Chester holiday rentals

We found 164 holiday rentals — enter your dates for availability
Discover a selection of 15 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.

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Why visit Chester

  • Coastal Charm: Enjoy the picturesque waterfront and serene beaches that make Chester a perfect spot for relaxation and family holidays.
  • Outdoor Activities: Explore scenic lakes, trails, and islands ideal for hiking, cycling, and water sports.
  • Community Spirit: Immerse yourself in the welcoming atmosphere of Chester, where locals share their love for the area.
  • Romantic Getaways: Experience the idyllic setting that offers a blend of tranquillity and adventure for couples.
  • Unique Spa Experiences: Indulge in relaxing treatments at local wellness centres, such as Nordic spas, for a rejuvenating holiday.

Popular types of accommodation in Chester

If you are unsure what type of accommodation you can expect in Chester, we have you covered. Enjoy a stay in Chester with ideal accommodation options including private holiday homes, cosy cottages, and stylish apartments. Explore local attractions, landmarks, and experiences that truly represent the charm of Chester, Nova Scotia, Canada, and indulge in unique offerings such as the Nordic spa for a complete holiday experience.

  • Private Holiday Homes: The most sought-after option in Chester, offering exclusive residences for a peaceful retreat.
  • Cottages: A charming choice providing cosy, countryside living experiences in a quaint setting.
  • Apartments: A popular selection for visitors, delivering modern, compact living spaces in central locations.
  • Villas: A luxurious option presenting spacious, well-appointed abodes for discerning holidaymakers.
  • Cabins: An affordable alternative, offering rustic, intimate spaces nestled in nature.**

Top attractions in and around Chester

Chester, Nova Scotia, offers a delightful blend of outdoor activities and coastal charm, perfect for family beach holidays. Visitors can explore scenic lakes and picturesque islands, or relax on serene beaches. The area is ideal for those seeking romance or adventure, with numerous trails and waterfront spots that invite exploration. Whether you're enjoying a leisurely stroll or engaging in water sports, Chester provides a memorable experience amidst its natural beauty.

  • Tancook Island: A charming island within Chester, Tancook Island offers stunning beaches and a serene outdoor atmosphere, perfect for leisurely strolls and picnics.
  • Bayswater Beach Provincial Park: Located a short drive from Chester, this picturesque beach park features golden sands and tranquil waters, ideal for swimming, sunbathing, and enjoying nature.
  • Mahone Bay Settlers Museum: This local museum showcases the rich cultural heritage of the area, providing fascinating insights into the lives of early settlers through engaging exhibits.

Things to do recommended for couples

Experience a romantic escape in Chester, Nova Scotia. Enjoy a charming stroll along scenic lanes and savour delightful local cuisine, perfect for couples seeking a cosy retreat.

Things to do recommended for families

Families will delight in exploring the scenic Chester waterfront, where children can enjoy the sandy beaches and playgrounds. Visit the local farmers' market for fresh produce and crafts, or embark on a family-friendly hike along the picturesque trails of the nearby scenic parks.

Things to do recommended for groups

Explore the rich maritime heritage of Chester, Nova Scotia with a guided group tour of the historic waterfront, followed by a lively seaside picnic and engaging local crafts 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

Whether you're journeying with a group, as a family, with your pets, or seeking extended stays, be sure to refine your search using the appropriate filters. Here are some Stayz booking pointers for you.

  • 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 get-togethers. Luckily, you can easily filter for all these options, and more, on Stayz.
  • Traveling to Chester with young kids: Traveling with young children can be challenging. You must prioritise their comfort and safety, as well as age-appropriate facilities, including a private swimming pool. It’s also wise to consider how close you are to family-friendly attractions.
  • Taking your pets with you to Chester: For many, a family holiday is not complete without their four-legged companion. If this resonates with you, have a look at Stayz accommodations that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels right 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 right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include preferences such as 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 retreat perfect for family-friendly outdoor and beach holidays. Explore its charming local attractions, scenic coastal neighbourhoods and relaxed atmosphere. Enjoy leisurely walks along its sandy shores and immerse yourself in the welcoming community spirit. The area promises a blend of recreation and tranquillity ideal for a memorable holiday experience.

