Chester vacation rentals

We found 155 vacation rentals — enter your dates for availability

Discover a selection of 16 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.

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Find out more about Chester

Why visit Chester

  • Stunning Beaches: Enjoy relaxing days at Chester's beautiful beaches, perfect for sunbathing and family fun.
  • Outdoor Adventures: Explore nearby lakes and state parks, offering plenty of recreational opportunities for all ages.
  • Charming Small Town Atmosphere: Experience the warmth of friendly locals in this picturesque coastal community.
  • Variety of Accommodations: Choose from cozy homes, charming cottages, and modern apartments that suit your style and budget.
  • Family-Friendly Activities: Engage in a range of activities that cater to both kids and adults, ensuring fun for everyone.

Popular types of accommodation in Chester

Planning a getaway to Chester? The next step is finding the perfect place to stay. Explore a variety of popular vacation rentals, including cozy private homes, charming cottages, and modern apartments. Whether you're interested in a Chester vacation home, a quaint vacation cottage, or a cabin for rent, you'll discover accommodations that suit your style and budget. Start your adventure in Chester with the ideal rental that feels just like home.

  • Houses: A top choice for travelers to Chester, offering spacious and comfortable settings for families, friends, or couples.
  • Cottages: These charming retreats provide a cozy atmosphere, perfect for a relaxing getaway in nature.
  • Apartments: An ideal option for those seeking convenience and flexibility, often located near local attractions.
  • Villas: Luxurious accommodations that offer ample space and upscale amenities for a lavish stay.
  • Cabins: A popular choice for those looking to immerse themselves in the great outdoors with rustic charm.**

Top attractions in and around Chester

Chester, Nova Scotia, is perfect for outdoor and family beach vacations, offering a variety of attractions like lakes, islands, and beaches. It's an ideal destination for travelers seeking outdoor adventures, romantic getaways, or family-friendly activities. Whether you want to relax by the shore or explore the natural beauty, Chester has something for everyone, making it a great choice for a memorable vacation.

  • Oak Island: Famous for its intriguing mystery and treasure hunt, Oak Island offers stunning outdoor experiences with beautiful beach vibes. Explore the island's captivating history while enjoying scenic views of the waters.
  • Lordly House Museum: This charming historical museum showcases the rich culture and heritage of Chester. Visitors can explore exhibits that highlight local history, making it a perfect spot for those interested in learning more about the area.
  • Bayswater Beach Provincial Park: A picturesque beach just a short drive away, Bayswater Beach Provincial Park features soft sands and refreshing ocean waves, ideal for sunbathing, picnicking, and leisurely strolls along the shore.

Things to do recommended for couples

Chester, Nova Scotia offers a charming getaway for couples. Enjoy a sunset walk along the picturesque waterfront, explore local art galleries, or indulge in a romantic dinner at a cozy bistro. Don't miss a boat tour of the stunning coastline for unforgettable memories together.

Things to do recommended for families

Families will love exploring the scenic Chester waterfront with its charming shops and eateries, taking a scenic boat tour of Mahone Bay, or enjoying outdoor activities at Graves Island Provincial Park, featuring picnic areas and beautiful hiking trails.

Things to do recommended for groups

Explore the charming village of Chester with a guided walking tour, enjoy fresh seafood at local eateries, or take a scenic boat tour of the picturesque coastline. Don't miss out on visiting the Chester Art Centre for a creative group workshop.

*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 traveling with a group, family, or pets, or if you're considering an extended stay, be sure to set your filters according to your specific needs. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chester with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Chester with young kids: Traveling with young kids can be demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chester: For many families, a vacation wouldn’t feel complete without their furry companions. If that resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chester: If you're in search of vacation rentals that offer special rates for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to enhance your search.

Where to stay near Chester

Chester, Nova Scotia, offers a delightful blend of outdoor adventures and family-friendly activities. Explore the charming small town atmosphere, breathe in the fresh air, and enjoy the beautiful beaches. Nearby state parks provide ample opportunities for recreation, making it an enjoyable destination for all ages. Experience the warmth of friendly locals and create lasting memories in this picturesque coastal community.

  • Mahone Bay: Located 10 miles from Chester, Mahone Bay is a charming coastal city that offers a delightful blend of outdoor activities and family-friendly experiences. Known for its picturesque waterfront, visitors can stroll along the scenic boardwalk, enjoy a round of golf at the local golf courses, or relax on the beautiful beaches. The area's attractions include cozy urban parks and stunning islands that are perfect for exploration. Mahone Bay’s vibrant arts scene and quaint shops make it a great destination for leisurely afternoons.
  • East Chester: Just 2 miles from Chester, East Chester is a quaint city that boasts breathtaking scenery and a tranquil beach experience. Travelers can enjoy shopping at local centers or spend time at the campground and recreational areas. The picturesque surroundings include serene lakes and a historic lighthouse, making it an ideal spot for outdoor enthusiasts looking to soak in the natural beauty of Nova Scotia. Whether you're hiking, picnicking, or simply relaxing by the water, East Chester offers a peaceful retreat.
  • Chester Islands: Located 3 miles from Chester, Chester Islands is a captivating destination that draws visitors for its stunning beaches and scenic landscapes. Outdoor lovers will appreciate the hiking trails and recreational areas, while the shopping centers provide unique local goods. The islands are surrounded by beautiful bays and offer plenty of opportunities for exploration and relaxation. With its tranquil atmosphere and natural beauty, Chester Islands is the perfect spot for a day of adventure or a serene escape.

