Oakland Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Oakland holiday rentals

Desk, free WiFi

Cabin in Oak Hill

Oakhill Pines Campground
3.0 star property
9.0 out of 10, Wonderful, (16 reviews)
"Staff was super welcoming and cabin was all set for us! "
Canada
Andrea
The price is HK$639
HK$729 total
includes taxes & fees
27 Feb - 28 Feb
Oakhill Pines Campground
Premium bedding, pillow-top beds, free WiFi

Cabin in Mahone Bay

Black Forest Cabins
3.0 star property
10.0 out of 10, Exceptional, (23 reviews)
"Great spot for a special night out … beds were super comfortable "
Canada
Caroline
The price is HK$1,165
HK$1,523 total
includes taxes & fees
1 Mar - 2 Mar
Black Forest Cabins
Outdoor spa tub

Chalet in Windsor Road

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
9.8 out of 10, Exceptional, (9 reviews)
"Everything was very clean!"
Canada
Max R.
The price is HK$852
HK$1,147 total
includes taxes & fees
8 Mar - 9 Mar
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Outdoor spa tub

Chalet in Chester Basin

Tiny homes in Chester Nova Scotia. Hosted by Dordean Suites
9.8 out of 10, Exceptional, (14 reviews)
"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! "
United States
Karil
The price is HK$851
HK$1,145 total
includes taxes & fees
4 Mar - 5 Mar
Tiny homes in Chester Nova Scotia. Hosted by Dordean Suites
Pool

Cabin in West Dublin

Shackup Cabin— Wood Fired Hot Tub & Near the beach
10.0 out of 10, Exceptional, (5 reviews)
"Fantastic little hideaway. Very comfortable and private"
Canada
Adam
The price is HK$1,313
HK$1,705 total
includes taxes & fees
2 Mar - 3 Mar
Shackup Cabin— Wood Fired Hot Tub & Near the beach
Interior

Cabin in La Have

Shackup A-frame— Private Hot Tub & Beach Access
10.0 out of 10, Exceptional, (4 reviews)
"Was an amazing weekend. Cabin was just as described."
United States
Adam H.
The price is HK$1,641
HK$2,132 total
includes taxes & fees
9 Mar - 10 Mar
Shackup A-frame— Private Hot Tub & Beach Access
Exterior detail

Apartment in Lunenburg

Red Roof Bed & Breakfast
9.6 out of 10, Exceptional, (9 reviews)
"We enjoyed our stay very much! "
Canada
Kimberley K.
The price is HK$1,022
HK$1,556 total
includes taxes & fees
27 Feb - 28 Feb
Red Roof Bed & Breakfast
1 bedroom, iron/ironing board, WiFi, bed sheets

Apartment in Bridgewater

ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV,
8.4 out of 10, Very good, (6 reviews)
"Great location. Surprisingly quiet given its proximity to a Main Street. "
United States
Jacqueline S.
The price is HK$719
HK$1,222 total
includes taxes & fees
7 Mar - 8 Mar
ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV,
Property grounds

Holiday Home in Western Shore

Oceanfront Luxury Magical Views Sunset and Sunrise
9.6 out of 10, Exceptional, (20 reviews)
"Excellent unit and very clean.The view was awesome.Highly recommended for a wonderful place to stay."
Canada
John S.
The price is HK$1,315
HK$2,201 total
includes taxes & fees
4 Mar - 5 Mar
Oceanfront Luxury Magical Views Sunset and Sunrise
1 bedroom, iron/ironing board, WiFi, bed sheets

Apartment in Lunenburg

Cozy Garden View Suite near Lunenburg Waterfront (Suite 6)
8.0 out of 10, Very good, (2 reviews)
"Perfect from start to finish! Great communication, check in was easy, room very clean, comfortable and quiet.Perfect location to walk and explore beautiful Lunenburg.We will definitely stay here again with any future trips.Thanks to the owner for your excellent communication."
United States
Big Dog Pots Pottery
The price is HK$741
HK$1,451 total
includes taxes & fees
27 Feb - 28 Feb
Cozy Garden View Suite near Lunenburg Waterfront (Suite 6)
Property grounds

Cottage in Chester

Indulge in luxurious bliss : private Hot Tub, kayaking. So much more
9.0 out of 10, Wonderful, (2 reviews)
"It was the perfect get away for myself after a rough week at work! Highly recommend. "
Canada
Michelle L.
The price is HK$1,593
HK$2,031 total
includes taxes & fees
29 Mar - 30 Mar
Indulge in luxurious bliss : private Hot Tub, kayaking. So much more
Terrace/patio

