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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Oakland vacation rentals

Property grounds

Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.

Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.
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.
$336 nightly
The price is $365
Jul 19 - Jul 20
Total with taxes and fees
Hilltop, relax and enjoy nature's aviary atop the Endless Mountains.
Smart TV, fireplace, books, music library

Quiet Lakefront Retreat nestled in the woods.

Quiet Lakefront Retreat nestled in the woods.
Montrose
10.0 out of 10, Exceptional, (103 reviews)
"It was very quiet and beautiful"
United States
Timothy G.
$175 nightly
The price is $190
Jul 20 - Jul 21
Total with taxes and fees
Quiet Lakefront Retreat nestled in the woods.
Exterior detail

Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres
Starlight
10.0 out of 10, Exceptional, (215 reviews)
"Great little cabin in a great location. "
United States
Michael M.
$325 nightly
The price is $353
Jul 24 - Jul 25
Total with taxes and fees
Handcrafted Riverfront Cabin on 10 acres
Property grounds

Waterfront Properties vacation rental

Waterfront Properties vacation rental
Windsor
9.8 out of 10, Exceptional, (70 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.
$274 nightly
The price is $310
Aug 11 - Aug 12
Total with taxes and fees
Waterfront Properties vacation rental
Interior

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.
$308 nightly
The price is $339
Jul 21 - Jul 22
Total with taxes and fees
Charming 120-year-old farmhouse by the creek
Property grounds

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.
$355 nightly
The price is $401
Jul 19 - Jul 20
Total with taxes and fees
Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit
Interior

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, (16 reviews)
"Perfect place to bring the family for a quiet ski holiday. "
United States
Pamela S.
$283 nightly
The price is $305
Aug 4 - Aug 5
Total with taxes and fees
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
Property grounds

Rustic 3-bedroom cottage in Windsor.

Rustic 3-bedroom cottage in Windsor.
Windsor
$244 nightly
The price is $292
Jul 21 - Jul 22
Total with taxes and fees
Rustic 3-bedroom cottage in Windsor.
Smart TV, video games

Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
10.0 out of 10, Exceptional, (8 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
$109 nightly
The price is $123
Jul 20 - Jul 21
Total with taxes and fees
Fireside Cabin at Osborne Creek
Property grounds

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.
$210 nightly
The price is $226
Jul 21 - Jul 22
Total with taxes and fees
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
House, Private Bathroom, Mountain View (Angler & Nature's Delight) | Lounge

Hale Eddy

Hale Eddy
2.0 star property
Hancock
$325 nightly
The price is $342
Jul 22 - Jul 23
Total with taxes and fees
Hale Eddy
Property grounds

Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
$345 nightly
The price is $374
Aug 3 - Aug 4
Total with taxes and fees
Susquehanna Waterfall Haven
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

Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres

10/10 Excellent
"Beautiful scenic cabin. With clear stream. Dog loved it. Very private. Was perfect for a couple day get away."
Peter G. 2-night trip
Posted 16 hours ago
Handcrafted Riverfront Cabin on 10 acres

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 $123 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?

Explore the area and family-friendly sights such as Animal Adventure Park, or get out into nature at a spot like Susquehanna River. 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.