Discover a selection of 1,000 vacation rentals in Chatham, NY that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $216 per night, and houses and cottages are popular options for a stay in Chatham. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chatham
Destination guide

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—perfect for a relaxing getaway.

Things to do

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:

  • Furnace Brook Winery at Hilltop Orchards (10.9 mi / 17.6 km)
  • Catamount Ski Area (14.9 mi / 24 km)
  • Bousquet Ski Area (16.5 mi / 26.5 km)
  • Cranwell Golf Club (16.8 mi / 27 km)
  • Ski Butternut (18.8 mi / 30.3 km)
  • Lake Taghkanic State Park (19.6 mi / 31.5 km)
Natural features

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 (15.1 mi / 24.4 km)
  • The Mount (16 mi / 25.8 km)
  • Housatonic River Walk (16.6 mi / 26.7 km)
  • Dutchman’s Landing (16.9 mi / 27.2 km)
  • Bash Bish Falls State Park (18.4 mi / 29.6 km)
  • Lake Taghkanic State Park (19.6 mi / 31.5 km)
How to get there

Transportation options to and around Chatham

The nearest airport is in Albany Intl. Airport (ALB), located 28.5 mi (45.9 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Hudson, NY (HCC-Columbia County), which is 7.7 mi (12.4 km) away.

What are the top vacation rentals in or near Chatham?

Whatever your vacation needs, you'll find a rental in or around Chatham that suits your style. Why not try these on for size?:

  • "Designers Own Year - Round Hudson Valley Getaway Cottage" is a favorite with guests. Around 14 miles from Chatham, it has 2 bedrooms and lots of useful amenities, including a microwave oven and an oven.
  • Another great option is "Luxury Barn Retreat. Year - Round Perfect Family Getaway", which is around 12 miles from Chatham. With 3 bedrooms, nearby museums and a wood stove, it has everything you need to make your stay comfortable.

For even more great options, use the search bar at the top of the page to find the perfect Chatham vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near Chatham?

We all deserve some "me time" from time to time. If you're ready to spend a couple of long mornings lingering in bed hugging a coffee, there's no shortage of excellent weekend getaways in and near Chatham. Check out a few of our favorites:

  • "Beauty In The Berkshires" is around 6 miles southeast of Chatham and the perfect place to recharge your batteries. You'll appreciate the convenient amenities here, including off-street parking options and a phone.
  • Alternatively, live it up with your gang at "Scandi - Style Modern Cabin In Chatham: Enjoy Summer Hygge In The Woods", which is around 3 miles to the northwest of Chatham. Take advantage of coffee and tea making facilities, a washing machine and more here.

Can I find studio apartments for rent in and around Chatham?

Studio apartments are a simple yet stylish choice, perfectly suited for traveling sweethearts or solo adventurers. Spend your days getting to know your surroundings and your nights relaxing in your comfy hideaway. The following options in or near Chatham are guaranteed to please:

  • After a fun-filled day of outdoor exploration, enjoy total comfort and privacy at "Berkshire Barn On 23 Wooded Acres 2br". A firepit and ski lift privileges are just two of the amenities on offer here.
  • Or, use "Martin Van Buren Lake Cottage 2" as a base to discover the best sights around you. This cozy stay comes with air conditioning, coffee and tea making facilities and more.

Can I find short term rentals in or near Chatham?

Whether you're searching for a compact apartment for you and a few friends or a townhouse with space for the whole family, short-term rentals are easy to find in and around Chatham. These properties make the perfect base for a short and sweet stay:

  • If you only need to stay a few nights, "Cozy Apartment Overlooking Our Small Farm. Family Friendly" is a fantastic choice. It's not too far from the center of Chatham, so you'll have easy access to all the best sights.
  • Alternatively, spend a few nights at "Secluded House With Picturesque Views In Historic Old Chatham". This comfy, centrally located property makes exploring the local sights easy.

What are the best romantic weekend getaways in or near Chatham?

