Oakland Holiday Rentals

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Holiday Rentals in Oakland

Charming Cave City Vacation Rental w/ Fire Pit!
3.0 star property
10.0 out of 10, Exceptional, (1)
"One of the BEST overnight stays we have ever experienced ! This place was EXCEPTIONAL !! "
United States
Tony
The price is AU$455
includes taxes & fees
26 Oct - 27 Oct
Charming Cave City Vacation Rental w/ Fire Pit!
Cozy Cottage Close To Mammoth Cave. Boat Ramp, Master Suite, Pergola. Serene.
9.4 out of 10, Exceptional, (53)
"Wonderful stay"
United States
Magdalena F.
The price is AU$293
includes taxes & fees
27 Oct - 28 Oct
Cozy Cottage Close To Mammoth Cave. Boat Ramp, Master Suite, Pergola. Serene.
Cave City's Honeycomb Hideout
9.8 out of 10, Exceptional, (14)
"The house was very clean, comfortable, well organized and located in a quiet neighborhood. The location was excellent for exploring Mammoth Cave and other points of interest. "
United States
Ira B.
The price is AU$432
includes taxes & fees
27 Oct - 28 Oct
Cave City's Honeycomb Hideout
Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
9.0 out of 10, Wonderful, (26)
"Easy check in. Extremely clean bungalow. Air conditioning was so awesome. Very comfortable bed. Thanks for sharing your place with us, we enjoyed our stay so much. If I return to Cave City I will definitely stay here again."
United States
Tracy
The price is AU$301
includes taxes & fees
26 Oct - 27 Oct
Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
Cozy Tiny Home at Traveler's Cellar Winery in Rockfield with Vineyard views.
10.0 out of 10, Exceptional, (11)
"Lovely place!"
United States
R
The price is AU$288
includes taxes & fees
26 Oct - 27 Oct
Cozy Tiny Home at Traveler's Cellar Winery in Rockfield with Vineyard views.
Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave
9.6 out of 10, Exceptional, (15)
"My husband and I really enjoyed our stay. We would absolutely book this again. "
United States
Carla V.
The price is AU$330
includes taxes & fees
29 Oct - 30 Oct
Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave
Hunts Bend Private Getaway!
10.0 out of 10, Exceptional, (8)
"A wonderful property in a great location!"
United States
Lance M.
The price is AU$476
includes taxes & fees
18 Nov - 19 Nov
Hunts Bend Private Getaway!
The Blue Nest: Downtown, WKU, Hospital & Garage
10.0 out of 10, Exceptional, (1)
"Comfortable, clean, cute! Great location for walking to downtown "
United States
Kim B.
The price is AU$451
includes taxes & fees
21 Nov - 22 Nov
The Blue Nest: Downtown, WKU, Hospital & Garage
Peaceful 2-bedroom home near Mammoth Cave.
10.0 out of 10, Exceptional, (15)
"Perfect size and location for a weekend visit to Mammoth Cave."
United States
Heidi H.
The price is AU$222
includes taxes & fees
3 Nov - 4 Nov
Peaceful 2-bedroom home near Mammoth Cave.
2 BR Beautiful new home near Mammoth Cave.
9.6 out of 10, Exceptional, (39)
"Very nice place to stay! Close to everything and very homey. Will definitely come back when in the area again! "
United States
Josie S.
The price is AU$222
includes taxes & fees
3 Nov - 4 Nov
2 BR Beautiful new home near Mammoth Cave.
Hilltopper Convenience: Modern Duplex Near WKU
3.0 star property
The price is AU$471
includes taxes & fees
30 Oct - 31 Oct
Hilltopper Convenience: Modern Duplex Near WKU
Wanderlust: Here for your outdoor adventure
9.4 out of 10, Exceptional, (24)
"Very cute very clean we really enjoyed our stay"
Canada
Carey F.
The price is AU$270
includes taxes & fees
27 Oct - 28 Oct
Wanderlust: Here for your outdoor adventure
Country setting with mature trees, large deck. Game/Rec room, Fire Pit and Grill
10.0 out of 10, Exceptional, (16)
"Lovely stay on a beautiful property!"
United States
Christine G.
The price is AU$363
includes taxes & fees
26 Oct - 27 Oct
Country setting with mature trees, large deck. Game/Rec room, Fire Pit and Grill
Peace And Quiet Of Country Living Yet Close To Modern Convenience.
9.8 out of 10, Exceptional, (159)
"Property exactly as described, loved the location and peacefulness of the area."
United States
Jerrod G.
The price is AU$301
includes taxes & fees
26 Oct - 27 Oct
Peace And Quiet Of Country Living Yet Close To Modern Convenience.
King bed in Tulip Glamping Aframe at Noble Pine Campground
9.2 out of 10, Wonderful, (21)
"great view. very nice A- frame cabin"
United States
dean v.
The price is AU$250
includes taxes & fees
26 Oct - 27 Oct
King bed in Tulip Glamping Aframe at Noble Pine Campground
NEW LISTING! Dickinson Room by Main Street Bed & Breakfast
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful,, clean, accomadating and friendly. Great place to relax after hours of driving. They have a very sweet dog and we are looking forward to breakfast before we get on our way."
United States
Mahina P.
The price is AU$273
includes taxes & fees
26 Oct - 27 Oct
NEW LISTING! Dickinson Room by Main Street Bed & Breakfast
Quiet Apartment
9.8 out of 10, Exceptional, (32)
"Very clean and conveniently located. "
United States
Karen J.
The price is AU$289
includes taxes & fees
29 Oct - 30 Oct
Quiet Apartment
Peaceful private 3 BR new home near Mammoth Cave.
9.8 out of 10, Exceptional, (29)
"This house is a perfect place to stay. So close to Mammoth State Park.."
United States
Nicole J.
The price is AU$245
includes taxes & fees
3 Nov - 4 Nov
Peaceful private 3 BR new home near Mammoth Cave.
Historical Studio near WKU Campus & Downtown BG!
9.8 out of 10, Exceptional, (12)
"Absolutely beautiful apartment! Great location & a comfortable stay"
United States
Ella F.
The price is AU$317
includes taxes & fees
2 Nov - 3 Nov
Historical Studio near WKU Campus & Downtown BG!
Exile on Main Street
10.0 out of 10, Exceptional, (57)
"Nice stay! As described. "
United States
Brad T.
The price is AU$434
includes taxes & fees
27 Oct - 28 Oct
Exile on Main Street
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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Top Oakland Hotel Reviews

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Oakland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as AU$222 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Oakland has to offer?

Charming 2-bedroom bungalow with WiFi, AC in serene Cave City. : This holiday home rental outside of Oakland has air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

What can I see and do in Oakland?

While exploring the area, visit family-friendly sights like Beech Bend Park, or get outside and enjoy nature at Mammoth Cave National Park. National Corvette Museum and NCM Motorsports Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Oakland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oakland. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for family gatherings.