Old Chatham vacation rentals

We found 216 vacation rentals — enter your dates for availability

Discover a selection of 6 homes and other vacation rentals in Old Chatham that are perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation homes have the best amenities for spending time at your vacation home, which might include a pool and a washer and dryer. You'll be able to choose a rental that has what everyone needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Old Chatham

Showing deals for:Feb 6 - Feb 13

Image gallery for Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Pool
10 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Ghent, NY

13% off
Price is CA $1,350
CA $12,036 total
includes taxes & fees
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

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Find out more about Old Chatham

Why visit Old Chatham

  • Scenic Outdoors: Old Chatham is perfect for outdoor enthusiasts, featuring serene lakes and nature reserves ideal for hiking and relaxation.
  • Historic Charm: Explore the quaint village of Chatham, with its historic houses and welcoming locals, offering a glimpse into its rich heritage.
  • Family-Friendly Activities: Enjoy a variety of excursions suitable for all ages, making it a great destination for families.
  • Romantic Getaways: The picturesque scenery provides a perfect backdrop for couples seeking a romantic retreat.
  • Diverse Accommodations: Choose from private vacation homes, charming cottages, and condos for a comfortable stay tailored to your needs.

Popular types of accommodation in Old Chatham

If you’re wondering about accommodation options in Old Chatham, you’re in the right place. Our most popular choices include Houses, Condos, and charming Cottages. Whether you’re searching for Old Chatham vacation rentals or reviews of nearby hotels, we’re here to provide you with all the information you need for a memorable stay. Discover the best of Chatham Centre and enjoy the comfort of holiday cottages tailored to your needs.

  • Houses: This is the top choice for visitors to Old Chatham, offering spacious accommodations perfect for families or groups.
  • Condos: A great option for those seeking modern amenities and convenience, these rentals are popular among travelers.
  • Cottages: For a quaint and picturesque stay, cottages are a charming choice that many guests adore.
  • Apartments: Ideal for solo travellers or couples, these rentals provide a comfortable and private space.
  • Cabins: Perfect for a rustic escape, cabins offer a cozy retreat amidst nature for those looking to unwind.**

Top attractions near Old Chatham

Old Chatham, New York, offers a picturesque escape perfect for outdoor enthusiasts and romantic getaways. Explore historic houses, serene lakes, and nature reserves that provide a blend of culture and family-friendly experiences. Whether you're seeking tranquility or adventure, there are plenty of attractions to discover in and around Old Chatham, ensuring a memorable vacation.

  • National Shrine of the Divine Mercy: Located 27.4km from Old Chatham, this serene shrine offers a peaceful atmosphere for reflection and spiritual connection, enriched by its beautiful architecture and gardens.
  • Hancock Shaker Village: Just 17.7km away, this historic village invites visitors to explore the Shaker way of life through its preserved buildings and engaging exhibits, highlighting unique crafts and sustainable living.
  • Art Omi International Arts Center - Fields Sculpture Park: Situated 14.5km from Old Chatham, this outdoor sculpture garden features contemporary art installations amidst picturesque landscapes, perfect for families and art enthusiasts alike.

Things to do recommended for couples

For a romantic getaway in Old Chatham, enjoy a concert at Tanglewood Music Center, ski at Jiminy Peak Mountain Resort, or indulge in wine tasting at Furnace Brook Winery. Each destination offers a unique blend of charm and entertainment, perfect for couples looking to create lasting memories.

Things to do recommended for families

Families will love exploring Kennedy Park, just 24.1km from Old Chatham, for wellness and relaxation. Shatford Memorial Park, located 16.1km away, offers a beautiful recreational area. Don't miss Zuzu's Wonderful Life Inc, a delightful sweet treat spot 29.0km from Old Chatham, perfect for family fun.

Things to do recommended for groups

Groups visiting Old Chatham can enjoy a captivating performance at the Mac-Haydn Theatre, explore the charming Zema's Nursery, or hit the greens at Wyndhurst Golf & Club for some outdoor fun. These activities offer a delightful blend of culture, shopping, and sports for everyone.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Old Chatham

If you're planning a trip with a group, family, or pets, or if you're interested in extended stays, be sure to refine your search based on your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Old Chatham with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Old Chatham with young kids: Traveling with young kids can present some challenges. It's important to prioritize their comfort and safety, along with ensuring there are suitable amenities for their age, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Old Chatham: For many, a family getaway wouldn’t feel complete without their furry companion. If you can relate, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Old Chatham: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Old Chatham

Old Chatham, New York, offers a delightful blend of outdoor adventures and romantic scenery, perfect for a relaxing getaway. Explore the charming Town of Chatham and its quaint village, where friendly locals welcome you with open arms. Enjoy family-friendly excursions and budget-friendly options, making it an ideal destination for all types of travellers. Don't miss the chance to experience the essential beauty and unique atmosphere that Old Chatham has to offer.

