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Oakland Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Oakland holiday rentals

A spacious living room with a grand piano, a chandelier, and a staircase leading to another level.

1. Jenny’s Southland Homestead, LLC

Jenny’s Southland Homestead, LLC
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$1,891
HK$6,272 total
includes taxes & fees
14 Oct - 15 Oct
Jenny’s Southland Homestead, LLC
A spacious living room with a grand piano, a chandelier, and a staircase leading to another level.

2. Jennys Southland Homestead, LLC

Jennys Southland Homestead, LLC
3.0 star property
Oakland
The price is HK$2,331
HK$6,213 total
includes taxes & fees
14 Oct - 15 Oct
Jennys Southland Homestead, LLC
A modern kitchen with grey cabinets, a coffee machine, and a built-in oven.

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, (13 reviews)
"The host was responsive, the home was clean & invting. We loved the location as well!"
United States
johnnie l.
The price is HK$734
HK$2,631 total
includes taxes & fees
13 Oct - 14 Oct
Hunts Bend: Feel the Season Change|5-Acre Retreat
A kitchen with wooden cabinets, a stainless steel refrigerator, a microwave, and a sink.

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, (186 reviews)
"Great place near Mammoth Cave"
United States
Richard R.
The price is HK$1,406
HK$2,083 total
includes taxes & fees
14 Oct - 15 Oct
Bluegrass Vineyard B&B, nestled next to the vineyard and winery
A kitchen with a blue wall, a brick backsplash, a stainless steel sink, a microwave, and a hanging light fixture.

5. Quiet Apartment

Quiet Apartment
Brownsville
9.8 out of 10, Exceptional, (46 reviews)
"The apartment is exactly as described - very quiet! The space was clean and welcoming. We’d definitely recommend this accommodation to others visiting the Mammoth Cave area."
United States
Mary Elizabeth W.
The price is HK$777
HK$1,479 total
includes taxes & fees
15 Oct - 16 Oct
Quiet Apartment
A neatly made bed with white linens, a wooden headboard, and two bedside lamps.

6. Wanderlust: Here for your outdoor adventure

Wanderlust: Here for your outdoor adventure
Brownsville
9.6 out of 10, Exceptional, (36 reviews)
"Great place with a great pet friendly yard!"
United States
Bailey B.
The price is HK$691
HK$1,367 total
includes taxes & fees
13 Oct - 14 Oct
Wanderlust: Here for your outdoor adventure
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.

7. Very clean & private

Very clean & private
Bowling Green
9.8 out of 10, Exceptional, (169 reviews)
"Great place and location!"
United States
Carla B.
The price is HK$1,059
HK$1,380 total
includes taxes & fees
22 Oct - 23 Oct
Very clean & private
A living room with a sectional sofa, a dining area with a table and chairs, a ceiling fan, and a kitchen in the background.

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$1,177
HK$2,885 total
includes taxes & fees
14 Oct - 15 Oct
< Half-mi to Mammoth Cave! Family Home w/ Yard
A modern kitchen with white cabinets, a granite countertop, a built-in oven, a microwave, a refrigerator, and a coffee maker.

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

Blue Nest: Your Modern Downtown Perch - Downtown BG
Bowling Green
9.8 out of 10, Exceptional, (7 reviews)
"A great place to stay!"
United States
Stephanie B.
The price is HK$622
HK$2,113 total
includes taxes & fees
18 Oct - 19 Oct
Blue Nest: Your Modern Downtown Perch - Downtown BG
A kitchen with granite countertops, wooden cabinets, a window, and a coffee maker.

10. 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, (14 reviews)
"Places clean as described. Had a great time."
United States
Jonathan G.
The price is HK$622
HK$1,550 total
includes taxes & fees
13 Oct - 14 Oct
Beautiful Bungalow in the Heart of BG. By WKU Campus. Close to Mammoth Cave.
A modern kitchen with dark wooden cabinets, stainless steel appliances, and a granite countertop.

