Oakland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Oakland Vacation
Book a custom vacation package to Oakland and prepare to experience this interesting city the way you want. Consider staying in the neighborhood of Garden Lots, which is good for watersports and a whole lot more. Fill your trip to Oakland with visits to some of its most popular attractions. Where to first? Head straight for Halifax and Southwestern Railway Museum. Don't put off exploring this destination any longer. The perfect Oakland vacation is a few quick clicks away with Expedia.
Top Oakland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Lark & Loon Inn
CA $525
per person
Dec 8 - Dec 12
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
10/10 Exceptional! (152 reviews)
Kevin and Leslie were wonderful hosts who served us a delicious breakfast - a most welcome treat after the typical hotel fare. The house is a beautifully renovated period home with large spacious bedrooms and private bathrooms. We were impressed with the attention to detail and the cleanliness. Kevin loves Nova Scotia and gave us many great recommendations for things to do and restaurants to visit.
Reviewed on Sep 14, 2026
Claymore inn & Suites
CA $518
per person
Nov 20 - Nov 24
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
8.4/10 Very good! (776 reviews)
Located in shopping center so close to amenities. But not particularly beautiful grounds. Breakfast was amazing. Staff friendly.
Reviewed on Sep 27, 2026
Elevate Rooms at 66 Montague
CA $456
per person
Dec 8 - Dec 12
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to Halifax (YHZ)
9/10 Wonderful! (7 reviews)
This place is a hidden GEM! I couldn't believe the space that was provided!
Will most certainly be back! The host Mike was lovely and helpful.
Reviewed on Sep 6, 2026
Ready to book your vacation to Oakland?
Oakland Hotel Deals
Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay
Mahone Bay NS
9.8/10 Exceptional! (35 reviews)
"Very beautiful view, totally breathtaking.Quiet part of th world!Lovely home, you will enjoy!"
Reviewed on Aug 23, 2026
Bridgewater Hotel
35 High St. Bridgewater NS
Fully refundableReserve now, pay when you stay
CA $119
CA $140 total
Oct 15 - Oct 16
includes taxes & fees
6/10 (529 reviews)
"It’s a good, clean place to stay in a great location. Staff was helpful with all our questions, check in was quick and easy, the room was basic and clean, parking was easy. Not much for amenities or activities at the hotel, but that’s not why we stayed there. Price was very reasonable. Quick access ..."
Reviewed on Sep 27, 2026
Travelodge by Wyndham Bridgewater
49 North St Bridgewater NS
Fully refundableReserve now, pay when you stay
CA $184
CA $223 total
Oct 11 - Oct 12
includes taxes & fees
8/10 Very good! (1,009 reviews)
"Great desk staff!"
Reviewed on Sep 28, 2026
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 can snap up a vacation package to this top destination from CA $441 on Expedia. However, how much your vacation to Oakland costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Oakland?
If you're hoping to book a cheap Oakland vacation package, consider visiting in January, February and November. You'll generally find better rates on hotels and flights during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Oakland?
With a well-planned itinerary, you can easily tick off the main Oakland attractions in a handful of days. But if you prefer to discover hidden spots or go on day tours, think about booking your Oakland vacation for longer.
How to find the best Oakland package deals?
Use Expedia's handy filters to help you find some fabulous Oakland package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Oakland package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights individually. Better still, you can tailor your Oakland escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Oakland?
If you've got your Oakland travel dates confirmed, book as soon as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Oakland?
- Choose your travel dates: The things you plan to do in Oakland and your favourite season will help you decide when to go.
- Figure out your budget: Make sure you have enough money to cover everything from transportation and meals to flights and experiences. Your hotel will likely be the largest expense during your trip to Oakland.
- Set the duration of your trip: Start by compiling a list of the attractions you'd like to experience in Oakland. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find an Oakland vacation 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.