  • East Chatham: Situated a mere 4.8km from Old Chatham, East Chatham is a charming city that beckons outdoor enthusiasts and couples seeking a romantic getaway. Known for its breathtaking natural landscapes, visitors can enjoy activities such as skiing in winter and hiking in summer. The local theatre and music concerts add a vibrant cultural touch to the experience. Nearby attractions include stunning lakes, majestic mountains, and the expansive national state park, offering a perfect backdrop for adventure and relaxation alike.
  • Malden Bridge: Located 3.2km from Old Chatham, Malden Bridge is a picturesque city known for its captivating scenery and outdoor activities. Ideal for couples and nature lovers, Malden Bridge offers various attractions, including music concerts and theatre performances that enrich the local culture. Visitors can explore enchanting lakes, towering mountains, and mesmerizing waterfalls, making it a perfect destination for those looking to immerse themselves in nature's beauty while enjoying romantic experiences.
  • North Chatham: Just 6.4km from Old Chatham, North Chatham is a delightful city that provides a blend of outdoor adventure and scenic charm. Nature enthusiasts will appreciate the tranquil lakes and striking monuments, while the nearby caves offer intriguing exploration opportunities. With a focus on education and culture, visitors can enjoy local music concerts and theatrical performances. North Chatham is an ideal spot for couples seeking a romantic escape amidst breathtaking landscapes and enriching experiences.

Best time to go to Old Chatham

If you're planning a trip to Old Chatham, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.6°F (-4.1°C)Light RainMostly CloudyModerately LowAverage
February26.2°F (-3.2°C)Light RainMostly CloudyAverageAverage
March34.2°F (1.2°C)Light RainMostly CloudyAverageSlightly Low
April45.7°F (7.6°C)Light RainMostly CloudyAverageSlightly Low
May57.4°F (14.1°C)Light RainMostly SunnyAverageAverage
June65.3°F (18.5°C)Light RainMostly SunnyModerately HighAverage
July71.6°F (22.0°C)Light RainMostly SunnyModerately HighSlightly High
August69.6°F (20.9°C)Light RainMostly SunnyModerately HighSlightly High
September62.6°F (17.0°C)Light RainMostly SunnyAverageAverage
October51.4°F (10.8°C)Light RainMostly SunnyAverageSlightly Low
November39.2°F (4.0°C)Light RainMostly SunnyModerately LowAverage
December31.1°F (-0.5°C)Light RainMostly CloudyModerately LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that meets your budget, feel free to use our filters to sort by price, location, and type of vacation rental.

Vrbo Trips: Effortless planning

Vrbo's groundbreaking Trip Board offers you a convenient way to plan your future travels, pick up right where you left off, or manage your itinerary with ease. You can easily access the properties you've saved or booked under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Choose a vacation rental for your Old Chatham getaway

Enjoy the museums and other features of Old Chatham. You'll find plenty to explore during your stay in the area. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Old Chatham

Do you want to find things to do while you're in the area? Although it can be tempting to stay in your comfortable vacation rental, you'll want to check out everything that makes Old Chatham a fun spot to vacation. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

  • 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 exciting outdoor activities or just want to take in the scenery, Old Chatham is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

  • 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)
  • Berkshire Botanical Garden (15.1 mi / 24.2 km)
  • The Mount (16 mi / 25.7 km)
  • Sleepy Hollow Lake (16 mi / 25.8 km)

Transportation 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 center. 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 vacation rental?
When considering a vacation rental in Old Chatham, New York, a popular area to stay in is the vicinity around the charming village centre. This area offers a delightful blend of tranquillity and proximity to local attractions, making it ideal for those seeking a peaceful retreat. Here, you will find a modest selection of properties, ranging from quaint cottages to larger family homes, allowing visitors to choose accommodations that best suit their needs.

Staying near the village centre puts you within easy reach of the Old Chatham Rural Cemetery, which is not only a serene spot for a leisurely stroll but also steeped in history. Additionally, the area boasts proximity to the beautiful Chatham Fish and Game Club, where outdoor enthusiasts can enjoy various recreational activities.

