Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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, (188 reviews)
"Very nice and close to Bowling Green activities .. would stay again. Especially loved separate bedroom and bathroom accommodations for two adults couple . Winery next door was very good and people very friendly."
United States
Kaye W.
The price is CA $250
CA $356 total
includes taxes & fees
Nov 17 - Nov 18
Bluegrass Vineyard B&B, nestled next to the vineyard and winery
A bedroom with a large bed, a view of a forest, and a modern design.

2. The Maple Retreat at Park Mammoth

The Maple Retreat at Park Mammoth
3.0 star property
Park City
9.2 out of 10, Wonderful, (23 reviews)
"Comfortable and nice location"
United States
Emily
The price is CA $247
CA $405 total
includes taxes & fees
Nov 24 - Nov 25
The Maple Retreat at Park Mammoth
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 CA $157
CA $476 total
includes taxes & fees
Nov 9 - Nov 10
Hunts Bend: Feel the Season Change|5-Acre Retreat
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, (172 reviews)
"Great place and location!"
United States
Carla B.
The price is CA $189
CA $233 total
includes taxes & fees
Nov 17 - Nov 18
Very clean & private
A modern room with a bed, a desk, and a kitchenette.

5. Quiet Apartment

Quiet Apartment
Brownsville
9.8 out of 10, Exceptional, (48 reviews)
"Accommodations were very nice: clean house, comfy bed, convenient amenities, and helpful, communicative host. Fantastic location."
United States
Anonymous traveller
The price is CA $138
CA $250 total
includes taxes & fees
Nov 9 - Nov 10
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, (37 reviews)
"Wonderful location. Peaceful and very clean. Owners were very accommodating."
United States
Margaret P.
The price is CA $123
CA $231 total
includes taxes & fees
Nov 9 - Nov 10
Wanderlust: Here for your outdoor adventure
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
The price is CA $210
CA $514 total
includes taxes & fees
Nov 9 - Nov 10
< Half-mi to Mammoth Cave! Family Home w/ Yard
A modern kitchen with dark wooden cabinets, stainless steel appliances, and a granite countertop.

8. 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, (14 reviews)
"Beautiful place with thoughtful touches throughout. The host was incredibly responsive and easy to communicate with. The open layout made it perfect for our family, and everyone enjoyed their stay—the kids loved it, and the adults did too. We would happily stay here again"
United States
Candance E.
The price is CA $166
CA $363 total
includes taxes & fees
Nov 17 - Nov 18
Cozy home on shady lot, minutes to Beech Bend, WKU, Corvette museum, hospitals
A gazebo with a fire pit, wooden benches, and string lights against a sunset backdrop.

9. 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, (23 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 CA $239
CA $530 total
includes taxes & fees
Nov 6 - Nov 7
The Mammoth Cave House, 3BR, 2 bath with 5 beds and VERY near 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, (67 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 CA $222
CA $434 total
includes taxes & fees
Nov 9 - Nov 10
Exile on Main Street
A modern kitchen with white cabinets, a granite countertop, a built-in oven, a microwave, a refrigerator, and a coffee maker.

11. 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 CA $129
CA $381 total
includes taxes & fees
Nov 9 - Nov 10
Blue Nest: Your Modern Downtown Perch - Downtown BG
A modern kitchen with a central island, dark cabinetry, stainless steel appliances, and a window with blinds.

12. Bluegrass BnB - New, Downtown BG 1 Bedroom Apartment

Bluegrass BnB - New, Downtown BG 1 Bedroom Apartment
College Hill Historic District
The price is CA $170
CA $322 total
includes taxes & fees
Nov 21 - Nov 22
Bluegrass BnB - New, Downtown BG 1 Bedroom Apartment
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.

13. 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 CA $278
CA $557 total
includes taxes & fees
Nov 17 - Nov 18
Entire House Family-Pets-Friendly Close to i65.
A wooden deck with a round table and four chairs, surrounded by trees.

14. 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, (73 reviews)
"Cabin is as described. Cozy."
United States
Deanna
The price is CA $133
CA $282 total
includes taxes & fees
Nov 9 - Nov 10
Cozy 1-bedroom cabin with WiFi, AC in charming Mammoth Cave Hiking in the area
A living room with a brown leather sofa, a brown leather chair, a round coffee table with a plant, a floor lamp, and a painting on the wall.

15. Toppers Landing - Steps away from WKU Campus

Toppers Landing - Steps away from WKU Campus
College Hill Historic District
The price is CA $130
CA $317 total
includes taxes & fees
Nov 8 - Nov 9
Toppers Landing - Steps away from WKU Campus
A single-story house with a front porch, a garage, and a well-maintained lawn.

16. 2 BR Beautiful new home near Mammoth Cave.

2 BR Beautiful new home near Mammoth Cave.
Cave City
9.8 out of 10, Exceptional, (104 reviews)
"Beautiful home that was very comfortable and clean. Very convenient location as well. We enjoyed our stay!"
United States
Rebecca M.
The price is CA $142
CA $213 total
includes taxes & fees
Nov 14 - Nov 15
2 BR Beautiful new home near Mammoth Cave.
A bedroom with a bed, two nightstands, a dresser, a fireplace, and two wall-mounted windows with wreaths.

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

Blue Belle: Storybook Spring Escape - Cozy 2BR
Bowling Green
9.8 out of 10, Exceptional, (17 reviews)
"There are some thoughtful touches by the engaging, cooperative host of this historic property. Would definitely stay there again."
United States
Kent D.
The price is CA $141
CA $438 total
includes taxes & fees
Nov 30 - Dec 1
Blue Belle: Storybook Spring Escape - Cozy 2BR
A kitchen with granite countertops, wooden cabinets, a window, and a coffee maker.

18. 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
8.2 out of 10, Very good, (16 reviews)
"Places clean as described. Had a great time."
United States
Jonathan G.
The price is CA $117
CA $274 total
includes taxes & fees
Nov 16 - Nov 17
Beautiful Bungalow in the Heart of BG. By WKU Campus. Close to Mammoth Cave.
A spacious living room with a beige sofa, patterned cushions, a glass coffee table, and large windows offering a view of the backyard.

19. 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 CA $127
CA $303 total
includes taxes & fees
Nov 16 - Nov 17
Quaint 2-bedroom Dog Friendly apartment with AC in Bowling Green
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)
"Check in was easy and the house was clean. We appreciated having access to a washer and dryer so we didn’t have to take wet swimsuits home with us after spending the day at Beech Bend."
United States
Anonymous traveller
The price is CA $268
CA $731 total
includes taxes & fees
Nov 9 - Nov 10
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

An outdoor patio area with stone walls, a barbecue grill, fire pits, and string lights.
Everhome Suites Bowling Green by Choice Hotels

Everhome Suites Bowling Green by Choice Hotels

Everhome Suites Bowling Green by Choice Hotels
Eastland Park

10/10 Excellent

Very nice hotel
Canada
Jacques
Reviewed July 27, 2026
Everhome Suites Bowling Green by Choice Hotels

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland vacation rentals we have selected for you start as low as CA $117 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 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.

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.