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Holiday Rentals in Oakland

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Our top choices for Oakland holiday rentals

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, (186 reviews)
"Great place near Mammoth Cave"
United States
Richard R.
The price is €240
includes taxes & fees
19 Oct - 20 Oct
Bluegrass Vineyard B&B, nestled next to the vineyard and winery

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 €319
includes taxes & fees
3 Nov - 4 Nov
Hunts Bend: Feel the Season Change|5-Acre Retreat

3. Quiet Apartment

Quiet Apartment
Brownsville
9.8 out of 10, Exceptional, (47 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 €170
includes taxes & fees
15 Nov - 16 Nov
Quiet Apartment

4. Wanderlust: Here for your outdoor adventure

Wanderlust: Here for your outdoor adventure
Brownsville
9.6 out of 10, Exceptional, (37 reviews)
"Great place with a great pet friendly yard!"
United States
Bailey B.
The price is €159
includes taxes & fees
16 Nov - 17 Nov
Wanderlust: Here for your outdoor adventure

5. 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 €161
includes taxes & fees
18 Oct - 19 Oct
Very clean & private

6. 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 €244
includes taxes & fees
18 Oct - 19 Oct
Blue Nest: Your Modern Downtown Perch - Downtown BG

7. < 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 €328
includes taxes & fees
26 Oct - 27 Oct
< Half-mi to Mammoth Cave! Family Home w/ Yard

8. 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 €220
includes taxes & fees
16 Nov - 17 Nov
Quaint 2-bedroom Dog Friendly apartment with AC in Bowling Green

9. 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 €207
includes taxes & fees
16 Nov - 17 Nov
Beautiful Bungalow in the Heart of BG. By WKU Campus. Close to Mammoth Cave.

10. 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 €278
includes taxes & fees
19 Oct - 20 Oct
Exile on Main Street

11. Toppers Landing - Steps away from WKU Campus

Toppers Landing - Steps away from WKU Campus
College Hill Historic District
The price is €212
includes taxes & fees
19 Oct - 20 Oct
Toppers Landing - Steps away from WKU Campus

12. 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 €244
includes taxes & fees
16 Nov - 17 Nov
Cozy home on shady lot, minutes to Beech Bend, WKU, Corvette museum, hospitals

13. Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave Hiking in the area

Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave Hiking in the area
Mammoth Cave
9.6 out of 10, Exceptional, (67 reviews)
"Cabin is as described. Cozy."
United States
Deanna
The price is €191
includes taxes & fees
21 Oct - 22 Oct
Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave Hiking in the area

14. 2 BR Beautiful new home near Mammoth Cave.

2 BR Beautiful new home near Mammoth Cave.
Cave City
9.8 out of 10, Exceptional, (102 reviews)
"The house was clean, welcoming, and we'll stocked for cooking. We loved our stay."
United States
celeif L.
The price is €150
includes taxes & fees
16 Nov - 17 Nov
2 BR Beautiful new home near Mammoth Cave.

15. 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 €345
includes taxes & fees
21 Oct - 22 Oct
The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave

16. Lovely 2- Bedroom Condo located in the heart of BG

Lovely 2- Bedroom Condo located in the heart of BG
Bowling Green
8.8 out of 10, Excellent, (21 reviews)
"The condo was nice and clean with all the amenities we needed for our stay. The location was great close to restaurants and shopping."
United States
benjamin
The price is €178
includes taxes & fees
16 Nov - 17 Nov
Lovely 2- Bedroom Condo located in the heart of BG

17. 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
16 Nov - 17 Nov
Drakes Creek: Summer Fun For Everyone!

18. 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 €309
includes taxes & fees
1 Nov - 2 Nov
The Maple Retreat at Park Mammoth

19. 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 €368
includes taxes & fees
16 Nov - 17 Nov
Entire House Family-Pets-Friendly Close to i65.

20. Comfortable/cozy apartment BGKY

Comfortable/cozy apartment BGKY
Bowling Green
7.4 out of 10, Good, (10 reviews)
"Loved it!"
United States
Kevin L.
The price is €176
includes taxes & fees
11 Nov - 12 Nov
Comfortable/cozy apartment BGKY
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

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as €156 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.