Chatham holiday rentals

We found 1,163 holiday 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 holiday rentals in Chatham that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for spending time at your holiday home, which might include parking and a garden. At the end of the day, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

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

Friendly Chatham will entice you

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

Sightseeing in and around Chatham

Are you searching for top things to see and do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Chatham has to offer. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 exciting outdoor activities or just want to take in the scenery, Chatham is a great place to get out in nature. These are some of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport 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 centre. 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 holiday home in Chatham?

The average price for a holiday 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 travelling. Simply enter your dates of travel into Vrbo and the number of guests to view your home 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 holiday home 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 holiday home in Chatham for?

The amount of time you can stay in a Chatham holiday home 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 holiday more enjoyable and convenient, such as kitchens and air conditioning. Some holiday homes may also offer weekly or monthly discounted prices, so you can stay even longer for less.

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