Chester holiday lettings

We found 175 holiday rentals — enter your dates for availability

Select from 41 homes, 24 cottages and other holiday rentals in Chester to find one that's perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the amenities that you expect for your stay, which might include a garden and hot tub. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Popular cities in Chester

Holiday rentals with weekly discounts - Chester

Showing deals for:14 Nov - 21 Nov

Why visit Chester

  • Stunning coastal scenery: Chester boasts breathtaking views of lakes, islands, and bays, perfect for nature lovers.
  • Outdoor activities: Enjoy a range of activities such as hiking, kayaking, and swimming, ideal for outdoor enthusiasts.
  • Rich cultural heritage: Explore historical sites and learn about the local history in this charming municipality.
  • Family-friendly attractions: Chester offers numerous activities suitable for families, ensuring fun for all ages.
  • Variety of accommodations: Choose from delightful cottages, spacious homes, and stylish apartments for a comfortable stay.

Popular types of accommodation in Chester

If you're pondering the ideal accommodation for your stay in Chester, look no further! Our most sought-after options include charming cottages, spacious private holiday homes, and stylish apartments. Whether you're seeking a quaint cottage rental or a modern house rental, Chester offers a variety of holiday rentals to suit every traveller's needs. Experience the comfort and convenience of our vacation homes, and make your visit to this historic city truly memorable.

  • Houses: The top choice for holidaymakers in Chester, these homes provide a comfortable and spacious environment, ideal for families, friends, or couples seeking a home-away-from-home experience.
  • Cottages: A charming option, cottages offer a quaint and picturesque retreat, perfect for enjoying the natural beauty of Chester while providing a cosy atmosphere.
  • Apartments: A convenient choice for those looking for self-catering options, apartments in Chester provide a practical base for exploring the area.**

Top attractions in Chester

Chester, Nova Scotia, is a delightful destination for outdoor enthusiasts and beach lovers, offering stunning scenery with its nearby lakes, islands, and bays. Visitors can enjoy a range of activities that showcase the area's natural beauty, making it an ideal spot for a relaxing holiday. Just minutes from Chester, you'll find various points of interest and attractions that cater to those seeking a memorable seaside experience.

  • Oak Island: Known for its intriguing legends and treasure hunts, Oak Island offers stunning outdoor experiences with beach vibes. Enjoy the natural beauty while exploring its scenic trails and coastal views.
  • Saint Margarets Bay: A picturesque bay perfect for outdoor enthusiasts, Saint Margarets Bay boasts beautiful beaches and breathtaking scenery. It’s ideal for swimming, kayaking, or simply relaxing by the water.
  • Swiss Air Flight 111 Memorial Bayswater: This poignant memorial honours the victims of the tragic flight. It provides a serene atmosphere for reflection while showcasing the local culture and community spirit.

Things to do recommended for couples

Chester, Nova Scotia, offers enchanting experiences for couples. Enjoy a romantic stroll along the picturesque waterfront, indulge in a candlelit dinner at a charming bistro, or explore the scenic trails together. Don't miss a sunset cruise on the bay, creating memories to last a lifetime.

Things to do recommended for families

Families can explore the picturesque Graves Island Provincial Park, where they can enjoy nature walks, picnics, and stunning views. This tranquil spot offers a perfect blend of relaxation and outdoor fun for all ages, making it an ideal destination for a memorable family vacation in Chester.

Things to do recommended for groups

Experience the scenic Chester Golf Club for a friendly round of golf, enjoy captivating performances at the Chester Playhouse theatre, and indulge in delightful spirits at Black Harbour Distillers Inc. for a taste of local charm and romance. Perfect for group bonding!

What do I need to keep in mind when booking a vacation in 'Chester

If you're planning a trip with friends, family, pets, or seeking extended stays, it's important to prioritise your preferences when filtering options. Here are some helpful booking tips for using Vrbo.

  • 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 filter for these options, and much more, on Vrbo.
  • Traveling to Chester with young kids: Travelling with young children can present its difficulties. It's important to prioritise their comfort and safety, as well as ensure access to suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Chester: For many, a family holiday isn’t truly complete without their furry companion by their side. 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 include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in Chester

Chester, Nova Scotia, is a charming municipality ideal for outdoor enthusiasts and those seeking stunning coastal scenery. With its friendly atmosphere and rich cultural heritage, visitors can enjoy family-friendly activities and explore historical sites. From spectacular oceanfront villas to cosy holiday rentals with fireplaces, Chester offers a perfect getaway for everyone. Discover the beauty of this delightful region and create lasting memories on your vacation.

