Oakland Holiday Rentals

  • 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

The Cozy Nolin Cabin in Mammoth Cave, KY makes for the Perfect Lakefront Getaway

The Cozy Nolin Cabin in Mammoth Cave, KY makes for the Perfect Lakefront Getaway
Mammoth Cave
10.0 out of 10, Exceptional, (31 reviews)
"We loved everything about this cabin and hope to come back!"
United States
Lauren D.
The price is HK$2,468
HK$5,088 total
includes taxes & fees
1 Apr - 2 Apr
The Cozy Nolin Cabin in Mammoth Cave, KY makes for the Perfect Lakefront Getaway

The Maple Retreat at Park Mammoth

The Maple Retreat at Park Mammoth
3.0 star property
Park City
9.2 out of 10, Wonderful, (15 reviews)
"Wonderful property and ambiance. "
United States
neil
The price is HK$1,518
HK$2,445 total
includes taxes & fees
20 Apr - 21 Apr
The Maple Retreat at Park Mammoth

2 Bedroom | Free Daily Breakfast! Pool

2 Bedroom | Free Daily Breakfast! Pool
Bowling Green
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 HK$1,585
HK$2,049 total
includes taxes & fees
5 Apr - 6 Apr
2 Bedroom | Free Daily Breakfast! Pool

Very clean & private

Very clean & private
Bowling Green
9.8 out of 10, Exceptional, (155 reviews)
"It was a very nice stay for the Holidays way better than a hotel room.Very clean cozy place to stay. The hosts are awesome!"
United States
james k.
The price is HK$1,057
HK$1,377 total
includes taxes & fees
1 Apr - 2 Apr
Very clean & private

4 Mi to Wku: Hilltopper's Hideaway w/ Grills!

4 Mi to Wku: Hilltopper's Hideaway w/ Grills!
3.0 star property
Bowling Green
4 Mi to Wku: Hilltopper's Hideaway w/ Grills!

Fabulous 2-bedroom cabin in charming Cub Run

Fabulous 2-bedroom cabin in charming Cub Run
Cub Run
10.0 out of 10, Exceptional, (21 reviews)
"This cabin was very well setup. The host responded quickly with a few of our questions we had. Overall, was very pleased. Had a great weekend of relaxation. "
United States
Jamie
The price is HK$931
HK$2,149 total
includes taxes & fees
1 Apr - 2 Apr
Fabulous 2-bedroom cabin in charming Cub Run

Charming 3-bedroom cabin with AC and WiFi at Barren River Lake in Lucas, KY

Charming 3-bedroom cabin with AC and WiFi at Barren River Lake in Lucas, KY
Lucas
10.0 out of 10, Exceptional, (8 reviews)
"A wonderful stay! Very comfortable. Lots of extra comforts provided. WillVisit again! "
United States
Melissa S.
The price is HK$1,530
HK$3,361 total
includes taxes & fees
7 Apr - 8 Apr
Charming 3-bedroom cabin with AC and WiFi at Barren River Lake in Lucas, KY

Beautiful Relaxing House w a private lake joining the Mammoth Cave National Park

Beautiful Relaxing House w a private lake joining the Mammoth Cave National Park
Mammoth Cave
10.0 out of 10, Exceptional, (53 reviews)
"The property was just as described and was perfect for our company retreat."
United States
Daphanee W.
The price is HK$2,643
HK$5,056 total
includes taxes & fees
6 Apr - 7 Apr
Beautiful Relaxing House w a private lake joining the Mammoth Cave National Park

Peaceful private 3 bedroom & 2 bathroom new home near Mammoth Cave.

Peaceful private 3 bedroom & 2 bathroom new home near Mammoth Cave.
Cave City
9.8 out of 10, Exceptional, (69 reviews)
"We enjoyed our stay. The house is beautiful. I would definitely stay here again. "
United States
Tonia E.
The price is HK$1,105
HK$1,658 total
includes taxes & fees
20 Apr - 21 Apr
Peaceful private 3 bedroom & 2 bathroom new home near Mammoth Cave.

Entire House Family-Pets-Friendly Close to i65.

Entire House Family-Pets-Friendly Close to i65.
Bowling Green
9.2 out of 10, Wonderful, (26 reviews)
"Lived the backyard and the fire pit. House was clean and plenty of room"
United States
Andrew D.
The price is HK$1,543
HK$3,207 total
includes taxes & fees
8 Apr - 9 Apr
Entire House Family-Pets-Friendly Close to i65.