Best time to go to Chester

If you're planning a trip to Chester, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from July to September, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.4°F (-2.0°C)Light RainMostly CloudyAverageAverage
February27.5°F (-2.5°C)Light RainMostly CloudyAverageSlightly Low
March32.0°F (0.0°C)Light RainMostly CloudyAverageAverage
April40.3°F (4.6°C)Light RainMostly CloudyAverageSlightly Low
May48.4°F (9.1°C)Light RainMostly CloudyAverageAverage
June56.5°F (13.6°C)Light RainMostly SunnyAverageSlightly High
July64.8°F (18.2°C)Light RainMostly SunnyHighSlightly High
August66.4°F (19.1°C)Light RainMostly SunnyHighSlightly High
September61.3°F (16.3°C)Light RainMostly SunnyHighAverage
October52.5°F (11.4°C)Light RainMostly SunnyLowAverage
November43.0°F (6.1°C)Light RainMostly CloudyLowSlightly Low
December34.9°F (1.6°C)Light RainMostly CloudyLowAverage

Booking with Vrbo is a breeze

Planning to save on your next getaway? Being open to adjusting your travel dates can really help, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental. We're here to help you find the best options.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new journeys, pick up right where you left off, and easily view and organize your travel plans. You can now find the properties you've saved and booked categorized under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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 best area to stay in Chester, Nova Scotia, Canada when booking a vacation rental?
When considering a vacation rental in Chester, Nova Scotia, the best area to stay is along the waterfront, where you'll find a charming blend of stunning views and local culture. This picturesque neighborhood not only offers easy access to the serene waters of Mahone Bay but also places you within walking distance of delightful cafes, artisanal shops, and local galleries.

One of the top attractions in this area is the Chester Playhouse, a beloved venue that hosts a variety of performances, from live theater to music events, providing a wonderful glimpse into the local arts scene. Additionally, the scenic Chester Golf Club, known for its breathtaking views and well-maintained course, is a great spot for golf enthusiasts looking to enjoy a round while soaking in the natural beauty of the region.
How much does it cost to rent a vacation home in Chester?
Prices for vacation rentals in Chester vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chester to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chester vacation house rentals?
You can find great discounts on house rentals in Chester on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Chester?
For renting a beach house in Chester, Nova Scotia, travelers should explore the picturesque neighborhoods along the Chester Basin, particularly around the Chester Golf Club and the charming waterfront village. Many vacation rentals in this area offer stunning views of the water, with properties often featuring large decks, private docks, and outdoor grills, great for enjoying the fresh coastal air and summer sunsets.

The area near the Chester Marina is also ideal, where visitors can find cozy cottages and modern homes that provide easy access to boating, sailing, and swimming. Many rentals here come equipped with amenities such as spacious living areas, fully equipped kitchens, and sometimes even kayaks or paddleboards for guests to use.

Additionally, the nearby seaside parks and walking trails, like those at the Chester Shore, provide opportunities for hiking and beachcombing, enhancing the beach house experience.
Where are the best Chester ski resort rentals?
For skiing in Chester, Nova Scotia, travelers will want to look towards nearby areas that provide convenient access to winter sports. The closest ski facilities are found in the greater Halifax region, particularly in areas like Martock and Wentworth. In these locations, visitors can find cozy chalets and cabins that cater to winter sports enthusiasts. Many of these properties come equipped with amenities such as fireplaces for warming up after a day on the slopes, hot tubs for relaxation, and fully stocked kitchens to prepare meals.

In the town of Windsor, which is approximately a half-hour drive from Chester and provides access to ski areas like Ski Martock, you can find vacation rentals that offer a blend of comfort and convenience. These accommodations often feature spacious living areas, ski storage options, and outdoor decks where guests can enjoy the winter scenery.

Additionally, the proximity to local dining options and shops in Windsor enhances the experience for travelers.
What is the most popular type of vacation rental accomodation in Chester?
In Chester, vacation houses are the most popular type of rental, with about 15 available throughout the area. These houses often feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking a relaxing getaway by the waterfront. Many of these properties also include outdoor spaces like decks or patios, allowing guests to enjoy the scenic views of the nearby harbor.

In addition to vacation houses, several cottages, apartments, and condos are scattered around Chester, offering travelers a variety of options. Cottages typically provide a quaint, rustic charm, while apartments and condos may offer more modern amenities.
Are there any family house rentals in Chester?
In Chester, Nova Scotia, there are several family-friendly house rentals available, making it a wonderful destination for families. The charming village offers a selection of homes that often feature spacious living areas, full kitchens ideal for preparing meals together, and outdoor spaces where children can play freely. Many of these properties also include amenities such as Wi-Fi and cozy fireplaces, enhancing the comfort of your stay.

