Default HTG hotel image

Oakland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 vacation 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, (30 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.
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
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 AED 384
AED 1,279 total
includes taxes & fees
3 Nov - 4 Nov
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 AED 658
AED 975 total
includes taxes & fees
19 Oct - 20 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, (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 AED 364
AED 692 total
includes taxes & fees
18 Oct - 19 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, (37 reviews)
"Great place with a great pet friendly yard!"
United States
Bailey B.
The price is AED 323
AED 640 total
includes taxes & fees
19 Oct - 20 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 AED 496
AED 646 total
includes taxes & fees
18 Oct - 19 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 AED 551
AED 1,350 total
includes taxes & fees
18 Oct - 19 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 AED 291
AED 989 total
includes taxes & fees
19 Oct - 20 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 AED 301
AED 745 total
includes taxes & fees
19 Oct - 20 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 AED 437
AED 999 total
includes taxes & fees
19 Oct - 20 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 AED 334
AED 833 total
includes taxes & fees
26 Oct - 27 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 AED 551
AED 1,158 total
includes taxes & fees
19 Oct - 20 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 AED 317
AED 856 total
includes taxes & fees
19 Oct - 20 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 AED 810
AED 1,274 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 AED 661
AED 1,413 total
includes taxes & fees
15 Nov - 16 Nov
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 AED 731
AED 1,540 total
includes taxes & fees
18 Oct - 19 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, (102 reviews)
"The house was clean, welcoming, and we'll stocked for cooking. We loved our stay."
United States
celeif L.
The price is AED 343
AED 561 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
8.0 out of 10, Very good, (1 review)
"The room was not set up for 4 adults as reserved. When I asked for this to be corrected it was not. The front desk never communicated to me about anything during my stay."
United States
Darrel
The price is AED 506
AED 658 total
includes taxes & fees
19 Oct - 20 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 AED 606
AED 1,898 total
includes taxes & fees
19 Oct - 20 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakland Hotel Reviews

Staybridge Suites Bowling Green by IHG

Staybridge Suites Bowling Green by IHG

10/10 Excellent
"perfect for families. Very friendly staff"
Thomas 3-night trip
Posted 11 hours ago
Staybridge Suites Bowling Green by IHG

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.