Chester holiday rentals

We found 198 holiday rentals — enter your dates for availability

Select from 52 homes, 23 cottages and other holiday rentals in Chester to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, which might include a garden and hot tub. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Popular Chester destinations on Stayz

A waterfront with boats docked, a dock with yellow chairs, and houses with a Canadian flag.

Chester

Chester
Chester

Find spaces that suit your style

Why visit Chester

  • Picturesque Waterfront: Enjoy serene walks along the scenic waterfront, taking in stunning views of the ocean and natural beauty.
  • Chester Playhouse: Experience local culture and entertainment at the charming Chester Playhouse, showcasing various performances.
  • Chester Commons: Explore the beautiful Chester Commons, perfect for recreational activities and enjoying the outdoors.
  • Relaxing Beaches: Unwind on Chester's pristine beaches, ideal for sunbathing and swimming in the inviting waters.
  • Rich History: Immerse yourself in the town’s historical charm, with quaint streets and local cuisine to savour.

Popular types of accommodation in Chester

Your Chester holiday rental adventure begins here in the charming town of Chester, Nova Scotia, Canada. Discover a selection of private holiday homes, cottages, and apartments nestled in a scenic setting, where local attractions and picturesque landmarks create memorable experiences. Explore house rentals and holiday rentals, all offering transparency, savings and reassurance for your perfect getaway in Chester.

  • Private Holiday Homes: Discover the charm of secluded private holiday homes, a top choice for those seeking a cosy retreat in Chester.
  • Cottages: Experience the rustic allure of traditional cottages, offering a quaint escape amidst scenic landscapes.
  • Apartments: Enjoy the modern convenience and compact elegance of apartments, perfect for a flexible holiday in this picturesque locale.**

Top attractions in Chester

Chester in Nova Scotia offers a delightful blend of beach, outdoor, and scenic attractions. Visitors can enjoy the picturesque water views and explore local highlights such as the Chester Playhouse. This charming town is perfect for those seeking a relaxing holiday surrounded by natural beauty, with its pristine lake, island, and beach settings contributing to an inviting atmosphere for exploration and leisure.

  • Bayswater Beach Provincial Park: Enjoy the stunning sandy shores and relaxed beach vibe at Bayswater Beach Provincial Park. It's perfect for sunbathing, picnicking, and taking leisurely strolls along the coastline, offering a serene escape amidst beautiful natural surroundings.
  • Tancook Island: Experience the charm of Tancook Island with its picturesque beaches and outdoor adventures. Ideal for hiking, cycling, and exploring the local flora and fauna, this island provides an idyllic setting for nature lovers and those seeking tranquility.
  • Ross Farm Museum: Step back in time at Ross Farm Museum, where you can immerse yourself in the rich culture and history of rural Nova Scotia. Engage with traditional farming practices, visit historic buildings, and participate in hands-on activities that celebrate the region's heritage.

Things to do recommended for couples

Chester, Nova Scotia, offers a charming escape for couples. Enjoy a scenic walk along the picturesque waterfront, indulge in a candlelit dinner at a local bistro, or explore the quaint shops together. For a touch of adventure, consider a kayak tour for two amidst stunning coastal views.

Things to do recommended for families

Families can explore beautiful coastal trails and enjoy picnics at local parks in Chester, Nova Scotia. The area offers delightful seaside walks and engaging experiences for children, ensuring a memorable family holiday steeped in local charm.

Things to do recommended for groups

Explore the charming seaside village of Chester by taking a scenic boat tour of the picturesque coastline or indulge in a local culinary experience at a quaint café. Don't miss the chance to visit the Chester Playhouse for an evening of entertainment with your group.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Chester

If you’re travelling with a group, as a family, bringing your pets along, or seeking longer stays, be sure to use the appropriate filters that match your priorities. Here are some helpful booking tips for Stayz.

  • Traveling to Chester with a group: Consider the number of bedrooms required, along with facilities like a fully-equipped kitchen or an outdoor area for group occasions. Thankfully, Stayz allows you to refine your search by these criteria and many others.
  • Traveling to Chester with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, alongside ensuring access to suitable amenities, like a private swimming pool. Additionally, it’s wise to think about your closeness to family-friendly attractions.
  • Taking your pets with you to Chester: For many, a family holiday feels incomplete without their beloved pet by their side. If this resonates with you, take a look at Stayz properties that welcome pets. Most pet-friendly accommodations supply feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Chester: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the ideal spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Chester

Chester, Nova Scotia, is a charming seaside municipality perfect for outdoor enthusiasts and families alike. Explore the picturesque Chester Commons, where you can enjoy stunning views and recreational activities. The friendly atmosphere and rich culture make it an ideal destination for a relaxing holiday. Stroll along the scenic waterfront, indulge in local cuisine, and immerse yourself in the area’s historical charm. Chester is the perfect base for experiencing the beauty of Nova Scotia’s coastline.

