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

Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Oakland vacation 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, (81 reviews)
"It was a cute and cozy stay. We would stay here again."
Canada
Julie
The price is CA $352
CA $435 total
includes taxes & fees
Oct 29 - Oct 30
Black Forest Cabins
A bright living room with a white sofa, a coffee table, and a potted plant.

2. One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (116 reviews)
"Wonderful property and extremely clean. Hosts were wonderful!"
United States
Dianne T.
The price is CA $200
CA $336 total
includes taxes & fees
Oct 17 - Oct 18
One bedroom fully equipped Mahone Bay luxury cottage
A wooden door with a view of an outdoor deck and a chair.

3. Oakhill Pines Campground

Oakhill Pines Campground
3.0 star property
Oak Hill
8.8 out of 10, Excellent, (37 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 $161
CA $184 total
includes taxes & fees
Sep 29 - Sep 30
Oakhill Pines Campground
A modern kitchen with white cabinetry, a wooden countertop, and a large mirror.

4. Mahone Bay Hide-Away

Mahone Bay Hide-Away
Mahone Bay
10.0 out of 10, Exceptional, (112 reviews)
"Comfortable cottage very close to town centre but also quiet and calm."
Canada
Richard
The price is CA $200
CA $332 total
includes taxes & fees
Oct 9 - Oct 10
Mahone Bay Hide-Away
A spacious living room with a white sofa, wooden coffee table, and a rustic wooden chest. A wooden staircase leads to another room.

5. Cozy Cape Located In The Beautiful Seaside Town of Mahone Bay

Cozy Cape Located In The Beautiful Seaside Town of Mahone Bay
Mahone Bay
10.0 out of 10, Exceptional, (23 reviews)
"This was our second stay at this cottage and are planning to make this a yearly event. The cottage has everything you need, well appointed and very cozy! Location is also great."
Canada
Brauna R.
The price is CA $285
CA $529 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Cape Located In The Beautiful Seaside Town of Mahone Bay
A view of a waterfront property with a dock and a small building.

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

Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
Western Shore
9.2 out of 10, Wonderful, (27 reviews)
"Beautiful spot!"
United States
Kirby D.
The price is CA $380
CA $626 total
includes taxes & fees
Sep 29 - Sep 30
Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,
A wooden building with a sign reading "The Knot."

7. Red Barn Bed & Breakfast

Red Barn Bed & Breakfast
Lunenburg
9.4 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay very much! "
Canada
Kimberley K.
The price is CA $180
CA $271 total
includes taxes & fees
Oct 12 - Oct 13
Red Barn Bed & Breakfast
A dock with boats, a clear blue lake, and a forested island.

8. Mermaid's Retreat - Caribou Lake Cottage!

Mermaid's Retreat - Caribou Lake Cottage!
Mahone Bay
9.8 out of 10, Exceptional, (6 reviews)
"This property would be excellent for older couples and handicapped people. There's a ramp leading to the cottage and grab bars inside. Very peaceful and such a wonderful couple who owns it."
Canada
Betty
The price is CA $250
CA $386 total
includes taxes & fees
Sep 29 - Sep 30
Mermaid's Retreat - Caribou Lake Cottage!
A wooden deck with white railings and steps leading to a house.

9. 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 CA $200
CA $375 total
includes taxes & fees
Oct 1 - Oct 2
Cozy Garden View Suite near Lunenburg Waterfront (Suite 6)
A tented accommodation with a bed, two chairs, and a view of a lake.

10. 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, (36 reviews)
"The dome was well appointed and beautifully decorated. I would highly recommend it to anyone who wants a comfortable, relaxing getaway."
Canada
LISA
The price is CA $314
CA $448 total
includes taxes & fees
Oct 4 - Oct 5
Luxury lakefront dome with private beach, close to nature and town!
A calm lake with boats docked at the pier, surrounded by trees.

