Chester Islands holiday rentals

We found 174 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Chester Islands to find one that's perfect for your trip. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as parking and a washer and dryer. You'll be 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 Islands

Showing deals for:13 Nov - 20 Nov

Interior
Exterior
Beach
Living area
Excellent
(7 reviews)

Anchorage House & Cottages - Bayswater Cottage

Hubbards

8% off
AU$1,646
for 7 nights, 1 cottage
AU$235 per night
includes taxes & fees
Anchorage House & Cottages - Bayswater Cottage
scarecrow festival Mahone Bay
Mahone Bay waterfront
livingroom
Exterior
Exceptional
(92 reviews)

On a quiet, narrow Lane walking distance to all amenities

Mahone Bay

8% off
AU$2,125
for 7 nights, 1 cottage
AU$304 per night
includes taxes & fees
On a quiet, narrow Lane walking distance to all amenities
Interior
Exterior
Room
Living area
Exceptional
(12 reviews)

The Garden Suite - View of Lunenburg Waterfront

Garden Lots

12% off
AU$1,994
for 7 nights, 1 room
AU$285 per night
includes taxes & fees
The Garden Suite - View of Lunenburg Waterfront
Private kitchen
Terrace/patio
Nearby Peggy's Cove
Living area
Exceptional
(100 reviews)

Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove

Indian Harbour

7% off
AU$2,129
for 7 nights, 1 cottage
AU$304 per night
includes taxes & fees
Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove
Living area
Interior
Exterior
Living area
Exceptional
(19 reviews)

Private cottage on the ocean with a beautiful view that you’ll love.

Heckmans Island

8% off
AU$3,276
for 7 nights, 1 cottage
AU$468 per night
includes taxes & fees
Private cottage on the ocean with a beautiful view that you’ll love.
Private kitchen
Interior
Exterior detail
Room
Wonderful
(12 reviews)

Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

Lunenburg

8% off
AU$1,639
for 7 nights, 1 apartment
AU$234 per night
includes taxes & fees
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

  • 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

Find the perfect holiday rental for your Chester Islands getaway

Learn about the unique charm of Chester Islands with a stay in a holiday home rental. This city has something for everyone. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Chester Islands

Do you want to discover attractions to visit in the area? Venture out of your holiday home and check out everything that makes Chester Islands a fun spot to go on holiday. These are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Chester Golf Club (1.7 mi / 2.7 km)
  • Shore Club Dance Hall (9.5 mi / 15.3 km)
  • For The Birds Nature Shop (11 mi / 17.7 km)
  • Have A Yarn (11.2 mi / 18 km)
  • Osprey Ridge Golf Course (18.1 mi / 29.1 km)
  • Lunenburg County Winery (19.6 mi / 31.5 km)

Exploring the natural features in Chester Islands

Whether you're looking for adventure or just want to spend some time taking in the scenery, Chester Islands is a great place to get outside. Here are some 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)
  • Meisners Beach (3.2 mi / 5.1 km)
  • Oak Island (5.4 mi / 8.7 km)
  • Bayswater Beach Provincial Park (6.4 mi / 10.3 km)
  • Hubbards Beach (9.5 mi / 15.3 km)
  • Queensland Beach Provincial Park (10.7 mi / 17.2 km)

Frequently asked questions

What is the best area to stay in Chester Islands when booking a holiday rental?
When considering a holiday rental in the Chester Islands, Nova Scotia, a popular area to stay is in the charming village of Chester itself. This picturesque community is known for its stunning waterfront views and vibrant arts scene, making it an ideal base for exploring the surrounding islands. In Chester, you'll find a variety of properties ranging from quaint cottages to modern homes, suiting different tastes and budgets.One of the main attractions in Chester is the Chester Playhouse, which offers a delightful array of performances, including theatre, music, and dance, showcasing local talent and providing a wonderful cultural experience. Additionally, the scenic Chester Marina is a superb spot for sailing enthusiasts and those who enjoy waterfront activities, providing a lovely backdrop for leisurely strolls or picnics.Another appealing area to consider is the nearby Big Tancook Island, accessible by ferry. This tranquil island is known for its breathtaking landscapes and opportunities for hiking and cycling, making it a great choice for nature lovers. While it has fewer rental properties compared to Chester, the serene atmosphere and natural beauty make it a rewarding choice for a getaway.
What are the top attractions in Chester Islands?
In Chester Islands, visitors can enjoy a variety of attractions that highlight the natural beauty and charm of the area. The stunning coastline offers opportunities for kayaking and sailing, with many rentals situated near the water providing easy access to these activities. The picturesque village of Chester is known for its historic architecture and vibrant arts scene, with local galleries and craft shops lining the streets.One of the top attractions is the Chester Marina, where guests can watch boats come and go while enjoying scenic views of the harbour. Nearby, Green Bay Beach is superb for sunbathing and swimming, making it a popular spot for families. For those interested in hiking, the surrounding trails offer breathtaking views of the landscape and the Atlantic Ocean.Additionally, the Chester Playhouse hosts various performances throughout the year, providing a taste of local culture and entertainment.
Are all fees included in the Chester Islands 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 Islands holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chester Islands 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 Islands holiday homes?
You can find great discounts on holiday homes in Chester Islands 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 Islands holiday home booking on Stayz?
To find Chester Islands 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 Islands?
A long-stay holiday home in Chester Islands 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 Islands holiday home?
Book your Chester Islands 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 Islands?
Prices for holiday homes in Chester Islands 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 Islands 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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