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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 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)
"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 £553
includes taxes & fees
31 Aug - 1 Sept
Bowling Green House w/ Shared Pool!
Coffee/tea maker, fridge, microwave, oven

2. 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 £176
includes taxes & fees
31 Aug - 1 Sept
Bluegrass Vineyard B&B, nestled next to the vineyard and winery
Property grounds

3. 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 £241
includes taxes & fees
24 Aug - 25 Aug
Hunts Bend: Feel the Season Change|5-Acre Retreat
Exterior

4. 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 £200
includes taxes & fees
21 Sept - 22 Sept
The Grove at Middlebrook
Smart TV, Netflix, Hulu, streaming services

5. 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 £132
includes taxes & fees
24 Aug - 25 Aug
Very clean & private
Coffee/tea maker, fridge, microwave, cookware/dishes/utensils

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 £139
includes taxes & fees
5 Sept - 6 Sept
Quiet Apartment
Exterior

7. 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 £118
includes taxes & fees
31 Aug - 1 Sept
2 BR Beautiful new home near Mammoth Cave.
Terrace/patio

8. 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 £296
includes taxes & fees
24 Aug - 25 Aug
Entire House Family-Pets-Friendly Close to i65.
2 bedrooms, iron/ironing board, free WiFi, bed sheets

9. 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 £227
includes taxes & fees
24 Aug - 25 Aug
Blue Belle: Storybook Spring Escape - Cozy 2BR
Smart TV, fireplace, books

10. 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 £371
includes taxes & fees
24 Aug - 25 Aug
Drakes Creek: Summer Fun For Everyone!
Dining

11. 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 £219
includes taxes & fees
24 Aug - 25 Aug
Charming KY Stay
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, (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 £264
includes taxes & fees
21 Sept - 22 Sept
The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave
Private kitchen

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

Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
Cave City
9.4 out of 10, Exceptional, (48 reviews)
"Perfect location for all the hiking trails and amazing coffee shop downtown!"
United States
Ami
The price is £157
includes taxes & fees
23 Aug - 24 Aug
Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
Smart TV

14. Mammoth Cave Getaway

Mammoth Cave Getaway
Cave City
9.8 out of 10, Exceptional, (51 reviews)
"Well kept adorable home not far from all the area has to offer."
United States
Janice C.
The price is £194
includes taxes & fees
23 Aug - 24 Aug
Mammoth Cave Getaway
Coffee/tea maker, fridge, microwave, oven

15. Beautiful Bungalow in the Heart of BG. By WKU Campus. Close to Mammoth Cave.

Beautiful Bungalow in the Heart of BG. By WKU Campus. Close to Mammoth Cave.
Bowling Green
8.0 out of 10, Very good, (10 reviews)
"Places clean as described. Had a great time."
United States
Jonathan G.
The price is £151
includes taxes & fees
31 Aug - 1 Sept
Beautiful Bungalow in the Heart of BG. By WKU Campus. Close to Mammoth Cave.
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, (89 reviews)
"It was the perfect spot for us to stay the one night!"
United States
Grace H.
The price is £124
includes taxes & fees
31 Aug - 1 Sept
Peaceful private 3 BR new home near Mammoth Cave.
Interior

17. Peaceful 2-bedroom home near Mammoth Cave.

Peaceful 2-bedroom home near Mammoth Cave.
Cave City
10.0 out of 10, Exceptional, (60 reviews)
"Great home in a quiet neighborhood and close to Mammoth Cave NP. Very clean and easy access to restaurants and shops. Definitely would stay here again. "
United States
Thomas M.
The price is £123
includes taxes & fees
1 Sept - 2 Sept
Peaceful 2-bedroom home near Mammoth Cave.
Outdoor dining

18. The Lodge at Mammoth Cave - Private Nature Retreat

The Lodge at Mammoth Cave - Private Nature Retreat
Cave City
10.0 out of 10, Exceptional, (16 reviews)
"Great location, very clean and perfect space for our family of 4. Loved the set up and the way it was decorated. "
United States
Ashley H.
The price is £204
includes taxes & fees
25 Aug - 26 Aug
The Lodge at Mammoth Cave - Private Nature Retreat
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, (88 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
The price is £145
includes taxes & fees
31 Aug - 1 Sept
Peaceful private 3 bedroom & 2 bathroom new home near Mammoth Cave.
Dining

20. Lil' Rock - close to Beech Bend

Lil' Rock - close to Beech Bend
Bowling Green
10.0 out of 10, Exceptional, (7 reviews)
"The house was exactly what we needed for our time in Bowing Green , hoping to be able to stay there again on our next trips."
United States
Christopher M.
The price is £286
includes taxes & fees
23 Aug - 24 Aug
Lil' Rock - close to Beech Bend
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
"This is an older hotel, but is maintained well. Great value for the price paid."
Erin 1-night trip
Posted 6 hours ago
Red Roof Inn & Suites Cave City

Find out more about Oakland

Oakland Holiday Homes information

Number of reviews
953
Accommodation
204 Holiday Homes
Lowest Price
£118
Highest Price
£553