  • Chester: Chester offers a delightful blend of outdoor adventure and urban conveniences. Nestled in a picturesque coastal region, it is ideal for families looking to unwind. You can enjoy a variety of activities including shopping at local centres, playing a round of golf, or simply relaxing at the beach. The urban park provides a peaceful retreat with stunning views, while the surrounding islands invite exploration. Chester's vibrant community and charming atmosphere make it a perfect base for discovering the beauty of Nova Scotia.
  • Western Shore: Western Shore is a charming coastal town that beckons families and outdoor enthusiasts alike. With its stunning beaches and access to lush golf courses, it's the perfect spot for a day of fun in the sun. The local private country club provides a welcoming atmosphere for golf lovers, while the nearby urban park offers recreational opportunities for all ages. Western Shore's natural beauty, combined with its family-friendly activities, creates an inviting environment for a memorable holiday.
  • Chester Islands: Chester Islands is a serene escape known for its breathtaking scenery and outdoor pursuits. This idyllic destination is perfect for those seeking relaxation by the beach or engaging in recreational activities. The islands provide a unique opportunity to explore nature, with stunning coastal views and tranquil spots ideal for picnics. Educational experiences are also available, making it a great choice for families looking to combine leisure with learning. Chester Islands promises an enchanting experience amid the beauty of the Atlantic.

Booking with Vrbo is simple

Are you hoping to make your next getaway more affordable? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you'll find that booking a longer stay can lead to considerable savings. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board provides you with a dedicated area to plan new getaways, pick up from where you last stopped, or easily view and manage your travel arrangements. You can now find the properties you've previously saved and booked categorised under Potential, Upcoming, or Current Trips. To start using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Find the perfect holiday rental for your Chester getaway

Learn about the unique charm of Chester with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Chester

Do you want to discover top things to see and do while you're in the area? Venture out of your holiday home and check out everything that makes Chester a one-of-a-kind holiday spot. These are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Chester Golf Club (6.9 mi / 11.1 km)
  • Shore Club Dance Hall (11.3 mi / 18.2 km)
  • Cocoa Organic Spa & Boutique (13 mi / 21 km)
  • Have A Yarn (13.1 mi / 21 km)
  • Lunenburg County Winery (14.5 mi / 23.4 km)
  • Bluenose Golf Club (17.8 mi / 28.7 km)

Exploring the natural features in Chester

Whether you're looking for adventure or just want to take in the scenery, Chester is a great place to get out in nature. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Graves Island Provincial Park (6 mi / 9.7 km)
  • Timber Lake (7.1 mi / 11.4 km)
  • Meisners Beach (7.3 mi / 11.8 km)
  • Oak Island (7.8 mi / 12.6 km)
  • Dauphinees Mill Lake (8.9 mi / 14.4 km)
  • Green Island (9 mi / 14.5 km)

Frequently asked questions

What is the best area to stay in Chester when booking a holiday rental?
Chester is among the most preferred areas to select a holiday property in Chester. Searching for some fun things to do here? Take time to visit Chester Golf Club and Graves Island Provincial Park.
What is the most popular type of holiday rental accommodation in Chester?
The most sought-after types of holiday rentals in Chester are houses. Ready for more choices? Vrbo has many options to match the unique needs of our guests, so you'll see properties in loads of sizes and shapes. The ideal home away from home is waiting for you — book yours today.
How much does it cost to rent a holiday rental in Chester?
The average price for a holiday home in Chester depends on several factors, like time of year, length of stay and property type. Whether you're looking for a sprawling villa with space for extended family or a cosy cabin perfect for just you and the kids, just enter your dates of travel to find stays that offer great value.
How much does it cost to rent a beach house in Chester?
Prices for beach houses in Chester may differ depending on the size and style of the property and when you're travelling. All you need to do is enter your travel dates into Vrbo and how many guests to view available options and prices. From there you can use the filters to narrow your search results by amenities, nearby activities, ratings and more.
What are popular rental amenities in Chester?
When it comes to rental amenities that people are searching for in Chester, a fridge, a microwave oven and off-street parking options rank highest. With Vrbo holiday homes, you'll discover options to match your taste and style, whether you're going away with friends, relatives or even pets.
Are there large group holiday rentals in Chester?
With eight properties that can sleep 10 or more guests in Chester, you don't have to keep your invite list short. From holidays with the extended family to special events like birthday parties and weddings, Vrbo will help you find a large group rental to suit the occasion.
What are the top attractions for families in Chester?
Keeping the kids entertained during your Chester holiday is a cinch with these exciting family-friendly attractions:

  • Oak Island
  • Chester Golf Club
  • Saint Margarets Bay

Can I find two-bedroom holiday rentals in Chester?
Chester has 14 two-bedroom properties to select from. Go for a holiday home with all the comfort and space you want at a price that won't break the bank on Vrbo.
Are there holiday rentals with WiFi in Chester?
Chester has 29 holiday rentals with WiFi, so you'll be able to stay connected when you're away. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to checking emails, these Vrbo homes make it easy to go online.
How old do you have to be to rent a holiday rental in Chester?
The minimum required age is usually 16, 18 or 21. It can change between properties on Vrbo, so look at the rules of your preferred Chester stay before you book.
How long can I rent a holiday rental in Chester for?
It's down to the Chester property. To see a list of options offering extended stays, just enter your travel dates and guest number into Vrbo's search page. Enjoy having the property to yourself, along with amenities such as a full kitchen, air conditioning and an outdoor space where the little ones can play. Keep your eyes open for long-term stays that offer discounted weekly or monthly prices.

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