Visitors can enjoy the beautiful coastal scenery, with nearby attractions like the picturesque Chester Golf Club and the serene waters of the Atlantic Ocean. Families may also explore local parks or take leisurely strolls along the waterfront, where they can appreciate the stunning views and vibrant community atmosphere.
Can I rent a vacation home with a pool or hot tub in Chester?
In Chester, Nova Scotia, there are several vacation homes available for rent that feature pools or hot tubs, providing a great option for travelers looking to relax and unwind. The area is known for its picturesque coastal scenery and charming village atmosphere. Many of these properties come equipped with amenities such as private pools, hot tubs, spacious outdoor decks, and fully equipped kitchens, making them superb for families or friends gathering for a getaway.

You can expect to find homes in scenic neighborhoods near the waterfront, allowing for easy access to local beaches and boating activities.
Can I find long-stay vacation rentals in Chester?
A long-stay vacation rental in Chester is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chester?
In Chester, Nova Scotia, there are several pet-friendly house rentals available, making it a great destination for travelers who wish to bring their furry companions. Visitors can expect a variety of amenities in these rentals, including spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy fresh air. Many properties also offer stunning views of the surrounding coastal landscape, with some featuring private decks or patios superb for relaxing after a day of exploring.

The neighborhood surrounding Chester provides ample opportunities for pet-friendly activities. The scenic Chester Golf Club and the nearby waterfront promenade are ideal for leisurely walks with pets, while the picturesque beaches in the area welcome dogs, especially during off-peak hours. Additionally, Chester's charming village atmosphere includes local shops and cafes that are often accommodating to pets, enhancing the overall experience for travelers.
Are there any remote work vacation rentals in Chester?
In Chester, Nova Scotia, there are several remote work-friendly vacation rentals available, with around 11 options to choose from. This charming coastal town offers a picturesque setting for those looking to blend work and leisure. Many of these properties provide essential amenities for remote work, including free Wi-Fi and dedicated workspaces, such as desks and desk chairs, ensuring a comfortable and productive environment.

Travelers can expect to find cozy accommodations that may feature additional comforts like fully equipped kitchens, spacious living areas, and outdoor spaces to relax after a day of work. Chester is also known for its scenic waterfront, quaint shops, and local dining options, making it an ideal location for those looking to explore the beauty of Nova Scotia while maintaining their work commitments. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chester vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chester with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chester?
In Chester, popular vacation rental amenities include kitchens, which allow guests to prepare their own meals, and onsite parking for convenience. Many rentals also feature coffee and tea makers for a cozy morning routine, as well as decks or patios where travelers can enjoy the pleasant surroundings. Additionally, some properties permit pets, making it easier for guests to bring their furry companions along for their stay.
When is the best time to visit Chester for a vacation rental?
The best time to visit Chester for a vacation rental is during the peak season from July to September. This vibrant period draws travelers seeking to enjoy the beautiful coastal scenery and the charming ambiance of this picturesque Nova Scotia village. With warm temperatures typically ranging from the mid-60s to low 80s Fahrenheit, it's an ideal time for outdoor activities, including sailing, kayaking, and exploring the stunning coastal trails.

July stands out as the most popular month, offering a lively option filled with community events, festivals, and opportunities to mingle with fellow vacationers. Visitors can engage in the local culture, sampling fresh seafood and enjoying the breathtaking views of the harbor.

For those looking for a more budget-friendly option, consider planning your trip in December. This quieter season provides a unique opportunity to experience Chester's cozy winter charm, with fewer crowds and a chance to enjoy peaceful walks along the waterfront. The town's holiday decorations create a magical setting, great for a serene getaway.

Ultimately, your choice of when to visit Chester will depend on whether you prefer the bustling energy of summer or the tranquil beauty of the winter months.
How early should I book a Chester vacation rental?
Book your Chester vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chester, Nova Scotia, Canada?
In Chester, Nova Scotia, visitors can enjoy a variety of attractions that highlight the area's natural beauty and maritime charm. The picturesque waterfront is a focal point, where travelers can stroll along the marina and admire the colorful boats and stunning views of Chester Basin. The nearby Chester Golf Club offers a scenic course with views of the ocean, making it a popular spot for golf enthusiasts.

The charming village itself features quaint shops and local galleries, particularly along the main street, where visitors can discover unique crafts and art by local artisans. The Chester Playhouse is a cultural gem, hosting a range of performances and events throughout the year, providing entertainment for all ages.

For those interested in outdoor activities, nearby beaches like Blandford Beach and the hiking trails in the surrounding areas offer opportunities for swimming, picnicking, and enjoying nature. Additionally, the historic St. Stephen's Anglican Church, with its beautiful architecture, adds a cultural touch to the area's attractions.
Can I change or cancel my Chester home rental booking on Vrbo?
To find Chester vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chester vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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