Holiday Rentals in Oakland

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Oakland holiday rentals

3.0 star property
9.8 out of 10, Exceptional, (14 reviews)
"Wonderful property and ambiance. "
United States
neil
The price is €235
includes taxes & fees
2 Mar - 3 Mar
The Maple Retreat at Park Mammoth
3.0 star property
10.0 out of 10, Exceptional, (1 review)
"One of the BEST overnight stays we have ever experienced ! This place was EXCEPTIONAL !! "
United States
Tony
The price is €272
includes taxes & fees
4 Mar - 5 Mar
Charming Cave City Vacation Rental w/ Fire Pit!
9.4 out of 10, Exceptional, (59 reviews)
"Wonderful stay"
United States
Magdalena F.
The price is €182
includes taxes & fees
2 Mar - 3 Mar
Cozy Cottage Close To Mammoth Cave. Boat Ramp, Master Suite, Pergola, Peaceful.
10.0 out of 10, Exceptional, (42 reviews)
"Perfect place to stay for our family trip to Mammoth Cave. "
United States
Taylor D.
The price is €367
includes taxes & fees
2 Mar - 3 Mar
log home Only 10 min from Mammoth Cave Nat Park

Cottage in Brownsville

Exile on Main Street
10.0 out of 10, Exceptional, (58 reviews)
"Nice stay! As described. "
United States
Brad T.
The price is €271
includes taxes & fees
2 Mar - 3 Mar
Exile on Main Street
10.0 out of 10, Exceptional, (3 reviews)
"Highly recommend booking your stay here! Our stay here was amazing! The property is quiet and beautiful. The cabins are brand new, clean, and full of thoughtful details. Communication was great, the owner is very nice and accommodating. The property had great outdoor living areas, including covered porch and firepit area."
United States
Jacob C.
The price is €237
includes taxes & fees
2 Mar - 3 Mar
The Maple Retreat - Junior Cabin
10.0 out of 10, Exceptional, (14 reviews)
"Every where I looked, I found something interesting, artistic. You can tell they've put in years of thought and work to make this place feel special!"
United States
Matt F.
The price is €338
includes taxes & fees
4 Mar - 5 Mar
A Kentucky Cottage - Charming Cottage One Mile From Mammoth Cave National Park
3.0 star property
The price is €132
includes taxes & fees
8 Mar - 9 Mar
Greer Room 1 Bedroom by Main Street Bed & Breakfast

Holiday Home in Bowling Green

Very clean & private
9.8 out of 10, Exceptional, (154 reviews)
"It was wonderful! Our son's kitchen was having repairs so we had Thanksgiving here it was wonderful!"
United States
james k.
The price is €153
includes taxes & fees
2 Mar - 3 Mar
Very clean & private
10.0 out of 10, Exceptional, (156 reviews)
"This home was very clean and check in was super easy. The winery is attached and was really fun. "
United States
Megan
The price is €204
includes taxes & fees
2 Mar - 3 Mar
Bluegrass Vineyard B&B, nestled next to the vineyard and winery

Holiday Home in Cave City

Home in Mammoth Cave
10.0 out of 10, Exceptional, (78 reviews)
"Another awesome stay thank you"
United States
Rach A.
The price is €254
includes taxes & fees
17 Mar - 18 Mar
Home in Mammoth Cave

Holiday Home in Cave City

Cave City's Honeycomb Hideout
9.8 out of 10, Exceptional, (15 reviews)
"Great place good location for a park visit. "
United States
Henry S.
The price is €235
includes taxes & fees
3 Mar - 4 Mar
Cave City's Honeycomb Hideout
10.0 out of 10, Exceptional, (52 reviews)
"House was clean and very cute! Loved the porch. We'd wake up every morning and have breakfast at the outdoor table! Kids loved the yard and sitting on the dock!"
United States
Danielle L.
The price is €539
includes taxes & fees
5 Mar - 6 Mar
Beautiful Relaxing House w a private lake joining the Mammoth Cave National Park
10.0 out of 10, Exceptional, (38 reviews)
"This house was exceptionally clean and so cozy. I would stay here again if I came back to this area. The hosts have made this property super convenient and it feels like home away from home. "
United States
clay n.
Chillin Time is a cozy pet friendly home 6 miles from Mammoth cave!

Holiday Home in Brownsville

Quiet Apartment
9.8 out of 10, Exceptional, (36 reviews)
"The place was beautiful and very quiet. We loved it. "
United States
Angela S.
The price is €162
includes taxes & fees
2 Mar - 3 Mar
Quiet Apartment

Cabin in Edmonson County

Redbird Hideaway With Hot Tub
9.6 out of 10, Exceptional, (9 reviews)
"We loved our stay with our two dogs at the Redbird Hideaway. The property felt secluded and cozy. We loved the charcoal grill , the fire pit, and all of the comforts of home but in the beautiful woods. The hot tub was clean and well maintained. Felt great after a day spent in Mammoth cave! We would stay again!"
United States
Karen E.
The price is €317
includes taxes & fees
2 Mar - 3 Mar
Redbird Hideaway With Hot Tub
10.0 out of 10, Exceptional, (21 reviews)
"Super great place to stay!"
United States
Jamie F.
The price is €350
includes taxes & fees
10 Mar - 11 Mar
Gorgeous New Cabin with 70Acres!Trails, Waterfalls and Amazing Rock Formations!
10.0 out of 10, Exceptional, (4 reviews)
"This was a great find! Well priced, spacious, good breakfast...no complaints!"
United States
Anonymous traveller
The price is €209
includes taxes & fees
2 Mar - 3 Mar
2 Bedroom | Free Daily Breakfast! Pool
10.0 out of 10, Exceptional, (19 reviews)
"Great place to get away in a secluded area. WiFi worked great and the cabin itself was great. Great place for sure!!"
United States
Jimmy D.
The price is €208
includes taxes & fees
2 Mar - 3 Mar
Fabulous 2-bedroom cabin in charming Cub Run
10.0 out of 10, Exceptional, (50 reviews)
"It was wonderful! Couldn’t have asked for better! Great house and set up in side and out. "
United States
Jenny C.
Private Getaway! Great for families and friends! Hot tub and Fire pit!
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.
Save an average of 15% on thousands of hotels when you're signed in

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, apart-hotels, 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 favorite 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 depends 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 €138 per night. Entering your travel dates in the search wizard you might find 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?

Beautiful Relaxing House w a private lake joining the Mammoth Cave National Park: This holiday home rental outside of Oakland is located in a rural location, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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 Fountain Square 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.