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.

Holiday rentals with weekly discounts - Chester

Showing deals for:6 Mar - 13 Mar

Image gallery for Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Front of Property
9.6 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)

Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Chester, NY

14% off
Price is £8,638
for 7 nights, 1 villa
£1,234 per night
includes taxes & fees
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Find spaces that suit your style

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. 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)
  • City Winery Hudson Valley (11.8 mi / 19.1 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)
  • Arrow Park Lake and Lodge (7.2 mi / 11.6 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)
  • Greenwood Lake (12.5 mi / 20.1 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 a holiday rental in Chester, New York, the area around Lake Highland is an excellent choice. This picturesque neighbourhood offers a serene atmosphere with stunning views of the water, making it a superb retreat for those looking to unwind in nature. Lake Highland is conveniently close to the charming Chester Town Park, where visitors can enjoy leisurely walks, picnics, and various recreational activities.

Another appealing option is the vicinity of the Hudson River, which provides a lovely backdrop for outdoor enthusiasts. Here, you can partake in kayaking or simply enjoy the scenic beauty of the river. The area is dotted with delightful properties, allowing for a range of rental options that cater to different preferences and budgets.
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 those seeking ski resort rentals near Chester, New York, the nearby area of the Catskills presents excellent options. Specifically, the towns of Tannersville and Hunter are popular choices, as they provide convenient access to the ski slopes of Hunter Mountain. In Tannersville, visitors can find a variety of holiday rentals, including cabins and chalets that often come equipped with amenities such as fireplaces, hot tubs, and fully stocked kitchens, great for unwinding after a day on the mountain.

In the Hunter area, many properties cater to families and groups, offering spacious rooms that may include multiple bedrooms and living areas designed for relaxation. Some rentals also feature outdoor spaces, such as decks or patios, allowing guests to enjoy the picturesque winter landscape.
What is the most popular type of holiday rental accomodation in Chester?
In Chester, holiday houses are quite popular, with several options available throughout the area. These properties typically offer spacious living arrangements, featuring multiple bedrooms, fully equipped kitchens, and outdoor spaces such as gardens or patios, ideal for enjoying the scenic surroundings. Additionally, there are several apartments and villas that cater to travellers looking for a more compact or luxurious stay. Apartments generally provide a homely atmosphere with essential amenities, while villas often come with upscale features like private pools or expansive views.
Are there any family house rentals in Chester?
In Chester, New York, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. This charming area offers a mix of spacious homes located in scenic surroundings, often featuring amenities such as fully equipped kitchens, large living rooms for family gatherings, and outdoor spaces ideal for play and relaxation.
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 and hot tubs. This charming town, set against the backdrop of the Catskill Mountains, offers a picturesque setting for a relaxing getaway. Many of these properties come with amenities such as private swimming pools, outdoor hot tubs, spacious decks for sunbathing, and fully equipped kitchens, making them ideal for families or groups looking to unwind in comfort.
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, offering a great retreat for travellers with furry companions. The area is known for its picturesque landscapes and proximity to outdoor activities, making it an attractive destination for nature lovers. Many of the holiday rentals here come equipped with amenities such as spacious backyards, modern kitchens, and comfortable living spaces, which provide a welcoming environment for both guests and their pets.
Are there any remote work holiday rentals in Chester?
In Chester, New York, there are several remote work holiday rentals available, suiting those looking to combine work with leisure. The area offers a serene environment, surrounded by the picturesque landscapes of the Hudson Valley. Many of these properties come equipped with essential amenities for remote work, such as Wi-Fi, dedicated desk space, and comfortable chair setups, ensuring a productive work atmosphere away from the office. 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 essential kitchen appliances such as microwaves, ovens, refrigerators, and stovetops. These features allow guests to prepare their own meals, enhancing the home-like experience while enjoying the scenic surroundings of the area. Many rentals also provide comfortable living spaces, ensuring a relaxing atmosphere after a day of exploring local attractions.
When is the best time to visit Chester for a holiday rental?
The best time to book a holiday rental in Chester is during the peak season from July to September. This period attracts a multitude of visitors eager to enjoy the refreshing summer weather and the vibrant community events that Chester is known for. With temperatures typically ranging from the mid-teens to low 20s Celsius, it's an ideal time for outdoor activities such as hiking in the nearby Hudson Valley or enjoying leisurely strolls around the picturesque lakes.

July stands out as the most popular month, offering a lively atmosphere filled with festivals, farmers' markets, and ample opportunities to engage with local culture. The warm days invite visitors to explore Chester's beautiful parks, take part in water activities, or simply relax and soak up the sun.

For those seeking a quieter and more budget-friendly experience, November is a wonderful option. The crisp autumn air brings the stunning colours of fall foliage, creating a serene backdrop for nature walks and photography. November allows visitors to enjoy Chester's charm without the hustle and bustle of the high season, making it a great time to appreciate the local scenery and community.
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, visitors can enjoy a variety of attractions that highlight the area's natural beauty and charm. The picturesque Chester Village offers quaint shops and local eateries that reflect the community's welcoming atmosphere. Just a short drive away is the scenic Harriman State Park, where outdoor enthusiasts can enjoy hiking, biking, and picnicking amidst stunning landscapes and tranquil lakes.
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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