  • Mahone Bay: Mahone Bay is a charming city that boasts a blend of coastal allure and urban sophistication. Just 16km away from Chester, it offers travellers a delightful outdoor, family, and beach experience. Stroll along the scenic boardwalk, enjoy a round of golf at one of the local courses, or simply relax on the sandy beaches. The city's attractions include a picturesque urban park and nearby islands that add to its natural beauty.
  • Chester Islands: Chester Islands, located a mere 5km from Chester, is an enchanting getaway that epitomises a blend of outdoor adventure and beachside tranquillity. Visitors can immerse themselves in the local shopping centre, explore the recreational areas, or take a hike along the well-maintained trails. The islands offer stunning views of the bay and the beach, with islands dotting the seascape to enhance the scenic allure.
  • Marriotts Cove: Marriotts Cove, just 3km from Chester, is a delightful city renowned for its outdoor and beachside splendour, complemented by breathtaking scenery. Engage in a round of golf on one of its courses or take a leisurely walk along the boardwalk. The local landmarks, including a serene lake, nearby island, and sandy beach, provide a perfect setting for exploring the natural environment and enjoying the coastal charm.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January28.4°F (-2.0°C)Light RainMostly CloudyAverageAverage
February27.5°F (-2.5°C)Light RainMostly CloudyAverageAverage
March32.0°F (0.0°C)Light RainMostly CloudyAverageSlightly Low
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 Stayz is simple