Apartment in LaHave

The Lookout Dome One - Private Hot Tub
10.0 out of 10, Exceptional, (21 reviews)
"Beautiful stay. "
Canada
Kyle M.
The price is HK$1,948
HK$3,158 total
includes taxes & fees
1 Mar - 2 Mar
The Lookout Dome One - Private Hot Tub
Interior

Apartment in LaHave

The Lookout Dome Two - Private Hot Tub
9.8 out of 10, Exceptional, (10 reviews)
"Great experience "
Canada
Nathan D.
The price is HK$1,948
HK$3,158 total
includes taxes & fees
1 Mar - 2 Mar
The Lookout Dome Two - Private Hot Tub
Iron/ironing board, WiFi, bed sheets

Holiday Home in Bridgewater

Private Balcony View Riverside Walk Prime Downtown
The price is HK$400
HK$1,021 total
includes taxes & fees
7 Mar - 8 Mar
Private Balcony View Riverside Walk Prime Downtown
TV

Apartment in Bridgewater

Winter Snack Bar | Backyard Access | Private Entry
10.0 out of 10, Exceptional, (1 review)
"Perfect place to stay. We will be back for sure."
Canada
Geoff M.
The price is HK$685
HK$1,355 total
includes taxes & fees
10 Mar - 11 Mar
Winter Snack Bar | Backyard Access | Private Entry
Interior

Apartment in Bridgewater

Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
9.4 out of 10, Exceptional, (3 reviews)
"As described and in a great location!"
United States
Erin E.
The price is HK$1,028
HK$1,977 total
includes taxes & fees
7 Mar - 8 Mar
Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
1 bedroom, WiFi

Apartment in Lunenburg

Luxury lakefront dome with private beach, close to nature and town!
9.8 out of 10, Exceptional, (10 reviews)
"Perfect spot for a peaceful getaway with a great view. "
Canada
Alan L.
The price is HK$1,570
HK$2,382 total
includes taxes & fees
9 Mar - 10 Mar
Luxury lakefront dome with private beach, close to nature and town!
Living area

Apartment in Bridgewater

Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
8.8 out of 10, Excellent, (3 reviews)
"Everything was clean. We'll set up Would stay again for sure"
Canada
Porter F.
The price is HK$1,028
HK$2,051 total
includes taxes & fees
7 Mar - 8 Mar
Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
Outdoor spa tub

Chalet in Chester Basin

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
10.0 out of 10, Exceptional, (18 reviews)
"Room was spotless so clean and cute with snacks and a cute card !! It was so perfect for a little get away. We stayed there after spending the day at the Sensea Nortic Spa, it was great to come back to more relaxation with the hot tub and adorable room! "
Canada
Isabel
The price is HK$852
HK$1,147 total
includes taxes & fees
8 Mar - 9 Mar
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Marina

Cottage in Hubbards

SUN, SAND, OCEAN, in Hubbards. What more do you need?
9.4 out of 10, Exceptional, (16 reviews)
"Lovely location. We enjoyed our stay and would go again."
United States
Angela C.
The price is HK$3,859
HK$6,114 total
includes taxes & fees
28 Feb - 1 Mar
SUN, SAND, OCEAN, in Hubbards. What more do you need?
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 Oakland Hotel Reviews

The Dockside Inn & Restaurant

The Dockside Inn & Restaurant

10/10 Excellent
"Amazing individuals, super understanding, respectful and just overall awesome. Highly reccomend for nova scotian hospitality!"
James 1-night trip
Posted 5 days ago
The Dockside Inn & Restaurant

Find out more about Oakland

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

Frequently asked questions

Can I find a holiday rental in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, 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 Oakland has to offer?

Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay: This highly rated holiday home rental in Oakland is located by the ocean, and has a fireplace, a patio 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. You can relax into your holiday with a garden and a selection of books.

What can I see and do in Oakland?

While exploring the area, visit family-friendly sights like Have A Yarn, or get outside and enjoy nature at Mahone Bay Swimming Pool. Cocoa Organic Spa & Boutique and Northern Sun Gallery & Gifts are a couple of places you'll find in the wider area.

What are holiday rentals like in Oakland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakland. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for a small group gathering.