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Oakland Vacation Rentals

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Our top choices for Oakland vacation rentals

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.
The price is CA $176
CA $316 total
includes taxes & fees
Aug 27 - Aug 28
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!

2. Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
The price is CA $299
CA $546 total
includes taxes & fees
Aug 17 - Aug 18
Susquehanna Waterfall Haven

3. Waterfront Properties vacation rental

Waterfront Properties vacation rental
Windsor
10.0 out of 10, Exceptional, (73 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.
The price is CA $176
CA $446 total
includes taxes & fees
Aug 12 - Aug 13
Waterfront Properties vacation rental

4. Rustic 3-bedroom cottage in Windsor.

Rustic 3-bedroom cottage in Windsor.
Windsor
The price is CA $174
CA $378 total
includes taxes & fees
Aug 12 - Aug 13
Rustic 3-bedroom cottage in Windsor.

5. 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)
"Home was lovely! Beautiful like the pictures and perfect for a weekend getaway. I’d recommend bringing your own bath products, but otherwise, would be happy to return! "
United States
Htet A.
The price is CA $229
CA $430 total
includes taxes & fees
Aug 17 - Aug 18
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!

6. Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres
Starlight
9.8 out of 10, Exceptional, (217 reviews)
"Very clean and cozy and the hosts were very responsive. It was a great escape for a few days with a beautiful landscape."
United States
Jennifer O.
The price is CA $246
CA $568 total
includes taxes & fees
Aug 24 - Aug 25
Handcrafted Riverfront Cabin on 10 acres

7. Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
10.0 out of 10, Exceptional, (12 reviews)
"Our host was just wonderful! He was attentive to our needs and went above and beyond by even bringing my grandson an air mattress & showing us his horses. The cabin was beautiful and the outdoor fireplace and hammock was great. The only problem we had was the television service was spotty even after our host tried to fix it. All in all, a wonderful visit."
United States
Heidi
The price is CA $139
CA $189 total
includes taxes & fees
Aug 23 - Aug 24
Fireside Cabin at Osborne Creek

8. 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.
The price is CA $232
CA $597 total
includes taxes & fees
Aug 8 - Aug 9
Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit

9. Quiet Lakefront Retreat nestled in the woods.

Quiet Lakefront Retreat nestled in the woods.
Montrose
10.0 out of 10, Exceptional, (104 reviews)
"Such a sweet space in a beautiful setting. Definitely will be back! "
United States
Rachel F.
The price is CA $183
CA $267 total
includes taxes & fees
Aug 22 - Aug 23
Quiet Lakefront Retreat nestled in the woods.

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.
The price is CA $236
CA $507 total
includes taxes & fees
Aug 20 - Aug 21
Charming 120-year-old farmhouse by the creek

11. Hale Eddy

Hale Eddy
2.0 star property
Hancock
The price is CA $232
CA $480 total
includes taxes & fees
Aug 25 - Aug 26
Hale Eddy

12. 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.
The price is CA $316
CA $532 total
includes taxes & fees
Aug 23 - Aug 24
Hilltop, relax and enjoy the Endless Mountains views

13. 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.
The price is CA $176
CA $317 total
includes taxes & fees
Aug 17 - Aug 18
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

Find out more about Oakland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Oakland. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Ski Elk Mountain, hike, walk or bike Rail to Trails, fish, or star gaze.: Visitors like this Oakland vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. 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.