Chester Islands Holiday Rentals

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Holiday Rentals in Chester Islands

Red Roof Bed & Breakfast
9.6 out of 10, Exceptional, (9)
"A lovely little cottage, with the added bonus of a gift shop filled with curious trinkets! Would definitely stay here again if I’m ever back in Lunenberg."
Raeleen
The price is NZ$337
includes taxes & fees
19 Oct - 20 Oct
Red Roof Bed & Breakfast
Wilson's Coastal Club - C2
10.0 out of 10, Exceptional, (6)
"Great cottage. Exactly as advertised - cozy furniture, lovely surroundings and gardens, easy parking. The beds are exceptionally comfy! Would stay again!"
Helen B.
The price is NZ$301
includes taxes & fees
22 Oct - 23 Oct
Wilson's Coastal Club - C2
Black Forest Cabins
3.0 star property
10.0 out of 10, Exceptional, (12)
"Great spot for a special night out … beds were super comfortable "
Caroline
The price is NZ$312
includes taxes & fees
17 Nov - 18 Nov
Black Forest Cabins
Overlooking the Stunning views of St.Margaret's Bay
9.6 out of 10, Exceptional, (19)
"Comfortable, relaxing place to stay that has great views and perfect location to visit different areas!"
Lisa H.
The price is NZ$462
includes taxes & fees
1 Nov - 2 Nov
Overlooking the Stunning views of St.Margaret's Bay
Tiny homes in Chester Nova Scotia. Hosted by Dordean Suites
9.8 out of 10, Exceptional, (13)
"There’s so much about Dordéan Suites to like: a contemporary, fun alternative to large, impersonal corporate roadside hotel. Loved our place, loved our stay! "
Karil
The price is NZ$295
includes taxes & fees
19 Oct - 20 Oct
Tiny homes in Chester Nova Scotia. Hosted by Dordean Suites
Anchorage House & Cottages - Bayswater Cottage
8.4 out of 10, Very good, (6)
"Wonderful cabin and great facility"
Ewan B.
The price is NZ$254
includes taxes & fees
22 Oct - 23 Oct
Anchorage House & Cottages - Bayswater Cottage
The Salt + Soul Suite – Cozy Apt 5
10.0 out of 10, Exceptional, (1)
"Cozy little space for short term stay. Fairly well equipped. Appliances in good shape. Clean and tastefully decorated. Noisy road. No yard. Well situated close to amenities."
Pam
The price is NZ$295
includes taxes & fees
20 Oct - 21 Oct
The Salt + Soul Suite – Cozy Apt 5
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
10.0 out of 10, Exceptional, (6)
"The cleanliness was impeccable, the hospitality was lovely. Everything one needs while away from home was supplied and then some ! Would definitely visit again !"
Carol
The price is NZ$295
includes taxes & fees
29 Oct - 30 Oct
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg
9.8 out of 10, Exceptional, (16)
"Lovely walking distance to the waterfront. Beautiful place to stay!"
Emma
The price is NZ$697
includes taxes & fees
20 Oct - 21 Oct
Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg
Spacious 1-Bedroom King Bed Suite w/ Outdoor Deck (Suite 3)
9.0 out of 10, Wonderful, (4)
"Great stay!!"
heather p.
The price is NZ$417
includes taxes & fees
19 Oct - 20 Oct
Spacious 1-Bedroom King Bed Suite w/ Outdoor Deck (Suite 3)
ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV,
10.0 out of 10, Exceptional, (4)
"Great location. Surprisingly quiet given its proximity to a Main Street. "
Jacqueline S.
The price is NZ$267
includes taxes & fees
27 Oct - 28 Oct
ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV,
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
8.4 out of 10, Very good, (30)
"Beautiful view, the property owner was very responsive, they even had water in the fridge. Was perfect for our relaxing family getaway! "
Ariele M.
The price is NZ$295
includes taxes & fees
29 Oct - 30 Oct
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
Shackup Cabin— Wood Fired Hot Tub & Near the beach
10.0 out of 10, Exceptional, (4)
"A beautiful private property nestled in the forest beside a small stream. The cabin is tastefully decorated, impressively constructed with timber framing, and comfortable. Through the giant windows, the view is fantastic and peaceful. We thoroughly enjoyed the outdoor hot tub and found our whole experience at the cabin calming and memorable."
Sean B.
The price is NZ$402
includes taxes & fees
6 Nov - 7 Nov
Shackup Cabin— Wood Fired Hot Tub & Near the beach
Juniper Bell Tent near Peggy's Cove
8.8 out of 10, Excellent, (3)
"Good for a nights stay and close to Peggy’s cove. Comfy and enough space"
Pamela M.
The price is NZ$251
includes taxes & fees
19 Oct - 20 Oct
Juniper Bell Tent near Peggy's Cove
Pet-Friendly Glamping Dome close to Peggy’s Cove!
10.0 out of 10, Exceptional, (4)
"It was a pleasure to stay here! It's well located, very cozy, spacious, and full of amenities. We felt nestled in a restful, secluded forest, yet not far off the main road. Our dog loved it here."
Claudia Franey J.
The price is NZ$426
includes taxes & fees
3 Nov - 4 Nov
Pet-Friendly Glamping Dome close to Peggy’s Cove!
Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
9.4 out of 10, Exceptional, (3)
"As described and in a great location!"
Erin E.
The price is NZ$432
includes taxes & fees
27 Oct - 28 Oct
Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
Log Cabin #2 - Hubbards Beach
10.0 out of 10, Exceptional, (1)
"As advertised and 2 minutes from the shore club."
Jody K.
The price is NZ$454
includes taxes & fees
20 Oct - 21 Oct
Log Cabin #2 - Hubbards Beach
Orchard Cabin #4 - Hubbards Beach
7.4 out of 10, Good, (6)
"Very cute property with a nice location. "
Nancy O.
The price is NZ$356
includes taxes & fees
19 Oct - 20 Oct
Orchard Cabin #4 - Hubbards Beach
Log Cabin #1 - Hubbards Beach
9.6 out of 10, Exceptional, (4)
"A wonderful cottage with character!! Comfy beds, nice pillows! Very rustic, very peaceful"
Lisa R.
The price is NZ$454
includes taxes & fees
19 Oct - 20 Oct
Log Cabin #1 - Hubbards Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Islands Hotel Reviews

Find out more about Chester Islands

Everything you need to know about Chester Islands holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester Islands holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester Islands holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester Islands holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester Islands. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester Islands holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester Islands holiday rentals we have selected for you start as low as NZ$251 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester Islands rentals

At Expedia, we put the best Chester Islands holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chester Islands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester Islands holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester Islands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chester Islands?

Yes, there are holiday rentals close to the most popular sights in Chester Islands, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chester Islands has to offer?

Family Home In the Heart of the Village of Chester: This holiday home rental outside of Chester Islands is located near the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

What’s there to see and do in Chester Islands?

Explore the area and family-friendly sights such as Shore Club Dance Hall, or get out into nature at a spot like Graves Island Provincial Park. In the wider area, you’ll find Chester Golf Club and Chester Playhouse.

What’s a holiday rental in Chester Islands like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester Islands. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a family getaway.