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Oakland Vacation Rentals

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Check prices for these dates

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

Our top choices for Oakland vacation rentals

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, (186 reviews)
"Great place near Mammoth Cave"
United States
Richard R.
$243 nightly
The price is $265
Oct 19 - Oct 20
Total with taxes and fees
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.
$319 nightly
The price is $347
Nov 9 - Nov 10
Total with taxes and fees
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, (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.
$171 nightly
The price is $189
Oct 18 - Oct 19
Total with taxes and fees
Quiet Apartment
A neatly made bed with white linens, a wooden headboard, and two bedside lamps.

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.
$158 nightly
The price is $174
Oct 19 - Oct 20
Total with taxes and fees
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.

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.
$155 nightly
The price is $176
Oct 18 - Oct 19
Total with taxes and fees
Very clean & private
A modern kitchen with white cabinets, a granite countertop, a built-in oven, a microwave, a refrigerator, and a coffee maker.

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.
$238 nightly
The price is $269
Oct 20 - Oct 21
Total with taxes and fees
Blue Nest: Your Modern Downtown Perch - Downtown BG
A living room with a sectional sofa, a dining area with a table and chairs, a ceiling fan, and a kitchen in the background.

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
$334 nightly
The price is $368
Oct 18 - Oct 19
Total with taxes and fees
< Half-mi to Mammoth Cave! Family Home w/ Yard
A spacious living room with a beige sofa, patterned cushions, a glass coffee table, and large windows offering a view of the backyard.

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.
$199 nightly
The price is $226
Oct 26 - Oct 27
Total with taxes and fees
Quaint 2-bedroom Dog Friendly apartment with AC in Bowling Green
A kitchen with granite countertops, wooden cabinets, a window, and a coffee maker.

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.
$179 nightly
The price is $203
Oct 20 - Oct 21
Total with taxes and fees
Beautiful Bungalow in the Heart of BG. By WKU Campus. Close to Mammoth Cave.
A spa room with a massage table, red chairs, and a window with a view of trees.

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.
$286 nightly
The price is $315
Oct 22 - Oct 23
Total with taxes and fees
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.

11. Toppers Landing - Steps away from WKU Campus

Toppers Landing - Steps away from WKU Campus
College Hill Historic District
$206 nightly
The price is $233
Oct 19 - Oct 20
Total with taxes and fees
Toppers Landing - Steps away from WKU Campus
A modern kitchen with dark wooden cabinets, stainless steel appliances, and a granite countertop.

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, (13 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.
$249 nightly
The price is $272
Nov 2 - Nov 3
Total with taxes and fees
Cozy home on shady lot, minutes to Beech Bend, WKU, Corvette museum, hospitals
A cozy cabin room with a wooden interior, a window with a forest scene curtain, a lamp, and a quilted bedspread featuring animal prints.

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, (68 reviews)
"Cabin is as described. Cozy."
United States
Deanna
$189 nightly
The price is $208
Oct 21 - Oct 22
Total with taxes and fees
Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave Hiking in the area
A single-story house with a front porch, a garage, and a well-maintained lawn.

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.
$147 nightly
The price is $162
Nov 2 - Nov 3
Total with taxes and fees
2 BR Beautiful new home near Mammoth Cave.
A gazebo with a fire pit, wooden benches, and string lights against a sunset backdrop.

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.
$328 nightly
The price is $362
Oct 21 - Oct 22
Total with taxes and fees
The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near Mammoth Cave
A two-story white building with black shutters, numbered doors, and a small front porch.

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
$171 nightly
The price is $193
Oct 18 - Oct 19
Total with taxes and fees
Lovely 2- Bedroom Condo located in the heart of BG
A spacious living room with a fireplace, large windows, and a kitchen in the background.

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.
$474 nightly
The price is $517
Oct 19 - Oct 20
Total with taxes and fees
Drakes Creek: Summer Fun For Everyone!
A bedroom with a large bed, a view of a forest, and a modern design.

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
$315 nightly
The price is $347
Nov 1 - Nov 2
Total with taxes and fees
The Maple Retreat at Park Mammoth
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.

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.
$384 nightly
The price is $419
Oct 18 - Oct 19
Total with taxes and fees
Entire House Family-Pets-Friendly Close to i65.
A kitchen with grey cabinets, a white stove, a microwave, and a dishwasher.

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.
$171 nightly
The price is $193
Oct 18 - Oct 19
Total with taxes and fees
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

Woodspring Suites Bowling Green I-65

Woodspring Suites Bowling Green I-65

8/10 Good
"Everything was great except that the fitted sheet kept coming off which is pretty annoying. Still without a doubt the best priced hotel, much better than expected for the price. I will stay there again."
Ken 1-night trip
Posted 15 hours ago
Woodspring Suites Bowling Green I-65

Find out more about Oakland

Everything you need to know about Oakland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oakland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $170 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Oakland?

Yes, we have vacation rentals near top local attractions in Oakland, or you can choose a more remote option if you're looking for relaxation.

What are some of the best vacation rentals that Oakland has to offer?

Charming 2-bedroom bungalow with WiFi, AC in serene Cave City. : This vacation 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 larger area.

What are vacation rentals like in Oakland?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Oakland. Vacation rentals offer amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.