Chatham vacation rentals

We found 1,164 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 17 homes and other vacation rentals in Chatham that are perfect for your trip. Whether you're going on vacation with family or friends, vacation homes have the best amenities for spending time at your vacation home, which might include WiFi and a fireplace. No matter what you're looking for, you'll be able to choose a rental for everyone's needs, including accessible or non-smoking choices.

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Friendly Chatham will entice you

Enjoy the theater scene and other features of Chatham. Travelers appreciate the restaurants in this welcoming city. Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Sightseeing in and around Chatham

Do you want to find things to do while you're in the area? Venture out of your vacation home and check out everything that makes Chatham a one-of-a-kind vacation spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Catamount Ski Area (14.9 mi / 24 km)
  • Bousquet Ski Area (16.5 mi / 26.5 km)
  • Ski Butternut (18.8 mi / 30.3 km)
  • Lake Taghkanic State Park (19.6 mi / 31.5 km)
  • Furnace Brook Winery at Hilltop Orchards (10.9 mi / 17.6 km)
  • Kennedy Park (16.3 mi / 26.2 km)

Exploring the natural landscape of Chatham

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

  • Naumkeag Museum (15.1 mi / 24.4 km)
  • The Mount (16 mi / 25.8 km)
  • Housatonic River Walk (16.6 mi / 26.7 km)
  • Bash Bish Falls State Park (18.4 mi / 29.6 km)
  • Lake Taghkanic State Park (19.6 mi / 31.5 km)
  • Hudson River (20.8 mi / 33.4 km)

Transportation options to and around Chatham

The nearest airport is in Hudson, NY (HCC-Columbia County), located 7.7 mi (12.4 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 16 mi (25.8 km) away.

Frequently asked questions

How much does it cost to rent a vacation rental in Chatham?

The average price for a vacation home in Chatham is based on a number of factors, such as length of stay, property type and season. Whether you prefer a sprawling villa with lots of space or a quaint cabin for just you and the kids, just add your dates of travel to find stays that offer great value.

How much does it cost to rent a beach house in Chatham?

Prices for beach houses in Chatham may vary depending on the size and type of the property and time of year you're traveling. Simply enter your dates of travel into Vrbo and the number of guests to view your rental options and prices. From there you can use our filters to tailor your search results by ratings, amenities, nearby activities and more.

What are the top attractions for families in Chatham?

Keep your kids busy at these popular family-friendly attractions in Chatham:

  • Shaker Museum and Library
  • Kinderhook Lake
  • High Falls Trail

How old do you have to be to rent a vacation rental in Chatham?

The minimum required age is typically 16, 18 or 21. It can change from one property to another on Vrbo, so look at the rules of your preferred Chatham stay before booking your escape.

How long can I rent a vacation rental in Chatham for?

The amount of time you can stay in a Chatham vacation rental for is up to each property. Just put in your dates of travel to find available options that offer long-term stays. They have all you require to make your extended vacation more enjoyable and convenient, such as kitchens and air conditioning. Some vacation rentals may also offer weekly or monthly discounted prices, so you can stay even longer for less.

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