Oakland Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Oakland holiday rentals

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
The price is S$179
includes taxes & fees
29 Apr - 30 Apr
Greer Room 1 Bedroom by Main Street Bed & Breakfast
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 S$408
includes taxes & fees
28 Apr - 29 Apr
Charming Cave City Vacation Rental w/ Fire Pit!
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
8.8 out of 10, Excellent, (16 reviews)
"Wonderful property and ambiance. "
United States
neil
The price is S$397
includes taxes & fees
19 Apr - 20 Apr
The Maple Retreat at Park Mammoth
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$179
includes taxes & fees
20 Apr - 21 Apr
America Room 1 Bedroom 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 S$247
includes taxes & fees
29 Apr - 30 Apr
Dupriest Room 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 S$587
includes taxes & fees
20 Apr - 21 Apr
Private Hot Tub, Arcade Game: Bee Spring Cabin
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 S$355
includes taxes & fees
20 Apr - 21 Apr
4 Mi to Mammoth Cave: Hand-built Cabin on 70 Acres
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$232
includes taxes & fees
4 May - 5 May
Dickinson Room by Main Street Bed & Breakfast
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$196
includes taxes & fees
20 Apr - 21 Apr
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

Wingate by Wyndham Bowling Green

Wingate by Wyndham Bowling Green

4/10 Poor
"Length of time to check in was disappointing. "
Dan 1-night trip
Posted 6 hours ago
Wingate by Wyndham 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. Ephram White Park and National Corvette Museum 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.