Oakland Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Oakland holiday rentals

Outdoor dining

Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave

Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave
Mammoth Cave
9.6 out of 10, Exceptional, (28 reviews)
"We absolutely loved our stay. It was quiet and beautiful!"
United States
Elana T.
The price is HK$743
HK$1,672 total
includes taxes & fees
15 Feb - 16 Feb
Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave
Terrace/patio

Peaceful Quiet Cozy Tiny Home W/Country Views. 20 min. to Downtown Bowling Green

Peaceful Quiet Cozy Tiny Home W/Country Views. 20 min. to Downtown Bowling Green
Rockfield
10.0 out of 10, Exceptional, (19 reviews)
"Lovely place!"
United States
R
The price is HK$633
HK$1,374 total
includes taxes & fees
15 Feb - 16 Feb
Peaceful Quiet Cozy Tiny Home W/Country Views. 20 min. to Downtown Bowling Green
Terrace/patio

Tiny Home Cabin @ Nolin Lake Close to Mammoth Cave. Couple's Retreat w/ Hot Tub

Tiny Home Cabin @ Nolin Lake Close to Mammoth Cave. Couple's Retreat w/ Hot Tub
Cub Run
9.0 out of 10, Wonderful, (66 reviews)
"Adorable and cozy, with excellent proximity to Mammoth Cave and Nolin Lake activities! Perfect spot for a weekend hiking getaway!"
United States
Shelby N.
The price is HK$570
HK$1,990 total
includes taxes & fees
15 Feb - 16 Feb
Tiny Home Cabin @ Nolin Lake Close to Mammoth Cave. Couple's Retreat w/ Hot Tub
Private kitchen

Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.

Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
Cave City
9.0 out of 10, Wonderful, (31 reviews)
"It was a great place for a quick stay. "
United States
Sarah B.
The price is HK$809
HK$1,823 total
includes taxes & fees
15 Feb - 16 Feb
Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
Interior

Gorgeous New Cabin with 70Acres!Trails, Waterfalls and Amazing Rock Formations!

Gorgeous New Cabin with 70Acres!Trails, Waterfalls and Amazing Rock Formations!
Cub Run
10.0 out of 10, Exceptional, (20 reviews)
"Super great place to stay!"
United States
Jamie F.
The price is HK$1,407
HK$3,231 total
includes taxes & fees
19 Feb - 20 Feb
Gorgeous New Cabin with 70Acres!Trails, Waterfalls and Amazing Rock Formations!
Exterior

2 BR Beautiful new home near Mammoth Cave.

2 BR Beautiful new home near Mammoth Cave.
Cave City
9.6 out of 10, Exceptional, (56 reviews)
"It was so close to the national park which was great for us"
United States
Morgan I.
The price is HK$587
HK$1,078 total
includes taxes & fees
16 Feb - 17 Feb
2 BR Beautiful new home near Mammoth Cave.
Interior

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, (37 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$1,069
HK$2,112 total
includes taxes & fees
16 Feb - 17 Feb
Chillin Time is a cozy pet friendly home 6 miles from Mammoth cave!
Property grounds

Nolin Cabin Experience w/ Hot Tub

Nolin Cabin Experience w/ Hot Tub
Grayson County
9.8 out of 10, Exceptional, (23 reviews)
"We thoroughly enjoyed, inside, and outside!"
United States
Kary R.
The price is HK$895
HK$2,417 total
includes taxes & fees
16 Feb - 17 Feb
Nolin Cabin Experience w/ Hot Tub
Interior

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, (48 reviews)
"Great place had fun will be back "
United States
Tim S.
The price is HK$891
HK$1,413 total
includes taxes & fees
5 Mar - 6 Mar
Peaceful private 3 BR new home near Mammoth Cave.
Smart TV

Fabulous 2-bedroom cabin in charming Cub Run

Fabulous 2-bedroom cabin in charming Cub Run
Cub Run
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 HK$1,330
HK$2,629 total
includes taxes & fees
16 Feb - 17 Feb
Fabulous 2-bedroom cabin in charming Cub Run
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

