Chatham vacation rentals

We found 1,318 vacation rentals — enter your dates for availability

Discover a selection of 14 homes and other vacation rentals in Chatham that are perfect for your trip. Whether you're going on vacation with family or friends, vacation homes have the best amenities for spending time at your vacation home, which might include WiFi and a fireplace. No matter what you're looking for, you'll be able to choose a rental for everyone's needs, including accessible or non-smoking choices.

Vacation rentals with weekly discounts - Chatham

Showing deals for:Jul 3 - Jul 10

Image gallery for Private pool on 8 acres. Minutes from Hudson, Copake Lake, OMI, Klocke & Olana!

Relax by the pool, antique on Warren St. or visit the beautiful area attractions
9.8 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)

Private pool on 8 acres. Minutes from Hudson, Copake Lake, OMI, Klocke & Olana!

Hudson

8% off
Price is $627
$4,392 for 7 nights
All fees included
Private pool on 8 acres. Minutes from Hudson, Copake Lake, OMI, Klocke & Olana!

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Find out more about Chatham

Why visit Chatham

  • Outdoor Adventures: Enjoy activities like hiking, fishing, and boating in the beautiful lakes and nature reserves.
  • Charming Town Atmosphere: Explore the welcoming neighborhoods filled with friendly locals and quaint shops.
  • Historic Sites: Visit historical landmarks that showcase the rich history of Chatham and its surroundings.
  • Romantic Getaways: Experience picturesque settings perfect for couples looking for a romantic escape.
  • Diverse Accommodation Options: Choose from a variety of vacation rentals, including cozy cottages and luxury homes.

Popular types of accommodation in Chatham

Planning a getaway to Chatham? You're in for a treat. Explore a variety of vacation rentals, including houses, condos, and charming cottages. Whether you're searching for apartments in Chatham or pet-friendly options, we have you covered. Discover the perfect house for rent that meets all your needs and enjoy a memorable stay in this picturesque destination.

  • Houses: The top choice for visitors to Chatham, offering spacious and comfortable accommodations ideal for families and groups.
  • Condos: A popular option for those seeking modern amenities and a community feel, perfect for couples or small families.
  • Cottages: A charming and quaint choice, these cozy retreats provide a peaceful escape in a picturesque setting.
  • Apartments: Convenient and versatile, apartments are great for travelers looking for a home-like experience in the heart of Chatham.
  • Cabins: Ideal for nature enthusiasts, cabins offer a rustic vibe and close access to outdoor adventures.**

Top attractions near Chatham

Chatham, New York, is the perfect destination for outdoor and romantic getaways, boasting beautiful lakes, historic sites, and nature reserves. Visitors can immerse themselves in local culture while enjoying scenic views and outdoor activities. Don't miss exploring the charming town of Chatham and considering local rentals for a comfortable stay. Whether you seek adventure or relaxation, Chatham offers a delightful experience for every traveler.

  • Martin Van Buren National Historic Site: Explore the home of the eighth President of the United States, showcasing the rich culture and history of the early 19th century. Enjoy guided tours and beautiful landscapes that reflect Van Buren's legacy.
  • Art Omi International Arts Center - Fields Sculpture Park: A vast outdoor sculpture garden featuring diverse contemporary art installations. Perfect for families, enjoy leisurely walks among stunning artworks while experiencing the beauty of nature.
  • Kinderhook Lake: A picturesque lake offering scenic views, ideal for romantic picnics or relaxing beach days. Enjoy outdoor activities like kayaking and fishing in a serene setting.

Things to do recommended for couples

For a romantic getaway in Chatham, enjoy a concert at Tanglewood Music Center, just 15 miles away, or savor wine at the charming Hudson Chatham Winery, only 4 miles from town. For adventurous couples, the Catamount Ski Area, also 15 miles away, offers thrilling skiing experiences.

Things to do recommended for families

Families can unwind at Lake Mansfield Park or Kennedy Park, both offering serene recreational areas just 16 miles from Chatham. Alternatively, Mosher Park, located 14 miles away, provides a perfect spot for relaxation and fun activities in a beautiful setting.

