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Holiday Homes in Oakland

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Oakland holiday homes

A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a sink.

1. 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, (184 reviews)
"Great place near Mammoth Cave"
United States
Richard R.
The price is €212
includes taxes & fees
4 Oct - 5 Oct
Bluegrass Vineyard B&B, nestled next to the vineyard and winery
A modern kitchen with grey cabinets, a coffee machine, and a built-in oven.

2. 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, (13 reviews)
"The host was responsive, the home was clean & invting. We loved the location as well!"
United States
johnnie l.
The price is €315
includes taxes & fees
20 Oct - 21 Oct
Hunts Bend: Feel the Season Change|5-Acre Retreat
A kitchen with a blue wall, a brick backsplash, a stainless steel sink, a microwave, and a hanging light fixture.

3. Quiet Apartment

Quiet Apartment
Brownsville
9.8 out of 10, Exceptional, (46 reviews)
"Quiet, clean apartment. Very comfortable and responsive host."
United States
Cheryl K.
The price is €168
includes taxes & fees
1 Oct - 2 Oct
Quiet Apartment
A living room with a sofa, armchair, and a coffee table. There are two framed pictures on the wall, a lamp on a side table, and a window with blinds.

4. Very clean & private

Very clean & private
Bowling Green
9.8 out of 10, Exceptional, (169 reviews)
"Everything about this home was excellent. "
United States
Sandra B.
The price is €159
includes taxes & fees
4 Oct - 5 Oct
Very clean & private
A single-story house with a front porch, a garage, and a well-maintained lawn.

5. 2 BR Beautiful new home near Mammoth Cave.

2 BR Beautiful new home near Mammoth Cave.
Cave City
9.8 out of 10, Exceptional, (96 reviews)
"The house was clean, welcoming, and we'll stocked for cooking. We loved our stay."
United States
celeif L.
The price is €138
includes taxes & fees
5 Oct - 6 Oct
2 BR Beautiful new home near Mammoth Cave.
A gazebo with a fire pit, wooden benches, and string lights against a sunset backdrop.

6. 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, (21 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 €321
includes taxes & fees
1 Oct - 2 Oct
The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave
A kitchen with granite countertops, wooden cabinets, a window, and a coffee maker.

7. 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, (13 reviews)
"Places clean as described. Had a great time."
United States
Jonathan G.
The price is €189
includes taxes & fees
5 Oct - 6 Oct
Beautiful Bungalow in the Heart of BG. By WKU Campus. Close to Mammoth Cave.
A wooden deck with a white table set with white ceramic cups and a sugar container. A white vase with flowers is on the left, and a blue and green striped pillow is on the right.

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)
"Great location for an extended family trip to Mammoth Caves!"
United States
Erin M.
The price is €357
includes taxes & fees
4 Oct - 5 Oct
Entire House Family-Pets-Friendly Close to i65.
A modern kitchen with granite countertops, a dining area with a table and chairs, a living room with a sofa and a TV, and a ceiling fan.

9. Peaceful 2-bedroom home near Mammoth Cave.

Peaceful 2-bedroom home near Mammoth Cave.
Cave City
10.0 out of 10, Exceptional, (69 reviews)
"Great house and convenient to park. Lots of space to relax and was quiet."
United States
Theodore
The price is €158
includes taxes & fees
12 Oct - 13 Oct
Peaceful 2-bedroom home near Mammoth Cave.
A spacious living room with a fireplace, large windows, and a kitchen in the background.

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 €494
includes taxes & fees
28 Oct - 29 Oct
Drakes Creek: Summer Fun For Everyone!
A bedroom with a bed, two nightstands, a dresser, a fireplace, and two wall-mounted windows with wreaths.

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

Blue Belle: Storybook Spring Escape - Cozy 2BR
Bowling Green
9.8 out of 10, Exceptional, (15 reviews)
"Our second time staying here and again it was a very welcoming, convenient place to stay with ample amenities, We visited family nearby and enjoyed the easy walk downtown and pleasant walks around the neighborhood."
United States
Laura W.
The price is €284
includes taxes & fees
19 Oct - 20 Oct
Blue Belle: Storybook Spring Escape - Cozy 2BR
A single-story house with a dark gray exterior, white trim, and a dark roof.

