A rocky shoreline with a forested area and a calm sea.

Oakland Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Oakland holiday rentals

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.

1. 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 HK$1,128
HK$1,477 total
includes taxes & fees
27 Oct - 28 Oct
Black Forest Cabins
A view of a waterfront property with a dock and a small building.

2. Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise
Western Shore
9.2 out of 10, Wonderful, (29 reviews)
"Beautiful spot!"
United States
Kirby D.
The price is HK$1,337
HK$2,454 total
includes taxes & fees
27 Oct - 28 Oct
Oceanfront Luxury Magical Views Sunset and Sunrise
A tented accommodation with a bed, a television, and a view of a body of water.

3. Luxury lakefront dome with private beach, close to nature and town!

Luxury lakefront dome with private beach, close to nature and town!
Lunenburg
10.0 out of 10, Exceptional, (43 reviews)
"Really clean, beautiful view, perfect place to relax"
Canada
Maxime
The price is HK$1,536
HK$2,223 total
includes taxes & fees
25 Oct - 26 Oct
Luxury lakefront dome with private beach, close to nature and town!
A staircase with wooden balusters and a handrail, leading to a landing with a red door.

4. 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 HK$997
HK$1,768 total
includes taxes & fees
5 Nov - 6 Nov
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)
A cozy cabin with a rustic interior, a wooden floor, a stove, a chair, and a view of a lake.

5. 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 HK$1,399
HK$2,188 total
includes taxes & fees
25 Oct - 26 Oct
Mermaid's Retreat - Caribou Lake Cottage!
A wooden deck with a hot tub surrounded by trees.

6. 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, (17 reviews)
"Unique property. Cozy warm and welcoming from the get go. Owners would respond to questions within minutes. Accommodations were immaculate and had everything we needed. They've literally thought of everything. Can't wait to visit again"
Canada
Sandra
The price is HK$1,003
HK$1,603 total
includes taxes & fees
26 Oct - 27 Oct
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A bedroom with a bed, a desk, a chair, a ceiling fan, and a kitchenette with a stove.

7. 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 HK$390
HK$1,005 total
includes taxes & fees
26 Oct - 27 Oct
Downtown Bridgewater Suite near River and Trails
A small cabin with a deck, a door, and a window.

8. 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 HK$1,003
HK$1,322 total
includes taxes & fees
26 Oct - 27 Oct
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A living room with a sofa, a table with a plant, and a window with blinds.

9. Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.

Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
Bridgewater
8.6 out of 10, Excellent, (14 reviews)
"A little hard to find as it is not well marked, although the actual unit was great. Clean and had everything we needed for our stay. Centrally located and easy to get where we needed. Would definitely stay again if in the area."
Canada
Alan
The price is HK$1,063
HK$1,872 total
includes taxes & fees
25 Oct - 26 Oct
Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
A dining area with a wooden table, chairs, and a chandelier. There is a living room with a sofa and a TV in the background.

10. Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater

Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
Bridgewater
8.6 out of 10, Excellent, (8 reviews)
"Great stay, comfortable place, quiet and close to shops. My only recommendation would be to add a photo of the exterior of the place to help identify it, even if it's only added to the check in info. Overall very nice."
Canada
Cheriee
The price is HK$1,119
HK$2,095 total
includes taxes & fees
8 Nov - 9 Nov
Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
A kitchen with wooden cabinets, a built-in oven, and a sink.

11. 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 HK$709
HK$1,179 total
includes taxes & fees
30 Oct - 31 Oct
Red Barn Bed & Breakfast
A hammock on a wooden deck overlooking a forested area with a clear sky.

12. The Eagle's Landing on Minamkeak Lake

The Eagle's Landing on Minamkeak Lake
Italy Cross
9.8 out of 10, Exceptional, (98 reviews)
"Lovely host. The property is not a cabin as posted but a lovely little separate room under the owner’s home. Everything was there for a comfortable stay. Loved listening to the loons call from the lake as we fell asleep."
Canada
Allyson
The price is HK$1,036
HK$1,641 total
includes taxes & fees
25 Oct - 26 Oct
The Eagle's Landing on Minamkeak Lake
A cozy outdoor seating area with wicker furniture, a small round table, and binoculars, overlooking a forested landscape and a body of water.

