Old Chatham holiday lettings

We found 207 holiday rentals — enter your dates for availability

Discover a selection of 8 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.

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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:

  • 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)
  • Furnace Brook Winery at Hilltop Orchards (9.6 mi / 15.4 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)
  • Art Omi International Arts Center - Fields Sculpture Park (9.1 mi / 14.7 km)
  • Mull Island (11.4 mi / 18.3 km)
  • Lenox Mountain Reserve (13 mi / 20.9 km)
  • Stockbridge Bowl (14.4 mi / 23.2 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, one of the most appealing areas to stay is the charming neighbourhood surrounding the picturesque town centre. This area offers a delightful mix of historic architecture and modern conveniences, making it a great base for exploring the region. Here, you can find a variety of properties, from quaint cottages to spacious homes, suiting different tastes and group sizes.

Nearby, visitors can enjoy the beauty of the Columbia County region, with attractions like the stunning Olana State Historic Site, which features a magnificent house and breathtaking views of the Hudson River. Additionally, the local area is renowned for its natural beauty, with numerous hiking trails and parks, great for outdoor enthusiasts.
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 those seeking ski resort rentals near Old Chatham, the closest significant skiing is found at the Catamount Ski Area, located roughly 20 miles away in Hillsdale. In this area, visitors can find a variety of accommodations, including cosy cabins and family-friendly chalets, which often feature amenities such as fully equipped kitchens, communal fire pits, and comfortable living spaces great for relaxation after a day on the slopes.

The nearby towns of Chatham and Great Barrington also offer additional options, with properties that cater to both skiing enthusiasts and those looking to explore the scenic beauty of the Berkshires. Many rentals here come with traditional New England charm, boasting wood-burning stoves, outdoor decks, and sometimes even hot tubs for unwinding in the evenings.

In Chatham, visitors can enjoy quaint shops and local dining, while Great Barrington provides a vibrant arts scene and access to the picturesque Bash Bish Falls State Park, which is ideal for winter hiking and photography.
What is the most popular type of holiday rental accomodation in Old Chatham?
In Old Chatham, holiday houses are the most popular type of holiday rental, with about 21 available throughout the area. These properties typically offer spacious living arrangements, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many of these holiday houses also feature outdoor spaces such as gardens or patios, superb for relaxing after a day of exploring the scenic surroundings. Additionally, there are several charming cottages that provide a quaint and cosy atmosphere, often located in peaceful neighbourhoods that enhance the rural charm of Old Chatham.
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 a family getaway. The area is known for its picturesque landscapes and charming rural character. Many of these homes provide spacious living areas, full kitchens for preparing family meals, and outdoor spaces where children can safely play.

Visitors can also enjoy amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay. The locale offers easy access to nearby attractions, including local farms and scenic parks, great for family outings and outdoor activities.
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 or hot tubs, making it an appealing option for travellers seeking relaxation. This charming area in New York offers a mix of scenic countryside and quaint village life. Many properties with pools provide spacious outdoor areas great for lounging, as well as fully equipped kitchens for those who enjoy self-catering.

Visitors can expect amenities such as comfortable living spaces, private gardens, and some rentals may even include additional features like fire pits or outdoor dining areas. The serene surroundings of Old Chatham allow for a peaceful retreat, while still being conveniently located near local attractions, including art galleries and nature trails.
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 for those looking to enjoy a getaway with their furry companions. The area is known for its picturesque rural landscapes, offering a peaceful retreat amidst nature. Many of the holiday homes here come with amenities such as spacious gardens, outdoor seating areas, and fully equipped kitchens, making them ideal for families or groups.

Visitors can explore the nearby scenic spots, including the picturesque Chatham Village and the surrounding countryside, which features walking trails and opportunities for outdoor activities. The area is also home to charming local shops and cafes, where pets are often welcomed, enhancing the overall experience for travellers with pets.
Are there any remote work holiday rentals in Old Chatham?
In Old Chatham, New York, there are around 21 remote work-friendly holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties come equipped with essential amenities for remote work, such as desks, comfortable office chairs, and high-speed Wi-Fi, ensuring a productive environment.

The area itself is known for its tranquil rural charm, surrounded by beautiful landscapes and outdoor recreational opportunities. Guests can enjoy spacious living areas and well-equipped kitchens, great for a comfortable stay. Additionally, the proximity to local attractions, including scenic parks and quaint shops, enhances the experience for those seeking a balance between work and relaxation. 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 kitchens, allowing guests to prepare their own meals. Many properties also feature desks and desk chairs, which cater to those needing a workspace during their stay. Additionally, a coffee or tea maker is often provided, great for enjoying a warm beverage at any time. For added comfort, many rentals come equipped with fireplaces, creating a cosy atmosphere, particularly during the colder months.
When is the best time to visit Old Chatham for a holiday rental?
The peak season for visiting Old Chatham is during the summer months, particularly from June to August. This is when the charming village comes alive with visitors seeking to enjoy the vibrant local culture, outdoor activities, and the beautiful natural surroundings. July is the most popular month, offering warm weather that averages between 15 to 30 degrees Celsius, great for exploring the scenic beauty of the area.

During these summer months, you can partake in a range of activities such as hiking, cycling, and visiting local farms and markets. The longer daylight hours and pleasant climate make it ideal for outdoor adventures, including leisurely strolls through the picturesque countryside and enjoying the delightful local cuisine at nearby eateries.

For those looking for a more budget-friendly option, consider visiting in November. This month allows you to experience the tranquil charm of Old Chatham without the crowds, as the fall colours provide a stunning backdrop for peaceful walks and quiet reflection.
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, New York, visitors can enjoy a charming rural atmosphere with several attractions that highlight the region's natural beauty and artistic spirit. The Old Chatham Country Store is a local favourite, offering a delightful selection of artisanal goods and a taste of the community's history.

Nearby, the picturesque Chatham Village is home to quaint shops and eateries, superb for leisurely strolls. For those who appreciate the arts, the surrounding areas host various galleries and studios, showcasing local talent.

Outdoor enthusiasts can explore the scenic landscapes of the nearby Taconic State Park, where hiking trails and picnic areas provide ample opportunities for recreation. In the autumn, the vibrant foliage attracts many visitors, making it a prime time for nature walks and photography.
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 cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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