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Holiday Homes in Oakland

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Check prices for these dates

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

Our top choices for Oakland holiday homes

Interior

1. Bowling Green House w/ Shared Pool!

Bowling Green House w/ Shared Pool!
Bowling Green
9.8 out of 10, Exceptional, (29 reviews)
"This house was awesome. Stayed in the pink room and it was beautiful to see the sunrise from our window. Thank you to the hosts for our lovely stay. Hope to return. I forgot to sign the guest book."
United States
Rachel
Bowling Green House w/ Shared Pool!
Exterior

2. 3-bedroom house near Barren River Lake

3-bedroom house near Barren River Lake
Scottsville
The price is €178
includes taxes & fees
18 Aug - 19 Aug
3-bedroom house near Barren River Lake
4 bedrooms, travel cot, free WiFi, bed sheets

3. Experience the best of Nolin Lake at this spacious lakefront retreat! With 4 bedrooms, room for 13 guests, two living areas, stunning lake views, and a semi-private dock, it's the perfect getaway for families& friends.

Experience the best of Nolin Lake at this spacious lakefront retreat! With 4 bedrooms, room for 13 guests, two living areas, stunning lake views, and a semi-private dock, it's the perfect getaway for families& friends.
Cub Run
10.0 out of 10, Exceptional, (1 review)
"Comfortable and spacious. A great place to get away from it all, literally. Plenty of room and amenities for a large family/group. A nice dock that comes in handy for a boat rental on the lake."
United States
Bruce B.
The price is €697
includes taxes & fees
12 Aug - 13 Aug
Experience the best of Nolin Lake at this spacious lakefront retreat! With 4 bedrooms, room for 13 guests, two living areas, stunning lake views, and a semi-private dock, it's the perfect getaway for families& friends.
Coffee/tea maker, fridge, microwave, oven

4. 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, (178 reviews)
"Great stay"
United States
Justin W.
Bluegrass Vineyard B&B, nestled next to the vineyard and winery
Coffee/tea maker, fridge, microwave, oven

5. 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 €289
includes taxes & fees
18 Aug - 19 Aug
Hunts Bend Private Getaway!
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 €252
includes taxes & fees
19 Aug - 20 Aug
The Grove at Middlebrook
Coffee/tea maker, fridge, microwave, cookware/dishes/utensils

7. 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 €165
includes taxes & fees
5 Sept - 6 Sept
Quiet Apartment
Exterior

8. 2 BR Beautiful new home near Mammoth Cave.

2 BR Beautiful new home near Mammoth Cave.
Cave City
9.8 out of 10, Exceptional, (85 reviews)
"Awesome place to stay. Great location! Very clean and as advertised "
United States
Joey
The price is €136
includes taxes & fees
12 Aug - 13 Aug
2 BR Beautiful new home near Mammoth Cave.
Smart TV, Netflix, Hulu, streaming services

9. Very clean & private

Very clean & private
Bowling Green
9.8 out of 10, Exceptional, (166 reviews)
"We enjoyed our stay. Having a full kitchen and fridge was nice and the bed was comfortable. And previous reviews were right, the shower had perfectly hot water! "
United States
Stephanie G.
The price is €156
includes taxes & fees
19 Aug - 20 Aug
Very clean & private
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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

Blue Belle: Storybook Spring Escape - Cozy 2BR
Bowling Green
9.8 out of 10, Exceptional, (14 reviews)
"Very charming in a historical part of town,with a park near by"
United States
Lynnette A.
The price is €271
includes taxes & fees
19 Aug - 20 Aug
Blue Belle: Storybook Spring Escape - Cozy 2BR
Smart TV, fireplace, books

11. 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 €475
includes taxes & fees
7 Sept - 8 Sept
Drakes Creek: Summer Fun For Everyone!
Property grounds

12. 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, (16 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 €332
includes taxes & fees
12 Aug - 13 Aug
The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave
Interior

13. Peaceful 2-bedroom home near Mammoth Cave.

Peaceful 2-bedroom home near Mammoth Cave.
Cave City
10.0 out of 10, Exceptional, (58 reviews)
"Great place, will stay again!"
United States
Darren B.
The price is €140
includes taxes & fees
19 Aug - 20 Aug
Peaceful 2-bedroom home near Mammoth Cave.
Private kitchen

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

Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
Cave City
9.2 out of 10, Wonderful, (47 reviews)
"Perfect location for all the hiking trails and amazing coffee shop downtown!"
United States
Ami
The price is €186
includes taxes & fees
22 Aug - 23 Aug
Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
Smart TV

15. Mammoth Cave Getaway

Mammoth Cave Getaway
Cave City
9.8 out of 10, Exceptional, (50 reviews)
"Great pet friendly location if visiting mammoth cave. "
United States
Cara L.
The price is €232
includes taxes & fees
23 Aug - 24 Aug
Mammoth Cave Getaway
Interior

16. 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, (88 reviews)
"It was the perfect spot for us to stay the one night!"
United States
Grace H.
The price is €140
includes taxes & fees
19 Aug - 20 Aug
Peaceful private 3 BR new home near Mammoth Cave.
Terrace/patio

17. 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.
Entire House Family-Pets-Friendly Close to i65.
Dining

18. 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 €259
includes taxes & fees
18 Aug - 19 Aug
Charming KY Stay
Smart TV

19. 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, (87 reviews)
"Had everything you needed for a short stay (or even a longer one!) outside Mammoth Cave. We only stayed one night, but enjoyed having the space for our kids."
United States
Christopher
Peaceful private 3 bedroom & 2 bathroom new home near Mammoth Cave.
Outdoor dining

20. Charming Cave City Vacation Rental w/ Fire Pit!

Charming Cave City Vacation Rental w/ Fire Pit!
Cave City
10.0 out of 10, Exceptional, (58 reviews)
"This was such a cozy house perfect for our little family getaway! We had everything we needed and the location was perfect for checking out the caves in the area. There were also plenty of great restaurants close by. "
United States
Christa G.
The price is €278
includes taxes & fees
15 Aug - 16 Aug
Charming Cave City Vacation Rental w/ 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.
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Top Oakland Hotel Reviews

Red Roof Inn & Suites Cave City

Red Roof Inn & Suites Cave City

10/10 Excellent
"Good"
Cameron 1-night trip
Posted 1 hour ago
Red Roof Inn & Suites Cave City

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