Oakland Holidays

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  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Top hotels in Oakland

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

65 Whitten Rd Augusta ME
Fully refundable
S$197
31 Aug - 1 Sept
includes taxes & fees
9.2/10 Wonderful! (1,016 reviews)
"We enjoyed our stay here. Alyssa at the front desk was really welcoming and helpful upon our arrival. Our room was clean and had everything we needed including a coffee maker, a large (dorm-sized) fridge with a REALLY good freezer, and a few toiletries. There was even a microwave in our room, although ..."

Reviewed on 10 Aug, 2026

Maine Evergreen Hotel, an Ascend Collection Hotel
Fireside Inn & Suites Waterville

Fireside Inn & Suites Waterville

376 Main Street Waterville ME
Fully refundableReserve now, pay when you stay
S$161
23 Aug - 24 Aug
includes taxes & fees
Fireside Inn & Suites Waterville
Senator Inn & Spa

Senator Inn & Spa

284 Western Ave Augusta ME
Fully refundableReserve now, pay when you stay
S$179
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (1,012 reviews)
"Upgraded and best stay ever while visiting family."

Reviewed on 9 Aug, 2026

Senator Inn & Spa
See all 574 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.

Stay near popular Oakland attractions

Tree Spirits

New England's only Absinthe Verte producer crafts spirits from local maple syrup, apple cider, and pear. Sample their unique creations, including Maine's sole Limoncello, during an intimate tasting experience.
See properties

Frequently asked questions

How much does an Oakland holiday package cost?
You'll find cheap prices on Expedia for your Oakland break. However, factors like the length of stay, hotel choice and season will influence how much your holiday to Oakland costs.
What are the cheapest months to go to Oakland?
To score cheap Oakland holiday packages, plan your trip outside of peak periods such as public holidays. You'll generally find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Oakland?
Generally, a handful of days is enough to visit the major sights during your Oakland holiday. However, if you prefer to have time to rest or take day trips, consider extending your trip.
How to find the best Oakland package deals?
Start your search for an Oakland package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Oakland package deal straight away, just change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oakland escape underway.
Is it cheaper to book an Oakland holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Oakland holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Oakland?
If you have your Oakland holiday dates finalized, book as soon as you can to grab some awesome deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Oakland?
  1. Choose when to go: Check your calendar and get your bags packed. Your favourite season and the type of activities available will also help you decide when to visit Oakland.
  2. Set a budget: Consider costs such as flights, meals and transportation when working out how much to put aside for your trip to Oakland. Then, pick a property that fits your budget, whether that's an economical option or a deluxe retreat.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to experience in Oakland. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a tailored Oakland holiday package.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.