Oakland Holidays

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Oakland Holiday

Our pick of the best Oakland Hotel Deals

Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Oakland
6.6/10 (4 reviews)
Fall Fun
"We were traveling through New England and were looking forward to spending some time exploring the pond. We’d already been at the coast and were headed to more mountains and hiking inland over the rest of the week. We arrived and found they had put the paddleboards and kayaks away for the season. ..."

Reviewed on 19 Oct. 2024

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Lakefront home on McGrath Pond - once featured on Maine Cabin Masters
Cozy Long Pond Cottage: private mooring & shared dock
Cozy Long Pond Cottage: private mooring & shared dock
Rome
9.8/10 Exceptional! (8 reviews)
Great
"The stay was a very nice place and we will be coming back with the whole family next time."

Reviewed on 12 Nov. 2024

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Cozy Long Pond Cottage: private mooring & shared dock
Central Maine Apartment offering 4 Seasons of Fun.
Central Maine Apartment offering 4 Seasons of Fun.
Oakland
The price is NZ$444 per night from 29 Dec to 30 Dec
NZ$444
includes taxes & fees
29 Dec - 30 Dec
9.8/10 Exceptional! (32 reviews)
Great little space!
"This clean, spacious, comfortable place was just what we needed for our time spent in Maine. Gary and Irma thought of everything!"

Reviewed on 9 Oct. 2024

Central Maine Apartment offering 4 Seasons of Fun.
See all 472 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 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.