Oakland Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to £335 when you book a flight and hotel together*
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Your Oakland Holiday

There's no better way to embark on an adventure than with one of our holiday packages to Oakland. The rich history and eclectic style are just a couple of the convincing reasons to visit this captivating city. Make your trip to Oakland even more fun and exciting by going sightseeing. Colby College, Belgrade Lakes Chain and Waterville Opera House are among the leading attractions worth exploring. Expedia can help you escape the everyday. Tailor your holiday to Oakland to match your travel style, whatever that may look like.

Oakland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Augusta State Airport (AUG)
Population
2,600
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
First Congregational Church, Colby College and Belgrade Lakes Chain

Our pick of the best Oakland Hotel Deals

Scenic Farm Stay Retreat in the heart of Belgrade Lakes Region! Pet Friendly!
Scenic Farm Stay Retreat in the heart of Belgrade Lakes Region! Pet Friendly!
Oakland, ME
Stay at this farm stay in Oakland. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Tree Spirits and Belgrade Lakes Chain are located ...
10/10 Exceptional! (1 review)
A great 1st exerience with Vrbo
"The property we rented was as advertised - 3 bedrooms and a 10-minute drive from Colby College, where we attended our college reunion. The house was older but had modern appliances, 2 bathrooms, a washer and dryer. The home is on a farm with horses and a mule on the premises, which we enjoyed. The ..."

Reviewed on 22 Jun 2025

Scenic Farm Stay Retreat in the heart of Belgrade Lakes Region! Pet Friendly!
Sister A-Frame in Woods B
Sister A-Frame in Woods B
Oakland, ME
Stay at this family-friendly holiday home in Oakland. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Tree Spirits and Belgrade Lakes ...
10/10 Exceptional! (1 review)
Cute place tucked in the woods
"Great stay. Would stay here again if in the area."

Reviewed on 4 Jun 2025

Sister A-Frame in Woods B
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
Oakland, ME
Stay at this cottage in Oakland. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Tree Spirits and Quarry Road Trails are located ...
9.4/10 Exceptional! (52 reviews)
"Had a very peacefully stay. Was a very nice weekend getaway during cancer treatments. Fishing and sitting by the water was soothing."

Reviewed on 18 Jun 2025

Weekly discounts avail. Get away from it all on the start of The Belgrade Lakes
See all 535 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does an Oakland travel package cost?
Live it up in Oakland from as low as . We offer a wonderful selection of rental cars, hotels and flights to suit your budget. You can score even more discounts when you add a few sightseeing tours to your travel package.
If I'm not able to travel, can I cancel my Oakland travel package?
Whether it's your hotel or flight, yes, you can amend or cancel it. Booked your Oakland travel package in the last 24 hours? You may be able to make changes or cancellations at no cost. For older bookings, you may be charged a fee by your airline, hotel or car rental company. For further information, check out our Customer Service Portal. We're here to help you each step of the way.
How do I get a cheap travel package to Oakland?
If you love amazing deals, combine your bookings into an Oakland travel package. Whether you need flights, hotels, rental cars or day tours, you can book everything in one place. You'll have a wealth of choice at your fingertips as well. Expedia has over 550 airlines and 1,000,000 hotel options across the globe to take your pick of. Fly with who you want, find a room where you like and save a packet --- now that's the perfect holiday!
Does Expedia offer Book Now, Pay Later Oakland holidays?
Expedia has joined forces with online lender Klarna to make booking your next break a bit easier on the wallet. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more money to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that fits into your budget. Check out these flexible payment options:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's monthly instalment plans. If paying small amounts each month works for you, choose this option during the checkout process.
  • Pay in instalments holidays: Into the idea of paying for your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you spot an awesome deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you lock in your getaway.

Where should I stay in Oakland?
Oakland is home to a number of top places to explore, such as Thomas College. Stay somewhere nearby and make sightseeing easier.
What are the top hotels in Oakland?
If it's your first visit to Oakland, reserve a room at Senator Inn & Spa or Hampton Inn Waterville. Both hotels offer comfy beds and are top options with many travellers.
How far in advance should I book my Oakland holiday?
Search Expedia to compare international fares as soon as you know your travel dates. You can normally purchase a ticket up to 12 months in advance. If you can't find your preferred air carrier, or you're booking late, fear not. Cheap tickets to Oakland sometimes appear a few weeks before departure.
What does an Expedia Oakland travel package include?
Choose from a combination of hotels, flights and rental cars. Once you've made your booking, you can also add on experiences and activities. Want to pick your fare class? That's easily done too. The choice is yours when it comes to organising your dream Oakland escape.
What should I know before booking an Oakland travel package?
Bundling your bookings into an Oakland travel package is the easiest way to organise your trip. Not only that, you'll save big when you combine your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with an Oakland Expedia travel package?
Yes, the choice is yours. We have access to over 550 airlines around the world, so you can customize your Oakland trip according to your travel preferences.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.