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
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 449 per night from Jun 15 to Jun 16
AED 449
AED 512 total
15 Jun - 16 Jun
includes taxes & fees
9.2/10 Wonderful! (865 reviews)
"Very comfortable suite was great for our family of five. We would choose this as our accommodations in the future!"

Reviewed on 2 June 2025

Best Western Plus Bridgewater Hotel & Convention Centre
Days Inn & Conference Center by Wyndham Bridgewater
Days Inn & Conference Center by Wyndham Bridgewater
2.5 out of 5
50 North Street, Hwy 103 and North Street, Bridgewater, NS
Fully refundableReserve now, pay when you stay
The price is AED 403 per night from Jun 7 to Jun 8
AED 403
AED 473 total
7 Jun - 8 Jun
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Overall stay was ok I have stayed there twice loved everything but the one thing they have work is GYM they Even dont have dumbbells or free weights . Machines for workout are broken . I hate that as i love to do workout"

Reviewed on 4 June 2025

Days Inn & Conference Center by Wyndham Bridgewater
See all 233 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.