Chester vacation rentals

We found 160 vacation rentals — enter your dates for availability

Discover a selection of 10 homes and other vacation rentals in Chester that are perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include air conditioning and a pool. Whatever you're looking for, you'll find a rental that has what everyone needs, including accessible or non-smoking choices.

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Find out more about Chester

Why visit Chester

  • Outdoor Adventures: Chester offers stunning national and state parks, perfect for hiking, fishing, and enjoying nature.
  • Scenic Lakes: Enjoy beautiful lakes that provide opportunities for swimming, kayaking, and picnicking.
  • Family-Friendly Attractions: The town is packed with activities suitable for families, ensuring fun for all ages.
  • Charming Neighborhoods: Explore welcoming neighborhoods filled with friendly locals and unique shops.
  • Diverse Accommodation Options: Choose from cozy cottages to modern condos, catering to every traveler's needs.

Popular types of accommodation in Chester

Planning a getaway to Chester? Discover a range of vacation rentals that cater to your needs, from spacious houses and cozy cottages to modern condos. Enjoy the comfort of bedroom apartments with laundry facilities, perfect for families or groups. With a variety of single-family rental listings, you’re sure to find the ideal spot to unwind and create lasting memories. Explore your options and make your Chester trip unforgettable.

  • Houses: The top choice for visitors, these spacious homes offer comfort and privacy, perfect for families and groups looking to enjoy Chester together.
  • Condos: A popular option, condos provide a mix of convenience and amenities, ideal for travelers seeking a home-away-from-home experience.
  • Cottages: Quaint and cozy, cottages in Chester are perfect for those wanting a charming retreat in nature.
  • Apartments: Modern and versatile, apartments are great for solo travelers or couples wanting easy access to local attractions.
  • Cabins: For a rustic getaway, cabins offer a unique experience amidst the beautiful landscapes of Chester.**

Top attractions near Chester

Chester, New York, is perfect for family vacations and offers a blend of entertainment and city experiences. Visitors can explore popular attractions like national and state parks, scenic lakes, and urban parks. The area's points of interest are ideal for travelers seeking outdoor adventures, cultural experiences, and beautiful scenery, making it a delightful destination for all types of vacationers.

  • United States Military Academy: Located 14 miles from Chester, this prestigious military institution offers a glimpse into the training of future leaders. Visitors can explore the stunning campus and learn about its rich history.
  • Bear Mountain State Park: Situated 15 miles away, this national park is perfect for outdoor enthusiasts, featuring scenic hiking trails, breathtaking views, and various recreational activities amidst nature.
  • Harness Racing Museum and Hall of Fame: Just 4 miles from Chester, this sports museum celebrates the history and culture of harness racing, offering exhibits that showcase the sport's legacy and its impact on American culture.

Things to do recommended for couples

Chester offers delightful romantic experiences for couples. Visit Brotherhood Winery for a charming atmosphere, enjoy luxury at The Golf Club at Mansion Ridge, or embrace adventure at Mount Peter Ski Area. Each location enhances your getaway with unique vibes perfect for a couple's retreat.

Things to do recommended for families

During your family vacation in Chester, New York, enjoy a day at The Rock Sports Complex for some athletic fun, visit the Castle Fun Center for arcade adventures, and unwind at Thomas Bull Memorial Park, a perfect spot for wellness and relaxation just 8 miles away.

Things to do recommended for groups

Experience thrilling races at the Orange County Fair Speedway, shop at the Monroe Federal Plaza Shopping Center for entertainment and family fun, and enjoy a captivating performance at the Paramount Theatre, where culture and romance come alive, all within a short drive from Chester.

*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 Chester

If you're traveling with a group, enjoying a family getaway, bringing your pets along, or planning an extended stay, be sure to set your preferences accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Chester with a group: Think about how many bedrooms you'll require, as well as any additional features like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Chester with young kids: Traveling with little ones 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 Chester: For many families, a vacation isn't truly enjoyable without their furry companions. If this resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chester: If you're in search of vacation rentals that offer special rates for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Chester

Chester, New York, offers a delightful blend of family-friendly attractions and charming neighborhoods perfect for small families. Explore the scenic beauty of the town, enjoy fun activities, and immerse yourself in the welcoming atmosphere created by friendly locals. Nearby regions present a variety of experiences, from budget-friendly options to a touch of luxury, ensuring that every traveler finds their perfect getaway in and around Chester.