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, opting for a longer stay can lead to substantial savings. To discover a Stayz property that suits your budget, feel free to utilise our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz’s Trip Board offers an easy-to-use platform for you to create new trips, continue from where you last left off, or review and arrange your travel plans. You can conveniently find your saved or booked properties organised under categories such as Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, please visit: https://www.stayz.com.au/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)
  • Bayswater Beach Provincial Park (9 mi / 14.4 km)
  • Mahone Bay Swimming Pool (9.8 mi / 15.7 km)
  • Hubbards Beach (11.1 mi / 17.8 km)
  • Queensland Beach Provincial Park (12.3 mi / 19.8 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 best area to stay in Chester when booking a holiday rental?
When considering a holiday rental in Chester, Nova Scotia, a popular area to stay is the charming waterfront neighbourhood. This picturesque locale offers a delightful blend of natural beauty and local culture, making it great for visitors looking to unwind and explore. The proximity to the marina provides easy access to boating activities, while the scenic views of the Atlantic Ocean add to the area's appeal.In addition to the stunning waterfront, Chester is renowned for its vibrant arts scene, with galleries and local crafts showcasing the talents of the region. A visit to the Chester Playhouse, a beloved local theatre, offers a chance to enjoy live performances and community events, further enriching your holiday experience.The area has a variety of holiday rental properties, from quaint cottages to more spacious homes, suiting different preferences and group sizes.
Where are the best areas for renting a beach house in Chester?
For renting a beach house in Chester, Nova Scotia, the picturesque waterfront area near Chester Basin offers an ideal setting. This region features charming cottages and modern homes with stunning views of the bay, many of which come equipped with amenities such as spacious decks, outdoor dining areas, and private access to the beach. Properties often include fully stocked kitchens and comfortable living spaces, superb for family gatherings or relaxing getaways.The village centre of Chester itself is another excellent option, known for its vibrant marina and local shops. Here, visitors can find quaint seaside cottages that may include features like kayaks for rent, barbecues for outdoor grilling, and proximity to local restaurants and cafés that serve fresh seafood.Additionally, the nearby Chester Golf Club and scenic hiking trails offer great opportunities for outdoor activities. Rentals in this area frequently highlight easy access to both the beach and the lush landscapes that characterise the region, making it a fantastic destination for a seaside retreat.
Where are the best Chester ski resort rentals?
For ski resort rentals near Chester, Nova Scotia, travellers should consider the nearby area of Martock, which is home to Ski Martock, one of the province's premier ski destinations. This ski area is less than half an hour's drive from Chester, making it a convenient choice for winter sports enthusiasts. In Martock, you can find a variety of rental properties, including cozy chalets and modern condos, often equipped with amenities such as fully stocked kitchens, fireplaces, and easy access to ski lifts. Many rentals here also offer outdoor spaces where guests can enjoy the snowy landscape.In Chester itself, while not directly a ski resort, visitors can find charming cottages and waterfront homes that provide a peaceful retreat after a day on the slopes. These properties typically feature amenities like hot tubs, fire pits, and stunning views of the coastline, making them a great option for those who appreciate both winter sports and seaside relaxation.Additionally, the surrounding areas, including Acadia University and local nature trails, offer opportunities for cross-country skiing and snowshoeing, ensuring a full winter experience.
What is the most popular type of holiday rental accomodation in Chester?
In Chester, holiday houses are the most popular type of holiday rental, with about 60 available throughout the area. These properties are often situated in charming neighbourhoods, providing easy access to local attractions such as the picturesque Chester Harbour and the nearby golf course. Most holiday houses feature spacious layouts, fully equipped kitchens, and outdoor areas, making them ideal for families or groups looking to enjoy a relaxed stay by the coast. Additionally, there are several apartments, cottages, and condos, which offer a range of amenities such as comfortable living spaces, laundry facilities, and sometimes even communal gardens.
Are there any family house rentals in Chester?
In Chester, Nova Scotia, there are several family-friendly house rentals available, making it an excellent choice for those travelling with loved ones. The charming village features properties that often come equipped with spacious living areas, fully stocked kitchens for preparing family meals, and outdoor spaces ideal for children to play and explore.Visitors can enjoy the nearby scenic waterfront, with opportunities for boating and kayaking, as well as local parks offering playgrounds and picnic areas. The area's proximity to attractions like the Chester Golf Club and the picturesque seaside offers a delightful mix of relaxation and recreation.
Can I rent a holiday home with a pool or hot tub in Chester?
In Chester, Nova Scotia, there are several holiday homes available for rent that feature pools and hot tubs, making it a delightful option for travellers seeking a relaxing getaway. The charming village is known for its beautiful waterfront and scenic views, and you can find these properties in various neighbourhoods, including those near the marina and along the picturesque coastline.Many of the rentals offer amenities such as private pools, hot tubs, outdoor patios, and fully equipped kitchens, ideal for families or groups looking to unwind after a day of exploring the area. Some properties may also provide access to gardens and outdoor dining spaces, enhancing the overall experience.Chester is a fantastic base for enjoying the surrounding natural beauty, with opportunities for boating, hiking, and visiting local shops and restaurants.
Are there pet-friendly house rentals in Chester?
In Chester, Nova Scotia, there are several pet-friendly house rentals available, making it an inviting destination for travellers with furry companions. The area is known for its picturesque coastal scenery and charming maritime atmosphere. Many of these holiday homes come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and outdoor decks or patios, superb for relaxing after a day of exploration.Chester offers easy access to nearby parks and waterfront areas where pets can enjoy the outdoors. The local Chester Village Green is a lovely spot for leisurely walks, and the scenic Chester Harbour provides opportunities for stunning seaside strolls. Additionally, the nearby Atlantic Ocean invites activities such as swimming and kayaking, ensuring a fun-filled stay for both pets and their owners.
Are there any remote work holiday rentals in Chester?
In Chester, Nova Scotia, there are numerous remote work-friendly holiday rentals available, with around 44 options to choose from. This charming coastal town offers a delightful setting for those looking to blend work and leisure. Many of the rentals come equipped with essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable living areas, ensuring a productive environment while enjoying the scenic beauty of the area.The town itself is known for its picturesque waterfront, quaint shops, and vibrant art scene. Visitors can explore local attractions like the Chester Golf Club and the picturesque Oak Island, which is just a short drive away. For outdoor enthusiasts, the surrounding region offers opportunities for hiking and sailing, making it a great spot for a balanced work-life experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Chester?
In Chester, popular holiday rental amenities include kitchens, allowing guests to prepare their own meals, which is particularly appealing for longer stays. Many properties also offer onsite parking, making it convenient for those travelling by car. A coffee and tea maker is typically available, ensuring that guests can enjoy their morning brews at their leisure. Additionally, many rentals feature a deck or patio, providing a lovely outdoor space for relaxation. For those travelling with pets, it's worth noting that several rentals in the area permit pets, making Chester a welcoming destination for furry companions.
When is the best time to visit Chester for a holiday rental?
The best time to visit Chester for a holiday rental is during the peak season from July to September. This lively period attracts a lot of visitors eager to enjoy the coastal charm of Chester, with its stunning waterfront views and vibrant community events. July, in particular, stands out as the most popular month, offering warm temperatures that range from 15 to 25 degrees Celsius, great for outdoor activities and exploration.During these summer months, you can partake in various activities, from sailing and kayaking to leisurely strolls along the picturesque harbour. The town buzzes with energy, as locals and tourists alike gather for festivals, art shows, and music events, making it an ideal time for those seeking a vibrant setting.For travellers looking for a more budget-friendly experience, consider visiting Chester in December. While this is the low season, the town's winter charm offers a unique perspective, with fewer crowds and a serene environment. During this time, you can enjoy cosy local cafés and the festive spirit of the holiday season.
What are the top attractions in Chester?
In Chester, Nova Scotia, visitors can enjoy a charming blend of coastal beauty and local culture. One of the main attractions is the picturesque Chester Harbour, where you can stroll along the waterfront and admire the array of boats. The Chester Playhouse is a cultural hub, hosting various performances throughout the year, showcasing local talent and providing a taste of the community's artistic spirit.Outdoor enthusiasts will appreciate the nearby seaside hiking trails, particularly those in the scenic area around the Chester Golf Club, which offers stunning views of the Atlantic Ocean. For a great experience, the nearby Bluenose II, a famous replica of a 1921 racing schooner, can often be seen in the waters, representing Nova Scotia's maritime heritage.Additionally, the quaint shops and cafes in the village centre provide a delightful atmosphere to relax and enjoy local cuisine.
Are all fees included in the Chester holiday homes prices shown on Stayz?
Stayz 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.
Are there any Chester holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chester with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Chester holiday homes?
You can find great discounts on holiday homes in Chester on Stayz, 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.
Can I change or cancel my Chester holiday home booking on Stayz?
To find Chester holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chester?
A long-stay holiday home in Chester is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Chester holiday home?
Book your Chester holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chester?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chester to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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