Oakland Vacations

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Find the Best Oakland Vacation Packages

Oakland Hotel Deals

Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay
Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay
Mahone Bay
9.8/10 Exceptional! (21 reviews)
Great place!
"Charming, spacious house. Easy check-in & well stocked kitchen. Lovely location. Overall a great visit!"

Reviewed on 3 September 2024

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Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay
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 AED 394 per night from Apr 20 to Apr 21
AED 394
AED 449 total
includes taxes & fees
20 Apr - 21 Apr
9.2/10 Wonderful! (844 reviews)
"Awesome"

Reviewed on 5 April 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
The price is AED 494 per night from Apr 16 to Apr 17
AED 494
AED 563 total
includes taxes & fees
16 Apr - 17 Apr
8.8/10 Excellent! (587 reviews)
"Really nice old property. Owners and staff very nice and helpful. Very quiet inn, didn’t hear a sound from other guests. They could use a carpeting upgrade throughout and new, firmer pillows would be great to match the very comfortable bed. All in all a great experience, thank you!"

Reviewed on 29 March 2025

Smugglers Cove Inn
See all 214 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 vacation 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 vacation to Oakland costs.
What are the cheapest months to go to Oakland?
If you’re hoping to book a cheap Oakland vacation 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 travelers.
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 vacation as a package?
You can enjoy significant savings on your Oakland escape by booking a customized vacation 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 vacation 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, favorite 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 vacation. 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 vacation package that brings all your bookings together.