Oakland Vacation Rentals

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Vacation Rentals in Oakland

Fridge, microwave, oven, stovetop
Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay
Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay
9.8 out of 10, Exceptional, (31)
"Charming, spacious house. Easy check-in & well stocked kitchen. Lovely location. Overall a great visit!"
Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay
Meeting facility
Black Forest Cabins
Black Forest Cabins
3.0 star property
10.0 out of 10, Exceptional, (11)
"Great spot for a special night out … beds were super comfortable "
$183 nightly
The price is $209
Nov 2 - Nov 3
Total with taxes and fees
Black Forest Cabins
Cabin, Multiple Beds, Shared Bathroom | Desk, free WiFi
Oakhill Pines Campground
Oakhill Pines Campground
3.0 star property
9.0 out of 10, Wonderful, (16)
"Great place"
Oakhill Pines Campground
Full-size fridge, microwave, oven, stovetop
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
10.0 out of 10, Exceptional, (113)
"Wonderful. Great cottage."
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
Terrace/patio
Family Home In the Heart of the Village of Chester
Family Home In the Heart of the Village of Chester
9.6 out of 10, Exceptional, (28)
"Spacious, clean, comfortable, and lots of room for people to spread out. We would happily return."
Family Home In the Heart of the Village of Chester
Fridge, microwave, oven, stovetop
One bedroom fully equipped Mahone Bay luxury cottage
One bedroom fully equipped Mahone Bay luxury cottage
10.0 out of 10, Exceptional, (101)
"Great cottage to use as a base to discover the area. Well equipped, quiet and close to restaurants and shopping."
One bedroom fully equipped Mahone Bay luxury cottage
Terrace/patio
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
9.6 out of 10, Exceptional, (34)
"Beautiful setting, very peaceful with lovely linens on the beds. The kitchen is fully stocked, the sitting room is comfortable and the outside decks are amazing. The little village of Chester was close by with a cozy pub offering live music on select nights and the local playhouse had local talent performing while we were there. We would stay again"
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Property grounds
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
10.0 out of 10, Exceptional, (98)
"The island is beautiful and exceeded our expectations. The house was clean and check in was easy. Phil was an excellent host. "
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
Exterior
Moonlight Cottage
Moonlight Cottage
9.2 out of 10, Wonderful, (16)
"Great time, went Peggy’s cove, Hubbard farm market, lunenburg and mahone bay"
Moonlight Cottage
View from property
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
8.4 out of 10, Very Good, (30)
"Beautiful view, the property owner was very responsive, they even had water in the fridge. Was perfect for our relaxing family getaway! "
$148 nightly
The price is $169
Oct 20 - Oct 21
Total with taxes and fees
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
Fridge, microwave, oven, stovetop
Tucked away on quiet street but short walk to Mahone Bay and all its amenities.
Tucked away on quiet street but short walk to Mahone Bay and all its amenities.
10.0 out of 10, Exceptional, (22)
"The place was clean, and host ensured we had no questions. "
Tucked away on quiet street but short walk to Mahone Bay and all its amenities.
Fireplace, books, stereo
A Quiet Riverside Cottage with 2 Fireplaces
A Quiet Riverside Cottage with 2 Fireplaces
10.0 out of 10, Exceptional, (71)
"Well organized and user friendly. Felt very comfortable there."
A Quiet Riverside Cottage with 2 Fireplaces
Exterior
Unique Ocean View Hilltop Retreat
Unique Ocean View Hilltop Retreat
10.0 out of 10, Exceptional, (177)
"Great hosts and amazing location"
Unique Ocean View Hilltop Retreat
Exterior
Lunenburg's Cupcake House
Lunenburg's Cupcake House
10.0 out of 10, Exceptional, (4)
"What can I say? Lovely hosts, gorgeous cozy property, comfy beds, well-equipped kitchen, thoughtful information pack, board games in the cupboard, everything spotless, and in a great location within a few minutes walk of Lunenberg’s waterfront, shops and restaurants. Even the flowers at the front were in full bloom and smelled amazing! We toured Canada for 5 weeks, as a family of 4, staying in 14 different locations, and this house was my favourite. Thank you so much for a lovely stay! I only...
Lunenburg's Cupcake House
Fridge, microwave, oven, stovetop
Amazing ocean view/ private road/close to bayswater beach.
Amazing ocean view/ private road/close to bayswater beach.
8.6 out of 10, Excellent, (47)
"Great property for a quiet get away"
Amazing ocean view/ private road/close to bayswater beach.
2 bedrooms, desk, WiFi, bed sheets
Oceanfront Luxury Magical Views Sunset and Sunrise
Oceanfront Luxury Magical Views Sunset and Sunrise
9.6 out of 10, Exceptional, (18)
"We took day trips from Holly’s home all week, but the view off the balcony was a delight to return to. "
Oceanfront Luxury Magical Views Sunset and Sunrise
Fridge, microwave, oven, stovetop
Modern oceanview vacation living in the deep bay
Modern oceanview vacation living in the deep bay
9.8 out of 10, Exceptional, (27)
"Clean, quiet cottage with fantastic views of the cove. We enjoyed our stay and would recommend it for anyone."
Modern oceanview vacation living in the deep bay
Outdoor dining
Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck
Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck
9.6 out of 10, Exceptional, (4)
"Beautiful location on the water, super friendly hosts. Location close to so many little towns with great food and amazing people. Trailer has everything that you need for your stay, they thought of everything. They made us feel welcome and we will be back for sure. We took our paddleboards out; he even lent us a fishing rod to use on the nearby Warf. "
Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck
Terrace/patio
Iconic Cabin on Lighthouse Route
Iconic Cabin on Lighthouse Route
10.0 out of 10, Exceptional, (3)
"Had a super comfortable stay. Kate had thought of everything you might need when away from home. Accommodation was better than we expected and all her suggestions of places to eat and visit were terrific. It was exactly what we were looking for. "
Iconic Cabin on Lighthouse Route
Exterior
Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg
Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg
9.8 out of 10, Exceptional, (16)
"Lovely walking distance to the waterfront. Beautiful place to stay!"
$351 nightly
The price is $400
Oct 15 - Oct 16
Total with taxes and fees
Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg
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

Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre

10/10 Excellent
"Good"
John 2-night trip
Posted 21 hours ago
Best Western Plus Bridgewater Hotel & Convention Centre

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Oakland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $169 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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?

Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay: Visitors like this Oakland vacation home rental. It is located by the ocean and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation 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 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.