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Oakland Holiday Rentals

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Oakland holiday rentals

Interior

1. Bowling Green House w/ Shared Pool!

Bowling Green House w/ Shared Pool!
Bowling Green
9.8 out of 10, Exceptional, (29 reviews)
"Beautiful farm setting just outside of downtown Bowling Green. The house has a lot of character in a good way. Plenty of parking."
United States
David K.
The price is HK$1,592
HK$5,975 total
includes taxes & fees
31 Aug - 1 Sept
Bowling Green House w/ Shared Pool!
Interior

2. Bowling Green House w/ Shared Pool!

Bowling Green House w/ Shared Pool!
3.0 star property
Oakland
The price is HK$1,991
HK$5,839 total
includes taxes & fees
31 Aug - 1 Sept
Bowling Green House w/ Shared Pool!
Private kitchen

3. 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, (180 reviews)
"Great stay"
United States
Justin W.
The price is HK$1,341
HK$1,917 total
includes taxes & fees
31 Aug - 1 Sept
Bluegrass Vineyard B&B, nestled next to the vineyard and winery
Exterior detail

4. Hunts Bend: Feel the Season Change|5-Acre Retreat

Hunts Bend: Feel the Season Change|5-Acre Retreat
Bowling Green
10.0 out of 10, Exceptional, (10 reviews)
"The host was responsive, the home was clean & invting. We loved the location as well!"
United States
johnnie l.
The price is HK$733
HK$2,620 total
includes taxes & fees
25 Aug - 26 Aug
Hunts Bend: Feel the Season Change|5-Acre Retreat
Property grounds

5. Cozy House with lots of charm!

Cozy House with lots of charm!
Bowling Green
10.0 out of 10, Exceptional, (48 reviews)
"Great stay enjoyed our self with most definitely stay again "
United States
Jennifer B.
The price is HK$1,073
HK$2,070 total
includes taxes & fees
26 Aug - 27 Aug
Cozy House with lots of charm!
Private kitchen

6. Quiet Apartment

Quiet Apartment
Brownsville
9.8 out of 10, Exceptional, (44 reviews)
"Quiet, clean apartment. Very comfortable and responsive host."
United States
Cheryl K.
The price is HK$776
HK$1,478 total
includes taxes & fees
25 Aug - 26 Aug
Quiet Apartment
Room

7. Wanderlust: Here for your outdoor adventure

Wanderlust: Here for your outdoor adventure
Brownsville
9.6 out of 10, Exceptional, (36 reviews)
"Very cute very clean we really enjoyed our stay"
Canada
Carey F.
The price is HK$690
HK$1,366 total
includes taxes & fees
25 Aug - 26 Aug
Wanderlust: Here for your outdoor adventure
Interior

8. < Half-mi to Mammoth Cave! Family Home w/ Yard

< Half-mi to Mammoth Cave! Family Home w/ Yard
3.0 star property
Brownsville
10.0 out of 10, Exceptional, (3 reviews)
"This place was very nice. It was very modern inside and a quiet country setting outside. We loved having a fire pit and being so close to the park. We would definitely stay here again."
United States
Amber
The price is HK$1,176
HK$2,882 total
includes taxes & fees
25 Aug - 26 Aug
< Half-mi to Mammoth Cave! Family Home w/ Yard
Living area

9. Very clean & private

Very clean & private
Bowling Green
9.8 out of 10, Exceptional, (167 reviews)
"Everything about this home was excellent. "
United States
Sandra B.
The price is HK$1,058
HK$1,378 total
includes taxes & fees
25 Aug - 26 Aug
Very clean & private
Private kitchen

10. Blue Nest: Your Modern Downtown Perch - Downtown BG

Blue Nest: Your Modern Downtown Perch - Downtown BG
Bowling Green
10.0 out of 10, Exceptional, (6 reviews)
"A great place to stay!"
United States
Stephanie B.
The price is HK$621
HK$2,120 total
includes taxes & fees
25 Aug - 26 Aug
Blue Nest: Your Modern Downtown Perch - Downtown BG
Room

11. Blue Belle: Storybook Spring Escape - Cozy 2BR

Blue Belle: Storybook Spring Escape - Cozy 2BR
Bowling Green
9.8 out of 10, Exceptional, (14 reviews)
"Great location and wonderful hospitality!"
United States
William J.
The price is HK$664
HK$2,417 total
includes taxes & fees
31 Aug - 1 Sept
Blue Belle: Storybook Spring Escape - Cozy 2BR
Exterior