  • Middletown: Located approximately 10 miles from Chester, Middletown is a vibrant city known for its family-friendly atmosphere and entertainment options. Visitors can enjoy a variety of activities, including shopping at the local shopping centers and malls. The city is also home to a popular theme park, providing fun for all ages. Nature enthusiasts can explore nearby lakes, making it an excellent spot for relaxation and recreation. With its bustling tourist precinct, Middletown offers a city-themed experience that caters to all ages.
  • Goshen: Just 4 miles from Chester, Goshen is another charming city that attracts families and entertainment seekers. Known for its welcoming environment, Goshen features a range of shopping centers and malls that are perfect for a leisurely day out. The city's highlights include a theme park and a modern square, which often hosts events and activities for visitors. With its rich history and vibrant community, Goshen provides an engaging city-themed experience that is sure to delight tourists.
  • Monroe: Monroe is located about 5 miles from Chester and is recognized for its family-friendly vibe and business-oriented attractions. The city features shopping malls and centers that offer a variety of retail options, along with resorts for those looking to unwind. Monroe's landscape is marked by the presence of a theme park, scenic lakes, and nearby mountains, making it an ideal destination for both adventure seekers and those looking to relax in nature. This city combines a family-friendly atmosphere with business-oriented experiences, appealing to a diverse range of visitors.

Best time to go to Chester

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.0°F (-2.2°C)Light RainMostly SunnyAverageAverage
February29.8°F (-1.2°C)Light RainMostly SunnySlightly LowSlightly Low
March37.4°F (3.0°C)Light RainMostly SunnyAverageSlightly Low
April48.7°F (9.3°C)Light RainMostly SunnyAverageSlightly Low
May59.4°F (15.2°C)Light RainMostly SunnyAverageAverage
June67.6°F (19.8°C)Light RainMostly SunnySlightly HighAverage
July73.9°F (23.3°C)Light RainMostly SunnySlightly HighSlightly High
August72.0°F (22.2°C)Light RainMostly SunnyAverageSlightly High
September64.9°F (18.3°C)Light RainMostly SunnySlightly HighAverage
October54.0°F (12.2°C)Light RainMostly SunnyAverageAverage
November42.1°F (5.6°C)Light RainMostly SunnySlightly LowAverage
December34.2°F (1.2°C)Light RainMostly SunnySlightly LowSlightly High

Booking with Vrbo is simple

Are you hoping to save on your upcoming travels? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your reservation. Being the planner truly has its rewards. When you join our travel rewards program, One Key, you’ll gain immediate access to exclusive member savings and the opportunity to earn and redeem OneKeyCash on eligible bookings. Sign up today and begin enjoying your savings.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a user-friendly platform for planning your travels, allowing you to create new trips, continue from where you last stopped, or easily view and manage your itinerary. You can organize your saved or booked properties under categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Travel to friendly Chester

Learn about the unique charm of Chester with a stay in a private vacation home. This welcoming and relaxing city is known for its shopping, restaurants and skiing. Are you looking for specific amenities for your getaway? Many of our vacation rentals feature full kitchens and laundry facilities.

Sightseeing in and around Chester

Are you hoping to find top things to see and do in the area? Venture out of your cozy vacation rental and check out everything that Chester has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • LEGOLAND® New York (2.3 mi / 3.8 km)
  • Goshen Historic Track (3.8 mi / 6.1 km)
  • Brotherhood Winery (7.4 mi / 11.9 km)
  • Mount Peter Ski Area (8.1 mi / 13 km)
  • Warwick Valley Winery and Distillery (10.1 mi / 16.2 km)
  • Ice Time Sports Complex (13.9 mi / 22.4 km)

Exploring the natural features in Chester

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Chester is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • The Rock Sports Complex (1.2 mi / 2 km)
  • Arrow Park Lake and Lodge (7.2 mi / 11.6 km)
  • Sterling Lake (10.8 mi / 17.3 km)
  • Lake Tiorati Beach (11.3 mi / 18.2 km)
  • Sterling Forest State Park (11.4 mi / 18.3 km)
  • Storm King Art Center (11.8 mi / 19 km)

Transportation to and around Chester

The nearest airport is in Stewart Intl. Airport (SWF), located 13.5 mi (21.7 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Caldwell, NJ (CDW-Essex County), which is 33.6 mi (54.1 km) away.

