Oakland Vacations from $323

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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.

The Latest Oakland vacation packages

Price found within the past 48 hours. Click for updated prices.
The Lord Nelson Hotel & Suites

The Lord Nelson Hotel & Suites

4.5 out of 5
Downtown Halifax
Price was $380, price is now $323 per person
$323
per person
Dec 4 - Dec 7
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
9.2/10 Wonderful! (1,807 reviews)
The room was clean and the staff friendly and helpful. The hotel is older so a few little things were not working such as the room safe (needed batteries) and outlet in the bathroom but great location!

Reviewed on Oct 13, 2025

Inn on the Lake

Inn on the Lake

3 out of 5
Price was $978, price is now $763 per person
$763
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
8.8/10 Excellent! (1,018 reviews)
Love the dining room

Reviewed on Oct 12, 2025

Lux Exec Home HFX Waterfront Pool Hot Tub

Lux Exec Home HFX Waterfront Pool Hot Tub

4.5 out of 5
Price was $1,350, price is now $1,111 per person
$1,111
per person
Dec 26 - Dec 29
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Halifax (YHZ)
10/10 Exceptional! (4 reviews)
Spacious very clean and all the amenitiies

Reviewed on Oct 12, 2025

Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
Price was $977, price is now $823 per person
$823
per person
Nov 19 - Nov 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
9.2/10 Wonderful! (2,049 reviews)
Enjoyed breakfast staff helpful

Reviewed on Oct 14, 2025

Nalu Retreat & Nordic Spa

Nalu Retreat & Nordic Spa

5 out of 5
Price was $1,105, price is now $940 per person
$940
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Halifax (YHZ)
9.8/10 Exceptional! (27 reviews)
Amazing place to stay. Ultra luxurious. Had everything, simply perfect. Booked cottage #2, best view ever!

Reviewed on Sep 15, 2025

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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! (22 reviews)
"The house was roomy enough for our family get together. The back porch needed some repairs. The kitchen was well equipped but poorly organized. A great place to enjoy Nova Scotia & grandchildren enjoyed the beaches"

Reviewed on Aug 30, 2025

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Executive Ocean Front Estate with 2 Acres Overlooking Waters of Mahone Bay
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
$105 nightly
The price is $123 total per night from Nov 1 to Nov 2
$123 total
Nov 1 - Nov 2
Total with taxes and fees
7.6/10 Good! (1,012 reviews)
"Breakfast was great,parking was very convenient and the room was clean and quiet. PERFECT!"

Reviewed on Oct 11, 2025

Days Inn & Conference Center by Wyndham Bridgewater
Bridgewater Hotel

Bridgewater Hotel

2.5 out of 5
35 High St., Bridgewater, NS
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $83 total per night from Oct 15 to Oct 16
$83 total
Oct 15 - Oct 16
Total with taxes and fees
5.8/10 (379 reviews)
Bathroom
"Tiles in bathroom need a scrub"

Reviewed on Oct 11, 2025

Bridgewater Hotel
See all 259 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.

Oakland Essential Information

Language
English
Currency
Canadian dollars
Top Sights
Fancy Lake Provincial Park, Ovens Natural Park and Osprey Ridge Golf Course

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Frequently asked questions

How much does an Oakland vacation package cost?
You'll find cheap prices from $323 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?
You can typically find lower rates and greater availability in November, December and January. Explore our cheap Oakland vacation packages and you could score some great off-season discounts.
How many days is enough for Oakland?
The ideal duration for your Oakland vacation depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to hit all the top sights and discover some hidden spots along the way.
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.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
Your Oakland break should be a relaxing escape from your daily routine, not a reason for money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.