Chester holiday lettings

We found 164 holiday rentals — enter your dates for availability
Discover a selection of 10 homes and other holiday rentals in Chester that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll have the best amenities for spending time at your home away from home, which might include a garden and pool. No matter what you're looking for, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

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Travel to friendly Chester

Learn about the unique charm of Chester with a stay in a holiday home rental. This welcoming and relaxing city is well known for its shopping, restaurants and skiing. LEGOLAND® New York and Woodbury Common Premium Outlets are just a couple of the must-see attractions in the area. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Chester

Are you hoping to discover attractions to visit in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Chester a fun spot to go on holiday. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 an active traveller or just want to appreciate the scenery, Chester is a great place to spend some time outside. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • The Rock Sports Complex (1.2 mi / 2 km)
  • Wickham Lake (5.7 mi / 9.2 km)
  • Arrow Park Lake and Lodge (7.2 mi / 11.6 km)
  • Orange County Arboretum (8 mi / 12.9 km)
  • Lake Tiorati Beach (11.3 mi / 18.2 km)
  • Sterling Forest State Park (11.4 mi / 18.3 km)

Transport to and around Chester

The nearest airport is in Newburgh, NY (SWF-Stewart Intl.), located 13.5 mi (21.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you might consider flying into 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 when booking a holiday rental?
When considering the best area to stay in Chester, New York, for a holiday rental, the charming village itself is an excellent choice. Chester boasts a delightful small-town atmosphere, great for those looking to relax and unwind. The area features a variety of properties, ranging from quaint cottages to more modern homes, suiting different tastes and budgets.

One of the village's highlights is the beautiful Chester Town Park, which offers scenic walking trails and lovely picnic spots. Additionally, outdoor enthusiasts will appreciate the proximity to the stunning Sterling Forest State Park, where you can explore hiking trails and enjoy breathtaking views.

Another appealing aspect of Chester is its vibrant local community, with a selection of inviting shops and eateries that reflect the area's character.
How much does it cost to rent a holiday home in Chester?
Prices for holiday 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 holiday 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, consider looking towards the nearby area of Mountain Creek in Vernon, New Jersey, which is a short drive away. This popular ski destination offers a variety of accommodations, including comfortable lodges and townhomes that provide easy access to the slopes. Many properties come equipped with amenities such as ski-in/ski-out access, hot tubs, and kitchen facilities, making them ideal for families or groups looking for convenience and comfort after a day on the mountain.

In Chester itself, you can find charming cabins and rustic lodges that offer a more secluded experience, often featuring fireplaces and outdoor decks to enjoy the picturesque surroundings. This area is known for its beautiful landscapes, so some rentals may also include hiking trails or proximity to local parks, superb for outdoor enthusiasts.

Additionally, the nearby town of Warwick offers further options, with quaint bed-and-breakfasts and holiday homes that provide a cosy atmosphere and easy access to local dining and shopping. Rentals here often feature spacious living areas, inviting gardens, and are well-suited for those looking to explore both the skiing and the charming rural setting of the Hudson Valley.
What is the most popular type of holiday rental accomodation in Chester?
In Chester, holiday houses are the most popular type of holiday rental, with around 21 available throughout the area. These houses typically offer spacious layouts, featuring multiple bedrooms, fully equipped kitchens, and often outdoor patios or decks for enjoying the scenic surroundings. Many are located in tranquil settings, making them superb for families or groups seeking a relaxing getaway. Additionally, there are several apartments and villas available, providing further options for those looking for different styles of accommodation.
Are there any family house rentals in Chester?
In Chester, New York, there are several family-friendly house rentals available, making it an excellent destination for groups seeking a relaxing getaway. The area features a variety of properties, many of which include spacious living rooms, fully equipped kitchens for preparing family meals, and outdoor areas great for children to play.

Visitors can enjoy easy access to nearby attractions such as the scenic Harriman State Park, ideal for hiking and outdoor activities, and the charming local shops and eateries in Chester. Additionally, some homes offer amenities like game rooms and private gardens, ensuring that families have a comfortable and enjoyable stay.
Can I rent a holiday home with a pool or hot tub in Chester?
In Chester, New York, there are several holiday homes available for rent that feature pools or hot tubs, making it a lovely choice for a relaxing getaway. The area is known for its scenic beauty and outdoor activities, with many properties located near the picturesque Lake Louise Marie or the surrounding hills.