Another appealing neighbourhood is the outskirts of Old Chatham, where you can experience the stunning natural beauty of the countryside. This area typically features a more spacious selection of vacation rentals, with picturesque views and an inviting rural atmosphere. You'll find yourself close to the scenic trails of the nearby Taconic State Park, great for hiking and enjoying the great outdoors.
How much does it cost to rent a vacation home in Old Chatham?
Prices for vacation 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 travelling 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.
Are there any discounts for Old Chatham vacation 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 skiing near Old Chatham, the closest renowned ski resort is Jiminy Peak, situated around a 30-minute drive away in Hancock, Massachusetts. Travellers looking for ski resort rentals should consider the areas surrounding Jiminy Peak, where you can find a variety of accommodations suiting different group sizes. Many of these properties are well-equipped with amenities such as fully furnished kitchens, living areas with fireplaces, and convenient ski storage, making them ideal for families or groups eager to hit the slopes.

In the nearby towns of Pittsfield and Lanesborough, visitors can discover charming cabins and larger homes that provide a rustic yet comfortable atmosphere. These rentals often feature essential amenities like Wi-Fi, laundry facilities, and outdoor spaces for relaxation after a day of skiing. Moreover, the proximity to local dining options and shops enhances the overall convenience for travellers.
What is the most popular type of vacation rental accomodation in Old Chatham?
In Old Chatham, vacation houses and cottages are the most popular types of rental accommodations, with several options available throughout the area. These properties provide a charming and rustic experience, often featuring spacious layouts, fully equipped kitchens, and inviting living areas. Many cottages come with outdoor spaces, such as gardens or patios, great for enjoying the serene surroundings. This quaint town is ideal for those seeking a peaceful getaway, with its picturesque landscapes and proximity to local attractions.
Are there any family house rentals in Old Chatham?
In Old Chatham, New York, there are several family-friendly house rentals available, making it a lovely spot for families to enjoy quality time together. Visitors can find homes with spacious living areas, well-equipped kitchens for preparing family meals, and outdoor spaces great for children to play. Many properties come with amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.
Can I rent a vacation home with a pool or hot tub in Old Chatham?
In Old Chatham, there are several vacation homes available for rent that feature pools and hot tubs, making it an appealing destination for those seeking relaxation and comfort. This picturesque town is located in the scenic landscapes of the Hudson Valley, providing a tranquil setting for a getaway.
Can I find long-stay vacation rentals in Old Chatham?
A long-stay vacation 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 that cater to travellers seeking a welcoming environment for their furry companions. The area is known for its picturesque rural charm, with vacation homes featuring amenities such as spacious gardens, fully equipped kitchens, and comfortable living spaces, making them ideal for families or groups. Many properties may also include features like outdoor patios or decks, providing a lovely spot to relax and enjoy the natural surroundings.
Are there any remote work vacation rentals in Old Chatham?
In Old Chatham, New York, there are several vacation rentals that cater to remote work needs. These properties typically feature dedicated office spaces equipped with desks and chairs, ensuring a productive work environment. High-speed Wi-Fi is commonly available, allowing for seamless connectivity. Many rentals also include amenities such as safes for securing personal items and comfortable living areas for relaxation after a day's work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Old Chatham vacation rentals with parking?
Vrbo offers a wide selection of vacation 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 vacation rental?
The best time to visit Old Chatham for a vacation rental is during the peak season from June to August, with July being particularly popular among travellers. This lively summer period invites visitors to enjoy the region's charming landscapes and partake in a variety of outdoor activities, such as hiking and exploring local farms and markets. The warm temperatures, often reaching the low 30s Celsius, create an inclusive setting superb for leisurely strolls and picnics in the idyllic countryside.

For those looking for a more tranquil experience, November offers a wonderful opportunity to enjoy the stunning fall colours as the leaves change. This month sees fewer crowds and allows for a peaceful retreat while still providing access to the area's natural beauty and quaint charm.
How early should I book a Old Chatham vacation rental?
Book your Old Chatham vacation 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 vacation 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 serene rural atmosphere with attractions that highlight the area's natural beauty and cultural heritage. The Old Chatham Country Store is a charming spot where travellers can find local goods and a friendly atmosphere, superb for a leisurely afternoon. Nearby, the Chatham Fish and Game Club offers opportunities for outdoor enthusiasts, including hiking and fishing.
Can I change or cancel my Old Chatham home rental booking on Vrbo?
To find Old Chatham vacation 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 vacation 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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