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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Oakland vacation rentals

House (5 Bedrooms) | Interior

1. Jennys Southland Homestead, LLC

Jennys Southland Homestead, LLC
3.0 star property
Oakland
The price is AED 1,091
AED 2,908 total
includes taxes & fees
31 Aug - 1 Sep
Jennys Southland Homestead, LLC
Room, 1 Bedroom | Private kitchen | Coffee/tea maker, fridge

2. America Room 1 Bedroom by Main Street Bed & Breakfast

America Room 1 Bedroom by Main Street Bed & Breakfast
2.0 star property
Glasgow
The price is AED 471
AED 519 total
includes taxes & fees
31 Aug - 1 Sep
America Room 1 Bedroom by Main Street Bed & Breakfast
House (3 Bedrooms) | Interior

3. < 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
31 Aug - 1 Sep
< Half-mi to Mammoth Cave! Family Home w/ Yard
Premium bedding, pillowtop beds, WiFi (free), bed sheets

4. 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 838
AED 1,310 total
includes taxes & fees
31 Aug - 1 Sep
The Maple Retreat at Park Mammoth
Room, 1 Bedroom | Private kitchen | Coffee/tea maker, fridge

5. Dupriest Room 1 Bedroom by Main Street Bed & Breakfast

Dupriest Room 1 Bedroom by Main Street Bed & Breakfast
3.0 star property
Glasgow
The price is AED 538
AED 700 total
includes taxes & fees
16 Sep - 17 Sep
Dupriest Room 1 Bedroom by Main Street Bed & Breakfast
Room, 1 Bedroom | Private kitchen | Coffee/tea maker, fridge

6. Greer Room 1 Bedroom by Main Street Bed & Breakfast

Greer Room 1 Bedroom by Main Street Bed & Breakfast
3.0 star property
Glasgow
10.0 out of 10, Exceptional, (1 review)
"I enjoyed my brief stay at the property. The check in process was unusual. I talked with the property manager via Ring and the place was unlocked. Also, I was initially unsure which room I would occupy. But everything got sorted out. The location is very, very close to the street, but the building, which apparently was constructed in 1810, was so well constructed that any noises from passing traffic could not be heard. The room was quiet and comfortable. The ambience of the place was...
United States
Michael Tim
The price is AED 471
AED 519 total
includes taxes & fees
31 Aug - 1 Sep
Greer Room 1 Bedroom by Main Street Bed & Breakfast
House (3 Bedrooms) | Interior

7. Charming Cave City Vacation Rental w/ Fire Pit!

Charming Cave City Vacation Rental w/ Fire Pit!
3.0 star property
Cave City
10.0 out of 10, Exceptional, (1 review)
"One of the BEST overnight stays we have ever experienced ! This place was EXCEPTIONAL !! "
United States
Tony
The price is AED 500
AED 1,181 total
includes taxes & fees
31 Aug - 1 Sep
Charming Cave City Vacation Rental w/ Fire Pit!
Studio | Private kitchen | Coffee/tea maker, fridge

8. Dickinson Room by Main Street Bed & Breakfast

Dickinson Room by Main Street Bed & Breakfast
3.0 star property
Glasgow
10.0 out of 10, Exceptional, (1 review)
The price is AED 506
AED 664 total
includes taxes & fees
31 Aug - 1 Sep
Dickinson Room by Main Street Bed & Breakfast
Cottage, 1 Bedroom | Private kitchen | Coffee/tea maker

9. Carroll Cottage 1 Bedroom by Main Street Bed & Breakfast

Carroll Cottage 1 Bedroom by Main Street Bed & Breakfast
3.0 star property
Glasgow
2.0 out of 10, (1 review)
"The bed sheets were not clean. Covered in both human and dog hair. Room was freezing. Looks to be an old converted shed sitting in a concrete pad. It was 5 degrees outside and we had a constant draft through the doors, windows, and cold air emitting straight from the floor. The home is old, which is no issue. There is a difference however between old and old/dirty/unkept. The floor was covered in dead bugs, spiderwebs, and dust. There was someone’s old food in n the mini fridge. Also, we are...
United States
Meesha
The price is AED 512
AED 564 total
includes taxes & fees
2 Sep - 3 Sep
Carroll Cottage 1 Bedroom by Main Street Bed & Breakfast
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

Drury Inn & Suites Bowling Green

Drury Inn & Suites Bowling Green

10/10 Excellent
"This hotel has some of the most competent and warmest staff I've ever seen. The hotel is spotless and comfortable. When we were informed of food served at 5.30 we expected snacks and instead found chicken fajitas and cocktails waiting. Nachos and hot dogs were also available. The 2nd night featured pasta pomadoro. The hotel is conveniently located to shopping and lots of fast food options. A huge thanks to Kayla and Matthew and all of the other staff."
Eulalia 2-night trip
Posted less than an hour ago
Drury Inn & Suites Bowling Green

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.