Oakland Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top 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 S$210 per night from 19 Jul to 20 Jul
S$210
19 Jul - 20 Jul
includes taxes & fees
8/10 Very Good! (724 reviews)
"Deffently will be staying there again."

Reviewed on 16 Jul, 2025

Travelodge 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 S$254 per night from 4 Aug to 5 Aug
S$254
4 Aug - 5 Aug
includes taxes & fees
9.2/10 Wonderful! (901 reviews)
"Nice place to stay"

Reviewed on 13 Jul, 2025

Best 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
8.8/10 Excellent! (643 reviews)
"Excellent location and staff. It was very clean."

Reviewed on 14 Jul, 2025

Get rates
Smugglers Cove Inn
See all 240 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.