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Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Oakland holiday rentals

House (5 Bedrooms) | Interior

1. Jennys Southland Homestead, LLC

Jennys Southland Homestead, LLC
3.0 star property
Oakland
Jennys Southland Homestead, LLC
Room, 1 Bedroom | Private kitchen

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 3.596.491 ₫
3.964.772 ₫ total
includes taxes & fees
14 Sept - 15 Sept
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 3.911.100 ₫
9.585.845 ₫ total
includes taxes & fees
8 Sept - 9 Sept
< Half-mi to Mammoth Cave! Family Home w/ Yard
Room

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 5.945.973 ₫
9.299.090 ₫ total
includes taxes & fees
14 Sept - 15 Sept
The Maple Retreat at Park Mammoth
Room, 1 Bedroom | Private kitchen

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 4.154.527 ₫
5.334.768 ₫ total
includes taxes & fees
8 Sept - 9 Sept
Dupriest Room 1 Bedroom by Main Street Bed & Breakfast
Room, 1 Bedroom | Private kitchen

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 3.596.491 ₫
3.964.772 ₫ total
includes taxes & fees
9 Sept - 10 Sept
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 3.546.064 ₫
8.384.355 ₫ total
includes taxes & fees
13 Sept - 14 Sept
Charming Cave City Vacation Rental w/ Fire Pit!
Studio | Private kitchen

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 3.906.485 ₫
5.061.325 ₫ total
includes taxes & fees
3 Sept - 4 Sept
Dickinson Room by Main Street Bed & Breakfast
Cottage, 1 Bedroom | Private kitchen

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 3.906.485 ₫
4.306.510 ₫ total
includes taxes & fees
9 Sept - 10 Sept
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
"Friendly unpretentious hotel. Great Breakfast and good beds"
Karthik 1-night trip
Posted 8 hours ago
Drury Inn & Suites Bowling Green

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 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.