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

Oakland Vacation Rentals

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Our top choices for Oakland vacation rentals

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 CA $213
CA $277 total
includes taxes & fees
Dec 13 - Dec 14
Black Forest Cabins

2. 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 CA $127
CA $185 total
includes taxes & fees
Nov 16 - Nov 17
Red Barn Bed & Breakfast

3. 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 CA $91
CA $202 total
includes taxes & fees
Nov 29 - Nov 30
Downtown Bridgewater Suite near River and Trails

4. Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise
Western Shore
9.2 out of 10, Wonderful, (29 reviews)
"Excellent location with beautiful marina and ocean view from the property. Very well maintained with excellent host Holly."
United States
Cynthia K G.
The price is CA $180
CA $338 total
includes taxes & fees
Dec 13 - Dec 14
Oceanfront Luxury Magical Views Sunset and Sunrise

5. 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 CA $169
CA $288 total
includes taxes & fees
Nov 14 - Nov 15
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

6. 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)
"Clean beyond belief!! Owners are amazing and we will def be going back."
United States
Leslie B.
The price is CA $179
CA $225 total
includes taxes & fees
Nov 15 - Nov 16
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

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

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Windsor Road
9.8 out of 10, Exceptional, (18 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 CA $179
CA $270 total
includes taxes & fees
Nov 15 - Nov 16
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

8. 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 CA $67
CA $189 total
includes taxes & fees
Nov 14 - Nov 15
Pretty Bachelor with Balcony near River & Trails

9. 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)
"This place exceeded expectations and was an absolute delight."
Canada
Sandie
The price is CA $275
CA $377 total
includes taxes & fees
Nov 15 - Nov 16
Luxury lakefront dome with private beach, close to nature and town!

10. 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, (15 reviews)
"Great location for us and very clean and spacious."
Canada
Christina
The price is CA $190
CA $315 total
includes taxes & fees
Dec 4 - Dec 5
Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.

11. King Bed Apt in Bridgewater near River and Trails

King Bed Apt in Bridgewater near River and Trails
Bridgewater
6.6 out of 10, (4 reviews)
"0"
Canada
Cassandra W.
The price is CA $100
CA $226 total
includes taxes & fees
Dec 1 - Dec 2
King Bed Apt in Bridgewater near River and Trails

12. Cozy Riverside Escape 1BR Near Trails and Parks

Cozy Riverside Escape 1BR Near Trails and Parks
Bridgewater
6.6 out of 10, (7 reviews)
"Love the quaint style of the suite in the converted older house. The air-conditioning worked very well; however, quite noisy (I don’t think there’s any way around that, however.) could use a couple of flatter pillows as options as the ones there were just too tall. And a couple extra towels would’ve been nice."
Canada
Karen
The price is CA $69
CA $162 total
includes taxes & fees
Nov 24 - Nov 25
Cozy Riverside Escape 1BR Near Trails and Parks

13. Mermaid's Retreat - Caribou Lake Cottage!

Mermaid's Retreat - Caribou Lake Cottage!
Mahone Bay
9.4 out of 10, Exceptional, (10 reviews)
"Fantastic property, location, and hosts. Will be booking again!"
Canada
Josh
The price is CA $250
CA $372 total
includes taxes & fees
Nov 14 - Nov 15
Mermaid's Retreat - Caribou Lake Cottage!

14. Large Backyard Oasis near River and Trails

Large Backyard Oasis near River and Trails
Bridgewater
6.8 out of 10, (5 reviews)
"Perfect place to stay. We will be back for sure."
Canada
Geoff M.
The price is CA $82
CA $191 total
includes taxes & fees
Nov 14 - Nov 15
Large Backyard Oasis near River and Trails

15. 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 $181
CA $335 total
includes taxes & fees
Nov 14 - Nov 15
Cozy Garden View Suite near Lunenburg Waterfront (Suite 6)

16. Relaxing King Bed Suite Close to Lunenburg Harbour (Suite 2)

Relaxing King Bed Suite Close to Lunenburg Harbour (Suite 2)
Lunenburg
9.4 out of 10, Exceptional, (8 reviews)
"It is a lovely place to stay! Very clean, very inviting."
Canada
Danette R.
The price is CA $175
CA $294 total
includes taxes & fees
Nov 14 - Nov 15
Relaxing King Bed Suite Close to Lunenburg Harbour (Suite 2)

17. 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 CA $203
CA $330 total
includes taxes & fees
Dec 1 - Dec 2
Spacious 1-Bedroom King Bed Suite w/ Deck (Suite 3)

18. 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 CA $200
CA $356 total
includes taxes & fees
Nov 29 - Nov 30
Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater

19. 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 CA $192
CA $352 total
includes taxes & fees
Nov 27 - Nov 28
Charming Heritage Suite w/ Cozy Sunroom & Deck (Suite 1)

20. Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour

Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour
Chester
Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour
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

Find out more about Oakland

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 Oakland. 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 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: You might want to consider this vacation home rental near Oakland, which 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. Northern Sun Gallery & Gifts and Have A Yarn 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.