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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Oakland vacation 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)
"A really memorable property! "
United States
Misti C.
The price is ￥32,342
￥121,415 total
includes taxes & fees
Aug 31 - Sep 1
Bowling Green House w/ Shared Pool!
House (5 Bedrooms) | Interior

2. Bowling Green House w/ Shared Pool!

Bowling Green House w/ Shared Pool!
3.0 star property
Oakland
The price is ￥40,467
￥118,658 total
includes taxes & fees
Aug 31 - Sep 1
Bowling Green House w/ Shared Pool!
Coffee/tea maker, fridge, microwave, oven

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, (179 reviews)
"Great stay"
United States
Justin W.
The price is ￥27,244
￥38,790 total
includes taxes & fees
Aug 30 - Aug 31
Bluegrass Vineyard B&B, nestled next to the vineyard and winery
Premium bedding, pillowtop beds, laptop workspace, WiFi (free)

4. The Maple Retreat at Park Mammoth

The Maple Retreat at Park Mammoth
3.0 star property
Park City
9.2 out of 10, Wonderful, (21 reviews)
"Comfortable and nice location"
United States
Emily
The price is ￥38,630
￥59,812 total
includes taxes & fees
Aug 18 - Aug 19
The Maple Retreat at Park Mammoth
House (3 Bedrooms) | Interior

5. < 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 ￥23,898
￥58,572 total
includes taxes & fees
Aug 21 - Aug 22
< Half-mi to Mammoth Cave! Family Home w/ Yard
Exterior

6. The Grove at Middlebrook

The Grove at Middlebrook
Smiths Grove
10.0 out of 10, Exceptional, (2 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 ￥30,111
￥43,558 total
includes taxes & fees
Sep 15 - Sep 16
The Grove at Middlebrook
Property grounds

7. Cozy House with lots of charm!

Cozy House with lots of charm!
Bowling Green
10.0 out of 10, Exceptional, (48 reviews)
"This property was perfect for our stay while attending bowtie nationals car show. Great communication and quick response on a couple questions we had before checking in. "
United States
Aron R.
The price is ￥21,795
￥42,061 total
includes taxes & fees
Aug 18 - Aug 19
Cozy House with lots of charm!
Smart TV, Netflix, Hulu, streaming services

8. 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 ￥21,508
￥28,008 total
includes taxes & fees
Aug 19 - Aug 20
Very clean & private
Terrace/patio

9. 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 ￥31,705
￥66,795 total
includes taxes & fees
Aug 18 - Aug 19
Entire House Family-Pets-Friendly Close to i65.
Interior

10. 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 ￥23,898
￥50,055 total
includes taxes & fees
Aug 20 - Aug 21
Exile on Main Street
Property grounds

11. 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 ￥25,810
￥57,081 total
includes taxes & fees
Sep 15 - Sep 16
The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave
Coffee/tea maker, fridge, microwave, oven

12. Hunts Bend Private Getaway!

Hunts Bend Private Getaway!
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 ￥14,896
￥53,238 total
includes taxes & fees
Aug 18 - Aug 19
Hunts Bend Private Getaway!
Coffee/tea maker, fridge, microwave, cookware/dishes/utensils

13. 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 ￥15,773
￥29,858 total
includes taxes & fees
Aug 18 - Aug 19
Quiet Apartment
Exterior

14. 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
9.4 out of 10, Exceptional, (19 reviews)
"Felt like a whimsical escape to the woods. Loved watching the frogs and wildlife. Hope to come back! Cute little cabin with lots of charm."
United States
Katherine
The price is ￥35,847
￥65,336 total
includes taxes & fees
Aug 18 - Aug 19
A Kentucky Cabin - Cozy Secluded Cabin One Mile From Mammoth Cave National Park
Apartment (3 Bedrooms) | Interior

15. Updated Apt: 1 Mi to Western Kentucky University!

Updated Apt: 1 Mi to Western Kentucky University!
3.0 star property
Bowling Green
10.0 out of 10, Exceptional, (1 review)
"Great area! Close to downtown. Easy entry and nice stay. "
United States
Lisa
Updated Apt: 1 Mi to Western Kentucky University!
Dining

16. Lil' Rock - close to Beech Bend

Lil' Rock - close to Beech Bend
Bowling Green
10.0 out of 10, Exceptional, (7 reviews)
"Very accommodating. Everything one may need for an extended stay. The neighbors are very sweet. Felt like home. "
United States
P U.
The price is ￥33,457
￥62,649 total
includes taxes & fees
Aug 24 - Aug 25
Lil' Rock - close to Beech Bend
Outdoor dining

17. 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, (22 reviews)
"Cottage was beautiful. Even had all the fixings for coffee in the am. Highly recommend. "
United States
Lisa J.
The price is ￥35,847
￥65,336 total
includes taxes & fees
Aug 18 - Aug 19
A Kentucky Cottage - Charming Cottage One Mile From Mammoth Cave National Park
Smart TV, fireplace, books

18. 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 ￥26,288
￥82,332 total
includes taxes & fees
Aug 24 - Aug 25
Drakes Creek: Summer Fun For Everyone!
Outdoor dining

19. Soothing 3-bedroom country house in peaceful Sweeden, KY

Soothing 3-bedroom country house in peaceful Sweeden, KY
Sweeden
10.0 out of 10, Exceptional, (8 reviews)
"This was the perfect location for us to stay before an impromptu visit to Mammoth Cave National Park. Located about a half hour drive from the park, this house met all our needs, with adequate sleeping space for our 3 adults and two kids. The extra touches to make our stay comfortable were much appreciated. We had a delicious take-out dinner from PJ's Roadhouse, located 4 minutes away - what a gem! We'll definitely keep this location in mind when we visit the area again!"
United States
Amber C.
The price is ￥31,545
￥39,517 total
includes taxes & fees
Aug 18 - Aug 19
Soothing 3-bedroom country house in peaceful Sweeden, KY
Smart TV, fireplace

20. Industrial Modern House for Sleep + Play

Industrial Modern House for Sleep + Play
Bowling Green
10.0 out of 10, Exceptional, (13 reviews)
"This home I cannot say enough how beautiful it is , it was perfect. I would definitely stay again when in town. And the hosts were very accommodating. "
United States
Sheila P.
The price is ￥79,660
￥134,261 total
includes taxes & fees
Aug 23 - Aug 24
Industrial Modern House for Sleep + Play
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

Drury Inn & Suites Bowling Green

Drury Inn & Suites Bowling Green

10/10 Excellent
"The staff were very friendly. Our room was very clean. The breakfast was delicious. The parking is very tight, because it shares a parking lot with a couple of restaurants. So, parking can be challenging. Other than that, our stay was perfect."
Shane 2-night trip
Posted 3 hours ago
Drury Inn & Suites 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:

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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 vacation rentals in Oakland?

Yes, we have vacation rentals near top local attractions in Oakland, or you can choose a more remote option if you're looking for relaxation.

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

Year-round 3BR/2BA Lake front - Nolin State Park (1mile) -Mammoth Cave (30min): This vacation home rental outside of Oakland is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a garden and 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 Mammoth Cave National Park. National Corvette Museum and NCM Motorsports Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Oakland?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Oakland. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.