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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, (184 reviews)
"Great place near Mammoth Cave"
United States
Richard R.
The price is £181
includes taxes & fees
28 Sept - 29 Sept
Bluegrass Vineyard B&B, nestled next to the vineyard and winery

2. Quiet Apartment

Quiet Apartment
Brownsville
9.8 out of 10, Exceptional, (45 reviews)
"Quiet, clean apartment. Very comfortable and responsive host."
United States
Cheryl K.
The price is £144
includes taxes & fees
28 Sept - 29 Sept
Quiet Apartment

3. Very clean & private

Very clean & private
Bowling Green
9.8 out of 10, Exceptional, (168 reviews)
"Everything about this home was excellent. "
United States
Sandra B.
The price is £136
includes taxes & fees
28 Sept - 29 Sept
Very clean & private

4. 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 £135
includes taxes & fees
28 Sept - 29 Sept
Wanderlust: Here for your outdoor adventure

5. 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, (12 reviews)
"The host was responsive, the home was clean & invting. We loved the location as well!"
United States
johnnie l.
The price is £259
includes taxes & fees
19 Oct - 20 Oct
Hunts Bend: Feel the Season Change|5-Acre Retreat

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 £208
includes taxes & fees
28 Sept - 29 Sept
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 £278
includes taxes & fees
28 Sept - 29 Sept
< Half-mi to Mammoth Cave! Family Home w/ Yard

8. 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, (64 reviews)
"Very cozy cabin , quiet , we enjoyed our stay"
United States
Beth H.
The price is £157
includes taxes & fees
28 Sept - 29 Sept
Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave Hiking in the area

9. Exile on Main Street

Exile on Main Street
Brownsville
9.8 out of 10, Exceptional, (65 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 £236
includes taxes & fees
28 Sept - 29 Sept
Exile on Main Street

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, (13 reviews)
"Places clean as described. Had a great time."
United States
Jonathan G.
The price is £154
includes taxes & fees
28 Sept - 29 Sept
Beautiful Bungalow in the Heart of BG. By WKU Campus. Close to Mammoth Cave.

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

Quaint 2-bedroom Dog Friendly apartment with AC in Bowling Green
Bowling Green
10.0 out of 10, Exceptional, (3 reviews)
"Overall good place to stay!"
United States
Annex Bar Grille P.
The price is £180
includes taxes & fees
5 Oct - 6 Oct
Quaint 2-bedroom Dog Friendly apartment with AC in Bowling Green

12. 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 £306
includes taxes & fees
28 Sept - 29 Sept
Entire House Family-Pets-Friendly Close to i65.

13. 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 £272
includes taxes & fees
28 Sept - 29 Sept
The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave

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, (93 reviews)
"It was the perfect spot for us to stay the one night!"
United States
Grace H.
The price is £122
includes taxes & fees
28 Sept - 29 Sept
Peaceful private 3 BR new home near Mammoth Cave.

15. 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 £118
includes taxes & fees
30 Sept - 1 Oct
2 BR Beautiful new home near Mammoth Cave.

16. Peace And Quiet Of Country Living Yet Close To Modern Convenience.

Peace And Quiet Of Country Living Yet Close To Modern Convenience.
Scottsville
9.8 out of 10, Exceptional, (174 reviews)
"Amazing property"
United States
Justin M.
The price is £149
includes taxes & fees
28 Sept - 29 Sept
Peace And Quiet Of Country Living Yet Close To Modern Convenience.

17. 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 £205
includes taxes & fees
1 Oct - 2 Oct
Mammoth Cave Getaway

18. 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 £402
includes taxes & fees
29 Sept - 30 Sept
Drakes Creek: Summer Fun For Everyone!

19. King bed in Tulip Glamping Aframe at Noble Pine Campground

King bed in Tulip Glamping Aframe at Noble Pine Campground
Mammoth Cave
9.6 out of 10, Exceptional, (37 reviews)
"Cozy, gorgeous place to spend a weekend. The host was great with communication, and it was such a fun and unique experience. I would totally stay again!"
United States
Angela Q.
The price is £127
includes taxes & fees
28 Sept - 29 Sept
King bed in Tulip Glamping Aframe at Noble Pine Campground

20. Peaceful Quiet Cozy Tiny Home W/Country Views. 20 min. to Downtown Bowling Green

Peaceful Quiet Cozy Tiny Home W/Country Views. 20 min. to Downtown Bowling Green
Rockfield
10.0 out of 10, Exceptional, (38 reviews)
"We loved the scenic location. We plan to stay here again!"
United States
William M.
The price is £136
includes taxes & fees
28 Sept - 29 Sept
Peaceful Quiet Cozy Tiny Home W/Country Views. 20 min. to Downtown Bowling Green
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 £122 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?

The Bunkhouse @Dragonfly Ranch is made to make you feel like home away from home: This holiday home rental outside of Oakland is located in a rural location, and has a garden, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of Access to hot tub in this rental home to help you unwind.

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.