Chester holiday homes

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your current months are April, 2024 and May, 2024.
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Discover a selection of 11 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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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
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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)
  • 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 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)
  • 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)
  • Bear Mountain State Park (15.1 mi / 24.3 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 home?

If you're organising 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 holiday home accommodation in Chester?

The most desirable types of holiday homes in Chester are villas. After something a little different? Bookabach 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 holiday home in Chester?

The average price for a holiday 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 cosy 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 Bookabach. 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 holiday home.

Are there pet-friendly holiday homes in Chester?

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

What are popular home amenities in Chester?

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

Are there holiday homes in Chester that welcome kids?

Bring the whole group together for fun-filled adventures in Chester at one of our three family-friendly holiday homes. 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 favourite 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 Centre
  • Harness Racing Museum and Hall of Fame
  • Arrow Park Lake and Lodge

Are there holiday homes with WiFi in Chester?

Chester has two holiday homes with WiFi, so you can stay connected during your holiday. 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 Bookabach homes make it a breeze to go online.

How can I find holiday homes with air conditioning in Chester?

Chester has three holiday homes where you can spend your days in air-conditioned comfort. To book a stay on Bookabach 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 holiday home in Chester?

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

How long can I rent a holiday home 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 Bookabach. 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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