Oakland Holiday Rentals from €127: Search Short-Term Rentals

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Our top choices for Oakland holiday rentals

A bedroom with a bed, a television mounted on the wall, a window with blinds, and a bedside table with a lamp.

1. Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!

Thompson

Anabel P.

includes taxes & fees

6 Dec - 7 Dec

A hot tub in a backyard with a wooden deck, a metal shed, and a house with lights.

2. Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!

Thompson

Tasha M.

includes taxes & fees

8 Nov - 9 Nov

A cozy cabin with wooden walls, a sofa, a desk with a computer, a refrigerator, and two windows.

3. Fireside Cabin at Osborne Creek

Port Crane

Matthew A.

includes taxes & fees

19 Nov - 20 Nov

A natural landscape with a pond, a wooden bridge, and a forested area.

4. Susquehanna Waterfall Haven

Susquehanna

includes taxes & fees

16 Nov - 17 Nov

A round table with a red umbrella, two white chairs, and a grassy area near a body of water with trees in the background.

5. Waterfront Properties vacation rental

Windsor

KURT N.

includes taxes & fees

6 Dec - 7 Dec

A two-story house with a front deck, a small garden, and a wooden swing set.

6. Olivia House is a old farm house that has been updated!

Susquehanna

Anna E.

includes taxes & fees

17 Nov - 18 Nov

A log cabin with a wooden door, a window, a bench, and a table.

7. Handcrafted Riverfront Cabin on 10 acres

Starlight

Joe M.

includes taxes & fees

9 Nov - 10 Nov

A cozy living room with a stone fireplace, wooden walls, a television, and a coffee table with decorative items.

8. Quiet Lakefront Retreat nestled in the woods.

Montrose

Grace D.

includes taxes & fees

2 Dec - 3 Dec

An open patio with a wooden pergola, two chairs, a small table with a bottle and glasses, and a view of a grassy yard with trees and a house in the distance.

9. Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!

Thompson

T.J. E.

includes taxes & fees

8 Nov - 9 Nov

10. Lakefront Home, Fast WiFi + Workspace, ideal for weeklong family friendly stays

New Milford

Gerald L.

includes taxes & fees

9 Nov - 10 Nov

A cozy living room with a sofa, a coffee table, and a lamp. There are large windows and a door leading to another room.

11. Hale Eddy

Hancock

includes taxes & fees

8 Nov - 9 Nov

A room with wooden ceiling beams, a skylight, a framed picture, and a window with a snowy forest view.

12. Charming 120-year-old farmhouse by the creek

Hancock

Paul C.

includes taxes & fees

10 Nov - 11 Nov

A rustic cabin with a stone wall and a wooden deck.

13. Hilltop, relax and enjoy the Endless Mountains views

Hallstead

Paula M.

includes taxes & fees

11 Nov - 12 Nov

A wooden cabin interior with a staircase, leather sofa, and a coffee table.

14. Modern Comforts Classic Cabin: Family/Fish Escape!

Deposit

"I would give this property 100 stars if I could. We were so grateful when we arrived and found this house to be even better than we expected. It is super cute, extremely clean and the perfect amount of space for our family of 5.This home met every need, and more! It was pristine, had the most adorable decorations, and was very comfortable and cozy. It was also well cared for (it was not beat up like many other properties we have stayed in). We had plenty of towels, coffee pods, toilet...

Kristin G.

includes taxes & fees

9 Nov - 10 Nov

A wooden cabin with a porch, a swing, and a view of the surrounding forest.

15. Modern Comforts Classic Cabin: Family/fish Escape!

Deposit

Ronald

includes taxes & fees

9 Nov - 10 Nov

A two-story house with a well-lit front porch and a dock extending into a body of water.

16. 12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

Montrose

Kaitlyn B.

includes taxes & fees

11 Nov - 12 Nov

View all properties

Find holiday rentals that suit your style

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, apart-hotels, 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 €127 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

Can I find a holiday rental 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?

Your Secluded Country Oasis - 70 Acres with Private Lake-Welcome to SkyFall!: This holiday home rental outside of Oakland is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Oakland?

While you're exploring the area, Susquehanna River and Heart Lake are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find Jimay's Flea Market and Shehawken Lake.

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 provide amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

Holiday Rentals in Oakland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakland holiday rentals

1. Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!

2. Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!

3. Fireside Cabin at Osborne Creek

4. Susquehanna Waterfall Haven

5. Waterfront Properties vacation rental

6. Olivia House is a old farm house that has been updated!

7. Handcrafted Riverfront Cabin on 10 acres

8. Quiet Lakefront Retreat nestled in the woods.

9. Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!

10. Lakefront Home, Fast WiFi + Workspace, ideal for weeklong family friendly stays

11. Hale Eddy

12. Charming 120-year-old farmhouse by the creek

13. Hilltop, relax and enjoy the Endless Mountains views

14. Modern Comforts Classic Cabin: Family/Fish Escape!

15. Modern Comforts Classic Cabin: Family/fish Escape!

16. 12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

Find holiday rentals that suit your style

Find out more about Oakland

Oakland holiday rentals: An excellent choice for every season

How to find incredible deals on Oakland rentals

Frequently Asked Questions

Can I find a holiday rental in Oakland?

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

What’s there to see and do in Oakland?

What’s a holiday rental in Oakland like?