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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 Sep - 27 Sep

Our top choices for Oakland holiday rentals

House (5 Bedrooms) | Interior

Bowling Green House w/ Shared Pool!

Bowling Green House w/ Shared Pool!
3.0 star property
Oakland
The price is 5.950.806 ₫
19.597.110 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Bowling Green House w/ Shared Pool!
Room, 1 Bedroom | Private kitchen | Fridge, coffee/tea maker

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 3.349.224 ₫
4.578.310 ₫ total
includes taxes & fees
23 Jun - 24 Jun
America Room 1 Bedroom by Main Street Bed & Breakfast
Apartment (3 Bedrooms) | Interior

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 3.079.323 ₫
8.513.670 ₫ total
includes taxes & fees
16 Jun - 17 Jun
Updated Apt: 1 Mi to Western Kentucky University!
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 5.098.649 ₫
8.211.626 ₫ total
includes taxes & fees
4 Jun - 5 Jun
The Maple Retreat at Park Mammoth
Room, 1 Bedroom | Private kitchen | Fridge, coffee/tea maker

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 3.477.266 ₫
5.525.113 ₫ total
includes taxes & fees
11 Jun - 12 Jun
Dupriest Room 1 Bedroom by Main Street Bed & Breakfast
Room, 1 Bedroom | Private kitchen | Fridge, coffee/tea maker

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 3.010.631 ₫
4.115.460 ₫ total
includes taxes & fees
4 Jun - 5 Jun
Greer Room 1 Bedroom by Main Street Bed & Breakfast
House (3 Bedrooms) | Interior

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 2.580.438 ₫
8.969.918 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Kentucky Vacation Rental: Half-mi to Mammoth Cave!
House (1 Bedroom) | Interior

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 2.264.466 ₫
7.733.941 ₫ total
includes taxes & fees
12 Jun - 13 Jun
4 Mi to Mammoth Cave: Hand-built Cabin on 70 Acres
Studio | Private kitchen | Fridge, coffee/tea maker

Dickinson Room by Main Street Bed & Breakfast

Dickinson Room by Main Street Bed & Breakfast
3.0 star property
Glasgow
The price is 3.270.004 ₫
5.241.792 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Dickinson Room by Main Street Bed & Breakfast
Cottage, 1 Bedroom | Private kitchen | Coffee/tea maker

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 3.270.004 ₫
4.470.018 ₫ total
includes taxes & fees
4 Jun - 5 Jun
Carroll Cottage 1 Bedroom by Main Street Bed & Breakfast
House (2 Bedrooms) | Interior

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 3.870.657 ₫
12.168.082 ₫ total
includes taxes & fees
4 Jun - 5 Jun
Private Hot Tub, Arcade Game: Bee Spring Cabin
House (3 Bedrooms) | Interior

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 2.842.452 ₫
8.449.189 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Charming Cave City Vacation Rental w/ Fire Pit!
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

Staybridge Suites Bowling Green by IHG

Staybridge Suites Bowling Green by IHG

10/10 Excellent
"This was a great stay in a homey atmosphere. Fun social hour, excellent breakfast, cheerful staff, excellent bedding. Simply a great place to stay!"
Frances 1-night trip
Posted 7 hours ago
Staybridge Suites Bowling Green by IHG

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.