Charming 2-bedroom cabin on Nolin Lake with WiFi, AC, fire pit

Charming 2-bedroom cabin on Nolin Lake with WiFi, AC, fire pit
Mammoth Cave
9.6 out of 10, Exceptional, (7 reviews)
"Beautiful place "
United States
Shawn S.
The price is HK$1,167
HK$2,246 total
includes taxes & fees
1 Apr - 2 Apr
Charming 2-bedroom cabin on Nolin Lake with WiFi, AC, fire pit

The Maple Retreat - Junior Cabin

The Maple Retreat - Junior Cabin
Park City
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 HK$2,107
HK$2,599 total
includes taxes & fees
12 Apr - 13 Apr
The Maple Retreat - Junior Cabin

A Kentucky Cabin - Cozy Secluded Cabin One Mile From Mammoth Cave National Park

A Kentucky Cabin - Cozy Secluded Cabin One Mile From Mammoth Cave National Park
Park City
9.2 out of 10, Wonderful, (15 reviews)
"Had a great time staying at this unique property."
United States
Andrew
The price is HK$1,958
HK$3,160 total
includes taxes & fees
5 Apr - 6 Apr
A Kentucky Cabin - Cozy Secluded Cabin One Mile From Mammoth Cave National Park

Merry Mammoth Cabin on 16 Acres with Hiking Trails and Direct Nolin Lake Access

Merry Mammoth Cabin on 16 Acres with Hiking Trails and Direct Nolin Lake Access
Mammoth Cave
The price is HK$1,304
HK$3,570 total
includes taxes & fees
11 Apr - 12 Apr
Merry Mammoth Cabin on 16 Acres with Hiking Trails and Direct Nolin Lake Access

Private Hot Tub, Arcade Game: Bee Spring Cabin

Private Hot Tub, Arcade Game: Bee Spring Cabin
3.0 star property
Bee Spring
6.0 out of 10, (1 review)
"The cabin was very nice. I called the host with a question and was disappointed in the friendliness of the conversation."
United States
Beth
The price is HK$1,152
HK$3,621 total
includes taxes & fees
6 Apr - 7 Apr
Private Hot Tub, Arcade Game: Bee Spring Cabin

Chillin Time is a cozy pet friendly home 6 miles from Mammoth cave!

Chillin Time is a cozy pet friendly home 6 miles from Mammoth cave!
Cave City
10.0 out of 10, Exceptional, (40 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.
The price is HK$1,072
HK$2,117 total
includes taxes & fees
5 Apr - 6 Apr
Chillin Time is a cozy pet friendly home 6 miles from Mammoth cave!

Peace And Quiet Of Country Living Yet Close To Modern Convenience.

Peace And Quiet Of Country Living Yet Close To Modern Convenience.
Scottsville
9.8 out of 10, Exceptional, (164 reviews)
"Awesome place! Super clean has everything! "
United States
jake S.
The price is HK$783
HK$1,509 total
includes taxes & fees
8 Apr - 9 Apr
Peace And Quiet Of Country Living Yet Close To Modern Convenience.

Peaceful private 3 BR new home near Mammoth Cave.

Peaceful private 3 BR new home near Mammoth Cave.
Cave City
9.8 out of 10, Exceptional, (55 reviews)
"Great place had fun will be back "
United States
Tim S.
The price is HK$893
HK$1,416 total
includes taxes & fees
13 Apr - 14 Apr
Peaceful private 3 BR new home near Mammoth Cave.

Bluegrass Vineyard B&B, nestled next to the vineyard and winery

Bluegrass Vineyard B&B, nestled next to the vineyard and winery
Smiths Grove
10.0 out of 10, Exceptional, (159 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 HK$1,339
HK$1,847 total
includes taxes & fees
8 Apr - 9 Apr
Bluegrass Vineyard B&B, nestled next to the vineyard and winery

Quiet Apartment

Quiet Apartment
Brownsville
9.8 out of 10, Exceptional, (37 reviews)
"The bed was so comfortable. "
United States
Paige H.
The price is HK$775
HK$1,459 total
includes taxes & fees
11 Apr - 12 Apr
Quiet Apartment
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

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

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?

Big Cabin on HorseRanch close to MammothCaves,Corvettes,WKU, BeechBend Buc-ees: This holiday home rental outside of Oakland is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Ephram White 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.