13. Luxury Coastal Dome - Private Hot Tub, Oceanfront Deck, Firepit & Parking

Luxury Coastal Dome - Private Hot Tub, Oceanfront Deck, Firepit & Parking
LaHave
10.0 out of 10, Exceptional, (14 reviews)
"We had a wonderful stay the hot tub and fire table were excellent."
Canada
Kenneth J
The price is HK$2,056
HK$3,286 total
includes taxes & fees
3 Nov - 4 Nov
Luxury Coastal Dome - Private Hot Tub, Oceanfront Deck, Firepit & Parking
Terrace/patio

14. Coastal Dome Escape - Oceanfront, Private Hot Tub, Firepit and Deck

Coastal Dome Escape - Oceanfront, Private Hot Tub, Firepit and Deck
LaHave
10.0 out of 10, Exceptional, (23 reviews)
"Absolutely breathtaking and magical. A one-of-a-kind enchanting, memorable experience."
United States
cipi s.
The price is HK$2,056
HK$3,286 total
includes taxes & fees
3 Nov - 4 Nov
Coastal Dome Escape - Oceanfront, Private Hot Tub, Firepit and Deck
A compact living space with a sofa, a dining table, and a TV mounted on the wall.

15. Abigael’s Apt Suite 1 BR 2 BED in Central Bridgewater

Abigael’s Apt Suite 1 BR 2 BED in Central Bridgewater
Bridgewater
9.0 out of 10, Wonderful, (2 reviews)
"Nice to have all the appliances and be able to do our laundry. Good location, Wilma was a responsive host. They need better signage - the building has a barber shop in it and 3 people coming for a haircut ended up knocking on our door because they couldn't find the entrance, which is through the Bubble Tea shop. Noisy in the day time but okay for sleeping."
Canada
Jeannie T.
The price is HK$1,662
HK$3,790 total
includes taxes & fees
5 Nov - 6 Nov
Abigael’s Apt Suite 1 BR 2 BED in Central Bridgewater
A staircase with wooden balusters and a handrail, leading to a landing with a red door.

16. Spacious 1-Bedroom King Bed Suite w/ Deck (Suite 3)

Spacious 1-Bedroom King Bed Suite w/ Deck (Suite 3)
Lunenburg
8.8 out of 10, Excellent, (6 reviews)
"Great stay!!"
Canada
heather p.
The price is HK$1,118
HK$1,925 total
includes taxes & fees
5 Nov - 6 Nov
Spacious 1-Bedroom King Bed Suite w/ Deck (Suite 3)
A wooden deck with white railings and steps leading to a house.

17. Cozy Garden View Suite near Lunenburg Waterfront (Suite 6)

Cozy Garden View Suite near Lunenburg Waterfront (Suite 6)
Lunenburg
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful room … very well done"
Canada
Camil
The price is HK$967
HK$1,914 total
includes taxes & fees
5 Nov - 6 Nov
Cozy Garden View Suite near Lunenburg Waterfront (Suite 6)
A staircase with wooden balusters and a handrail, leading to a landing with a red door.

18. Charming Heritage Suite w/ Cozy Sunroom & Deck (Suite 1)

Charming Heritage Suite w/ Cozy Sunroom & Deck (Suite 1)
Lunenburg
9.8 out of 10, Exceptional, (9 reviews)
"very easy and clean. the spot is beautiful for checking out lunenburg"
Canada
Naomi M.
The price is HK$1,058
HK$2,042 total
includes taxes & fees
5 Nov - 6 Nov
Charming Heritage Suite w/ Cozy Sunroom & Deck (Suite 1)
A porch with colorful Adirondack chairs and a wooden deck.

19. Log Cabin #1 - Hubbards Beach

Log Cabin #1 - Hubbards Beach
Hubbards
9.8 out of 10, Exceptional, (6 reviews)
"Nothing else to add."
Canada
Blair
The price is HK$2,289
HK$3,049 total
includes taxes & fees
25 Oct - 26 Oct
Log Cabin #1 - Hubbards Beach
A residential area with a house, a swimming pool, and a marina with boats.

20. 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, (25 reviews)
"Sweet location. Easy check-in via lockbox. Had everything we needed. Clean. Only area for improvement is the pullout sofa. Mattress not usable. Two main bedrooms were great."
Canada
Sue
The price is HK$2,210
HK$3,888 total
includes taxes & fees
31 Oct - 1 Nov
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

Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

10/10 Excellent
"Staff were extremely helpful and friendly. Room was clean and warm. Didn't wake up in time for breakfast."
Bonnie 2-night trip
Posted 15 hours ago
Travelodge by Wyndham Bridgewater

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?

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: This holiday home rental outside of Oakland 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

What can I see and do in Oakland?

While exploring the area, visit family-friendly sights like For The Birds Nature Shop, or get outside and enjoy nature at Mahone Bay Swimming Pool. Northern Sun Gallery & Gifts and Have A Yarn 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.