Old Chatham holiday homes

We found 221 holiday rentals — enter your dates for availability

Discover a selection of 6 homes and other holiday rentals in Old Chatham that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday homes have the amenities that you need and want for your stay, which might include Wi-Fi and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Choose a holiday rental for your Old Chatham getaway

Enjoy the museums and other features of Old Chatham. This city has something for everyone. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Old Chatham

Are you hoping to discover top things to see and do while you're in the area? Venture out of your holiday home and check out everything that makes Old Chatham a one-of-a-kind holiday spot. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Bousquet Ski Area (14.5 mi / 23.4 km)
  • Jiminy Peak Mountain Resort (15.9 mi / 25.6 km)
  • Wyndhurst Golf & Club (16.5 mi / 26.6 km)
  • Catamount Ski Area (19.4 mi / 31.3 km)
  • Hudson Chatham Winery (9.8 mi / 15.8 km)
  • Brookview Station Winery (9.9 mi / 16 km)

Exploring the natural features in Old Chatham

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Old Chatham is a great place to get outside. These are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Berkshire Botanical Garden (15.1 mi / 24.2 km)
  • The Mount (16 mi / 25.7 km)
  • Sleepy Hollow Lake (16 mi / 25.8 km)

Transport 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 centre. 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 holiday home accommodation in Old Chatham?
The most sought-after types of holiday homes in Old Chatham are houses. Looking for something different? Bookabach has plenty of options to match our guests’ requirements, so you’ll see holiday properties in all shapes and sizes. The ideal fit is ready and waiting for you — grab yours today.
How much does it cost to rent a holiday home in Old Chatham?
Season, length of stay and property type are some factors that can influence the price of a holiday home. Simply click on your travel dates to find your ideal match. From comfy cottages to sprawling villas, all Bookabach holiday homes offer terrific value.
How much does it cost to rent a beach house in Old Chatham?
Prices for beach houses in Old Chatham will vary depending on the type and size of the property and when you plan to travel. Simply enter your travel dates into Bookabach and how many guests to see available options and prices. From there you can use our filter tool to refine your search results by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday homes in Old Chatham?
Yes, there are. You can pick from nine holiday homes that allow pets in Old Chatham. Lots of our pet-friendly holiday homes even come with space outdoors for your fur child to have fun in, complimentary treats, doggie beds and proximity to parks and green space. Apply the “Pets allowed” filter to find a holiday home on Bookabach that’s pawfect.
Can I rent a house with a pool in Old Chatham?
Check the “pool” box in our handy filter tool and choose from four houses with private pools in Old Chatham on Bookabach. Morning dip, sunset soak or midnight swim? Free time is up to you when your holiday home boasts a swimming pool.
What are popular home amenities in Old Chatham?
Mountain views, a barbecue grill and a water view rank as the most popular home amenities in Old Chatham. Whether you’re taking a trip on your own, with your other half or a group of family members, Bookabach will help you find a holiday home that fits your tastes with all the features you’re looking for.
Are there large group holiday homes in Old Chatham?
Old Chatham has two holiday homes that can accommodate 10 or more people. These properties come with the privacy and space you need to enjoy good times with your favourite people.
Are there holiday homes in Old Chatham that welcome kids?
With nine family-friendly holiday properties available in Old Chatham, now is the perfect time to introduce the kids to the excitement of travel. Simply check our “Properties good for families” filter to search for stays packed with conveniences ideal for families on the move, like extra bedrooms, patios, entertainment areas and hot tubs.
What are the top attractions for families in Old Chatham?
Keep the kids amused at these top family-friendly attractions in Old Chatham:

  • Shaker Museum and Library
  • Kinderhook Lake
  • Mount Lebanon Shaker Village

Are there one-bedroom holiday homes in Old Chatham?
Old Chatham has two one-bedroom homes on offer. Often located in prime areas due to their smaller size, a one-bedroom home is great if you’re getting away with a buddy or your partner. And with plenty of home comforts like wireless internet and more privacy than a standard hotel, you’ll be able to kick back while enjoying this exciting destination.
Can I find two-bedroom holiday homes in Old Chatham?
You can pick from three two-bedroom homes in Old Chatham. Give your little ones the second room or maybe fill it with a couple of your favourite people. There’s a comfy spot for whoever’s fortunate enough to be joining your journey.
Are there holiday homes with WiFi in Old Chatham?
Old Chatham has five holiday homes with WiFi, so you can stay connected during your trip. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming TV shows with the family to scrolling social media, these Bookabach homes make it easy to go online.
How can I find holiday homes with air conditioning in Old Chatham?
Work out your travel dates and then use our filter tool to see holiday homes with air conditioning in Old Chatham on Bookabach. With nine air-conditioned properties available, you can enjoy a cool and comfortable stay.
How old do you have to be to rent a holiday home in Old Chatham?
It’s advisable to check with the Old Chatham holiday home you want on Bookabach as the minimum age varies. However, typically it’s 16, 18 or 21.
How long can I rent a holiday home in Old Chatham for?
It really depends on the Old Chatham property. To browse a list of options offering extended stays, simply enter your dates and number of people into Bookabach. Enjoy having the place to yourself, as well as comforts such as a fully-equipped kitchen and outdoor spaces where the kids can run around and play. Keep your eyes open for any long-term stays that offer discounted weekly or monthly prices.

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