Book Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

Family Home In the Heart of the Village of Chester

Family Home In the Heart of the Village of Chester

Chester
Located in Chester, this vacation home is near the beach, within a 5-minute walk of Tancook Island and Lordly House Museum.
Opens in a new windowFamily Home In the Heart of the Village of Chester
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

Hubbards
Located in Northwest Cove, this vacation home is by the ocean, a 2-minute drive from Southwest Cove Lake and 7 minutes from Awalt Lake.
Opens in a new windowPrivate Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
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.

Mahone Bay
A stay at this vacation home places you in the heart of Mahone Bay, within a 10-minute walk of Northern Sun Gallery & Gifts and Have A Yarn.
Opens in a new windowTucked away on quiet street but short walk to Mahone Bay and all its amenities.
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Lunenburg's Cupcake House

Lunenburg's Cupcake House

Lunenburg
With a stay at this vacation home in Lunenburg (Old Town Lunenburg), you'll be steps from Hillcrest Cemetery and 2 minutes by foot from Lunenburg Academy.
Opens in a new windowLunenburg's Cupcake House
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

Hubbards
A stay at this vacation home places you in the heart of Fox Point, within a 5-minute drive of Black Harbour Distillers Inc. and Fox Point Beach.
Opens in a new window4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
Unique Ocean View Hilltop Retreat

Unique Ocean View Hilltop Retreat

Lunenburg
When you stay at this vacation home in First South, you'll be by the sea, within a 5-minute drive of Pearl Theatre and Halifax and Southwestern Railway ...
Opens in a new windowUnique Ocean View Hilltop Retreat
Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise

Western Shore
The price is AU$455 per night from 30 Nov to 1 Dec
AU$455
30 Nov - 1 Dec
includes taxes & fees
Located in Western Shore, this vacation home is on the waterfront, within a 15-minute drive of Oak Island and Mahone Bay Waterfront.
Opens in a new windowOceanfront Luxury Magical Views Sunset and Sunrise
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

Lunenburg
When you stay at this vacation home in Lunenburg, you'll be by the sea, within a 15-minute walk of Pearl Theatre and Lunenburg Waterfront.
Opens in a new windowRemodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg
Oceanfront 3-Bedroom Captain's House

Oceanfront 3-Bedroom Captain's House

Rose Bay
Located in Feltzen South, this vacation home is within a 15-minute drive of Ovens Natural Park and Indian Path Commons.
Opens in a new windowOceanfront 3-Bedroom Captain's House
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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.

Oakland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oakland vacation homes are the perfect way for you to wing it.

Holiday houses in Oakland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oakland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oakland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oakland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oakland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oakland Holiday Homes essential information

Accommodation
67 Holiday Homes
Lowest Price
AU$133
Highest Price
AU$455
Popular accommodation
Family Home In the Heart of the Village of Chester, Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia, Tucked away on quiet street but short walk to Mahone Bay and all its amenities., Lunenburg's Cupcake House, 4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort, Unique Ocean View Hilltop Retreat, Oceanfront Luxury Magical Views Sunset and Sunrise , Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg, Oceanfront 3-Bedroom Captain's House

Top trending hotels in Oakland

Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

2 out of 5
49 North St, Bridgewater, NS
Fully refundableReserve now, pay when you stay
The price is AU$201 per night from 14 Nov to 15 Nov
AU$201
14 Nov - 15 Nov
includes taxes & fees
Located in Bridgewater, Travelodge by Wyndham Bridgewater is within a 5-minute drive of Bridgewater Mall and Bridgewater Memorial Arena.
Opens in a new windowTravelodge by Wyndham Bridgewater
Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre

3.5 out of 5
527 Highway 10 Exit 12, Cookville, NS
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 27 Nov to 28 Nov
AU$186
27 Nov - 28 Nov
includes taxes & fees
Located in Cookville, Best Western Plus Bridgewater Hotel & Convention Centre is within a 5-minute drive of Cookville Provincial Park and Bridgewater Mall.
Opens in a new windowBest Western Plus Bridgewater Hotel & Convention Centre
Smugglers Cove Inn

Smugglers Cove Inn

4 out of 5
139 Montague Street, Lunenburg, NS
Fully refundableReserve now, pay when you stay
With a stay at Smugglers Cove Inn in Lunenburg (Old Town Lunenburg), you'll be steps from Lunenburg Waterfront and Knaut Rhuland House Museum.
Opens in a new windowSmugglers Cove Inn
Save an average of 15% on thousands of hotels when you're signed in
The Homeport Motel

The Homeport Motel

2 out of 5
167 Victoria Road, Lunenburg, NS
Fully refundableReserve now, pay when you stay
The price is AU$133 per night from 14 Nov to 15 Nov
AU$133
14 Nov - 15 Nov
includes taxes & fees
With a stay at The Homeport Motel in Lunenburg, you'll be a 4-minute walk from Pearl Theatre and 10 minutes by foot from Halifax and Southwestern Railway ...
Opens in a new windowThe Homeport Motel
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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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^Subject to availability and chosen travel dates.