Things to do recommended for groups

Experience the charm of Chatham by catching a show at the Mac-Haydn Theatre, hiking the scenic High Falls Trail just 9 miles away, or having an adventure at the Catamount Aerial Adventure Park, located 14 miles from town. Perfect for group fun and bonding.

*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 Chatham

If you're traveling with a group, family, or pets, or if you're seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chatham with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. The good news is that you can easily filter for all of these options and more on Vrbo.
  • Traveling to Chatham with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chatham: For many families, a getaway wouldn’t be the same without their furry companion. If that resonates with you, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chatham: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Be sure to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Chatham

Chatham, New York, offers a delightful blend of outdoor adventures and romantic scenery, making it an ideal vacation spot. Explore the charming neighborhoods filled with friendly faces and family-friendly atmospheres. Nearby areas promise relaxing getaways with luxury homes and historical sites, perfect for those seeking a budget-friendly escape. Whether you're looking for coastal retreats or simply a peaceful respite, Chatham and its surroundings guarantee a memorable experience.

  • Ghent: Located a mere 3 miles from Chatham, Ghent is a charming city that beckons travelers with its stunning outdoor scenery and romantic ambiance. Known for its picturesque landscapes, visitors can enjoy activities such as skiing at the nearby ski resorts, making it a prime destination for winter sports enthusiasts. The area's natural landmarks, including serene lakes and majestic mountains, provide perfect backdrops for a day of exploration or relaxation at the beach. Whether you're looking for a cozy getaway or an adventure in nature, Ghent has something for everyone.
  • Hudson: Situated 13 miles from Chatham, Hudson is a vibrant city that offers a delightful blend of outdoor adventure and scenic beauty. This city is a haven for thrill-seekers and nature lovers alike, with accessible ski fields and resorts that attract winter sports fans. The city's surrounding landscapes featuring lakes and mountains create an idyllic setting for hiking and exploration. With its bustling tourist precinct filled with unique shops and local eateries, Hudson is perfect for those seeking both adventure and a taste of local culture.
  • East Chatham: Just 5 miles from Chatham, East Chatham is an inviting city known for its outdoor adventures and romantic charm. Visitors can immerse themselves in the local arts scene by attending theater performances or music concerts, all while enjoying the stunning natural surroundings. With nearby attractions like a national state park, beautiful lakes, and mountains, East Chatham offers endless opportunities for hiking, skiing, and enjoying nature. This city is an excellent choice for those looking to blend outdoor fun with cultural experiences.

Best time to go to Chatham

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January24.6°F (-4.1°C)Light RainMostly CloudyAverageAverage
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 SunnyAverageAverage
July71.6°F (22.0°C)Light RainMostly SunnySlightly HighSlightly High
August69.6°F (20.9°C)Light RainMostly SunnySlightly HighSlightly High
September62.6°F (17.0°C)Light RainMostly SunnySlightly HighAverage
October51.4°F (10.8°C)Light RainMostly SunnySlightly LowSlightly Low
November39.2°F (4.0°C)Light RainMostly SunnySlightly LowAverage
December31.1°F (-0.5°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you aiming to save on your upcoming travel plans? Keeping your travel dates flexible can be a great way to take advantage of fluctuating prices. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to utilize our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options for your needs.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy-to-use platform where you can plan new trips, continue from where you last stopped, or organize your travel arrangements. You'll see your saved or booked properties neatly organized into categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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 for a relaxing getaway.

