Oakland Vacations from $376
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Your Oakland Vacation
The fascinating city of Oakland is calling. Uncover both its hidden gems and highlights with a Oakland vacation package that's custom made for you. In the mood to explore the sights but not sure where to start? Any trip to Oakland should include Ephram White Park. Don't put off visiting this destination any longer. The perfect Oakland vacation is only a few clicks away with Expedia.
The Latest Oakland Vacation Packages
- Laurel Point Resort
Dec 13 - Dec 17Laurel Point Resort + Flight
Chalet Village4 nights2.5 star property9.0/10 - Wonderful (368 reviews)Roundtrip • Boston (BOS) - Knoxville (TYS)BOS - TYS • Nonstop TYS - BOS • Nonstop - River Terrace Resort & Convention Center
Dec 26 - Dec 31River Terrace Resort & Convention Center + Flight
Downtown Gatlinburg5 nights3.5 star property7.8/10 - Good (1,015 reviews)"The staff was wonderful. They do need to tell you about the elevators that will take you up a level instead of walking up a very steep hill. The location is great. The rooms were clean, but does need some renovation."Reviewed November 6, 2026Roundtrip • Philadelphia (PHL) - Knoxville (TYS)PHL - TYS • Nonstop TYS - PHL • 1 stop - 1 Hotel Nashville
Jan 15 - Jan 181 Hotel Nashville + Flight
Downtown Nashville3 nights5.0 star property9.4/10 - Exceptional (1,006 reviews)Roundtrip • Boston (BOS) - Nashville (BNA)BOS - BNA • Nonstop BNA - BOS • Nonstop$1,171$774found 1 day agoper traveler - Hotel Indigo Gatlinburg Downtown by IHG
Dec 26 - Dec 30Hotel Indigo Gatlinburg Downtown by IHG + Flight
Downtown Gatlinburg4 nights3.5 star property9.6/10 - Exceptional (851 reviews)"Loving the wood floor. most of hotels I've stayed used carpet, which is not friendly to allergic people, and besides, wood floor can be better cleaned up than carpet floor. Bed is bigger than I expected, some hotels say queen size but actually felt like double size, this hotel has the true queen size bed, pillow are comfortable as well. Bathroom: love the rain shower, plenty of counter space, towels are big and thick but slightly harsh instead of soft, shampoo and body wash smell ok. ac/heating:..."Reviewed November 7, 2026Roundtrip • Boston (BOS) - Knoxville (TYS)BOS - TYS • Nonstop TYS - BOS • 1 stop$1,258$872found 1 day agoper traveler - Sentral Sobro
Jan 20 - Jan 26Sentral Sobro + Flight
Downtown Nashville6 nights4.0 star property8.6/10 - Excellent (2,214 reviews)Roundtrip • Boston (BOS) - Nashville (BNA)BOS - BNA • Nonstop BNA - BOS • Nonstop$1,294$904found 1 day agoper traveler
Where to stay in and around Oakland
Bowling Green
For travelers seeking a memorable trip, Bowling Green is an ideal base to explore the vibrant culture and outdoor adventures of Kentucky. Here, you can immerse yourself in the thrilling world of motor racing at the National Corvette Museum, enjoy family fun at Beech Bend Park, or take in the scenic beauty near Western Kentucky University. Located about 11 miles by car from Oakland, Bowling Green offers easy access and a diverse range of activities, making it a smart choice for your stay.
Smiths Grove
Plan your stay in Smiths Grove, a top-rated choice for family and nature travelers looking for a blend of outdoor adventure and budget-friendly options. This charming city is near attractions like Mammoth Cave National Park, where you can explore stunning cave systems, and the National Corvette Museum, perfect for car enthusiasts. With a recreational area and campground close by, Smiths Grove offers a vibrant getaway. Located about 2 miles from Oakland, it’s a smart choice for your vacation accommodations.
Martinsville
If you are a traveler with a love for family adventures and outdoor experiences, look no further than Martinsville, nestled in Oakland, Kentucky. This charming village offers easy access to exciting attractions like the National Corvette Museum and Barren River Lake, ideal for a day of exploration. You can also enjoy some thrills at Beech Bend Park. With its welcoming atmosphere and convenient location, Martinsville is a smart choice for your next getaway.
Plum Springs
Immerse yourself in Plum Springs, where families and adventure seekers can easily access thrilling attractions like the National Corvette Museum and Beech Bend Park. This charming village offers a budget-friendly base for exploring the nearby national park and camping opportunities, making it perfect for outdoor enthusiasts. Located about 8 miles from Oakland, Plum Springs is a smart choice for your vacation, providing a memorable experience in a scenic setting.
Brownsville
Travelers visiting the area often choose Brownsville, especially families and nature enthusiasts seeking close proximity to stunning outdoor experiences. With attractions like the Mammoth Cave National Park and Nolin Lake State Park, visitors can immerse themselves in breathtaking scenery and adventure. Just about an 11-mile drive from Oakland, Brownsville offers a budget-friendly base perfect for exploring the natural wonders of Kentucky. It’s an excellent choice for your vacation stay.
Oakland Hotel Deals
MainStay Suites Bowling Green North
MainStay Suites Bowling Green North
SureStay Hotel by Best Western Bowling Green North
SureStay Hotel by Best Western Bowling Green North"Stay literally anywhere else. The room was unsafe and the door was literally opened even when “closed.” The open door allowed bugs that came in from the outside. I was immediately greeted by a room that reeked of pet urine and musk. I tried turning on the light switch when I walk into the room, but there is no light that is plugged in/works until you get to almost halfway through the room. The fridge didn’t work. The drawers didn’t work and the smoke alarm beeped the entire trip. I tried getting...
Embassy Suites by Hilton Bowling Green
Embassy Suites by Hilton Bowling Green
Super 8 by Wyndham Bowling Green North
Super 8 by Wyndham Bowling Green North
"I travel a lot and this was the best place I’ve stayed in a while. It was basically a one bedroom condo, full kitchen, huge. The staff was outstanding! Great location and price too. Highly recommend!!"
SpringHill Suites by Marriott Bowling Green
SpringHill Suites by Marriott Bowling Green
La Quinta Inn & Suites by Wyndham Bowling Green
La Quinta Inn & Suites by Wyndham Bowling Green"Wish I could stay longer! Best hotel in town … especially the I-65 area!"
Frequently Asked Questions
How much does an Oakland vacation package cost?
You'll find cheap prices from $376 on Expedia for your Oakland escape. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
November, December and January are great times to look for cheap Oakland vacation packages. Opting to travel in less busy periods means you can generally find better prices on hotels and flights.
How many days is enough for Oakland?
Typically, a handful of days is enough to see the top attractions during your Oakland vacation. However, if you'd like to have more time to relax or take day tours, think about extending your trip.
How to find the best Oakland package deals?
Begin your search for an Oakland package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Oakland package deal straight away, just tweak 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 vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays separately. Better still, you can customize your Oakland trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Oakland?
If you're planning a spur-of-the-moment Oakland adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
Your Oakland break should be an escape from your daily routine, not a reason for money-related stress. So to allow you extra flexibility, we've partnered with online lender Affirm to offer 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 aren't any hidden costs or late payment fees to worry about.