Chester holiday homes

We found 135 holiday rentals — enter your dates for availability

Discover a selection of 13 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.

Holiday rentals with weekly discounts - Chester

Showing deals for:19 Dec - 26 Dec
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Why visit Chester

  • Stunning waterfront: Enjoy Chester’s picturesque waterfront, ideal for relaxation and scenic strolls.
  • Chester Zoo: Visit the local zoo for a fun day out with family and a chance to see diverse wildlife.
  • Outdoor activities: Engage in various outdoor pursuits like kayaking, swimming, and hiking in beautiful surroundings.
  • Local culture: Experience the vibrant Chester Rows and attend the lively Chester Show for a taste of community spirit.
  • Charming neighbourhoods: Explore quaint streets filled with friendly locals, boutique shops, and delightful dining options.

Top attractions in and around Chester

Chester, Nova Scotia, is a fantastic spot for outdoor and family vacations, offering beautiful lakes, islands, and beaches. You can explore local attractions like the Chester Zoo, enjoy various activities, and take in the stunning scenery. Don't miss out on the Chester Show and the vibrant Chester Rows for a taste of local culture. Whether you're after adventure or relaxation, Chester has something for everyone to enjoy.

  • Oak Island: A stunning island located 4.8km from Chester, known for its beautiful beaches and outdoor vibes. It's a perfect spot for a leisurely day of sunbathing, swimming, or exploring coastal trails.
  • The Moorings Gallery: Situated 14.5km from Chester, this art gallery showcases local and international artists, providing a rich cultural experience. The gallery hosts various exhibitions and offers a glimpse into the artistic spirit of the region.
  • Amicus Gallery: Located within Chester, this charming gallery features a diverse collection of art that highlights local talent. Its inviting atmosphere makes it a lovely place to appreciate creativity and culture.

Things to do recommended for couples

Chester, Nova Scotia, offers a delightful romantic getaway. Dance the night away at the Shore Club, indulge in relaxation at Cocoa Organic Spa, and sip exquisite wines at Lunenburg County Winery. Each experience is perfect for creating cherished memories with your partner.

Things to do recommended for families

Families will love the Mahone Bay Swimming Pool for a splashy day of fun, while Graves Island Provincial Park offers a serene spot for relaxation and wellness, just a short distance from Chester. Enjoy the beautiful outdoors together.

Things to do recommended for groups

Experience the charm of Chester by catching a show at the Chester Playhouse, enjoying a round at the Chester Golf Club, or exploring local crafts at Have A Yarn, just 16.1km away. Perfect activities for your group to enjoy the local culture and outdoor vibes.

*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 heading off on a trip with a group, family, or pets, or if you're planning for an extended stay, it’s important to use the right filters to suit your 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 features like a full kitchen or outdoor area for group gatherings. The good news is, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Chester with young kids: Navigating travel with young children can present its challenges. It's important to prioritize their comfort and safety, along with ensuring access to 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 holiday wouldn’t be the same without their furry companion. If that resonates with you, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that your whole family feels comfortable and at home.
  • Planning for a long term stay visiting Chester: If you’re in search of holiday rentals with special offers for stays of a month or more, you’ve come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Chester

Chester, Nova Scotia, offers a delightful mix of outdoor adventures and family-friendly experiences. Explore the charming waterfront, relax in scenic parks, and enjoy local dining options. The nearby region is perfect for those seeking a laid-back atmosphere with friendly locals, ensuring a memorable getaway. From river activities to exploring quaint neighbourhoods, Chester is your ideal spot for a relaxing break filled with new discoveries.

  • Mahone Bay: Mahone Bay is a picturesque town located 16.1km from Chester, renowned for its vibrant outdoor and family-friendly atmosphere. This charming coastal community boasts stunning views and a delightful boardwalk that invites leisurely strolls. Visitors can explore the local shopping centre and enjoy a variety of shops and eateries. Notable attractions include the beautiful beaches and nearby islands, making Mahone Bay a perfect spot for beach lovers and those looking to unwind in a scenic environment.
  • Robinsons Corner: Situated 3.2km away from Chester, Robinsons Corner offers a serene escape with its breathtaking scenery and outdoor experiences. This quaint city features a recreational area ideal for families and nature enthusiasts alike. The local shopping centre provides convenient access to various retail options. Proximity to stunning beaches, picturesque bays, and a national park enhances the area’s appeal, making it a fantastic destination for those seeking both relaxation and adventure.
  • Martins Point: Located 8.0km from Chester, Martins Point is a tranquil retreat perfect for outdoor enthusiasts and beachgoers. This charming city features a recreational area and campground, making it ideal for families looking to connect with nature. Visitors can enjoy the local shopping centre while being drawn to the area’s beautiful beaches and stunning island views. With its scenic surroundings, Martins Point provides a delightful experience for those wanting to soak up the natural beauty of Nova Scotia.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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

Keen to save some dollars on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. You can also enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental. We're here to help you find the perfect spot.

Vrbo Trips: Planning made easy

Vrbo's clever Trip Board offers you a handy space to plan new adventures, pick up right where you left off, or keep track of your travel arrangements. You can easily find properties you've saved and booked in the Potential, Upcoming, or Current Trips sections. To start using Trip Boards, simply 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)
  • Cocoa Organic Spa & Boutique (9.4 mi / 15.2 km)
  • Have A Yarn (9.5 mi / 15.3 km)
  • Shore Club Dance Hall (11 mi / 17.7 km)
  • Bluenose Golf Club (12.6 mi / 20.2 km)
  • Osprey Ridge Golf Course (16.3 mi / 26.3 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)
  • Hollahan Lake (6.8 mi / 11 km)
  • Callender Lake (8.2 mi / 13.3 km)
  • Bayswater Beach Provincial Park (9 mi / 14.4 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.

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