Chester holiday homes

We found 162 holiday rentals — enter your dates for availability
Discover a selection of 16 homes and other holiday rentals in Chester that are perfect for your trip. Holiday rentals offer the best amenities for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Chester

  • Scenic outdoor adventures: Experience Chester's stunning landscapes with picturesque lakes, charming islands, and beautiful beaches perfect for relaxation and exploration.
  • Family-friendly activities: Enjoy a variety of activities suitable for all ages, including picnics by the water and engaging water sports.
  • Charming village atmosphere: Stroll through the quaint Chester village, soaking in the friendly local vibe and unique shops.
  • Inviting beaches: Relax on Chester's inviting beaches, ideal for sunbathing, swimming, and creating cherished memories with loved ones.
  • Leisurely strolls: Take leisurely walks along scenic paths, offering stunning views and a peaceful environment for unwinding.

Top attractions in and around Chester

Chester, Nova Scotia, offers a delightful blend of outdoor adventures and family-friendly activities, making it an ideal destination for beach holidays. Visitors can explore scenic lakes, charming islands, and stunning beaches that cater to those seeking romance and relaxation. Whether you're enjoying a picnic by the water or engaging in water sports, Chester's natural beauty and inviting atmosphere promise memorable experiences for everyone.

  • Oak Island: A mysterious island known for its intriguing history and legends, Oak Island offers stunning beaches and outdoor activities, perfect for nature lovers and adventure seekers.
  • St. Stephen's Church: This historic church showcases beautiful architecture and a rich cultural heritage, providing a serene space for reflection and community gatherings.
  • Lordly House Museum: Explore local history at this charming museum, featuring artefacts and exhibits that celebrate Chester's past, alongside a picturesque garden.

Things to do recommended for couples

Chester offers a delightful escape for couples. Enjoy a scenic walk along the waterfront, explore charming local shops, or indulge in a romantic dinner at a waterfront restaurant. Don't miss a sunset cruise on the bay for an unforgettable view of the stunning Nova Scotia coastline.

Things to do recommended for families

Families in Chester, Nova Scotia can enjoy activities such as beach picnics, local farmer’s markets, and interactive exhibits at community centres, all within a short drive from town. Experience local charm and create lasting memories during your family holiday.

Things to do recommended for groups

Explore the charming seaside village of Chester, enjoy a scenic boat tour of Mahone Bay, or indulge in fresh seafood at local eateries. For a unique experience, take a group hike along the picturesque trails of the nearby Bluenose Coastal Trail.

*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

Whether you're journeying with a group, travelling as a family, bringing your pets along or seeking extended stays, be sure to select filters that align with your specific needs. Here are some Vrbo booking pointers to help you out.

  • Traveling to Chester with a group: Consider how many bedrooms you'll need, as well as features like a fully-equipped kitchen or an outdoor area ideal for group gatherings. Luckily, you can refine your search for all these options and more on Vrbo.
  • Traveling to Chester with young kids: Traveling with little ones can be demanding. You must prioritise their comfort and safety, ensuring they have access to age-suitable facilities, such as a private pool. It’s also wise to consider how close you are to attractions that cater to families.
  • Taking your pets with you to Chester: For many, a family holiday isn’t quite the same without their furry companion. If this 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 holiday rentals with great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider including features like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Chester

Chester, Nova Scotia offers a delightful blend of outdoor and family-friendly experiences. Wander through the charming Chester village, relax on its inviting beaches, and enjoy the friendly local atmosphere. The area is perfect for leisurely strolls, scenic views, and quality time with loved ones, making it a superb destination for a relaxed holiday from New Zealand.

