Old Chatham holiday lettings

We found 215 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.

Holiday rentals with weekly discounts - Old Chatham

Showing deals for:23 Jan - 30 Jan

Image gallery for Gorgeous large renovated historic home on 10 acres with pool

Property grounds
10 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)

Gorgeous large renovated historic home on 10 acres with pool

Chatham, NY

8% off
Price is £5,745
for 7 nights, 1 home
£821 per night
includes taxes & fees
Gorgeous large renovated historic home on 10 acres with pool

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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:

  • Furnace Brook Winery at Hilltop Orchards (9.6 mi / 15.4 km)
  • 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)

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)
  • Berkshire Botanical Garden (15.1 mi / 24.2 km)
  • The Mount (16 mi / 25.7 km)
  • Sleepy Hollow Lake (16 mi / 25.8 km)
  • Naumkeag Museum (16.3 mi / 26.3 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 best area to stay in Old Chatham when booking a holiday rental?
When considering a holiday rental in Old Chatham, New York, the area around the village centre is an excellent choice. This charming neighbourhood offers a delightful blend of rural tranquility and convenient access to local amenities. Staying here allows you to enjoy the picturesque landscape of the Hudson Valley while being just a short distance from enticing attractions.

One of the top points of interest nearby is the Old Chatham Country Store, where you can find a selection of local produce, artisanal goods, and unique gifts. It's a superb spot to experience the local culture and perhaps pick up some treats for your stay. Additionally, the area is known for its scenic beauty, with numerous trails and parks nearby, ideal for outdoor activities like hiking and birdwatching.
How much does it cost to rent a holiday home in Old Chatham?
Prices for holiday rentals in Old Chatham vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Old Chatham to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Old Chatham holiday house rentals?
You can find great discounts on house rentals in Old Chatham on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best Old Chatham ski resort rentals?
For ski resort rentals near Old Chatham, travellers should consider the nearby areas of Windham and Hunter, both of which offer excellent access to ski slopes. Windham, located approximately 30 minutes away, features a variety of rental options, including cosy chalets and modern condos that cater to different group sizes. Many properties here come equipped with amenities such as fireplaces, full kitchens, and some even include hot tubs, providing a great retreat after a day on the slopes.

Hunter, slightly further afield, is another popular choice, known for its vibrant ski community. Here, visitors can find charming mountain lodges and holiday homes that often boast scenic views of the surrounding mountains. Many rentals in this area feature convenient amenities like ski storage, laundry facilities, and spacious living areas, making them ideal for families or groups of friends.
What is the most popular type of holiday rental accomodation in Old Chatham?
In Old Chatham, holiday houses and cottages are the most popular types of rental accommodations, with several available throughout the area. These properties typically offer a charming and rustic experience, often featuring multiple bedrooms, cosy living spaces, and fully equipped kitchens. Many also include outdoor areas such as gardens or patios, ideal for enjoying the tranquil surroundings.
Are there any family house rentals in Old Chatham?
In Old Chatham, New York, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. The area features a variety of spacious homes located among the scenic beauty of the countryside. Many of these properties boast amenities such as expansive living rooms, fully equipped kitchens for home-cooked meals, and outdoor spaces superb for kids to play and explore.
Can I rent a holiday home with a pool or hot tub in Old Chatham?
In Old Chatham, there are several holiday homes available for rent that feature pools and hot tubs, making it a delightful option for those seeking a relaxing getaway. This picturesque area, known for its charming countryside and quaint atmosphere, offers a range of amenities in these properties. Many rentals come with private pools, outdoor seating areas, and hot tubs, ideal for unwinding after a day of exploring. Additionally, fully equipped kitchens and spacious living areas provide comfort and convenience for families or groups.
Can I find long-stay holiday rentals in Old Chatham?
A long-stay holiday rental in Old Chatham is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Old Chatham?
In Old Chatham, there are several pet-friendly house rentals available, making it an ideal destination for travellers looking to bring their furry companions along. Many of these holiday homes feature amenities that enhance comfort and convenience, such as spacious backyards, fully equipped kitchens, and comfortable living areas. Some properties may even offer additional features like pet-friendly furnishings or nearby walking paths to accommodate your pet's needs.
Are there any remote work holiday rentals in Old Chatham?
In Old Chatham, New York, there are several remote work holiday rentals available, making it a suitable destination for those who wish to blend work and leisure. Many of these properties offer amenities tailored for remote work, including dedicated office spaces, desks with chairs, and reliable Wi-Fi to ensure a productive environment. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Old Chatham holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Old Chatham with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Old Chatham?
In Old Chatham, popular rental amenities typically include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature coffee makers, cookware, dishware, and utensils, which enhance the home-like experience. Additional conveniences often found in these rentals are dishwashers and microwaves, making it easier for travellers to enjoy their stay without the hassle of extensive cleaning or meal preparation.
When is the best time to visit Old Chatham for a holiday rental?
The best time to visit Old Chatham for a holiday rental is during the peak season from June to August. This vibrant period attracts travellers looking to immerse themselves in the beauty of the Hudson Valley, with opportunities for outdoor activities such as hiking, cycling, and visiting local farmers' markets. The warm summer temperatures, typically ranging from the mid-teens to low 30s Celsius, make it an ideal time for enjoying the lush landscapes and scenic views.

July is particularly popular, as the community comes alive with a variety of events and festivals. Visitors can enjoy delightful summer evenings, superb for stargazing or attending local art exhibitions, all while relishing the charming atmosphere of this quaint town.

For those seeking a more budget-friendly experience, consider planning your visit in November. This month offers a quieter, more reflective vibe, allowing you to appreciate the stunning autumn colours that adorn the surrounding hills. The crisp air is invigorating and ideal for peaceful walks, and you may find good value accommodation options during this time.
How early should I book a Old Chatham holiday rental?
Book your Old Chatham holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Old Chatham?
In Old Chatham, visitors can enjoy a tranquil rural atmosphere with several charming attractions. The Old Chatham Country Store is a local favourite, offering a taste of the area's history alongside artisanal goods and provisions. The nearby Chatham Brewing provides an excellent opportunity to sample locally crafted beers in a relaxed setting. Nature enthusiasts can explore the surrounding countryside, with scenic walking trails and beautiful landscapes superb for outdoor activities. The area is also known for its art galleries and antique shops, showcasing the creativity and heritage of the region.
Can I change or cancel my Old Chatham home rental booking on Vrbo?
To find Old Chatham holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Old Chatham holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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