Frequently asked questions

What is the best area to stay in Chester, New York, United States of America when booking a vacation rental?
When considering the best area to stay in Chester, New York, a great choice is the charming neighborhood surrounding the historic downtown. This area is not only picturesque, with its quaint buildings and local shops, but it also provides easy access to several attractions. Visitors can enjoy the scenic beauty of the nearby Harriman State Park, which offers numerous trails for hiking and biking, as well as opportunities for fishing and picnicking. Additionally, the nearby Chester Historical Society is a lovely spot to learn about the local heritage.

Another appealing neighborhood is the area close to the Greenwood Lake, where you can immerse yourself in outdoor activities such as boating, swimming, and lakeside relaxation. This region tends to have a variety of vacation rental properties, allowing travelers to find the great place that suits their needs while enjoying the natural beauty and vibrant community spirit Chester has to offer.
How much does it cost to rent a vacation home in Chester?
Prices for vacation rentals in Chester 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 Chester 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 Chester vacation house rentals?
You can find great discounts on house rentals in Chester 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 Chester ski resort rentals?
For the best ski resort rentals near Chester, New York, travelers should consider accommodations in the nearby area of the Catskills, particularly around the towns of Tannersville and Hunter. These towns are home to popular ski resorts and offer a variety of rental options, including cozy cabins and modern chalets that cater to different group sizes.

In Tannersville, guests can find properties that feature amenities such as fireplaces, spacious living rooms, and outdoor decks with scenic views of the surrounding mountains. Many rentals here are also equipped with kitchens, allowing for home-cooked meals after a day on the slopes. Additionally, several properties are conveniently located near the ski lifts, making it easy to access the slopes.

Hunter, just a short drive from Chester, offers a mix of traditional mountain lodges and contemporary condos. Many of these accommodations come with added perks, such as hot tubs, game rooms, and access to shared amenities like pools and fitness centers. The vibrant town atmosphere in Hunter provides local dining options and shops, enhancing the overall experience for travelers.

Both Tannersville and Hunter offer proximity to outdoor activities beyond skiing, including hiking trails and scenic viewpoints. This makes the area not only ideal for winter sports enthusiasts but also for those looking to explore the natural beauty of the Catskills throughout the year.
What is the most popular type of vacation rental accomodation in Chester?
In Chester, vacation houses are among the most popular rental options, with several available throughout the area. These homes typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking to enjoy a home-like experience. Many vacation houses also come with outdoor spaces, such as decks or gardens, superb for relaxing after a day of exploring the scenic beauty of the Hudson Valley region.

Apartments and villas are also available, providing additional choices for travelers. Apartments usually offer cozy accommodations with essential amenities, while villas tend to provide a more luxurious experience, often featuring upscale furnishings and additional amenities like pools or hot tubs.
Are there any family house rentals in Chester?
In Chester, New York, there are several family-friendly vacation rentals that cater to those traveling with children. The area is surrounded by picturesque landscapes, making it an excellent choice for families seeking both adventure and relaxation. Many of these homes feature spacious living areas, well-equipped kitchens for family meals, and outdoor spaces where kids can run and play.

Visitors can enjoy nearby attractions such as the scenic Sterling Forest State Park, which offers hiking trails and picnic spots, or explore the charming local community with its family-friendly activities. With amenities like air conditioning and Wi-Fi commonly available, families can expect a comfortable and enjoyable stay in Chester.
Can I rent a vacation home with a pool or hot tub in Chester?
In Chester, New York, there are several vacation homes available for rent that feature pools and hot tubs, making it an appealing destination for travelers seeking relaxation and leisure. The area offers a mix of charming properties, many of which are located in scenic settings, providing a tranquil atmosphere.

