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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Oakland vacation rentals

Property grounds

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

Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
Thompson
10.0 out of 10, Exceptional, (17 reviews)
"This is the perfect place for you to come and relax. "
United States
Anabel P.
$179 nightly
The price is $193
Aug 18 - Aug 19
Total with taxes and fees
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
Property grounds

2. Waterfront Properties vacation rental

Waterfront Properties vacation rental
Windsor
10.0 out of 10, Exceptional, (74 reviews)
"The owners were very attentive and willing to answer any question we had with very quick responses. The owners gave many recommendations for food in the area when asked. The place fit our needs perfectly. Will rent this place again if in the area again."
United States
Tyler J.
$286 nightly
The price is $323
Aug 21 - Aug 22
Total with taxes and fees
Waterfront Properties vacation rental
Interior

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

Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
Thompson
10.0 out of 10, Exceptional, (17 reviews)
"We loved our stay here! Great place, beautiful views, wished we could’ve stayed longer. Thank you!!"
United States
T.J. E.
$268 nightly
The price is $289
Aug 20 - Aug 21
Total with taxes and fees
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
Property grounds

4. Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
$346 nightly
The price is $375
Sep 1 - Sep 2
Total with taxes and fees
Susquehanna Waterfall Haven
Property grounds

5. Rustic 3-bedroom cottage in Windsor.

Rustic 3-bedroom cottage in Windsor.
Windsor
$204 nightly
The price is $247
Sep 13 - Sep 14
Total with taxes and fees
Rustic 3-bedroom cottage in Windsor.
Property grounds

6. Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit

Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit
Nineveh
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful location, clean, host was very helpful answering questions about the property / surrounding area."
United States
Kiel P.
$366 nightly
The price is $414
Aug 19 - Aug 20
Total with taxes and fees
Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit
Exterior detail

7. Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres
Starlight
9.8 out of 10, Exceptional, (219 reviews)
"Great little cabin in a great location. "
United States
Michael M.
$325 nightly
The price is $353
Aug 24 - Aug 25
Total with taxes and fees
Handcrafted Riverfront Cabin on 10 acres
Smart TV, video games

8. Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
10.0 out of 10, Exceptional, (12 reviews)
"Great location, great host, and great property. "
United States
Matthew A.
$119 nightly
The price is $134
Aug 18 - Aug 19
Total with taxes and fees
Fireside Cabin at Osborne Creek
Smart TV, fireplace, books, music library

9. Quiet Lakefront Retreat nestled in the woods.

Quiet Lakefront Retreat nestled in the woods.
Montrose
10.0 out of 10, Exceptional, (106 reviews)
"Such a sweet space in a beautiful setting. Definitely will be back! "
United States
Rachel F.
$175 nightly
The price is $190
Aug 19 - Aug 20
Total with taxes and fees
Quiet Lakefront Retreat nestled in the woods.
Interior

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

Charming 120-year-old farmhouse by the creek
Hancock
9.0 out of 10, Wonderful, (26 reviews)
"This is really a beautiful place to stay, we definitely will return in summer. "
United States
Paul C.
$310 nightly
The price is $341
Aug 25 - Aug 26
Total with taxes and fees
Charming 120-year-old farmhouse by the creek
House (3 Bedrooms) | Interior

11. Modern Comforts Classic Cabin- Family&fish Escape!

Modern Comforts Classic Cabin- Family&fish Escape!
3.0 star property
Deposit
10.0 out of 10, Exceptional, (1 review)
"House was great, hosts were very helpful"
United States
Ronald
$533 nightly
The price is $586
Aug 18 - Aug 19
Total with taxes and fees
Modern Comforts Classic Cabin- Family&fish Escape!
House, Private Bathroom, Mountain View (Angler & Nature's Delight) | Lounge

12. Hale Eddy

Hale Eddy
2.0 star property
Hancock
$325 nightly
The price is $342
Sep 8 - Sep 9
Total with taxes and fees
Hale Eddy
TV, books

13. Modern Comforts Classic Cabin- Family&Fish Escape!

Modern Comforts Classic Cabin- Family&Fish Escape!
Deposit
10.0 out of 10, Exceptional, (2 reviews)
"This is a great home! The rooms have comfortable beds and furniture. Extremely clean. No sulphur smell from water. Located at the end of a cul-de-sac on one of the nicest streets in Deposit. This home will not disappoint you."
United States
Mark
$546 nightly
The price is $601
Aug 18 - Aug 19
Total with taxes and fees
Modern Comforts Classic Cabin- Family&Fish Escape!
Property grounds

14. Hilltop, relax and enjoy the Endless Mountains views

Hilltop, relax and enjoy the Endless Mountains views
Hallstead
9.0 out of 10, Wonderful, (11 reviews)
"We needed a place to stay for the 6 of us attending the funeral of our mother and this vintage home was the perfect place for us. It offered tranquil views which was just what we needed. "
United States
Paula M.
$349 nightly
The price is $379
Aug 18 - Aug 19
Total with taxes and fees
Hilltop, relax and enjoy the Endless Mountains views
Exterior

15. 12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos

12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
Montrose
9.8 out of 10, Exceptional, (34 reviews)
"We really enjoyed our stay. The place is even better than the pictures and the host Julia was excellent."
United States
Blake T.
$1,679 nightly
The price is $1,824
Sep 7 - Sep 8
Total with taxes and fees
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
Terrace/patio

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

Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!
Thompson
9.4 out of 10, Exceptional, (13 reviews)
"Cool place to chilaxx"
United States
Luis R.
$179 nightly
The price is $193
Aug 18 - Aug 19
Total with taxes and fees
Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!
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

Colonial Brick Inn & Suites

Colonial Brick Inn & Suites

8/10 Good
"Great price. Bed was a little hard, AC worked good, but may noise (crackling paper sound). Stayed for one day only."
Kurt 1-night trip
Posted 13 hours ago
Colonial Brick Inn & Suites

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 $134 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?

Mountain Views, Private Pond, Mins 2 Elk Mountain: Visitors like this Oakland vacation home rental. It is located on the waterfront and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games.

What’s there to see and do in Oakland?

While you're exploring the area, Susquehanna River and Oquaga Lake are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Heart Lake 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.