12. Blueberry Cottage - Downtown Park City

Blueberry Cottage - Downtown Park City
Park City
10.0 out of 10, Exceptional, (12 reviews)
"Great stay. Cute homey house. Loved the little screened porch. Nice for morning coffee. Close to the expressway for quick on and off."
United States
Mary L.
The price is €358
includes taxes & fees
1 Oct - 2 Oct
Blueberry Cottage - Downtown Park City
A dining room with a wooden table and benches, a window with a view, and a sign reading "MAGNOLIA ROOM".

13. Lil' Rock - close to Beech Bend

Lil' Rock - close to Beech Bend
Bowling Green
10.0 out of 10, Exceptional, (10 reviews)
"Our stay was wonderful. The house is warm & family-friendly."
United States
Melissa S.
The price is €351
includes taxes & fees
1 Oct - 2 Oct
Lil' Rock - close to Beech Bend
A modern kitchen with a central island, wooden cabinets, and a dining area with a brown leather couch and a chandelier.

14. 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, (94 reviews)
"It was the perfect spot for us to stay the one night!"
United States
Grace H.
The price is €154
includes taxes & fees
5 Oct - 6 Oct
Peaceful private 3 BR new home near Mammoth Cave.
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a dining table set with white plates and glasses.

15. 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, (52 reviews)
"Perfect location for all the hiking trails and amazing coffee shop downtown!"
United States
Ami
The price is €189
includes taxes & fees
12 Oct - 13 Oct
Charming 2-bedroom bungalow with WiFi, AC in serene Cave City.
A modern living room with a wooden coffee table, a black sofa, and a flat-screen TV on a wooden stand.

16. Mammoth Cave Getaway

Mammoth Cave Getaway
Cave City
9.8 out of 10, Exceptional, (53 reviews)
"Well kept adorable home not far from all the area has to offer."
United States
Janice C.
The price is €228
includes taxes & fees
27 Oct - 28 Oct
Mammoth Cave Getaway
A park with a gazebo, outdoor seating, and a small shed.

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

Charming Cave City Vacation Rental w/ Fire Pit!
Cave City
10.0 out of 10, Exceptional, (65 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 €289
includes taxes & fees
13 Oct - 14 Oct
Charming Cave City Vacation Rental w/ Fire Pit!
A modern living room with a gray sectional sofa, a round coffee table, and a dining area with a wooden table and chairs.

18. Home in Mammoth Cave

Home in Mammoth Cave
Cave City
10.0 out of 10, Exceptional, (91 reviews)
"Amazing property and very responsive hosts. We have zero complaints."
United States
Kim
The price is €261
includes taxes & fees
15 Oct - 16 Oct
Home in Mammoth Cave
A living room with a large flat-screen TV, a ceiling fan, and a sofa.

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, (96 reviews)
"Extremely clean and close to Mammoth Cave National Park!"
United States
Emily
The price is €193
includes taxes & fees
25 Oct - 26 Oct
Peaceful private 3 bedroom & 2 bathroom new home near Mammoth Cave.
Living area

20. Charming 3-bedroom house "Cavern" with tons of amenities in Cave City.

Charming 3-bedroom house "Cavern" with tons of amenities in Cave City.
Cave City
9.6 out of 10, Exceptional, (23 reviews)
"The location and size of this property was perfect for our stop to visit Mammoth Caves!"
United States
Curt B.
The price is €240
includes taxes & fees
1 Oct - 2 Oct
Charming 3-bedroom house "Cavern" with tons of amenities in Cave City.
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

10/10 Excellent
"Great place to stay."
Donna 1-night trip
Posted 5 hours ago
Everhome Suites Bowling Green by Choice Hotels

Find out more about Oakland

Oakland Holiday Homes information

Number of reviews
1,098
Accommodation
216 Holiday Homes
Lowest Price
€138
Highest Price
€494