Chester holiday lettings

We found 150 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

  • Stunning coastal views: Enjoy breathtaking scenery along Chester's picturesque coastline, featuring charming islands and serene lakes.
  • Outdoor adventures: Engage in a variety of recreational activities, from hiking to water sports, perfect for nature enthusiasts.
  • Family-friendly activities: Discover numerous attractions tailored for families, ensuring fun for visitors of all ages.
  • Charming accommodation: Choose from a range of delightful holiday rentals, including cosy cottages and stylish apartments.
  • Inviting community vibe: Experience the warm hospitality of Chester's friendly locals, enhancing your getaway.

Popular types of accommodation in Chester

If you're considering a getaway to Chester, you'll find a delightful range of holiday rentals to suit your needs. The most sought-after options include charming houses, cosy cottages, and stylish apartments. Whether you're searching for rentals in Chester or specifically holiday rentals in Chester, our platform ensures you have transparent information and the best savings for a memorable stay.

  • Houses: The top choice for holidaymakers in Chester, these homes offer spacious and comfortable stays perfect for families, friends, or couples.
  • Cottages: Charming and quaint, cottages provide a delightful atmosphere for those seeking a cozy retreat in the heart of Chester.
  • Apartments: A convenient option for solo travellers or couples, apartments in Chester offer modern amenities and easy access to local attractions.
  • Villas: Luxurious and often spacious, villas in Chester are ideal for those looking for a lavish getaway.
  • Cabins: Rustic and inviting, cabins cater to those wanting a peaceful escape surrounded by nature.**

Top attractions in and around Chester

Chester, Nova Scotia, is perfect for outdoor enthusiasts and families seeking a city-themed getaway. With its picturesque lakes, charming islands, and beautiful beaches, the area offers a variety of attractions for those wanting to immerse themselves in nature and enjoy scenic views. Whether you're travelling alone or with loved ones, Chester provides an inviting atmosphere to explore its natural wonders and create memorable experiences.

  • Oak Island: A picturesque island just 1.9km from Chester, Oak Island offers splendid outdoor experiences with its stunning beaches and tranquil vibes, perfect for leisurely walks and picnics.
  • St. Stephen's Church: Situated in the heart of Chester, this historic church showcases magnificent architecture and rich cultural heritage, making it a serene spot for reflection and appreciation of local traditions.
  • Amicus Gallery: Located in Chester, this charming gallery features an array of local artworks, providing a vibrant cultural experience and insight into the artistic community.

Things to do recommended for couples

Chester offers delightful romantic experiences for couples! Dance the night away at the Shore Club, unwind at Cocoa Organic Spa, or indulge in fine wines at Lunenburg County Winery. Each spot provides a unique atmosphere, perfect for creating cherished memories together.

Things to do recommended for families

During your family vacation in Chester, Nova Scotia, explore the serene Graves Island Provincial Park for relaxation or head to the Mahone Bay Swimming Pool for a fun-filled day of outdoor swimming and sports activities. Both spots are perfect for creating lasting family memories.

Things to do recommended for groups

Groups visiting Chester, Nova Scotia can enjoy a round of golf at the Chester Golf Club, catch a family-friendly show at the Chester Playhouse, or browse unique crafts at Have A Yarn, located 6.2km away. These experiences offer a delightful mix of sport, culture, and local charm.

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, or seeking longer stays, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chester with a group: Think about how many bedrooms you'll require, along with features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all of these options, and more, on Vrbo.
  • Traveling to Chester with young kids: Journeys with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable facilities, 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, a family holiday isn't truly finished without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most 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 offering discounts 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 accommodations. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or even a private pool to your search criteria.

Where to stay near Chester

Chester, Nova Scotia, offers a delightful blend of outdoor adventures and family-friendly activities. Visitors can explore the scenic coastline, relax in charming nearby villas, and soak in the warm atmosphere of friendly locals. Ideal for a rejuvenating getaway, Chester’s surroundings are perfect for recreation and historical exploration, ensuring a memorable experience for all. Don’t miss the spectacular oceanfront views and the inviting vibe of this lovely community.

  • Lunenburg: Located 7.5km from Chester, Lunenburg is a charming city renowned for its stunning outdoor scenery and family-friendly atmosphere. Visitors are drawn to its picturesque boardwalk and vibrant recreational areas, perfect for leisurely strolls and family outings. The local shopping centre offers unique crafts and local produce, ensuring a delightful shopping experience. Notable landmarks include the beautiful beaches and the nearby national park, which provide ample opportunities for exploration and relaxation. Lunenburg's historic architecture and rich maritime heritage make it a must-visit destination on your Nova Scotia itinerary.
  • Mahone Bay: Situated 6.2km from Chester, Mahone Bay is a delightful coastal city famed for its idyllic beaches and family-oriented activities. The charming boardwalk invites visitors to enjoy leisurely walks while soaking in the scenic views. Mahone Bay features an array of shopping options, from quaint boutiques to larger shopping centres, catering to diverse tastes. The area’s stunning islands and beaches provide perfect spots for sunbathing, swimming, and beachcombing. Mahone Bay’s picturesque landscapes and friendly local atmosphere make it an ideal retreat for families and outdoor enthusiasts alike.
  • Chester Islands: Just 1.9km from Chester, the Chester Islands are a serene escape for those seeking outdoor adventures and breathtaking scenery. Visitors can enjoy a round of golf or explore the educational opportunities offered in this tranquil environment. Recreational areas abound, providing plenty of space for picnics and nature walks. With pristine beaches and a lovely urban park nearby, the islands offer a perfect setting for relaxation and exploration. The natural beauty and peaceful ambiance of Chester Islands make it a hidden gem worth discovering during your visit to the region.

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 CloudyAverageAverage
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 CloudyAverageSlightly Low
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

Are you hoping to save on your next getaway? Being flexible with your travel dates can often lead to better prices, as they do vary. Additionally, opting for a longer stay can typically result in significant savings. To discover the perfect Vrbo accommodation that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient area for you to plan new journeys, manage your ongoing arrangements, or review and organise your bookings. The properties you've saved or reserved are now categorised into Potential, Upcoming, or Current Trips. To discover Trip Boards, please visit: https://www.vrbo.com/en-gb/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)
  • 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)
  • 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)
  • Fox Point Lake (8.8 mi / 14.2 km)
  • Bayswater Beach Provincial Park (9 mi / 14.4 km)
  • Little Lake (9.1 mi / 14.6 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 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.
How much does it cost to rent a holiday home in Chester?
Prices for holiday 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 holiday 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, 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.
Can I find long-stay holiday rentals in Chester?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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 Vrbo.
Are there any Chester holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 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 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.
How early should I book a Chester holiday rental?
Book your Chester holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Chester home rental booking on Vrbo?
To find Chester holiday 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 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 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, Vrbo 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 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 holiday 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 VrboCareℱ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCareℱ, 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 VrboCareℱ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCareℱ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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