12. The Grove at Middlebrook

The Grove at Middlebrook
Smiths Grove
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay. The home was beautiful and very comfortable. 30 minutes from Mammoth Cave . Enjoyed meals at Grammy’s and Kristin’s."
United States
Keely
The price is HK$1,482
HK$2,152 total
includes taxes & fees
23 Sept - 24 Sept
The Grove at Middlebrook
Dining

13. Charming KY Stay

Charming KY Stay
Bowling Green
8.8 out of 10, Excellent, (6 reviews)
"We enjoyed our stay at this property. The home was clean and well-equipped with all of the amenities we needed. The location was perfect, offering easy access to local attractions and restaurants."
United States
Jennifer H.
The price is HK$857
HK$2,376 total
includes taxes & fees
25 Aug - 26 Aug
Charming KY Stay
Terrace/patio

14. Entire House Family-Pets-Friendly Close to i65.

Entire House Family-Pets-Friendly Close to i65.
Bowling Green
9.0 out of 10, Wonderful, (31 reviews)
"The best is the back yard. We had such nice relaxing evenings outback with a fire. The TV was a bonus as we were interested in watching playoff hockey. Worked out well. Would definitely rent this place again. Very clean and charming. Close to everything we were hoping to see."
United States
Leslie W.
The price is HK$1,560
HK$3,270 total
includes taxes & fees
25 Aug - 26 Aug
Entire House Family-Pets-Friendly Close to i65.
Room

15. The Maple Retreat at Park Mammoth

The Maple Retreat at Park Mammoth
3.0 star property
Park City
9.2 out of 10, Wonderful, (22 reviews)
"Comfortable and nice location"
United States
Emily
The price is HK$1,788
HK$2,796 total
includes taxes & fees
25 Aug - 26 Aug
The Maple Retreat at Park Mammoth
Living area

16. Drakes Creek: Summer Fun For Everyone!

Drakes Creek: Summer Fun For Everyone!
Bowling Green
10.0 out of 10, Exceptional, (27 reviews)
"Beautiful, spotless home on a gorgeous wooded lot, minutes from everything Bowling Green has to offer. We had quick communication from owners, super easy check-in, and everything we needed for our stay. Would definitely rent again!"
United States
Anthony G.
The price is HK$1,294
HK$4,051 total
includes taxes & fees
25 Aug - 26 Aug
Drakes Creek: Summer Fun For Everyone!
Interior

17. Exile on Main Street

Exile on Main Street
Brownsville
9.8 out of 10, Exceptional, (62 reviews)
"We stayed as an overnight during our trip to TN. It was close to Mamoth Cave. "
United States
Joey S.
The price is HK$1,176
HK$2,472 total
includes taxes & fees
31 Aug - 1 Sept
Exile on Main Street
Exterior

18. 2 BR Beautiful new home near Mammoth Cave.

2 BR Beautiful new home near Mammoth Cave.
Cave City
9.8 out of 10, Exceptional, (90 reviews)
"Awesome place to stay. Great location! Very clean and as advertised "
United States
Joey
The price is HK$726
HK$1,233 total
includes taxes & fees
31 Aug - 1 Sept
2 BR Beautiful new home near Mammoth Cave.
Property grounds

19. The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave

The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave
Brownsville
10.0 out of 10, Exceptional, (17 reviews)
"Great property close to Mammoth Cave. Host was great and we had everything we needed for a great weekend."
United States
Cheryl Y.
The price is HK$1,270
HK$2,809 total
includes taxes & fees
23 Sept - 24 Sept
The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave
Interior

20. Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave Hiking in the area

Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave Hiking in the area
Mammoth Cave
9.6 out of 10, Exceptional, (57 reviews)
"Very cozy cabin and great host!"
United States
Mason D.
The price is HK$706
HK$1,634 total
includes taxes & fees
30 Aug - 31 Aug
Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave Hiking in the area
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

Everhome Suites Bowling Green by Choice Hotels

Everhome Suites Bowling Green by Choice Hotels

8/10 Good
"Pros: Rooms were very clean and we really appreciated the fact that there was no carpet. The room amenities were nice. Property was well kept and there was a nice outdoor pool/grill area with party lights that was very active. There was a nice selection of food in the lobby if you were doing an extended stay. Cons: The beds were less comfortable than we hoped and we could hear the person above us walking around heavily. I would stay here again, just making sure I asked for the top floor."
James 2-night trip
Posted less than an hour ago
Everhome Suites Bowling Green by Choice Hotels

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:

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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?

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.