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Chatham, New York, United States of America

Chatham holiday lettings

We found 636 holiday rentals — enter your dates for availability

Discover a selection of 500 holiday rentals in Chatham that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at £ 81 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.
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Houses

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Cottages

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Bungalows

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Flats

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Cabins

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Farmhouses

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Estates

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Studios

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Resorts

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Find the best place to stay — Chatham

Modern Cozy Wooded Retreat On 30 Private Acres

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
£ 208 avg/night
(14)

Clatter Hall

Sleeps 8 · 4 Bedrooms · 3 Bathrooms
£ 449 avg/night
(1)

CLOSE TO SKIING /HOT TUB /FIBER OPTIC WIFI

Sleeps 6 · 3 Bedrooms · 3 Bathrooms
£ 1,131 avg/night
(26)

Spectacular All Seasons Retreat with Amazing Views

Sleeps 14 · 7 Bedrooms · 4 Bathrooms
£ 1,295 avg/night
(37)

Eames Inspired Lake House in the Woods on 30 Private Acres

Sleeps 8 · 2 Bedrooms · 4 Bathrooms
£ 245 avg/night
(1)

Home Sweet Home in a Best Place to Live Locale

Sleeps 4 · 2 Bedrooms · 1 Bathroom
£ 81 avg/night

Search 636 holiday rentals

Top rated rentals — Chatham
Stayed Apr 2021

Wonderful weekend getaway!

The property was extremely clean. Bill answered any questions within a quick timeframe and provided us with lots of nearby attractions. We loved sitting by the fire at night and was a perfect way to end our day. We would definitely go back in the fut...

Kelsey K.
Kelsey K.
Stayed Apr 2021

Fantastic retreat!

We loved everything about this house. It is a new house, beautifully decorated and with every kind of detail, including lots of books for our avid 7-year old reader. We loved waking up with the woodpeckers, and breathe nature from our bed. The area i...

Maria Jose Hierro H.
Maria Jose Hierro H.
Stayed Apr 2021

Great weekend getaway

We had a great weekend! The communication with Chris could not have been better. The instructions about the house were very straightforward. And that’s before we even got there. The house was perfect for our family. My husband who is very particular ...

Maryfrances H.
Maryfrances H.
Stayed Mar 2021

A true sanctuary

This property is a true sanctuary. The pond is absolutely beautiful and provides such a peaceful respite. The house is perfectly designed and welcoming. My 7-year old said she wanted to live there forever! We had a fantastic time at this home and lik...

Tricia M.
Tricia M.
Stayed Mar 2021

Relaxing family getaway in Berkshires

We had a wonderful two weeks in this great house just outside Sheffield. The garden is huge and kids adored the space to run around outside - or in the basement games room if weather got a bit wet. Everything was clean and well equipped inside. Lots...

Mungo W.
Mungo W.
Stayed Mar 2021

Relaxing get-away

Studio is cozy but well-appointed and very clean. I loved the decor - nice spashes of color and elements of nature felt very cheery. Close to restaurants and town, and yet very quiet and feels secluded. We enjoyed exploring the property. We hope to m...

Jean C.
Jean C.

Massachusetts

Stayed Mar 2021

Nice house and location

The house and location are nice. Lots of great outdoor space, the side deck was great for catching the sunset and we saw lots of deer and other wildlife on the property! Location felt central and easy without being in the thick of things. Chatham i...

Corinne I.
Corinne I.
Stayed Feb 2021

The perfect quiet retreat

It has been tough to work from home and stare at the same walls that we're also living in. We needed a change of scenery and needed a quiet getaway, someplace where we could work during the day and relax and feel at home at night. We found that with ...

Kristina B.
Kristina B.
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Destination guide

Head to the friendly city of Chatham

Enjoy the theatre scene and other features of Chatham. Travellers appreciate the restaurants in this welcoming city. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities

Sightseeing in and around Chatham

Are you searching for things to do while you're in the area? Venture out of your holiday home and check out everything that makes Chatham a fun spot to go on holiday. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Furnace Brook Winery at Hilltop Orchards (9.8 mi / 15.7 km)
  • Catamount Ski Area (12.7 mi / 20.4 km)
  • Pleasant Valley Wilderness Sanctuary (13.7 mi / 22.1 km)
  • Kennedy Park (14.8 mi / 23.9 km)
  • Bousquet Ski Area (15.6 mi / 25 km)
  • Greenock Country Club (15.7 mi / 25.3 km)
Natural features

Exploring the natural landscape of Chatham

Whether you're an outdoor enthusiast or just want to take in the scenery, Chatham is a great place to get outside. Here are some of the area’s most enchanting features, all within 30 miles (48.2 km) of the city centre:

  • Berkshire Botanical Garden (11.7 mi / 18.8 km)
  • Lake Mansfield Park (13.5 mi / 21.7 km)
  • Kennedy Park (14.8 mi / 23.9 km)
  • Taconic Trail State Park (15.1 mi / 24.3 km)
  • Pittsfield State Forest (15.7 mi / 25.2 km)
  • Wood's Pond (16.1 mi / 25.9 km)
How to get there

Transport options to and around Chatham

Fly into Hudson, NY (HCC-Columbia County), the closest airport, located 8.3 mi (13.4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 15 mi (24.1 km) away.

Can I find a vacation rental around Chatham?

Yes, our 2021 property listings offer a large selection of 636 vacation rentals near Chatham. From 444 houses to 50 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chatham for a holiday or a weekend are on Vrbo.