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:

  • Catamount Ski Area (14.9 mi / 24 km)
  • Bousquet Ski Area (16.5 mi / 26.5 km)
  • Wyndhurst 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)
  • Hudson Chatham Winery (4.4 mi / 7 km)

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:

  • Art Omi International Arts Center - Fields Sculpture Park (4.4 mi / 7 km)
  • Kinderhook Lake (7.1 mi / 11.5 km)
  • Queechy Lake (9.7 mi / 15.5 km)
  • Sleepy Hollow Lake (11.8 mi / 19.1 km)
  • Mull Island (12 mi / 19.4 km)
  • Berkshire Botanical Garden (13.9 mi / 22.4 km)

Transportation options to and around Chatham

The nearest airport is in Hudson, NY (HCC-Columbia County), located 7.7 mi (12.4 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 16 mi (25.8 km) away.

Frequently asked questions

How much does it cost to rent a vacation home in Chatham?
Prices for vacation rentals in 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 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 Chatham vacation house rentals?
You can find great discounts on house rentals in 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 areas for renting a beach house in Chatham?
For renting a beach house in Chatham, travelers should focus on the scenic areas along the coastline, particularly around Chatham Lighthouse Beach. This area offers beautiful views of the Atlantic Ocean and convenient access to sandy shores. Many rental properties near the beach feature amenities such as outdoor decks or patios, great for enjoying the ocean breeze, as well as spacious living areas and fully equipped kitchens for family meals after a day in the sun.

In addition to Lighthouse Beach, the nearby properties along Hardings Beach provide a quieter, family-friendly atmosphere with easy access to soft sands and warm waters. Rentals in this vicinity often come with amenities like private yards, outdoor grills, and sometimes even access to community facilities like pools or tennis courts.

Travelers might also consider options near the Chatham Fish Pier, where they can enjoy a vibrant local atmosphere with seafood restaurants and shops. Rentals in this area typically offer charming coastal decor, cozy interiors, and the convenience of walking to local attractions. Find your rental near the beach in Chatham.
Where are the best Chatham ski resort rentals?
For skiing near Chatham, the closest resort is Jiminy Peak, located about 30 minutes away in Hancock, Massachusetts. Travelers looking for rentals in this area should consider the quaint surroundings of both Chatham and nearby towns like New Lebanon and Hancock. In New Lebanon, visitors can find cozy cabins and modern vacation homes equipped with amenities such as full kitchens, fireplaces, and spacious living areas that are superb for relaxing after a day on the slopes. Many properties also feature outdoor spaces for enjoying the fresh mountain air.

In Hancock, it's common to find ski-in/ski-out accommodations or lodges that provide convenient access to Jiminy Peak. These properties often include amenities like hot tubs, game rooms, and fitness centers, suiting families and larger groups looking for both comfort and entertainment. Additionally, the region offers stunning views of the Berkshires, adding to the appeal of the rentals.

For those looking to combine skiing with local culture, Chatham itself is home to charming shops and restaurants, and rentals in this area may also feature unique architectural styles and historic character.
What is the most popular type of vacation rental accomodation in Chatham?
In Chatham, vacation houses are a popular option, with several available throughout the area. These houses typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for comfort and convenience. Many of these properties also include outdoor spaces like decks or gardens, great for enjoying the fresh air and scenic surroundings. Additionally, mobile homes, chalets, apartments, and cabins are also prevalent, providing a variety of choices to suit different preferences.
Are there any family house rentals in Chatham?
In Chatham, New York, there are several family-friendly house rentals available, making it an excellent choice for families looking to unwind together. The area features spacious homes with multiple bedrooms, allowing for comfortable accommodations for larger groups. Many of these properties come equipped with full kitchens, enabling families to prepare meals together, as well as inviting outdoor spaces where children can play and explore.

Visitors to Chatham can enjoy the charming atmosphere of the town, with nearby attractions such as the picturesque Chatham Village and the scenic landscapes of the Berkshires. Families can take advantage of local parks, hiking trails, and recreational activities, ensuring a memorable stay filled with both relaxation and adventure.
Can I rent a vacation home with a pool or hot tub in Chatham?
In Chatham, New York, there are several vacation homes available for rent that include pools or hot tubs, making it a great choice for travelers seeking relaxation and leisure during their stay. This charming town is located in the picturesque Hudson Valley, providing a serene backdrop for your getaway. Many of these properties offer inviting outdoor spaces, where guests can enjoy refreshing swims or unwind in hot tubs amidst beautiful natural surroundings.