Quiet Apartment

Quiet Apartment
Brownsville
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 HK$774
HK$1,465 total
includes taxes & fees
15 Feb - 16 Feb
Quiet Apartment
Terrace/patio

Redbird Hideaway With Hot Tub

Redbird Hideaway With Hot Tub
Edmonson County
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 HK$1,141
HK$2,654 total
includes taxes & fees
16 Feb - 17 Feb
Redbird Hideaway With Hot Tub
Outdoor dining

A Kentucky Cottage - Charming Cottage One Mile From Mammoth Cave National Park

A Kentucky Cottage - Charming Cottage One Mile From Mammoth Cave National Park
Park City
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 HK$1,563
HK$2,680 total
includes taxes & fees
15 Feb - 16 Feb
A Kentucky Cottage - Charming Cottage One Mile From Mammoth Cave National Park
Terrace/patio

10 Point Landing - 10 Point Landing Glamping with Queen Bed & Bath

10 Point Landing - 10 Point Landing Glamping with Queen Bed & Bath
Horse Cave
9.6 out of 10, Exceptional, (4 reviews)
"Everything was perfect for our first glamping experience. Host communicated well and all the instructions were exact. We would definitely stay again!!!"
United States
Kabira Y.
The price is HK$813
HK$985 total
includes taxes & fees
16 Feb - 17 Feb
10 Point Landing - 10 Point Landing Glamping with Queen Bed & Bath
Interior

Charming Cave City Vacation Rental w/ Fire Pit!

Charming Cave City Vacation Rental w/ Fire Pit!
3.0 star property
Cave City
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 HK$844
HK$2,509 total
includes taxes & fees
16 Feb - 17 Feb
Charming Cave City Vacation Rental w/ Fire Pit!
Interior

Peaceful 2-bedroom home near Mammoth Cave.

Peaceful 2-bedroom home near Mammoth Cave.
Cave City
10.0 out of 10, Exceptional, (26 reviews)
"Good stay, communication good, gave great recommendations on local attractions. "
United States
Anonymous traveller
The price is HK$601
HK$1,094 total
includes taxes & fees
19 Feb - 20 Feb
Peaceful 2-bedroom home near Mammoth Cave.
Smart TV

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, (63 reviews)
"We enjoyed our stay. The house is beautiful. I would definitely stay here again. "
United States
Tonia E.
The price is HK$691
HK$1,192 total
includes taxes & fees
17 Feb - 18 Feb
Peaceful private 3 bedroom & 2 bathroom new home near Mammoth Cave.
Exterior

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, (163 reviews)
"beautiful area on 200 acres to explore, would definitely do it again"
United States
jalen r.
The price is HK$782
HK$1,506 total
includes taxes & fees
15 Feb - 16 Feb
Peace And Quiet Of Country Living Yet Close To Modern Convenience.
1 bedroom, WiFi, bed sheets

Wanderlust: Here for your outdoor adventure

Wanderlust: Here for your outdoor adventure
Brownsville
9.6 out of 10, Exceptional, (27 reviews)
"Very cute very clean we really enjoyed our stay"
Canada
Carey F.
The price is HK$688
HK$1,361 total
includes taxes & fees
16 Feb - 17 Feb
Wanderlust: Here for your outdoor adventure
Outdoor dining

Cozy Cottage Close To Mammoth Cave. Boat Ramp, Master Suite, Pergola, Peaceful.

Cozy Cottage Close To Mammoth Cave. Boat Ramp, Master Suite, Pergola, Peaceful.
Cub Run
9.4 out of 10, Exceptional, (59 reviews)
"Very clean and cozy. Met our needs for the 1 night we were there."
United States
Beth D.
The price is HK$732
HK$1,729 total
includes taxes & fees
17 Feb - 18 Feb
Cozy Cottage Close To Mammoth Cave. Boat Ramp, Master Suite, Pergola, Peaceful.
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

La Quinta Inn & Suites by Wyndham Bowling Green

La Quinta Inn & Suites by Wyndham Bowling Green

10/10 Excellent
"Clean. And friendly staff "
Kathy 1-night trip
Posted 15 hours ago
La Quinta Inn & Suites by Wyndham Bowling Green

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?

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 Southern Kentucky Performing Arts Center 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.