Chester apartments
We found 43 apartments — enter your dates for availability
Explore Chester condo rentals

Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, NY
Sleeps 4 · 1 bedroom · 1 bathroom

Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
Sleeps 6 · 2 bedrooms · 2 bathrooms

Cozy studio on 36 acres close to everything in Warwick
Sleeps 2 · 1 bathroom

The 5-Star Peaceful Pool Retreat Only 5 mins from Legoland
Sleeps 4 · 1 bedroom · 1 bathroom

Charming 2-bedroom apartment in the Village of Warwick
Sleeps 5 · 2 bedrooms · 1 bathroom
Find spaces that suit your style
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- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What's it like to stay at an apartment in Chester?
You'll find plenty of places to stay in Chester with 21 accommodation options. Though there aren't many apartments, we can help you find similar accommodation. When you search for a place to stay on Expedia, you can use the filters to search for a kitchen— one of the conveniences often found in an apartment. Even filter by similar property types like holiday homes, condos or cabins. You might want to visit the area's shops and enjoy its restaurants. While in the region, visit favourite sights such as Woodbury Common Premium Outlets.
How do you know if an apartment is a good option for you?
An apartment features a kitchen for convenient meals, and is usually more spacious than a traditional hotel room. Apartments are a good option for solo travellers who want to stay in at night and plan out their next day, but also for families who want the conveniences of home.
What can I expect from the weather during my trip to Chester?
Weather is only one factor, but it can really affect your travel plans, especially if you are planning a longer stay in Chester. The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Chester are January, February, March and April, with each month seeing an average of 16 cm of snowfall.
What should I see and do in Chester?
Chester is known for its restaurants and shops. Cultural attractions include Museum Village and Sugar Loaf Performing Arts Center, whereas The Rock Sports Complex is one spot to enjoy nature. While here, Castle Fun Center and Goosepond Mountain State Park are other places worth a visit.
What's the best way to get to and around Chester?
Knowing a bit about the transportation options can save you time when you get to your destination. Fly into Newburgh, NY (SWF-Stewart Intl.), which is located 13.5 mi (21.7 km) from the heart of the city. Otherwise, you can search for flights to Caldwell, NJ (CDW-Essex County), which is 33.6 mi (54.1 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.