Travelers can expect amenities such as spacious patios, fully equipped kitchens for home-cooked meals, and comfortable living areas to enhance their experience. The area is also known for its quaint downtown, filled with local shops and restaurants, which adds to the appeal of staying in Chatham.
Can I find long-stay vacation rentals in Chatham?
A long-stay vacation rental in Chatham is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chatham?
In Chatham, visitors can find several pet-friendly house rentals that cater to those traveling with furry companions. Many of these properties offer spacious backyards and outdoor areas, great for pets to enjoy the fresh air. Travelers can expect amenities such as fully equipped kitchens, cozy living spaces, and sometimes even features like fireplaces or outdoor seating areas for relaxation.

Chatham is known for its charming small-town atmosphere, with local shops, cafes, and beautiful parks nearby.
Are there any remote work vacation rentals in Chatham?
In Chatham, New York, there are several options for remote work vacation rentals, with around 16 properties available to suit your needs. Many of these rentals are equipped with amenities specifically designed for remote workers, including free Wi-Fi, dedicated desk spaces, and comfortable desk chairs, ensuring a productive environment during your stay.

The charming village of Chatham offers a quaint atmosphere with easy access to local cafes and restaurants that can serve as alternative workspaces. Additionally, the surrounding areas provide beautiful landscapes and recreational opportunities for relaxation after a day of work, making it an ideal location for those looking to blend productivity with leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chatham vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chatham with parking available—perfect for families or travelers 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 Chatham?
In Chatham, popular vacation rental amenities include fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also feature outdoor spaces such as decks or patios, superb for enjoying the fresh air and surrounding natural beauty. Onsite parking is commonly available, making it convenient for travelers with vehicles. Additionally, rentals often provide coffee and tea makers, ensuring guests can enjoy their morning brews at their leisure.
When is the best time to visit Chatham for a vacation rental?
The peak season for visiting Chatham falls between July and September, when the charming town transforms into a vibrant hub for travelers seeking both relaxation and adventure. This summer period is especially popular, with visitors flocking to enjoy the warm weather and partake in various outdoor activities such as hiking, biking, and exploring the stunning landscapes of the Hudson Valley.

July stands out as the most popular month, where you can expect a delightful atmosphere filled with lively events and gatherings. The temperatures typically range from the mid-60s to the low 80s Fahrenheit, making it an ideal time for outdoor barbecues, picnics in the park, or leisurely strolls through the picturesque downtown area.

For those looking for a more budget-friendly option, consider planning your visit in November. While this month marks the low season, it also offers a unique charm as the fall foliage transitions into a peaceful winter landscape. Enjoy the tranquility of Chatham while taking in the serene beauty of the surroundings, great for cozy evenings by the fire.

Ultimately, your choice of when to visit Chatham will depend on your preference for bustling summer activities or the quiet, reflective atmosphere of the shoulder season.
How early should I book a Chatham vacation rental?
Book your 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 Chatham, New York, United States of America?
In Chatham, New York, visitors can enjoy a variety of attractions that showcase the charm of this small town and its surrounding areas. The heart of Chatham features quaint shops and local eateries, superb for exploring on foot. The Chatham Marketplace is a popular stop for fresh produce and artisanal goods.

Nature lovers will appreciate the nearby Chatham Fish & Game Club, which offers opportunities for fishing and hiking. Additionally, the beautiful Olana State Historic Site, located just a short drive away, provides stunning views of the Hudson River and features a historic house museum designed by famed artist Frederic Edwin Church.

For those interested in the arts, the Crandell Theatre in downtown Chatham is a historic venue that often hosts films and community events. The town is also close to the scenic Taconic State Park, which offers trails for hiking and biking, making it an ideal spot for outdoor enthusiasts.
Can I change or cancel my Chatham home rental booking on Vrbo?
To find 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 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.
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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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