  • Chester: Nestled along the picturesque shores of Nova Scotia, Chester is a charming town that captivates visitors with its stunning outdoor experiences. Known for its beautiful beaches and scenic boardwalk, this family-friendly destination offers a plethora of activities, including golfing and leisurely beach strolls. The local attractions, such as the urban park and nearby islands, provide perfect opportunities for exploration and relaxation. Whether you're enjoying a sunny day at the beach or indulging in local cuisine, Chester promises a delightful holiday experience.
  • Chester Islands: An idyllic escape just off the coast of Chester, the Chester Islands are a haven for nature lovers and beach enthusiasts. The islands boast breathtaking scenery and a tranquil environment, perfect for outdoor adventures. Visitors can explore numerous hiking trails or spend a relaxing day at the beach, while the nearby shopping centre offers delightful local boutiques. The combination of stunning bays and lush landscapes makes Chester Islands an ideal spot for those seeking a peaceful retreat surrounded by nature.
  • Fox Point: Located in close proximity to Chester, Fox Point is a delightful community that offers a mix of beach fun and family-oriented activities. With its scenic boardwalk and vibrant recreational areas, visitors can enjoy a variety of outdoor pursuits. The local attractions, including beautiful beaches and serene bays, provide ample opportunities for relaxation and exploration. Fox Point is the perfect destination for families looking to create lasting memories while enjoying the stunning natural beauty of Nova Scotia.

Booking with Stayz is simple

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay often results in significant savings. To discover the ideal Stayz property that fits your budget, utilise our filters to refine your search by price, location, and type of holiday rental.

Stayz Trips: Planning made easy

Stayz’s innovative Trip Board provides you with a dedicated space to craft new journeys, pick up where you last left off, or comfortably review and organise your plans. You can now locate properties you’ve previously saved or booked under Potential, Upcoming, or Current Trips. To access Trip Boards, please visit: https://www.stayz.com.au/trips

**Based on Vrbo properties bookings.

Find the perfect holiday rental for your Chester getaway

Learn about the unique charm of Chester with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Chester

Do you want to discover top things to see and do while you're in the area? Venture out of your holiday home and check out everything that makes Chester a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Chester Golf Club (6.9 mi / 11.1 km)
  • Shore Club Dance Hall (11.3 mi / 18.2 km)
  • Cocoa Organic Spa & Boutique (13 mi / 21 km)
  • For The Birds Nature Shop (13 mi / 21 km)
  • Have A Yarn (13.1 mi / 21 km)
  • Bluenose Golf Club (17.8 mi / 28.7 km)

Exploring the natural features in Chester

Whether you're looking for adventure or just want to take in the scenery, Chester is a great place to get out in nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Graves Island Provincial Park (6 mi / 9.7 km)
  • Timber Lake (7.1 mi / 11.4 km)
  • Oak Island (7.8 mi / 12.6 km)
  • Noonan Lake (9 mi / 14.5 km)
  • Bear Lake (9.7 mi / 15.6 km)
  • Skinner Lake (10.5 mi / 16.8 km)

Frequently asked questions

What is the best area to stay in Chester when booking a holiday home?
Chester is among the most preferred areas to select a holiday property in Chester. Searching for some fun things to do here? Take time to visit Chester Golf Club and Graves Island Provincial Park.
What is the most popular type of holiday home accommodation in Chester?
The most sought-after types of holiday homes in Chester are houses. Ready for more choices? Stayz has many options to match the unique needs of our guests, so you'll see properties in loads of sizes and shapes. The ideal home away from home is waiting for you — book yours today.
How much does it cost to rent a holiday home in Chester?
The average price for a holiday home in Chester depends on several factors, like time of year, length of stay and property type. Whether you're looking for a sprawling villa with space for extended family or a cosy cabin perfect for just you and the kids, just enter your dates of travel to find stays that offer great value.
How much does it cost to rent a beach house in Chester?
Prices for beach houses in Chester may differ depending on the size and style of the property and when you're travelling. All you need to do is enter your travel dates into Stayz and how many guests to view available options and prices. From there you can use the filters to narrow your search results by amenities, nearby activities, ratings and more.
What are popular home amenities in Chester?
When it comes to home amenities that people are searching for in Chester, a fridge, a microwave oven and off-street parking options rank highest. With Stayz holiday homes, you'll discover options to match your taste and style, whether you're going away with friends, relatives or even pets.
Are there large group holiday homes in Chester?
With eight properties that can sleep 10 or more guests in Chester, you don't have to keep your invite list short. From holidays with the extended family to special events like birthday parties and weddings, Stayz will help you find a large group home to suit the occasion.
What are the top attractions for families in Chester?
Keeping the kids entertained during your Chester holiday is a cinch with these exciting family-friendly attractions:

  • Oak Island
  • Chester Golf Club
  • Saint Margarets Bay

Can I find two-bedroom holiday homes in Chester?
Chester has 14 two-bedroom properties to select from. Go for a holiday home with all the comfort and space you want at a price that won't break the bank on Stayz.
Are there holiday homes with WiFi in Chester?
Chester has 29 holiday homes with WiFi, so you'll be able to stay connected when you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to checking emails, these Stayz homes make it easy to go online.
How old do you have to be to rent a holiday home in Chester?
The minimum required age is usually 16, 18 or 21. It can change between properties on Stayz, so look at the rules of your preferred Chester stay before you book.
How long can I rent a holiday home in Chester for?
It's down to the Chester property. To see a list of options offering extended stays, just enter your travel dates and guest number into Stayz's search page. Enjoy having the property to yourself, along with amenities such as a full kitchen, air conditioning and an outdoor space where the little ones can play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

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