Chester vacation rentals

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your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of 11 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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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. LEGOLAND® New York and Woodbury Common Premium Outlets are just a couple of the must-sees in the area. 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)
  • Castle Fun Center (0.8 mi / 1.2 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)
  • Lake Tiorati Beach (11.3 mi / 18.2 km)
  • Storm King Art Center (11.8 mi / 19 km)
  • Harriman State Park (12.6 mi / 20.3 km)
  • Lake Welch Beach (13.6 mi / 21.9 km)
  • Upper Greenwood Lake (14.2 mi / 22.9 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 when booking a vacation rental?

If you're organizing a trip to Chester, Sugar Loaf is one of the most desired places to stay. Whether you choose a villa, cottage or other property style, you'll always have the entire place to yourself.

What is the most popular type of vacation rental accommodation in Chester?

The most desirable types of vacation rentals in Chester are villas. After something a little different? Vrbo has numerous options to match our guests' unique requirements, so you'll see properties in all shapes and sizes. The ideal home away from home is waiting for you — find yours today.

How much does it cost to rent a vacation rental in Chester?

The average price for a vacation home in Chester can vary depending on factors like property type, season and length of stay. Whether you're searching for a sprawling villa with space for the whole family or a cozy cottage just enough for two, just add your dates of travel to see some great-value stays.

How much does it cost to rent a beach house in Chester?

When you travel and the size and style of the property will help determine the cost of your beachside stay. Enter your Chester travel dates to view your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use our filters to choose the features and amenities you want in your vacation home.

Are there pet-friendly vacation rentals in Chester?

With three vacation rentals that allow pets, your furry best friend can join you on your Chester getaway. Use our filter tool to browse our pet-friendly vacation rentals and find your pawfect digs on Vrbo.

What are popular rental amenities in Chester?

When it comes to rental amenities that people prefer in Chester, a fireplace, a barbecue grill and a garden are at the top of the list. With Vrbo vacation homes, there are choices to fit your style and taste, whether you're going on a vacation with family, friends or even pets.

Are there vacation rentals in Chester that welcome kids?

Bring the whole group together for fun-filled adventures in Chester at one of our three family-friendly vacation rentals. A lot of these stays provide amenities that are suitable for trips with the little ones, like dining rooms, extra bedrooms and outdoor spaces. Just check the "Properties good for families" filter box and choose your favorite option.

What are the top attractions for families in Chester?

You'll find loads of fun things to do and see with the family in Chester, such as:

  • Castle Fun Center
  • Harness Racing Museum and Hall of Fame
  • Arrow Park Lake and Lodge

Are there vacation rentals with WiFi in Chester?

Chester has two vacation rentals with WiFi, so you can stay connected during your vacation. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming TV shows with the family to sending emails, these Vrbo homes make it a breeze to go online.

How can I find vacation rentals with air conditioning in Chester?

Chester has three vacation rentals where you can spend your days in air-conditioned comfort. To book a stay on Vrbo that has this perk, choose your travel dates and use the handy filters to select the "air conditioning" box.

How old do you have to be to rent a vacation rental in Chester?

You'll need to check with the Chester vacation rental you're looking at on Vrbo as the minimum age differs. However, normally it's 16, 18 or 21.

How long can I rent a vacation rental in Chester for?

It all depends on the Chester property. To view all available options offering extended stays, just enter your travel dates and number of guests into Vrbo. You can enjoy having the whole property to yourself, along with home comforts such as a kitchen, air conditioning and an outdoor space where your little ones can play. Keep your eyes open for any long-term stays that offer discounted weekly or monthly prices.

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