Oakland Holidays

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Your Oakland Holiday

Build a custom holiday package to Oakland and prepare to experience this incredible city the way you want. Think about spending some time in the neighbourhood of Garden Lots, which is good for watersports and lots more. Want to sightsee but unsure where to begin? Every trip to Oakland should include Halifax and Southwestern Railway Museum. Stop dreaming and start doing. Browse the multitude of options on Expedia today and finally put your Oakland holiday plans into action!

Oakland Holiday

Oakland Essential Information

Language
English
Currency
Canadian dollars
Top Sights
Fancy Lake Provincial Park, Ovens Natural Park and Halifax and Southwestern Railway Museum

Our pick of the best Oakland Hotel Deals

Bridgewater Hotel

Bridgewater Hotel

2.5 out of 5
35 High St. Bridgewater NS
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 14 Nov to 15 Nov
AU$119
14 Nov - 15 Nov
includes taxes & fees
6/10 (562 reviews)
"The staff was great!!! Pool was not useable and the property is outdated/rundown looking. The room wasn't bad but could have been cleaner. For the price , I would stay there again. Restaurant on site and close to all amenities was great!"

Reviewed on 12 Nov 2026

Bridgewater Hotel
Days Inn & Conference Center by Wyndham Bridgewater

Days Inn & Conference Center by Wyndham Bridgewater

2.5 out of 5
50 North Street Bridgewater NS
Fully refundableReserve now, pay when you stay
The price is AU$148 per night from 19 Nov to 20 Nov
AU$148
19 Nov - 20 Nov
includes taxes & fees
7.6/10 Good! (1,000 reviews)
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Reviewed on 12 Nov 2026

Days Inn & Conference Center 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$195 per night from 26 Nov to 27 Nov
AU$195
26 Nov - 27 Nov
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
"The staff were so friendly and helpful. The food was excellent! The morning breakfast had lots of choice and the restaurant at the hotel was great!"

Reviewed on 11 Nov 2026

Best Western Plus Bridgewater Hotel & Convention Centre
See all 291 properties in Oakland
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does an Oakland holiday package cost?
You'll find cheap prices on Expedia for your Oakland escape. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Oakland costs.
What are the cheapest months to go to Oakland?
If you're hoping to book a cheap Oakland holiday package, consider planning a trip in January, February and November. You'll typically find better prices on hotels and flights during these months — perfect for budget-conscious travellers.
How many days is enough for Oakland?
Usually, a handful of days is enough to explore the major attractions during your Oakland holiday. However, if you'd like to have some time to relax or go on day tours, think about extending your itinerary.
How to find the best Oakland package deals?
Landing a cheap Oakland package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most affordable Oakland package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Oakland holiday as a package?
You can enjoy significant savings on your Oakland escape by booking a customised holiday package. Check the "Package" heading, then select your destination and travel dates to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Oakland?
If you're considering a spur-of-the-moment Oakland adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Oakland?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to travel to Oakland.
  2. Set your budget: Factor in expenses like flights, food and transportation when calculating how much to set aside for your trip to Oakland. Then, pick a property that works with your budget, whether that's a low-cost option or a more upscale retreat.
  3. Decide how long to go for: Now that you know more about Oakland, you can figure out the perfect length of your holiday. Put together a rough itinerary and give yourself enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find an Oakland holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.