Old Chatham vacation rentals

We found 198 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 11 - Dec 18

Welcome!
Property grounds
3 season Sunroom
Dining area and small sitting are with flat screen TV. Stairs to second floor
Exceptional
(6 reviews)

Grand Estate w/ Mountain Views by Evergreen Home

Ghent

12% off
$794
$5,557 for 7 nights
All fees included
Grand Estate w/ Mountain Views by Evergreen Home
Private kitchen
Terrace/patio
Game room
Pool
Exceptional
(5 reviews)

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

Hillsdale

8% off
$747
$5,229 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
Kitchen with stainless steel appliances
Exceptional
(8 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Richmond

13% off
$395
$2,762 for 7 nights
All fees included
Berkshires Colonial on 2 Acres by Evergreen Home
Pool
Patio accessible from dining/kitchen
Walnut dining table seats ten
Front Door entrance
Exceptional
(47 reviews)

Designer Home with Panoramic Views near Hudson

Ghent

9% off
$500
$3,503 for 7 nights
All fees included
Designer Home with Panoramic Views near Hudson
Interior
Interior
Living area
Room
Exceptional
(41 reviews)

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

Stephentown

8% off
$218
$1,525 for 7 nights
All fees included
A MAGIC SPOT: Booking all year. A perfect, private, quiet mountaintop location.
Terrace/patio
Living area
Living area
Living area
Exceptional
(8 reviews)

Modern Log Chalet - 10 acres, views, and a pond!

Chatham

8% off
$364
$2,549 for 7 nights
All fees included
Modern Log Chalet - 10 acres, views, and a pond!
Coming up the path from down by the creek
Property grounds
Living room
Living room
Exceptional
(13 reviews)

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

Chatham

9% off
$221
$1,549 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!
Exterior
Exceptional
(10 reviews)

Family Fun in The Berkshires at Beautiful Hygge House

Richmond

9% off
$472
$3,307 for 7 nights
All fees included
Family Fun in The Berkshires at Beautiful Hygge House
Exterior
Interior
Exterior
Room
Exceptional
(6 reviews)

Chatham Cozy Country Retreat

Chatham

8% off
$175
$1,228 for 7 nights
All fees included
Chatham Cozy Country Retreat
Entry and living room
Dining
Interior
Living Room, wow!
Exceptional
(17 reviews)

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

Richmond

18% off
$330
$2,309 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 is the most popular type of vacation rental accommodation in Old Chatham?
Cottages are the most popular style of vacation rental in Old Chatham, according to our data. Even if you have a different idea about what you want, Vrbo has vacation homes in all shapes and sizes. Look over our options to find your perfect Old Chatham pad.
How much does it cost to rent a vacation rental in Old Chatham?
The average price for a vacation home in Old Chatham is based on several factors, such as length of stay, property type and season. Whether you'd like a sprawling villa with space for the whole family or a quaint cottage for just you and your sweetheart, just add your travel dates to find some great-value stays.
How much does it cost to rent a beach house in Old Chatham?
Prices for beach houses in Old Chatham can differ depending on the size and type of the property and when you're traveling. All you need to do is enter your travel dates into Vrbo and how many guests to view available options and prices. From there you can use our filter tool to narrow your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Old Chatham?
With nine vacation rentals that welcome four-legged guests, your happy hound can join in the fun on your Old Chatham break. Use our filter tool to browse our pet-friendly vacation rentals and find a stay that's pawfect on Vrbo.
Can I rent a house with a pool in Old Chatham?
Grab your swimming gear and inflatable swan, because there are four houses with a private pool in Old Chatham. Book one of these popular vacation homes and you'll enjoy pool days every day. Simply enter your dates into Vrbo, then check the "pool" filter to find the perfect place to make a splash!
What are popular rental amenities in Old Chatham?
When it comes to rental amenities that people are on the lookout for in Old Chatham, tennis, a barbecue grill and a swimming pool are the most popular. With Vrbo vacation rentals, there are options to suit your style and taste, whether you're going on a trip with friends, relatives or even pets.
Are there large group vacation rentals in Old Chatham?
With two vacation rentals that can sleep 10 or more guests in Old Chatham, there's no need to limit the invite list. From family vacations to events like anniversary parties and weddings, Vrbo can help you find a large group rental to match the occasion.
Are there vacation rentals in Old Chatham that welcome kids?
Old Chatham has nine family-friendly vacation homes to pick from. And securing a stay that welcomes kiddos is a breeze with our "Properties good for families" filter. On top of having the entire place to yourselves, you'll also get access to conveniences and perks such as bunk beds, kitchens and private pools.
What are the top attractions for families in Old Chatham?
Have a day out with the family at Shaker Museum and Library. This awesome attraction is situated near the center of Old Chatham.
Are there one-bedroom vacation rentals in Old Chatham?
There are two one-bedroom properties in Old Chatham to pick from. A one-bedroom vacation home is a superb choice if it's only two of you or if you're traveling alone. Add in more convenience, privacy and space than a standard hotel, and you're bound to have a break to remember.
Can I find two-bedroom vacation rentals in Old Chatham?
Select from three two-bedroom properties in Old Chatham. Give the kids the second room or maybe fill it with a couple of your besties. There's a spot for whoever's lucky enough to be coming along.
Are there vacation rentals with WiFi in Old Chatham?
Pick from five vacation rentals with WiFi in Old Chatham. If you'd like to disconnect from the world on your break, but still need to be connected to the web, these properties have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find vacation rentals with air conditioning in Old Chatham?
Old Chatham has nine vacation rentals where you'll be able to kick back in air-conditioned comfort. To find a stay on Vrbo that has this perk, enter your desired travel dates and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in Old Chatham?
You'll need to check with the Old Chatham vacation property you'd like on Vrbo as the age limit differs. However, typically it's 16, 18 or 21.
How long can I rent a vacation rental in Old Chatham for?
The amount of time you can rent an Old Chatham vacation rental for depends on the property. Just put in your dates of travel to browse options that offer extended stays. They include all you require to make your extended getaway more comfortable and convenient, such as air conditioning and kitchens. Some Vrbo vacation rentals may also offer discounted weekly or monthly prices, so you can have a longer stay for less.
Does Vrbo offer discounts for vacation homes in Old Chatham?
On Vrbo, you'll find amazing bargains and discounts for Old Chatham. Take a look at our newly listed homes, as well as our weekly and monthly discounts on vacation rentals. Whether you're off on a short getaway or an extended escape, Vrbo offers lots of options for every budget and style.

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