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Chester Islands Vacation Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chester Islands vacation rentals

A wooden deck with a hot tub surrounded by trees.

1. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Windsor Road
10.0 out of 10, Exceptional, (16 reviews)
"The cleanliness was impeccable, the hospitality was lovely. Everything one needs while away from home was supplied and then some ! Would definitely visit again !"
Canada
Carol
The price is AED 515
AED 673 total
includes taxes & fees
18 Oct - 19 Oct
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A small cabin with a deck, a door, and a window.

2. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Chester Basin
10.0 out of 10, Exceptional, (23 reviews)
"Hot tub is Devine, everything is clean and thoughtfully provided. Basket of snacks was a sweet treat! We enjoyed the large deck and privacy very much ♥️we will definitely be back "
Canada
Suzanne
The price is AED 515
AED 673 total
includes taxes & fees
26 Oct - 27 Oct
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A bright living room with a white sofa, a coffee table, and a potted plant.

3. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (118 reviews)
"Wonderful property and extremely clean. Hosts were wonderful!"
United States
Dianne T.
The price is AED 515
AED 863 total
includes taxes & fees
17 Oct - 18 Oct
One bedroom fully equipped Mahone Bay luxury cottage
A sunset view through a window with bare trees and a distant shoreline.

4. 4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
Hubbards
8.6 out of 10, Excellent, (60 reviews)
"Beautiful place to stay. Host was very easy to communicate with."
United States
Jeff T.
The price is AED 459
AED 609 total
includes taxes & fees
20 Oct - 21 Oct
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
A bedroom with a wooden ceiling, a bed with white bedding, a nightstand, a dresser, a chair, a window with a view of trees, and a patterned rug.

5. Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (89 reviews)
"It was a cute and cozy stay. We would stay here again."
Canada
Julie
The price is AED 867
AED 1,077 total
includes taxes & fees
13 Oct - 14 Oct
Black Forest Cabins
A sandy beach with people walking along the shore.

6. Downtown Bridgewater Suite near River and Trails

Downtown Bridgewater Suite near River and Trails
Bridgewater
9.4 out of 10, Exceptional, (3 reviews)
"This property was comfortable and convenient and we enjoyed our stay here."
United States
Marty
The price is AED 179
AED 465 total
includes taxes & fees
19 Oct - 20 Oct
Downtown Bridgewater Suite near River and Trails
A modern kitchen with white cabinetry, a wooden countertop, and a large mirror.

7. Mahone Bay Hide-Away

Mahone Bay Hide-Away
Mahone Bay
10.0 out of 10, Exceptional, (114 reviews)
"Comfortable cottage very close to town centre but also quiet and calm."
Canada
Richard
The price is AED 515
AED 866 total
includes taxes & fees
13 Oct - 14 Oct
Mahone Bay Hide-Away
A wooden building with a sign reading "The Knot."

8. Red Barn Bed & Breakfast

Red Barn Bed & Breakfast
Lunenburg
9.4 out of 10, Exceptional, (13 reviews)
"We enjoyed our stay very much! "
Canada
Kimberley K.
The price is AED 394
AED 623 total
includes taxes & fees
19 Oct - 20 Oct
Red Barn Bed & Breakfast
A wooden cabin in a snowy forest.

9. Pet-Friendly Glamping Dome close to Peggy’s Cove!

Pet-Friendly Glamping Dome close to Peggy’s Cove!
Seabright
10.0 out of 10, Exceptional, (19 reviews)
"Great place and location and the owners were very helpful!"
Canada
Judy
The price is AED 667
AED 892 total
includes taxes & fees
14 Oct - 15 Oct
Pet-Friendly Glamping Dome close to Peggy’s Cove!
A sauna with a view of the sea, wooden walls, and a stone heater.

10. Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax

Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax
Boutiliers Point
9.6 out of 10, Exceptional, (27 reviews)
"Check in staff were very friendly and showed us around the cabin and facilities. Cabin was clean, had all required items for cooking and enjoying the stay."
United States
Kristopher H.
The price is AED 595
AED 796 total
includes taxes & fees
15 Oct - 16 Oct
Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax
A view of a waterfront property with a dock and a small building.

11. Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise
Western Shore
9.2 out of 10, Wonderful, (28 reviews)
"Beautiful spot!"
United States
Kirby D.
The price is AED 824
AED 1,409 total
includes taxes & fees
13 Oct - 14 Oct
Oceanfront Luxury Magical Views Sunset and Sunrise
A beach with clear water, a sandy shore, and a forested island in the distance.

12. Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail

Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail
Ingramport
9.8 out of 10, Exceptional, (122 reviews)
"The cottage was so sweet and the host thought of everything Clean and cozy would stay again and again ! Great location too quiet and close enough to Halifax or other tourist destinations"
United States
Kristyn P.
The price is AED 636
AED 1,314 total
includes taxes & fees
13 Oct - 14 Oct
Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail
A small, two-story cabin with a deck, large windows, and a fireplace.

13. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Chester Basin
9.8 out of 10, Exceptional, (17 reviews)
"Amenities are fantastic, very private"
Canada
francesco c.
The price is AED 515
AED 673 total
includes taxes & fees
11 Nov - 12 Nov
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A staircase with wooden balusters and a handrail, leading to a landing with a red door.

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

Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)
Lunenburg
9.0 out of 10, Wonderful, (14 reviews)
"Loved our stay. Nice and clean, quiet and peaceful. Amazing yard. Basics were excellent (Bed, Tv & facilities). Definitely recommend."
Canada
Patrick
The price is AED 459
AED 817 total
includes taxes & fees
1 Nov - 2 Nov
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)
A small white cabin with green trim and a porch, surrounded by greenery.

15. Orchard Cabin #4 - Hubbards Beach

Orchard Cabin #4 - Hubbards Beach
Hubbards
7.2 out of 10, Good, (7 reviews)
"Very cute property with a nice location. "
United States
Nancy O.
The price is AED 646
AED 861 total
includes taxes & fees
13 Oct - 14 Oct
Orchard Cabin #4 - Hubbards Beach
A wooden deck with a table, a chair, and a sofa.

16. Oceanfront Kayaking retreat close to Lunenburg

Oceanfront Kayaking retreat close to Lunenburg
Lunenburg
9.8 out of 10, Exceptional, (7 reviews)
"We had a really nice stay here! This is a great place if you’re looking for a peaceful and tranquil getaway while still being close enough to town. The property feels wonderfully remote and quiet, yet it’s only about a 15-minute drive to Lunenburg. The place itself is spacious, comfortable, and has a beautiful view."
Canada
Anshika
Oceanfront Kayaking retreat close to Lunenburg
A calm lake with boats docked at the pier, surrounded by trees.

17. Lake Mushamush Cottage!

Lake Mushamush Cottage!
Lower Northfield
9.4 out of 10, Exceptional, (13 reviews)
"Very clean, well-stocked, hospitable and comfortable space."
Canada
Rita
The price is AED 399
AED 690 total
includes taxes & fees
15 Oct - 16 Oct
Lake Mushamush Cottage!
A dining table with blue plates, a bottle, and a glass.

18. Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach

Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach
Boutiliers Point
10.0 out of 10, Exceptional, (1 review)
"Awesome cabin, great staff who were welcoming and helpful. Great location close to all major attractions"
Canada
Christopher
The price is AED 624
AED 835 total
includes taxes & fees
25 Oct - 26 Oct
Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach
A sandy beach with people walking along the shore.

19. Pretty Bachelor with Balcony near River & Trails

Pretty Bachelor with Balcony near River & Trails
Bridgewater
2.0 out of 10, (1 review)
The price is AED 221
AED 552 total
includes taxes & fees
19 Oct - 20 Oct
Pretty Bachelor with Balcony near River & Trails
A dock with boats, a clear blue lake, and a forested island.

20. Mermaid's Retreat - Caribou Lake Cottage!

Mermaid's Retreat - Caribou Lake Cottage!
Mahone Bay
9.8 out of 10, Exceptional, (7 reviews)
"Fantastic property, location, and hosts. Will be booking again!"
Canada
Josh
The price is AED 644
AED 1,007 total
includes taxes & fees
13 Oct - 14 Oct
Mermaid's Retreat - Caribou Lake Cottage!
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

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

10/10 Excellent
"Great place"
Angela 1-night trip
Posted 4 hours ago
Oak Island Resort & Conference Centre

Frequently asked questions

Can I find vacation rentals in Chester Islands?

Yes, you can find vacation rentals close to top points of interest in Chester Islands, or you can go with a more remote option if you're looking for a relaxing stay.

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

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: Visitors like this Chester Islands vacation home rental. It is located by the ocean and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Oak Island. In the larger area, you’ll find Chester Golf Club and Chester Art Center.

What’s a vacation rental in Chester Islands like?

Vacation rentals are private properties you can book for several days or longer in Chester Islands. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a small group gathering.