11. Lake Mushamush Cottage!

Lake Mushamush Cottage!
Lower Northfield
9.6 out of 10, Exceptional, (10 reviews)
"Very clean, well-stocked, hospitable and comfortable space."
Canada
Rita
The price is CA $209
CA $334 total
includes taxes & fees
Sep 29 - Sep 30
Lake Mushamush Cottage!
A red building with a sign reading "ADAMS & KNICKLE LTD."

12. Ocean Sanctuary - The Salty Cribb Cabin

Ocean Sanctuary - The Salty Cribb Cabin
Rose Bay
9.4 out of 10, Exceptional, (6 reviews)
"When we arrived after a long trip we found the rooms were clean, welcoming and attractive. The cabin was well equipped and everything worked. Beautiful location, always enjoyed the drive up to Lunenberg."
United States
Paul K.
Ocean Sanctuary - The Salty Cribb Cabin
A sandy beach with people walking along the shore.

13. 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 $85
CA $197 total
includes taxes & fees
Oct 1 - Oct 2
Downtown Bridgewater Suite near River and Trails
A small cabin with a deck, a door, and a window.

14. 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 CA $200
CA $260 total
includes taxes & fees
Sep 30 - Oct 1
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
A wooden deck with a hot tub surrounded by trees.

15. 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 CA $200
CA $260 total
includes taxes & fees
Oct 5 - Oct 6
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
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.

16. 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
9.0 out of 10, Wonderful, (6 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 CA $200
CA $372 total
includes taxes & fees
Oct 4 - Oct 5
Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
A bedroom with a bed, bedside lamps, a nightstand, and a large abstract painting on the wall.

17. ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV,

ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV,
Bridgewater
8.8 out of 10, Excellent, (9 reviews)
"Clean, spacious and modern place."
Canada
Anthony
The price is CA $225
CA $339 total
includes taxes & fees
Sep 29 - Sep 30
ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV,
A living room with a sofa, a table with a plant, and a window with blinds.

18. 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, (12 reviews)
"Great location for us and very clean and spacious."
Canada
Christina
The price is CA $190
CA $332 total
includes taxes & fees
Oct 4 - Oct 5
Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
A cozy living room with a white sofa, patterned cushions, and large windows overlooking a body of water.

19. The Salty Cribb - Private oceanfront vacation home just minutes from Lunenburg

The Salty Cribb - Private oceanfront vacation home just minutes from Lunenburg
Rose Bay
10.0 out of 10, Exceptional, (29 reviews)
"We had a great time - the house was clean, beautiful and in a great location as a base for our family as we ventured on the South Shore."
United States
Hayley B.
The price is CA $256
CA $581 total
includes taxes & fees
Oct 8 - Oct 9
The Salty Cribb - Private oceanfront vacation home just minutes from Lunenburg
A cabin with a dock extending into a lake, surrounded by dense forest.

20. The Eagle's Landing on Minamkeak Lake

The Eagle's Landing on Minamkeak Lake
Italy Cross
9.8 out of 10, Exceptional, (97 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 CA $185
CA $292 total
includes taxes & fees
Sep 29 - Sep 30
The Eagle's Landing on Minamkeak Lake
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

Days Inn & Conference Center by Wyndham Bridgewater

Days Inn & Conference Center by Wyndham Bridgewater

8/10 Good
"The property was very central and quiet."
Joan 2-night trip
Posted 2 hours ago
Days Inn & Conference Center by Wyndham Bridgewater

Find out more about Oakland

Everything you need to know about Oakland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland vacation rental for you. At Expedia, you can take your pick from private vacation 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 Oakland vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. 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 Oakland vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland vacation rentals we have selected for you start as low as CA $184 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland vacation 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 Oakland 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 Oakland vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. 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 a vacation rental in Oakland?

Yes, there are vacation rentals near well known local attractions in Oakland, or you can select a more secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Oakland?

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: Visitors like this Oakland 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 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. Oak Island and Lunenburg Academy are a couple of places you'll find in the larger area.

What are vacation rentals like in Oakland?

Vacation rentals are privately owned accommodations you can stay in for several days or longer in Oakland. Vacation rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.