  • Mahone Bay: Located a mere 16km from Chester, Mahone Bay is a picturesque city renowned for its stunning natural scenery and vibrant outdoor activities. Families flock here for beach outings and engaging experiences, such as exploring the scenic boardwalk and playing a round of golf. Local attractions include beautiful beaches, charming islands, and a lovely urban park that invite visitors to unwind and soak in the coastal charm. Mahone Bay's friendly atmosphere and breathtaking waterfront views make it a perfect destination for a relaxing day trip.
  • Robinsons Corner: Just 3km away from Chester, Robinsons Corner offers a delightful blend of outdoor activities and scenic beauty. This charming city is perfect for those seeking a day of exploration and leisure. Visitors can enjoy recreational areas, shop at local centres, and experience the vibrant community spirit. Nearby landmarks include a stunning bay, a national park, and serene islands, making it an ideal spot for nature lovers and those looking to immerse themselves in the area's natural beauty.
  • Martins Point: A short 8km from Chester, Martins Point is a romantic getaway known for its outdoor adventures and beautiful beaches. This idyllic city is perfect for couples looking to enjoy quality time together while engaging in activities like golfing or relaxing at a country private club. The nearby islands and urban parks provide plenty of opportunities to explore and connect with nature, making Martins Point a charming destination for a leisurely 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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January28.4°F (-2.0°C)Light RainMostly CloudyAverage
February27.5°F (-2.5°C)Light RainMostly CloudyAverage
March32.0°F (0.0°C)Light RainMostly CloudyAverage
April40.3°F (4.6°C)Light RainMostly CloudyAverage
May48.4°F (9.1°C)Light RainMostly CloudyAverage
June56.5°F (13.6°C)Light RainMostly SunnyAverage
July64.8°F (18.2°C)Light RainMostly SunnyHigh
August66.4°F (19.1°C)Light RainMostly SunnyHigh
September61.3°F (16.3°C)Light RainMostly SunnyHigh
October52.5°F (11.4°C)Light RainMostly SunnyLow
November43.0°F (6.1°C)Light RainMostly CloudyLow
December34.9°F (1.6°C)Light RainMostly CloudyLow

Booking with Vrbo is simple

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

Vrbo Trips: Planning as easy as it gets

Vrbo's groundbreaking Trip Board offers you a dedicated space to design new trips, pick up where you paused, or organise your plans with ease. Your previously saved and booked properties are now categorised as Potential, Upcoming, or Current Trips. To access your Trip Boards, please visit: https://www.bookabach.co.nz/trips

**Based on Vrbo properties bookings.

Why people love visiting theatrical Chester

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

Sightseeing in and around Chester

Are you searching for attractions to visit in the city? Venture out of your holiday home and experience everything that makes Chester a fun spot to go on holiday. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Chester Golf Club (0.9 mi / 1.4 km)
  • For The Birds Nature Shop (9.4 mi / 15.1 km)
  • Have A Yarn (9.5 mi / 15.3 km)
  • Shore Club Dance Hall (11 mi / 17.7 km)
  • Osprey Ridge Golf Course (16.3 mi / 26.3 km)
  • Cocoa Organic Spa & Boutique (9.4 mi / 15.2 km)

Exploring the natural features in Chester

Whether you're an adventurous traveller or just want to appreciate the scenery, Chester is a great place to get outside. These are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Graves Island Provincial Park (2 mi / 3.2 km)
  • Oak Island (3.4 mi / 5.5 km)
  • Meisners Beach (4.6 mi / 7.4 km)
  • Callender Lake (8.2 mi / 13.3 km)
  • Bayswater Beach Provincial Park (9 mi / 14.4 km)
  • Mahone Bay Swimming Pool (9.8 mi / 15.7 km)

Transport to and around Chester

Fly into Halifax, NS (YHZ-Stanfield Intl.), the closest airport, located 42.8 mi (68.8 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Chester?
Houses are the most popular style of holiday home in Chester, according to our data. Even if you have a different vision in mind, Bookabach has holiday 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 holiday home in Chester?
The average price for a holiday home 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 cosy 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 Bookabach. Did someone just say "hot tub"? Use the filters to select the features and amenities you want in your holiday home.
Are there pet-friendly holiday homes in Chester?
With nine holiday homes that host pets, your happy hound can join you on your Chester break. Use our filter tool to browse our pet-friendly holiday homes and find a stay that'll set tails wagging on Bookabach.
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 holiday homes and you'll enjoy pool days every day. Simply enter your travel dates into Bookabach, then use the "pool" filter to find the perfect place to make a splash!
What are popular home amenities in Chester?
The most popular home amenities people search for in Chester include an ocean view, tennis and a firepit. Whether you're going on holiday with friends, family or even pets, Bookabach holiday properties come with the best amenities for making new memories with your loved ones.
Are there large group holiday homes 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 holiday homes in Chester that welcome kids?
Bring the entire family together for an epic adventure in Chester at one of our nine family-friendly holiday homes. 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 favourite.
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 holiday homes 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 holiday homes with WiFi in Chester. Check the "WiFi" box when searching on Bookabach and stay connected on your holiday.
How can I find holiday homes with air conditioning in Chester?
Choose from six Bookabach holiday homes 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 holiday home in Chester?
The minimum age allowed can differ across properties on Bookabach, so check the rules of the holiday home in Chester you're considering. But in general, it's 16, 18 or 21.
How long can I rent a holiday home in Chester for?
How long you can book a holiday home in Chester is up to the property. Just enter your chosen travel dates to look at a list of options offering extended stays. With a range of amenities like kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find somewhere just right to call your home away from home in Chester.