Oakland Holiday Rentals

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Our top choices for Oakland holiday rentals

3.0 star property
7.4 out of 10, Good, (1381)
"Its called the affordable suites. "
United States
Naomi
The price is NZ$138
includes taxes & fees
14 Dec - 15 Dec
Affordable Suites of America Detroit-Warren
9.6 out of 10, Exceptional, (5)
"Our host was amazing w"
United States
Taxes & Notary B.
The price is NZ$1,913
includes taxes & fees
1 Jan - 2 Jan 2026
Spacious 5-bedroom house with Jacuzzi, Game room & WIFI in delightful Southfield

Holiday Home in West Bloomfield Township

Luxury Guest place: very close to lake and downtown
7.6 out of 10, Good, (22)
"Amazing "
United States
Demarco F.
The price is NZ$389
includes taxes & fees
13 Dec - 14 Dec
Luxury Guest place: very close to lake and downtown
9.6 out of 10, Exceptional, (5)
"This was a great spot on the lake with a cozy fireplace. Great if your hunting in local area and also want to get some fishing in."
United States
Paula
The price is NZ$435
includes taxes & fees
15 Dec - 16 Dec
Cozy 2-bedroom bungalow on Lake St Clair with plenty of room to dock your boat!
9.4 out of 10, Exceptional, (3)
"This house is nicely remodeled, it’s in a good location and was safe for our family. We had a few cleanliness issues, that we addressed and the property manager communicated back with us. Overall we would stay there again."
United States
Edith J.
The price is NZ$644
includes taxes & fees
15 Dec - 16 Dec
Luxury House Perfect location-3BR Sterling Heights
9.4 out of 10, Exceptional, (13)
"The stay was great! "
Canada
Dustin L.
The price is NZ$258
includes taxes & fees
15 Dec - 16 Dec
Air-Conditioned Studio | Pool
9.2 out of 10, Wonderful, (57)
"My sisters and I visit my mom in her twice a year"
United States
Pamela N.
The price is NZ$500
includes taxes & fees
15 Dec - 16 Dec
Spacious Farmhouse with Breakfast- Ella’s Place
9.4 out of 10, Exceptional, (21)
"It was the perfect location for all our needs. House was great place relax too"
United States
Tamara Y.
Home in Royal Oak w/ pool & sauna & dream garage
9.0 out of 10, Wonderful, (2)
"It was a nice clean property and the host was great at answering all questions very quickly."
United States
Graeme B.
The price is NZ$776
includes taxes & fees
13 Dec - 14 Dec
Spacious 4BR Home w/ WiFi & A/C – Family-Friendly Stay in Sterling Heights

Holiday Home in New Baltimore

6-Bedrooms, 1.5-Bath Ranch Style Unit
2.0 star property
10.0 out of 10, Exceptional, (1)
"The host was amazing! So welcoming and very generous. He made our stay so much better, I could not recommend this or any of his properties enough! Thanks John! "
United States
Keegan D.
The price is NZ$930
includes taxes & fees
23 Dec - 24 Dec
6-Bedrooms, 1.5-Bath Ranch Style Unit

Holiday Home in rochester hills

private and spacious
10.0 out of 10, Exceptional, (82)
"Beautiful home, very kind hostess. Enjoyed our stay very much !"
United States
Kathy J.
The price is NZ$253
includes taxes & fees
23 Dec - 24 Dec
private and spacious

Holiday Home in Birmingham

Luxury House 3BR Downtown Birmingham
10.0 out of 10, Exceptional, (7)
"Great Host, easy booking and great communication. The household was very welcoming and reflected the photo's and descriptions as listed. I will definitely keep this property in mind for future trips."
United States
Ladarryll C.
The price is NZ$503
includes taxes & fees
16 Dec - 17 Dec
Luxury House 3BR Downtown Birmingham
9.0 out of 10, Wonderful, (6)
"We had a good visit, house was as described, owner very responsive. "
United States
J S.
The price is NZ$656
includes taxes & fees
15 Dec - 16 Dec
Charming 3-bedroom house in peaceful White Lake Township on Pontiac Lake
9.6 out of 10, Exceptional, (14)
"Great cozy place"
United States
Lawrence R.
Calm & Cozy 3BR King Bed Free Wifi | Washer Dryer
9.6 out of 10, Exceptional, (48)
"This was easily the most well-kept VRBO rental we have experienced. Description is accurate, and communication was good. Much appreciated!"
United States
Maureen F.
Secluded Getaway, Relax & Energize, Wildlife, Nature Trail, Fun Kids Playground!
9.4 out of 10, Exceptional, (52)
"Overall a great value for the location. Easy in and out checkin/checkout. Comfy beds and everything you need in the kitchen for an at home stay. "
United States
Pat D.
The price is NZ$348
includes taxes & fees
6 Jan - 7 Jan 2026
2BR Family-Sized Lower Suite with Private Entrance & Big Backyard. Pet-Friendly!
3.0 star property
3 Mi to Dtwn Royal Oak: Getaway w/ Fenced Yard!
The price is NZ$298
includes taxes & fees
14 Dec - 15 Dec
Cozy 1-bedroom condo near downtown Clawson with WiFi, AC

Holiday Home in Village of Clarkston

Spacious 5-bedroom house in peaceful Clarkston with AC
2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a Fabulous stay! Was welcomed by a Gorgeous house decorated for the holidays!! Such a wonderful surprise! Very cozy and accommodating for our trip! "
United States
Diana H.
Spacious 5-bedroom house in peaceful Clarkston with AC
10.0 out of 10, Exceptional, (8)
"House was as advertised. Close to several local restaurants and bars. "
United States
James S.
The price is NZ$325
includes taxes & fees
14 Dec - 15 Dec
Welcome to, Days Inn Paradise located in Clinton Townshipship Michigan.
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

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as NZ$138 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there 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 are some of the best holiday rentals that Oakland has to offer?

Luxury House 3BR Downtown Birmingham: This holiday home rental outside of Oakland is equipped with a fireplace, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, an oven and a microwave, so that you can cook with friends or family.

What’s there to see and do in Oakland?

Explore the area and family-friendly sights such as Canterbury Village, or get out into nature at a spot like Addison Oaks County Park. Other places in town to visit include Twin Lakes Golf Course and Paint Creek Trail.

What’s a holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals feature 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, holiday rentals can provide a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for family trips.