Chester, Chester, NS, Canada

Chester, Chester, NS, Canada

We found 84 vacation rentals — enter your dates for availability


Find the best place to stay — Chester

Where to stay around Chester, CA?

Our 2018 property listings offer a large selection of 84 vacation rentals near Chester. From 44 houses to 33 cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chester for a holiday or a weekend are on HomeAway.

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.

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.

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.

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.