Default HTG hotel image

Chester Islands Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chester Islands vacation rentals

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, (11 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 CA $200
CA $260 total
includes taxes & fees
Aug 30 - Aug 31
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

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, (21 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 CA $200
CA $260 total
includes taxes & fees
Sep 8 - Sep 9
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

3. 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, (52 reviews)
"Have use of all the facilities (laundry) was extremely helpful when travelling with a toddler."
Canada
Lisa
The price is CA $200
CA $260 total
includes taxes & fees
Sep 21 - Sep 22
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

4. Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.8 out of 10, Exceptional, (73 reviews)
"A beautiful, unique gem for the same price as a cookie cutter room in a chain hotel. Really nice place, wish we could stay longer."
Canada
paul
The price is CA $337
CA $418 total
includes taxes & fees
Sep 14 - Sep 15
Black Forest Cabins

5. Oakhill Pines Campground

Oakhill Pines Campground
3.0 star property
Oak Hill
8.8 out of 10, Excellent, (29 reviews)
"Check in and out was easy cute family that runs the place. Campground was very clean well-maintained fun areas for families for kids to play in the park fun pool washroom we're clean and maintained regularly. Definitely recommend for family fun."
Canada
David
The price is CA $108
CA $123 total
includes taxes & fees
Sep 28 - Sep 29
Oakhill Pines Campground

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

Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax
Boutiliers Point
9.8 out of 10, Exceptional, (24 reviews)
"Everything was clean and cozy very quiet and friendly staff "
Canada
Adele S.
The price is CA $190
CA $255 total
includes taxes & fees
Sep 2 - Sep 3
Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax

7. Newly built cabin in Fox Point (Hubbards) close to several beaches and trails

Newly built cabin in Fox Point (Hubbards) close to several beaches and trails
Hubbards
The price is CA $144
CA $201 total
includes taxes & fees
Sep 14 - Sep 15
Newly built cabin in Fox Point (Hubbards) close to several beaches and trails

8. 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 CA $200
CA $260 total
includes taxes & fees
Sep 7 - Sep 8
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

9. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (113 reviews)
"It was perfect. Very relaxed stay close to town. Thanks"
Canada
James
One bedroom fully equipped Mahone Bay luxury cottage

10. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (64 reviews)
"Immaculately clean and cozy! We had a lovely stay."
United States
Kathryn H.
The price is CA $225
CA $365 total
includes taxes & fees
Sep 18 - Sep 19
One bedroom fully equipped Mahone Bay luxury cottage

11. Orchard Cabin #4 - Hubbards Beach

Orchard Cabin #4 - Hubbards Beach
Hubbards
7.4 out of 10, Good, (6 reviews)
"Very cute property with a nice location. "
United States
Nancy O.
The price is CA $242
CA $317 total
includes taxes & fees
Sep 13 - Sep 14
Orchard Cabin #4 - Hubbards Beach

12. Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Western Shore
9.4 out of 10, Exceptional, (25 reviews)
"Beautiful spot!"
United States
Kirby D.
The price is CA $535
CA $829 total
includes taxes & fees
Sep 6 - Sep 7
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

13. SUN, SAND, OCEAN, in Hubbards. What more do you need?

SUN, SAND, OCEAN, in Hubbards. What more do you need?
Hubbards
9.6 out of 10, Exceptional, (17 reviews)
"Lovely location. We enjoyed our stay and would go again."
United States
Angela C.
The price is CA $295
CA $552 total
includes taxes & fees
Sep 6 - Sep 7
SUN, SAND, OCEAN, in Hubbards. What more do you need?

14. Mahone Bay Hide-Away

Mahone Bay Hide-Away
Mahone Bay
10.0 out of 10, Exceptional, (108 reviews)
"Close to restaurants, sights, many walking distance. Clean, bright, lodgings. Welcoming and helpful hosts. Would recommend to anyone "
Canada
Nancy R.
The price is CA $225
CA $368 total
includes taxes & fees
Sep 8 - Sep 9
Mahone Bay Hide-Away

15. 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, (10 reviews)
"Amazing place! Very cozy, clean, and relaxing. We really enjoyed our stay and would definitely come back!"
Canada
Sulaiman B.
The price is CA $259
CA $343 total
includes taxes & fees
Sep 2 - Sep 3
Pet-Friendly Glamping Dome close to Peggy’s Cove!

16. Red Barn Bed & Breakfast

Red Barn Bed & Breakfast
Lunenburg
9.4 out of 10, Exceptional, (10 reviews)
"We enjoyed our stay very much! "
Canada
Kimberley K.
The price is CA $199
CA $295 total
includes taxes & fees
Sep 20 - Sep 21
Red Barn Bed & Breakfast

17. Log Cabin #1 - Hubbards Beach

Log Cabin #1 - Hubbards Beach
Hubbards
9.6 out of 10, Exceptional, (5 reviews)
"A wonderful cottage with character!! Comfy beds, nice pillows! Very rustic, very peaceful"
Canada
Lisa R.
The price is CA $375
CA $492 total
includes taxes & fees
Sep 8 - Sep 9
Log Cabin #1 - Hubbards Beach

18. SUN, SAND, OCEAN in Hubbards Nova Scotia

SUN, SAND, OCEAN in Hubbards Nova Scotia
Hubbards
9.4 out of 10, Exceptional, (10 reviews)
"Cottage location was ideal for seeing sites in the area. We loved sitting on the dock, watching sunsets and relaxing. We would definitely recommend this rental."
Canada
Gloria L.
The price is CA $325
CA $597 total
includes taxes & fees
Sep 6 - Sep 7
SUN, SAND, OCEAN in Hubbards Nova Scotia

19. Lake Mushamush Cottage!

Lake Mushamush Cottage!
Lower Northfield
9.8 out of 10, Exceptional, (8 reviews)
"Beautiful spot we had the best time!!"
Canada
Patricia C.
The price is CA $209
CA $332 total
includes taxes & fees
Aug 30 - Aug 31
Lake Mushamush Cottage!

20. Downtown Bridgewater Suite near River and Trails

Downtown Bridgewater Suite near River and Trails
Bridgewater
9.0 out of 10, Wonderful, (2 reviews)
"Excellent kitchenette having everything needed to cook for yourself -ceiling fans needed a serious cleaning but not a dealbreaker"
Canada
Tim
The price is CA $91
CA $205 total
includes taxes & fees
Aug 30 - Aug 31
Downtown Bridgewater Suite near River and Trails
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Islands Hotel Reviews

Find out more about Chester Islands

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester Islands. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Mahone Bay Hide-Away : Visitors like this Chester Islands vacation home rental. It offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 larger area, you’ll find Chester Golf Club and Chester Playhouse.

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.