Photo by Annette Babek

Chester vacation rentals

We found 330 vacation rentals — enter your dates for availability

Discover a selection of 5 apartments and other vacation rentals in Chester that are perfect for your trip. Whether you're staying in a vacation rental with friends, family, or just with your pet, you'll have the best amenities for spending time at your home away from home, which might include a pool and a washer and dryer. You'll be able to choose a rental that has what everyone needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Chester

Showing deals for:Jul 25 - Aug 1
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Artsy Chester will entice you

Enjoy the theater scene and other features of Chester. One of the city's many top draws is its parks. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Chester

Are you searching for things to do while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Chester a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Machimoodus State Park (6.5 mi / 10.5 km)
  • Dinosaur Place at Nature's Art (13.7 mi / 22 km)
  • Château le' Gari' (14.4 mi / 23.2 km)
  • Brownstone Exploration & Discovery Park (14.6 mi / 23.5 km)
  • Powder Ridge Mountain Park and Resort (15 mi / 24.2 km)
  • TPC River Highlands (17.8 mi / 28.7 km)

Exploring the natural features in Chester

Whether you're an active traveler or just want to take in the scenery, Chester is a great spot to appreciate mother nature. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Dinosaur State Park (6.9 mi / 11 km)
  • Goose Island (8.3 mi / 13.3 km)
  • Westbrook Town Beach (8.7 mi / 14 km)
  • Clinton Town Beach (9.4 mi / 15.2 km)
  • Chalker Beach (9.5 mi / 15.3 km)
  • Harvey's Beach (10 mi / 16 km)

Traveling to and around Chester

The nearest airport is in New Haven, CT (HVN-Tweed - New Haven Regional), located 23.1 mi (37.2 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into New London, CT (GON-Groton - New London), which is 23.1 mi (37.2 km) away.

Frequently asked questions

What is the best area to stay in Chester when booking a vacation rental?
If you’re heading for Chester, Chester Center is among the most popular locations to stay. Whatever your style of travel, Vrbo is bound to have a vacation rental here that’s just right for you.
What is the most popular type of vacation rental accommodation in Chester?
Based on our research, apartments are considered the most popular type of property in Chester. But naturally, everyone’s idea of an epic trip will differ. Vrbo has vacation homes of all shapes, sizes and budgets, and we’ll help you discover your ideal match.
How much does it cost to rent a vacation rental in Chester?
Different factors can influence how much you’ll pay for a vacation rental in Chester, such as the type of property, season and length of stay. But, all of our vacation homes have one thing in common — exceptional value. Simply enter your travel dates to find your home away from home.
How much does it cost to rent a beach house in Chester?
Prices for beach houses in Chester can vary depending on the size and style of the property and when you’re traveling. All you need to do is enter your travel dates into Vrbo and how many guests to see your options and prices. From there you can use our filters to refine your search results by ratings, nearby activities, amenities and more.
Are there pet-friendly vacation rentals in Chester?
There certainly are. You can pick from two vacation homes that allow pets in Chester on Vrbo. Our furry friends also deserve a little time out, so simply use our search function for pet-friendly vacation rentals to find a pad where your pup can lap up the fun.
What are popular rental amenities in Chester?
When it comes to rental amenities that people search for in Chester, a fireplace, a garden and a nearby waterfront rank the highest. With Vrbo vacation homes, you’ll enjoy options to suit your style and taste, whether you’re going away with family members, friends or even pets.
Are there large group vacation rentals in Chester?
You’ll find two vacation rentals in Chester that can accommodate a group of five or more people. From family reunions to a special event, these stays have ample space to kick back with your favorite people.
Are there vacation rentals in Chester that welcome kids?
Chester has two family-friendly vacation rentals to pick from. And securing a stay that welcomes kids is simple with Vrbo’s “Properties good for families” filter. As well as having the whole place to yourselves, you can also look forward to perks and amenities like bunk beds, kitchens and private pools.
What are the top attractions for families in Chester?
There’s no room for boredom during your Chester trip with these family-friendly attractions to explore:

  • Norma Terris Theater
  • Chester Creek Marina

How old do you have to be to rent a vacation rental in Chester?
You’ll have to check with the Chester vacation rental you’re looking at on Vrbo as the age limit varies. However, generally it’s 16, 18 or 21.
How long can I rent a vacation rental in Chester for?
How long you can rent a vacation rental in Chester is up to the property. Just enter your selected travel dates to view a list of options offering extended stays. With a range of amenities like kitchens and air conditioning, as well as some offering weekly or monthly discounts, you’re sure to get someplace just right to call your home away from home in Chester.
Does Vrbo offer discounts for vacation homes in Chester?
Weekend adventure or a much-needed extended vacation, Vrbo has some fantastic deals and discounts in Chester to match your style and your budget. Browse our weekly and monthly discounts on vacation rentals, or check out what’s recently been added with one of our newly listed homes. Whatever you’re after, you’ll find the ideal place to stay — at an affordable rate.

More Vacation Rentals ideas

People also search for