Chester Vacation Rentals, Nova Scotia: Whole House to Yourself

Discover a selection of 13 homes and other vacation rentals in Chester that are perfect for your trip. Vacation rentals provide the best amenities for you and your friends, family, or even pets, such as WiFi and a hot tub. You're sure to find a rental for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

Find the best place to stay - Chester

Mid century modern home for rent in sought after Chester

Sleeps 6 · 2 bedrooms · 1 bathroom

Top rated rentals - Chester

Soak away all your worries while soaking in a sunset in the hot tub.

Totally eclipse of the sun

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.
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Why people love visiting artsy Chester

Come and experience Chester and its theater scene, entertainment and art galleries. Renowned for its wildlife, bird watching and golfing, this city welcomes all visitors. A vacation rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Take a trip back in time around Chester

You'll find all manner of attractions within easy reach of your Chester vacation rental. The Lordly House Museum is a well-preserved example of Georgian architecture, dating back to 1806. A tour around the lavish interior of this white clapboard house will give you a vivid sense of local upper-class life in the 19th century. For a further immersive trip back in time, head to the Halifax Citadel National Historic Site. The entire history of Nova Scotia's capital is intertwined with this imposing, star-shaped fort, which has been lovingly restored to the splendor of its Victorian period.

Aquatic adventures in Chester

Chester's shimmering waters provide a backdrop for all manner of aquatic pursuits. If your budget won't quite stretch to a private yacht, jump in a kayak and explore nearby secluded coves and uninhabited islands. A major highlight of the local events calendar is Chester Race Week, which takes place each August. The focal point is Canada's largest keelboat regatta, and street food, raucous boat parties and live music performances ensure that the fun continues long after the sun goes down. If you're hankering for evening entertainment at any other time of year, the Chester Playhouse presents everything from stirring dramas and lavish musicals to jazz concerts and comedy shows, so be sure to check what's on when you're in town.

Soak up the summer sun in Chester

Chester vacation rentals are in especially high demand during the peak summer season of June to August, when the local population effectively doubles. Vacationers are drawn here by the promise of long balmy days, plenty of sunshine and late sunsets. Late spring and early fall are also great times to visit – you'll likely find a freshness in the air, but you might land a great deal on accommodation. Winters can be bitingly cold, with a good chance of snow between December and February.

Commune with nature in Chester

Nova Scotia is an enchanting destination for those seeking to escape the hustle and bustle of urban life. In and around Chester you'll find soft sandy bays, rocky coastal paths, fragrant forest and pristine parklands. Nearby Graves Island Provincial Park is a particularly unspoiled spot to get away from it all, with its tranquil oceanfront hiking trails and picturesque picnic spots. Bird watchers should pack their binoculars, as you might catch sight of swooping shore birds or even a rare piping plover.

Transportation to and around Chester

Fly into Stanfield Intl. Airport (YHZ), the closest airport, located 42.8 mi (68.8 km) from the city center.

Frequently asked questions

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

Houses are the most popular style of vacation rental in Chester, according to our data. Even if you have a different vision in mind, Vrbo has vacation homes in many shapes and sizes. Take a look at our options to find your perfect match.

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

The average price for a vacation rental in Chester depends on several factors, including length of stay, property type and season. Whether you'd like a villa with space for extended family or a cozy cabin for you and your other half, just add your travel dates to see some great-value stays.

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

When you travel and the style and size of the property will help determine the cost of your beachside escape. Enter your Chester travel dates to see your options on Vrbo. Did someone just say "hot tub"? Use the filters to select the features and amenities you want in your vacation home.

Are there pet-friendly vacation rentals in Chester?

With nine vacation rentals that host pets, your happy hound can join you on your Chester break. Use our filter tool to browse our pet-friendly vacation rentals and find a stay that'll set tails wagging on Vrbo.

Can I rent a house with a pool in Chester?

Grab your swimsuit and swim ring, because there are two houses with a private pool in Chester. Make a booking at one of these superb vacation rentals and you'll enjoy pool days every day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place to make a splash!

What are popular rental amenities in Chester?

The most popular rental amenities people search for in Chester include an ocean view, tennis and a firepit. Whether you're going on vacation with friends, family or even pets, Vrbo vacation properties come with the best amenities for making new memories with your loved ones.

Are there large group vacation rentals in Chester?

You'll find five properties in Chester that can sleep five or more people. From family getaways to special occasions like birthday parties, these stays have ample space to kick back with the people that matter the most.

Are there vacation rentals in Chester that welcome kids?

Bring the entire family together for an epic adventure in Chester at one of our nine family-friendly vacation rentals. A lot of these stays come with conveniences that are perfect for trips with youngsters, such as full kitchens, multiple bedrooms and swimming pools. Just check the "Properties good for families" filter and pick out your favorite.

What are the top attractions for families in Chester?

Keep the kids amused at these fabulous family-friendly attractions in Chester:

Bayswater Beach Provincial Park
Lordly House Museum
Oak Island

Are there vacation rentals with WiFi in Chester?

Whether you'd like to keep up with the latest news, look over emails or post a pic to social media, there are seven vacation homes with WiFi in Chester. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.

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

Choose from six Vrbo vacation rentals with air conditioning in Chester offering that cool, cool breeze and extra level of comfort. Simply enter your chosen travel dates and then make use of our filter tool to locate properties with air conditioning.

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

The minimum age allowed can differ across properties on Vrbo, so check the rules of the vacation rental in Chester you're considering. But in general, it's 16, 18 or 21.