Photo by Annette Babek

Chester holiday rentals

We found 323 holiday rentals — enter your dates for availability

Discover a selection of holiday rentals in Chester that are perfect for your trip. Whether you're staying in a holiday rental with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a fireplace. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Chester

Showing deals for:21 Nov - 28 Nov
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Theatrical Chester will entice you

Enjoy the theatre 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 looking for attractions to see while you're in town? Venture out of your cosy holiday rental and experience everything that Chester has to offer. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Chatfield Hollow State Park (6.2 mi / 9.9 km)
  • Machimoodus State Park (6.5 mi / 10.5 km)
  • Chamard Vineyards (7.7 mi / 12.4 km)
  • Dinosaur Place at Nature's Art (13.7 mi / 22 km)
  • Brownstone Exploration & Discovery Park (14.6 mi / 23.5 km)
  • Powder Ridge Mountain Park and Resort (15 mi / 24.2 km)

Exploring the natural features in Chester

Whether you're an active traveller or just want to appreciate the scenery, Chester is a great spot to appreciate mother nature. These are some of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Chatfield Hollow State Park (6.2 mi / 9.9 km)
  • 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)
  • Harvey's Beach (10 mi / 16 km)

Travelling 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 centre. If you're unable to find a flight that fits your schedule, you can 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 holiday rental?
One of the more popular neighbourhoods to get a holiday home in Chester is Chester Centre. Discover a dream stay with Vrbo and explore this area like a local.
What is the most popular type of holiday rental accommodation in Chester?
The most desirable types of holiday rentals in Chester are apartments. Ready for more choices? Vrbo has many options to match the unique needs of our guests, so you'll see holiday properties in all shapes and sizes. The ideal home away from home is waiting for you — book yours today.
How much does it cost to rent a holiday rental in Chester?
Different things affect what you'll pay for your holiday rental in Chester, such as the type of property, length of stay and season. But, all our holiday homes have something in common — amazing value. Just add your travel dates to find your perfect fit.
How much does it cost to rent a beach house in Chester?
When you travel and the style and size of the property will influence how much you'll pay for your beachside holiday rental. Click on your Chester travel dates to view your available options on Vrbo. Did someone just say "hot tub"? Use the filters to pick the features and amenities you want in your holiday home.
Are there pet-friendly holiday rentals in Chester?
Pack up a suitcase for your pooch because Chester has two holiday rentals that open their doors to pets. Let your happy hound have fun with the family at one of our pet-friendly holiday rentals on Vrbo. Simply enter your destination and travel dates, then check the "Pets allowed" filter box.
What are popular rental amenities in Chester?
When it comes to rental amenities that guests look for in Chester, a nearby waterfront, a barbecue grill and nearby museums are the most popular. With Vrbo holiday homes, you'll discover options to match your taste and style, whether you're taking a trip with your partner, your family or even pets.
Are there large group holiday rentals in Chester?
Take your pick of two Vrbo properties in Chester that can accommodate a group of five or more people. You'll get all the space and privacy you need to hang out with your favourite people — and nobody else.
Are there holiday rentals in Chester that welcome kids?
With two family-friendly holiday homes to choose from in Chester, now is a great time to introduce your children to the joys of travel. Just check our "Properties good for families" filter to browse stays packed with conveniences perfect for travelling families, like living rooms, yards, bunk beds and entertainment areas.
What are the top attractions for families in Chester?
Keeping the kids happy during your holiday in Chester is easy with these family-friendly attractions:

  • Essex Steam Train
  • Connecticut River Museum
  • Stay and Play LLC

How old do you have to be to rent a holiday rental in Chester?
It's advisable to check with the Chester holiday home you're considering on Vrbo as the age limit differs. However, generally it's 16, 18 or 21.
How long can I rent a holiday rental in Chester for?
It's up to the Chester property. To see all available options offering extended stays, simply type your dates and number of guests into the Vrbo search page. Look forward to having the entire place to yourself, along with home comforts like air conditioning, a fully-equipped kitchen and outdoor spaces where the little ones can play. Keep an eye out for long-term stays that offer weekly or monthly discounts.

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