11. Cozy home on shady lot, minutes to Beech Bend, WKU, Corvette museum, hospitals

Cozy home on shady lot, minutes to Beech Bend, WKU, Corvette museum, hospitals
Bowling Green
10.0 out of 10, Exceptional, (12 reviews)
"This place is amazing! We felt completely at home and Jerri and Pat were amazing hosts! It was clean with modern decor and amenities. They truly thought of everything from the forgotten home essentials, games, and so much more. My girls loved the snack basket! The location was so close to all the tourist sites. We would definitely come back and stay"
United States
Jennifer U.
The price is HK$934
HK$2,133 total
includes taxes & fees
13 Oct - 14 Oct
Cozy home on shady lot, minutes to Beech Bend, WKU, Corvette museum, hospitals
A spacious living room with a beige sofa, patterned cushions, a glass coffee table, and large windows offering a view of the backyard.

12. Quaint 2-bedroom Dog Friendly apartment with AC in Bowling Green

Quaint 2-bedroom Dog Friendly apartment with AC in Bowling Green
Bowling Green
9.6 out of 10, Exceptional, (4 reviews)
"Overall good place to stay!"
United States
Annex Bar Grille P.
The price is HK$706
HK$1,771 total
includes taxes & fees
19 Oct - 20 Oct
Quaint 2-bedroom Dog Friendly apartment with AC in Bowling Green
A spa room with a massage table, red chairs, and a window with a view of trees.

13. Exile on Main Street

Exile on Main Street
Brownsville
9.8 out of 10, Exceptional, (66 reviews)
"The house is very cute and is very convenient for getting to Mammoth Cave. We loved the hot tub and the owner was available to answer any questions and helped us with entering the house. We had a great time."
United States
Donna Mary C.
The price is HK$1,177
HK$2,474 total
includes taxes & fees
13 Oct - 14 Oct
Exile on Main Street
A living room with a brown leather sofa, a teal armchair, a coffee table, a floor lamp, and a ceiling fan.

14. Toppers Landing - Steps away from WKU Campus

Toppers Landing - Steps away from WKU Campus
College Hill Historic District
The price is HK$677
HK$1,830 total
includes taxes & fees
13 Oct - 14 Oct
Toppers Landing - Steps away from WKU Campus
A bedroom with a large bed, a view of a forest, and a modern design.

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$1,730
HK$2,721 total
includes taxes & fees
18 Oct - 19 Oct
The Maple Retreat at Park Mammoth
A gazebo with a fire pit, wooden benches, and string lights against a sunset backdrop.

16. 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, (22 reviews)
"Great Value for our family of five! The host was great with communication. We selected this location to stay at during a visit to Mammoth Cave and had a great time!"
United States
Becky B.
The price is HK$1,271
HK$2,734 total
includes taxes & fees
13 Oct - 14 Oct
The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near 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.

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, (32 reviews)
"The houses location to the local sites is fantastic. The interior of the home could use remodeling and cleanliness could be better. The neighborhood is ok, but road is loud at night. People riding the motorcycles up and down the road can keep you up at night."
United States
Jessica B.
The price is HK$1,562
HK$3,290 total
includes taxes & fees
13 Oct - 14 Oct
Entire House Family-Pets-Friendly Close to i65.
A single-story house with a front porch, a garage, and a well-maintained lawn.

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, (101 reviews)
"The house was clean, welcoming, and we'll stocked for cooking. We loved our stay."
United States
celeif L.
The price is HK$734
HK$1,198 total
includes taxes & fees
18 Oct - 19 Oct
2 BR Beautiful new home near Mammoth Cave.
A stone staircase leading to a cave entrance with metal railings.

19. Comm Accessible 1BR King Suite | Breakfast Included

Comm Accessible 1BR King Suite | Breakfast Included
Bowling Green
The price is HK$1,082
HK$1,405 total
includes taxes & fees
18 Oct - 19 Oct
Comm Accessible 1BR King Suite | Breakfast Included
A spacious living room with a fireplace, large windows, and a kitchen in the background.

20. 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$1,321
HK$4,092 total
includes taxes & fees
13 Oct - 14 Oct
Drakes Creek: Summer Fun For Everyone!
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

La Quinta Inn & Suites by Wyndham Bowling Green

La Quinta Inn & Suites by Wyndham Bowling Green

10/10 Excellent
"Clean"
Donald 1-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham 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:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

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.