Oakland Vacation Packages
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Your Oakland Vacation
Say bye-bye to planning hassles and hello to a Oakland vacation package. With everything organized before you leave, you can focus on discovering this city, starting with Soulard, which is great for distilleries and craft breweries, bars and pubs and markets. Ready to venture out and explore? Grants Farm, Magic House - St. Louis Childrens Museum and Saint Louis Galleria Mall are just three of the top places to visit during your trip to Oakland. Your dream Oakland vacation is a couple of clicks away. Browse flights, accommodations and more on Expedia for a getaway that's tailored to suit your style.
Top Oakland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Wildwood Hotel
Price was CA $1,313, price is now CA $923 per person
CA $923
per person
Jul 29 - Aug 1
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
9.2/10 Wonderful! (1,657 reviews)
Everything was good, except the air conditioning was so loud,we couldn't sleep at all.
Reviewed on Jun 11, 2026
The Cheshire
Price was CA $1,455, price is now CA $1,255 per person
CA $1,255
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to St. Louis (STL)
8.8/10 Excellent! (1,007 reviews)
The Cheshire is an interesting experience. It is definitely one-of-a-kind. The problem is that the rooms are outdated. The a/c in my room was very loud. The ceiling tiles were dirty. The walls are very thin and I could hear everything the neighbor was saying. The pool is nice but is loud if your room faces it. Parking is convenience. Breakfast is average hotel continental breakfast - nothing special. The pub is cool. The place needs a refresh and an update, which can be accomplished while maintaining its cool medieval throwback vibe.
Reviewed on Jun 10, 2026
The Westin St. Louis
Downtown St. Louis
Price was CA $1,412, price is now CA $1,257 per person
CA $1,257
per person
Jul 29 - Aug 1
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
8.6/10 Excellent! (1,003 reviews)
Several lights in the room did not work, only 1 bottle of water for 3 guests, valet didn’t lock my car that was sitting out front, had to go to desk to remind, breakfast was just ok, but overpriced.
Reviewed on Jun 8, 2026
Ameristar Casino Resort and Spa
Price was CA $1,245, price is now CA $1,109 per person
CA $1,109
per person
Jul 29 - Aug 1
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to St. Louis (STL)
8.6/10 Excellent! (1,008 reviews)
The beds are super comfortable and the rooms are nicely laid out. However, for the price it is not worth it. You cannot get breakfast until 8 am, there is no shuttle service anywhere and no formal parking format. For the price you pay and the "resort fee" you would expect a valet or some sort of structured parking arrangement.
Reviewed on Jun 14, 2026
Oakland Hotel Deals
Hyatt Regency St. Louis at The Arch
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jun 19 to Jun 20
CA $208
CA $246 total
Jun 19 - Jun 20
includes taxes & fees
8.6/10 Excellent! (4,123 reviews)
"Had a wonderful stay at the Hyatt. The staff was extremely friendly and the service was great. They were able to upgrade my room to a higher floor with a perfect view of the Arch! Only one complaint, only 2 elevators were working on our side of the building and it took a long time to come downstairs ..."
Reviewed on Jun 14, 2026
Clayton Plaza Hotel & Extended Stay
7750 Carondelet Avenue St. Louis MO
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Jun 21 to Jun 22
CA $140
CA $164 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (3,269 reviews)
"It was a wonderful hotel to stay at with functioning appliances. The breakfast was to die for (get the waffles)."
Reviewed on Jun 15, 2026
Pear Tree Inn St. Louis Near Union Station
2211 Market Street St. Louis MO
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from Jun 21 to Jun 22
CA $172
CA $201 total
Jun 21 - Jun 22
includes taxes & fees
8.8/10 Excellent! (2,032 reviews)
"The pool was sooo dirty couldn't see the bottom. Sooo many kids in the hot tub it wasn't usable. The bathroom in the room was really small."
Reviewed on Jun 15, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
