

18% off
$336
$2,349 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

  • 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)
  • Lenox Mountain (13.3 mi / 21.5 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 are the best areas to stay in a vacation rental in Old Chatham?
Vacation rentals in Old Chatham offer a selection of properties throughout the area, providing a peaceful retreat for various trip types. You'll find options that cater to different needs, all offering the space and privacy of a whole home. Most vacation rentals in Old Chatham are houses, with a few cottages available.
What are the most popular vacation rentals in Old Chatham?
The most popular vacation rentals in Old Chatham are houses, which make up the majority of available properties. These homes are favored by guests seeking ample space, privacy, and the comforts of a full residence, making them ideal for families and groups. A selection of cottages also provides cozy options for those looking for a charming stay.
What amenities do vacation rentals in Old Chatham usually offer?
Vacation rentals in Old Chatham typically offer a range of amenities designed for comfort and convenience. You'll often find fully equipped kitchens, laundry facilities with washers, and air conditioning for a pleasant stay. Many properties also include free parking, high-speed internet, and fireplaces, perfect for cozy evenings. Additionally, a selection of vacation rentals provides outdoor spaces like patios or yards, and some feature balconies or terraces for enjoying the surroundings.
Are there family-friendly vacation rentals in Old Chatham?
Yes, Old Chatham offers several family-friendly vacation rentals, primarily houses and a few cottages. These properties are well-suited for families, providing the space and amenities needed for a comfortable stay. Many family-friendly vacation rentals in Old Chatham come with fully equipped kitchens, laundry facilities, and dining tables for shared meals. Some also offer amenities like high chairs, travel cribs, and outdoor play areas, making it easier to travel with children.
Are there pet-friendly vacation rentals in Old Chatham?
Yes, you can find several pet-friendly vacation rentals in Old Chatham, mainly houses and a few cottages. These properties welcome your furry companions, ensuring everyone in the family can enjoy the trip. Many pet-friendly vacation rentals in Old Chatham offer secured yards, providing a safe outdoor space for pets to play. It's a great way to explore the area without leaving your pets behind.
What are the best areas for group vacation rentals in Old Chatham?
For groups planning a trip, Old Chatham offers several vacation rentals that provide ample space and amenities. Most of these are houses, which are ideal for accommodating larger parties. These properties often feature multiple bedrooms and bathrooms, large dining areas, and plenty of parking, ensuring everyone has room to relax and socialize. The whole-home experience allows groups to enjoy privacy and shared moments together.
What are the best luxury vacation rentals in Old Chatham?
Old Chatham features a selection of luxury vacation rentals, predominantly houses, designed for an elevated stay. These upscale properties often come with premium amenities such as private pools, hot tubs, and fireplaces, offering a refined and comfortable experience. You'll find these luxury vacation rentals provide spacious interiors, high-end finishes, and often expansive outdoor areas for relaxation and entertainment.
Are there any budget-friendly vacation rentals in Old Chatham?
Yes, Old Chatham offers a selection of budget-friendly vacation rentals, including houses and cottages, that provide great value for your stay. These properties often feature essential amenities like fully equipped kitchens, laundry facilities, and free parking, helping guests manage their expenses. Opting for a vacation rental, especially a private home, allows groups to split costs and enjoy more space than traditional accommodations, making it a smart choice for value-conscious guests.
Are there any vacation rentals in Old Chatham with a pool?
Yes, you can find several vacation rentals in Old Chatham with pools, primarily houses. These properties offer a refreshing amenity for guests to enjoy during their stay. The pools available include private pools, outdoor pools, and some even feature heated pools, providing options for different preferences and times of year. Having a pool adds an extra layer of relaxation and fun to your vacation rental experience.
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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