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Check prices for these dates

Tonight
1 Dec - 2 Dec
Tomorrow
2 Dec - 3 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Holiday Rentals in Oakland

Exterior
The Maple Retreat at Park Mammoth

The Maple Retreat at Park Mammoth

3.0 star property
Park City
9.8 out of 10, Exceptional, (13)
"Wonderful property and ambiance. "
United States
neil
The price is 4.325.468 ₫
7.208.606 ₫ total
includes taxes & fees
2 Dec - 3 Dec
The Maple Retreat at Park Mammoth
House (2 Bedrooms) | Interior
Walk to Wku, Bars & Dining! Updated Duplex Home

Walk to Wku, Bars & Dining! Updated Duplex Home

3.0 star property
Bowling Green
10.0 out of 10, Exceptional, (1)
"Super location, super clean, good information before arrival, newly renovated and would definitely stay there again"
Denmark
Jakob
The price is 2.741.960 ₫
6.859.118 ₫ total
includes taxes & fees
2 Dec - 3 Dec
Walk to Wku, Bars & Dining! Updated Duplex Home
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 2.926.779 ₫
3.742.776 ₫ total
includes taxes & fees
2 Dec - 3 Dec
America 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
The price is 2.926.779 ₫
3.742.776 ₫ total
includes taxes & fees
4 Dec - 5 Dec
Greer Room 1 Bedroom by Main Street Bed & Breakfast
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 3.432.459 ₫
4.389.245 ₫ total
includes taxes & fees
2 Dec - 3 Dec
Dupriest Room 1 Bedroom by Main Street Bed & Breakfast
House (1 Bedroom) | Interior
Hilltopper Convenience: Modern Duplex Near WKU

Hilltopper Convenience: Modern Duplex Near WKU

3.0 star property
Bowling Green
The price is 2.109.200 ₫
6.141.463 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Hilltopper Convenience: Modern Duplex Near WKU
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 3.913.093 ₫
5.003.813 ₫ total
includes taxes & fees
31 Dec - 1 Jan 2026
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)
"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 3.179.619 ₫
4.066.274 ₫ total
includes taxes & fees
2 Dec - 3 Dec
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
"Easy check in. Clean room. Quiet night. "
Rory 1-night trip
Posted 18 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 Fountain Square 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.