Oakland Vacation Rentals from $164: Search Short-Term Rentals

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Our top choices for Oakland vacation rentals

A log cabin with a wooden deck, a cozy bedroom with a bed and a sofa, and a dining area with a table and chairs.

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

Thompson

Anabel P.

$234 nightly

Oct 25 - Oct 26

Total with taxes and fees

A rustic outdoor seating area with lounge chairs and a fire pit.

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

Thompson

Tasha M.

$239 nightly

Oct 25 - Oct 26

Total with taxes and fees

An outdoor seating area with a fire pit, chairs, and a table.

3. Rustic 3-bedroom cottage in Windsor.

Windsor

$224 nightly

Oct 24 - Oct 25

Total with taxes and fees

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

4. Susquehanna Waterfall Haven

Susquehanna

$342 nightly

Oct 22 - Oct 23

Total with taxes and fees

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

Michael B.

$330 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

6. Fireside Cabin at Osborne Creek

Port Crane

Matthew A.

$145 nightly

Oct 25 - Oct 26

Total with taxes and fees

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

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

Susquehanna

Anna E.

$329 nightly

Nov 3 - Nov 4

Total with taxes and fees

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

8. Handcrafted Riverfront Cabin on 10 acres

Starlight

Joe M.

$334 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

9. Quiet Lakefront Retreat nestled in the woods.

Montrose

Grace D.

$177 nightly

Oct 23 - Oct 24

Total with taxes and fees

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

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

Hancock

Paul C.

$286 nightly

Oct 22 - Oct 23

Total with taxes and fees

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.

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

Thompson

T.J. E.

$367 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

New Milford

Gerald L.

$571 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

13. Hale Eddy

Hancock

$320 nightly

Nov 3 - Nov 4

Total with taxes and fees

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

14. Hilltop, relax and enjoy the Endless Mountains views

Hallstead

Paula M.

$360 nightly

Oct 22 - Oct 23

Total with taxes and fees

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

15. 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.

$617 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

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

Deposit

Ronald

$607 nightly

Oct 26 - Oct 27

Total with taxes and fees

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

17. 12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

Montrose

Kaitlyn B.

$1,628 nightly

Nov 1 - Nov 2

Total with taxes and fees

18. Spacious Well Furnished A-Frame with Sauna in Union Dale, Pennsylvania

Union Dale

$912 nightly

Oct 22 - Oct 23

Total with taxes and fees

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Top Oakland Hotel Reviews

Colonial Brick Inn & Suites

8/10 Good

"Clean and convenient for the area."

Seasons on Oak Short walk to best Fly Fishing in Northeast Cozy Cabin Deposit NY

8/10 Good

"Clean rooms. Nice instruction booklet - only missing wifi information. Didn't know what to do with towels/dishes but since they had a dish washer and washing machine, I put my items there. Great amenities! Would definitely stay again!"

Mountain Views, Private Pond, Mins 2 Elk Mountain

8/10 Good

"Thoroughly enjoyed our time spent here.. We took multiple daily walks along the paths in the woods with our two dogs. A peaceful pond is just a short walk from the house where fish were caught. The fire pit out front was a nice touch to enjoy an early evening fire with a view.We always travel with our dogs and are grateful when a homeowner allows them. Upon making the reservation we were asked that both dogs be crated if we went out. It would have been nice to read in the description, prior to reserving, that a pet owner may be asked to crate their dogs. We ended up buying a crate for our one dog that is not crate trained and we were leery about how she would handle being crated. We were lucky that she did fine. There was a bit of miscommunication in regards to placing our trash in the garage and being picked up on one of the days we were there. Prior to our arrival I asked if we were to take the trash out to be picked up. Was told no and that they would get back to us on how it was to be handled and we never heard back. Upon arrival we then saw the bin at the end of the driveway and not in the garage as pictured and noted.We did get a timely response when we were given the wrong code to enter the house and appreciate being given the correct code so quickly to get us in. We thoroughly enjoyed being away from daily life and just relaxing. Memorable rides through the countryside with the Fall leaves changing their colors. Again, thank you!"

Spacious Luxury lodge near Elk Mountain ski resort on a private lake

10/10 Excellent

"This property was amazing for our group. The house and amenities were in great condition. The game room and sauna got a lot of use! Both paddle boats were broken but there was plenty of other options with paddles and life jackets for kids of all ages."

Find out more about Oakland

Everything you need to know about Oakland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Oakland vacation 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 low season months. For more hustle and bustle, you may prefer to visit Oakland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $164 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland vacation 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 vacation.

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 vacation rental in Oakland?

Yes, we give you a choice of vacation rentals close to well known points of interest in Oakland, or you can choose a secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Oakland?

Your Secluded Country Oasis - 70 Acres with Private Lake-Welcome to SkyFall!: Visitors like this Oakland vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 larger area, you’ll find Jimay's Flea Market and Shehawken Lake.

What’s a vacation rental in Oakland like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Oakland. Vacation rentals provide amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you to travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.

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Check prices for these dates

Our top choices for Oakland vacation rentals

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

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

3. Rustic 3-bedroom cottage in Windsor.

4. Susquehanna Waterfall Haven

5. Waterfront Properties vacation rental

6. Fireside Cabin at Osborne Creek

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

8. Handcrafted Riverfront Cabin on 10 acres

9. Quiet Lakefront Retreat nestled in the woods.

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

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

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

13. Hale Eddy

14. Hilltop, relax and enjoy the Endless Mountains views

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

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

17. 12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

18. Spacious Well Furnished A-Frame with Sauna in Union Dale, Pennsylvania

Find vacation rentals that suit your style

Top Oakland Hotel Reviews

Colonial Brick Inn & Suites

Fairfield by Marriott Inn & Suites New Milford

Chestnut Inn at Oquaga Lake

Seasons on Oak Short walk to best Fly Fishing in Northeast Cozy Cabin Deposit NY

Mountain Views, Private Pond, Mins 2 Elk Mountain

Handcrafted Riverfront Cabin on 10 acres

Quiet Lakefront Retreat nestled in the woods.

Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River

Spacious Luxury lodge near Elk Mountain ski resort on a private lake

Find out more about Oakland

Frequently asked questions

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