Oakland Holiday Rentals

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Oakland holiday rentals

Interior

Bowling Green House w/ Shared Pool!

Bowling Green House w/ Shared Pool!
3.0 star property
Oakland
The price is S$950
includes taxes & fees
8 Jun - 9 Jun
Bowling Green House w/ Shared Pool!
Private kitchen

Dickinson Room by Main Street Bed & Breakfast

Dickinson Room by Main Street Bed & Breakfast
3.0 star property
Glasgow
The price is S$237
includes taxes & fees
3 Jun - 4 Jun
Dickinson Room by Main Street Bed & Breakfast
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4 Mi to Mammoth Cave: Hand-built Cabin on 70 Acres

4 Mi to Mammoth Cave: Hand-built Cabin on 70 Acres
3.0 star property
Brownsville
The price is S$413
includes taxes & fees
12 Jun - 13 Jun
4 Mi to Mammoth Cave: Hand-built Cabin on 70 Acres
Premium bedding, pillow-top beds, laptop workspace, free WiFi

The Maple Retreat at Park Mammoth

The Maple Retreat at Park Mammoth
3.0 star property
Park City
9.0 out of 10, Wonderful, (17 reviews)
"Beautiful place right by the park! the views and nature are breath taking. The cabin is beautiful and clean and services are phenomenal."
United States
MARIA
The price is S$398
includes taxes & fees
4 Jun - 5 Jun
The Maple Retreat at Park Mammoth
Private kitchen

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 S$250
includes taxes & fees
3 Jun - 4 Jun
Dupriest Room 1 Bedroom by Main Street Bed & Breakfast
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Kentucky Vacation Rental: Half-mi to Mammoth Cave!

Kentucky Vacation Rental: Half-mi to Mammoth Cave!
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 S$418
includes taxes & fees
2 Jun - 3 Jun
Kentucky Vacation Rental: Half-mi to Mammoth Cave!
Private kitchen

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 S$199
includes taxes & fees
4 Jun - 5 Jun
Carroll Cottage 1 Bedroom by Main Street Bed & Breakfast
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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 S$410
includes taxes & fees
3 Jun - 4 Jun
Charming Cave City Vacation Rental w/ Fire Pit!
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Private Hot Tub, Arcade Game: Bee Spring Cabin

Private Hot Tub, Arcade Game: Bee Spring Cabin
3.0 star property
Bee Spring
6.0 out of 10, (1 review)
"The cabin was very nice. I called the host with a question and was disappointed in the friendliness of the conversation."
United States
Beth
The price is S$590
includes taxes & fees
2 Jun - 3 Jun
Private Hot Tub, Arcade Game: Bee Spring Cabin
Private kitchen

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 S$184
includes taxes & fees
3 Jun - 4 Jun
Greer Room 1 Bedroom by Main Street Bed & Breakfast
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Updated Apt: 1 Mi to Western Kentucky University!

Updated Apt: 1 Mi to Western Kentucky University!
3.0 star property
Bowling Green
10.0 out of 10, Exceptional, (1 review)
"Great area! Close to downtown. Easy entry and nice stay. "
United States
Lisa
The price is S$425
includes taxes & fees
16 Jun - 17 Jun
Updated Apt: 1 Mi to Western Kentucky University!
Private kitchen

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 S$187
includes taxes & fees
24 Jun - 25 Jun
America Room 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
"The breakfast provided was plentiful and very tasty. The first night there was no hot water available but it was soon fixed and I received a 20% discount on my bill for the inconvenience! The front desk staff was very helpful and answered all questions promptly. Housekeeping staff did a great job and gave us extra towels when asked.We appreciated our stay there and had a restaurant on each side of the hotel within walking distance. We would definitely use them again!"
Wendy 3-night trip
Posted 9 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.