Travellers can expect a variety of amenities in these rentals, including private pools, hot tubs for unwinding after a day of exploration, and spacious outdoor areas superb for family gatherings or barbecues. Many homes also come equipped with fully stocked kitchens, modern appliances, and comfortable living spaces.
Can I find long-stay holiday rentals in Chester?
A long-stay holiday rental in Chester 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 Chester?
In Chester, New York, there are several pet-friendly house rentals available, making it a suitable destination for travellers with pets. Many of these holiday homes come equipped with desirable amenities such as spacious living areas, fully equipped kitchens, and outdoor spaces, allowing for a comfortable stay. Some properties may even feature fenced yards, providing a safe area for pets to roam freely.

The charming town is surrounded by beautiful natural landscapes, offering opportunities for outdoor activities with your furry friends. Nearby parks and trails, such as the scenic Chester Town Park, are great for leisurely walks or picnics with pets. Additionally, the area's tranquil atmosphere and close-knit community add to the appeal, making it a great choice for those looking to enjoy a relaxing getaway with their pets.
Are there any remote work holiday rentals in Chester?
In Chester, New York, there are numerous holiday rentals suitable for remote work, with around 27 options available. Many of these properties provide essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable living areas that cater to those balancing work and leisure. Travellers can expect features like well-equipped kitchens for convenient meal preparation, cosy lounges for relaxation, and often access to outdoor spaces for a breath of fresh air during breaks.

The area is known for its beautiful natural surroundings, including nearby parks and lakes, offering a superb backdrop for those looking to unwind after a workday. Chester itself has a charming community vibe with local shops and eateries, making it easy to enjoy the local culture while working remotely. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chester holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chester 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 Chester?
In Chester, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties also feature decks or patios, great for enjoying the serene surroundings. Travellers can expect cosy fireplaces, which add warmth and charm, especially during the cooler months. Air conditioning is commonly available to ensure comfort during the warmer weather. Additionally, onsite parking is typically provided, making it convenient for those travelling by car.
When is the best time to visit Chester for a holiday rental?
The best time to visit Chester for a holiday rental is during the peak season from July to September. This period is particularly vibrant, attracting families and adventure seekers eager to enjoy the wonderful outdoor activities that Chester has to offer. With warm temperatures averaging between 20 and 30 degrees Celsius, it's an ideal time for hiking, biking, and exploring the scenic beauty of the Hudson Valley.

July stands out as the most popular month, as visitors flock to the area to partake in local festivals and events, making it a lively and engaging time to experience Chester's charm. The abundant recreational opportunities, combined with the community's welcoming atmosphere, create a memorable holiday.

If you're looking for a more budget-friendly option, consider visiting in November. This month offers a quieter experience, allowing for peaceful walks along the picturesque trails and a chance to enjoy the tranquil beauty of the changing seasons without the hustle and bustle of the high season.

Ultimately, your choice of when to visit Chester will depend on whether you prefer the lively summer atmosphere filled with activities or the serene, reflective experience of the autumn months.
How early should I book a Chester holiday rental?
Book your Chester 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 Chester?
In Chester, New York, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local charm. The picturesque Sterling Forest State Park, located just a short drive away, offers numerous hiking trails, picnic areas, and stunning views of the surrounding landscape, making it a superb spot for outdoor enthusiasts.

The quaint downtown area features unique shops and eateries, where travellers can sample local cuisine and browse handmade goods. The nearby Chester Historical Society provides insight into the town's rich history, while the scenic Lake Stahahe offers opportunities for fishing and relaxing by the water.

For those seeking a bit of adventure, the nearby Mountain Creek Resort in Vernon, New Jersey, is a popular destination for skiing in the winter and mountain biking in the summer, providing year-round recreational activities.
Can I change or cancel my Chester home rental booking on Vrbo?
To find Chester 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 Chester 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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