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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Oakland holiday rentals

Interior

Bowling Green Farmhouse 10 Mi to Mammoth Cave

Bowling Green Farmhouse 10 Mi to Mammoth Cave
3.0 star property
Oakland
The price is RM940
RM1,844 total
includes taxes & fees
9 Jul - 10 Jul
Bowling Green Farmhouse 10 Mi to Mammoth Cave
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 RM520
RM710 total
includes taxes & fees
8 Jul - 9 Jul
Greer Room 1 Bedroom by Main Street Bed & Breakfast
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
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, (19 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 RM936
RM1,462 total
includes taxes & fees
8 Jul - 9 Jul
The Maple Retreat at Park Mammoth
Private kitchen

Dickinson Room by Main Street Bed & Breakfast

Dickinson Room by Main Street Bed & Breakfast
3.0 star property
Glasgow
The price is RM532
RM847 total
includes taxes & fees
8 Jul - 9 Jul
Dickinson Room by Main Street Bed & Breakfast
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 RM540
RM858 total
includes taxes & fees
2 Jul - 3 Jul
Dupriest Room 1 Bedroom by Main Street Bed & Breakfast
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 RM611
RM1,497 total
includes taxes & fees
26 Jul - 27 Jul
Kentucky Vacation Rental: Half-mi to Mammoth Cave!
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 RM554
RM1,309 total
includes taxes & fees
27 Jul - 28 Jul
Charming Cave City Vacation Rental w/ Fire Pit!
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 RM508
RM694 total
includes taxes & fees
7 Jul - 8 Jul
Carroll Cottage 1 Bedroom by Main Street Bed & Breakfast
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 RM712
RM1,883 total
includes taxes & fees
12 Jul - 13 Jul
Private Hot Tub, Arcade Game: Bee Spring Cabin
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 RM467
RM639 total
includes taxes & fees
2 Jul - 3 Jul
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

The Hotel Sync

The Hotel Sync

10/10 Excellent
"Laundry room was great"
Zach 2-night trip
Posted 9 hours ago
The Hotel Sync

Find out more about Oakland

Search for holiday rentals in Oakland on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

Look no further and take a look at our great range of rental properties in Oakland!

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 Southern Kentucky Performing Arts Center 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.