Discover a selection of 105 vacation rentals in Chester, NS, CA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $116 per night, and cottages and houses are popular options for a stay in Chester. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Chester
Destination guide

Chester – a chic seaside retreat

Perched on the rugged Nova Scotian coast, the picture-postcard village of Chester was founded in 1759 by New England planters. A stately, gentile vibe persists to this day, with an abundance of lavish seafront mansions and a harbor invariably dotted with gleaming yachts and gently bobbing sail boats. Take a leisurely stroll down its winding alleyways and you'll find chic fashion boutiques, alluring art galleries and welcoming restaurants serving fresh seafood delicacies like decadent lobster rolls and hearty fish chowders. Chester vacation rentals include everything from cozy clapboard cottages to sprawling family homes, so you'll easily find one to suit your exact needs.

Things to do

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.

Natural features

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.

How to get there

How to get to and around Chester

The nearest airport is in Halifax, NS (YHZ-Stanfield Intl.), located 42.9 mi (69.1 km) from the city center.

How many vacation rentals are available around Chester, NS, CA?

Our 2021 property listings offer a large selection of 105 vacation rentals around Chester. From 36 cottage rentals to 87 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Chester?

Vrbo offers a large selection of vacation rentals near lovely places in Chester. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Chester Playhouse: 193 vacation rentals
  • St. Stephen's Church: 189 vacation rentals
  • Lordly House Museum: 187 vacation rentals
  • Chester Golf Club: 192 vacation rentals
  • Chester Art Center: 189 vacation rentals

But there are many other points of interest around Chester listed on Vrbo where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Cottages in Chester?

Yes, of course. Vrbo has 36 Cottages in Chester. Our other popular types of vacation rentals in Chester include:

  • Houses: 87 rentals available
  • Bungalows: 36 rentals available
  • Cabins: 37 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Condos/Apartments and more.

Can I find a vacation rental with pool in Chester?

Yes, you can select your preferred vacation rental with pool among our 12 vacation rentals with pool available in Chester. Please use our search bar to access the selection of vacation rentals available.