Travelers can expect amenities such as private pools, hot tubs, spacious outdoor areas for lounging, and fully equipped kitchens suitable for preparing meals. Some rentals may also include additional features like fire pits and outdoor dining spaces, great for enjoying the beautiful surroundings.
Can I find long-stay vacation rentals in Chester?
A long-stay vacation rental in Chester 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 Chester?
In Chester, New York, travelers will find several pet-friendly house rentals that cater to those looking to enjoy the beauty of the Hudson Valley with their furry companions. Many of these vacation homes come equipped with amenities such as spacious backyards, full kitchens, and cozy living areas, providing a comfortable environment for both pets and their owners.

The area around Chester is known for its scenic landscapes, including nearby hiking trails and parks that are superb for outdoor adventures with pets. For example, the nearby Minnewaska State Park Preserve offers miles of trails and stunning views, making it an excellent destination for nature lovers and their pets.
Are there any remote work vacation rentals in Chester?
In Chester, New York, there are several vacation rentals that cater to remote workers. These properties often feature essential amenities such as high-speed Wi-Fi, dedicated workspaces, and comfortable living areas. Many rentals offer a quiet atmosphere, which is great for focusing on work while enjoying the scenic beauty of the area.

Travelers can expect well-equipped kitchens for preparing meals, along with cozy spaces ideal for relaxation after a day of work. The town itself is located in a picturesque region, providing opportunities for outdoor activities and exploration during breaks. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chester 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 Chester?
In Chester, popular vacation rental amenities typically include kitchens, allowing guests to prepare their own meals. Many rentals also feature decks or patios, providing outdoor spaces for relaxation and enjoying the scenic surroundings. Fireplaces are common as well, adding a cozy touch to the accommodations, especially during cooler months. Air conditioning is available in many properties to ensure comfort during warmer weather. Additionally, onsite parking is often provided, making it convenient for guests traveling by car.
When is the best time to visit Chester for a vacation rental?
The best time to visit Chester for a vacation rental is during the peak summer months of July to September. This season is a favorite among travelers seeking outdoor adventures and family-friendly activities, as Chester offers a beautiful setting for hiking, kayaking, and enjoying the stunning views of the nearby lakes and mountains. July, in particular, draws many visitors eager to soak up the sun and participate in local events and festivals.

During the summer, temperatures in Chester generally range from the mid-60s to mid-80s Fahrenheit, creating a comfortable climate for outdoor exploration and sightseeing. The lush greenery and vibrant landscapes make it an excellent backdrop for leisurely walks and picnics in the local parks.

If you're looking for a more budget-friendly option, consider visiting Chester in November. This month sees fewer tourists, allowing for a more peaceful experience. You can enjoy the beauty of autumn as the leaves change color, making it a great time for scenic drives and quiet reflection.
How early should I book a Chester vacation rental?
Book your Chester 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 Chester, New York, United States of America?
In Chester, New York, visitors can enjoy a variety of attractions that showcase the area's natural beauty and charm. The historic downtown area features quaint shops and local eateries, providing a great spot for leisurely strolls and dining. Nearby, the picturesque Chester Town Park offers walking trails, picnic areas, and a beautiful lake ideal for fishing or kayaking.

For outdoor enthusiasts, the nearby Harriman State Park is a significant draw, offering miles of hiking trails, scenic views, and opportunities for camping and wildlife observation. The park is great for a day trip, allowing visitors to immerse themselves in the stunning landscape of the Hudson Valley.

Additionally, the scenic views from the top of the nearby Bear Mountain and the proximity to the Hudson River make this area attractive for those seeking outdoor adventures.
Can I change or cancel my Chester home rental booking on Vrbo?
To find Chester 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 Chester 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.

Frequently asked questions

Are there vacation rentals in Chester?
Yes, you can find vacation rentals in Chester close to Castle Fun Center, or you can go with a more remote option if you'd like a relaxing place to stay. The shops and restaurants are several reasons why visitors like Chester. Make sure you have time to check out the ski areas and coffeehouses during your trip.
How many vacation rentals are there in Chester?
Expedia has 10 vacation rentals for your stay in Chester.
What can I see and do in Chester?
Family-friendly attractions include Castle Fun Center, whereas The Rock Sports Complex is a spot to enjoy the outdoors. While here, Museum Village and Goosepond Mountain State Park are other places worth a visit.
What are vacation rentals like in Chester?
Vacation rentals are privately owned properties you can reserve for several days or more in Chester. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a popular option for a family trip or a small group gathering.

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