A lake surrounded by trees with autumn leaves.

Oakland Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Oakland holiday rentals

A large rock surrounded by lush greenery and flowering plants.

1. Wilson Lake Inn & Suites

Wilson Lake Inn & Suites
2.0 star property
Wilton
The price is S$278
includes taxes & fees
26 Oct - 27 Oct
Wilson Lake Inn & Suites
A two-story building with a green sign reading 'Wilson Lake Inn.'

2. Wilson Lake Inn

Wilson Lake Inn
3.0 star property
Wilton
9.0 out of 10, Wonderful, (2 reviews)
"Clean room . Quiet! Close to what we were in the area for."
United States
Patricia
The price is S$260
includes taxes & fees
20 Oct - 21 Oct
Wilson Lake Inn
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

Maine Evergreen Hotel, an Ascend Collection Hotel

Maine Evergreen Hotel, an Ascend Collection Hotel

10/10 Excellent
"Surprisingly good!!"
MICHAEL 1-night trip
Posted 3 hours ago
Maine Evergreen Hotel, an Ascend Collection Hotel

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. Oakland is known for its shopping and restaurants. Make sure you have time to check out the monuments while you're in the area.

How many holiday rentals will I find in Oakland?

Choose from 31 Expedia holiday rentals in Oakland for a memorable holiday.

What can I see and do in Oakland?

Belgrade Lakes Chain and Messalonskee Lake are a couple of lovely local spots to get outside and enjoy nature. East Pond and Great Pond are other places to visit while you're in town.

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 offer extras such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.