Whether spent in a log cabin or a beach house, a romantic weekend getaway is one of the best ways to add some zing to your relationship. Whisk your other half off for a couple of relaxing days at one of these popular escapes in or near Chatham:

  • Sneak away on Friday for a couple of nights of passion at "Designers Own Year - Round Hudson Valley Getaway Cottage". Approximately 14 miles from Chatham, this property comes with plenty of nice touches, like beauty services and a fireplace.
  • Alternatively, spend your break enjoying each other's company at "Luxury Barn Retreat. Year - Round Perfect Family Getaway", around 12 miles from Chatham. A sauna and a restaurant dining guide will help ramp up the romance.

What are the best houses for rent with a pool in or near Chatham?

A pool is often a nonnegotiable when choosing where to spend your vacation, especially if you're traveling with kids who are full of beans. Check out these houses with a pool in or near Chatham and fill your days with splashing good fun:

  • Switch to vacay mode at "Secluded House With Picturesque Views In Historic Old Chatham", where your main priority will be enjoying the pool. Amenities such as cable/satellite TV services and a video library help make this retreat a guest favorite.
  • Spend leisurely days splashing about or catching a few peaceful moments by the water at "19th Century Farm House On 300 Acre Farm". This vacation home is another guest favorite and comes with a garden, towels and more.

Not sure what the weather's like in Chatham? It has a humid continental climate, with average summertime temperatures ranging from 55 ºF to 80 ºF. If you're searching for more inspiration on places to stay in this amazing destination, use the search bar at the top of the page and adjust the filters to browse through our entire range of Chatham vacation rentals.

What are the best large family vacation rentals in or near Chatham?

Grammy and Pop, Aunty Monique ... You can put them on your invitation list when you lock in a large family vacation rental in or near Chatham. Get all your loved ones together at one of these spacious getaways:

  • Around 12 miles to the south of Chatham, "Luxury Barn Retreat. Year - Round Perfect Family Getaway" has 3 bedrooms that sleep up to 8 guests. Amenities here include a dishwasher and a separate dining area.
  • "Beauty In The Berkshires" is another vacation rental your crew will love. You'll be able to invite as many as 16 people to this retreat which offers 6 bedrooms, childrens activities, a separate dining area and more. It's located 6 miles to the southeast of central Chatham.

We know it's tempting, but don't spend all your time socializing with the fam indoors. Head out and discover the area's family-friendly attractions, starting with Catamount Aerial Adventure Park.

Can I find family cabin rentals in or near Chatham?

Vacation with your kids in a family cabin rental in or near Chatham and get set to create some wonderful new memories together. Check out these options:

  • "Newly Renovated Cabin In The Country" - Enjoy fun and good times with your gang at this escape, which is around 4 miles east of the center of Chatham. A separate dining area and towels are among its family-friendly amenities.
  • "Cozy Copake Lake Cabin" - This stay is also ideal for families and is around 14 miles south of Chatham. Offering beach sun loungers, a barbecue grill and more, it'll get your group's stamp of approval.

For more options, use the search bar at the top of the page and adjust the filters to find the Chatham vacation rental that's perfect for your needs.

Can I find two-bedroom vacation rentals in or near Chatham?

It's easy to plan a wonderful getaway with Vrbo. Whether you prefer a cute cabin or a stylish apartment, you'll find great two-bedroom options in or near Chatham: Here are a couple of our personal faves:

  • "The Pinetop Cabin | Modern ∙ Surrounded By Trees ∙ Sustainably" is a winning choice for smaller groups. In addition to two bedrooms, this delightful stay offers amenities like a kitchen and a garden.
  • "Home Sweet Home In A Best Place To Live Locale" is another lovely two-bedroom retreat. It comes with a garden, a kitchen and more.

What are the best three-bedroom vacation rentals in or near Chatham?

You could easily fit a small crowd into the three-bedroom getaways available on Vrbo. If you're traveling with family or friends, consider these options in or near Chatham:

  • It won't take you long to see why "Scandi - Style Modern Cabin In Chatham" is popular with many travelers. This sizable retreat comes with a kitchen and a garden and makes vacationing with friends and family a breeze.
  • Alternatively, check out the spacious retreat that is "Close To Skiing Heated Pool /hot Tub". Stretch out with your favorite people and enjoy its many conveniences, including a kitchen and a firepit.