Oakland Vacation Rentals

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Vacation Rentals in Oakland

Handcrafted Riverfront Cabin on 10 acres
10.0 out of 10, Exceptional, (174)
"Beautiful cabin on very nice property. Great place to just relax. "
United States
Mary P.
$271 nightly
The price is $295
Oct 29 - Oct 30
Total with taxes and fees
Handcrafted Riverfront Cabin on 10 acres
Equestrian House Suites
3.0 star property
$610 nightly
The price is $665
Oct 28 - Oct 29
Total with taxes and fees
Equestrian House Suites
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast
10.0 out of 10, Exceptional, (11)
"Charming cabin, newly built with outstanding attention to detail. Rachel was a wonderful host and very accommodating. We thoroughly enjoyed our stay and plan to return in the future."
United States
Rick M.
Cozy Cabin built 2024 in Deposit,NY Short walk to best Fly Fishing in Northeast
Ski Elk Mountain, hike, walk or bike Rail to Trails, fish, or star gaze.
9.8 out of 10, Exceptional, (57)
"Very quiet lake i loved it . The property was well maintained and the Scenery was great we had a deer come right in the back yard "
United States
James D.
Ski Elk Mountain, hike, walk or bike Rail to Trails, fish, or star gaze.
Elk Mountain Vacation Home on 21 Acres
9.8 out of 10, Exceptional, (45)
"It’s our 4th year at Union Dales at this property. Simply amazing, rustic clean house, nature, privacy, beautiful trails, peace and quiet. "
United States
Luda C.
Elk Mountain Vacation Home on 21 Acres
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
9.8 out of 10, Exceptional, (29)
"We really enjoyed our stay. The place is even better than the pictures and the host Julia was excellent."
United States
Blake T.
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
Your Secluded Country Oasis - 70 Acres with Private Lake-Welcome to SkyFall!
10.0 out of 10, Exceptional, (79)
"We loved this place. It was so quiet and there was so much to do despite it raining most of our stay. Our hike to the waterfall was lovely. There are beautiful fish in the lake. The kids loved the game room! Adults loved the hot tub! We would definitely stay again!"
United States
Jennifer M.
Your Secluded Country Oasis - 70 Acres with Private Lake-Welcome to SkyFall!
DISCOUNT LAST MINUTE Elk Mountain Estate Manor in beautiful PA-Groups and Events
9.8 out of 10, Exceptional, (95)
"We booked at the last minute due to another rental falling through. The booking process was smooth and Laura was a gracious and amazing host. The property is beautiful and spacious! We can’t wait to visit again "
United States
Kolbie T.
DISCOUNT LAST MINUTE Elk Mountain Estate Manor in beautiful PA-Groups and Events
Spectacular Catskill Mountain River Front Custom Log Home
10.0 out of 10, Exceptional, (72)
"Great Location"
United States
David S.
Spectacular Catskill Mountain River Front Custom Log Home
A-Frame Retreat I 34 Acres I Lake/Camping/Hot Tub
5.6 out of 10, (5)
"House is very private and set back from the road. It has a unique design. Teens loved the loft. It’s definitely a work in progress but it’s adequate for a small group who just wants to ski and have a place nearby to sleep and eat. "
United States
Brian M.
A-Frame Retreat I 34 Acres I Lake/Camping/Hot Tub
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
10.0 out of 10, Exceptional, (189)
"We really enjoyed our stay! Jim and Tracy were fantastic and very nice! The cabin is so peaceful. If, you are looking for a peaceful getaway this is the place to go to! You will love it!"
United States
Alexis M.
Charming Country Cottage Located On Cute Farm, Minutes From The Delaware River
Breathtaking 44+ Acre Country Estate
10.0 out of 10, Exceptional, (36)
"We had a great family vacation here, coming in from various parts of the country. The fire pit, fishing, pickle ball, pool, hot tub, bald eagles, shooting stars and scenic views were just a few of the highlights! Gorgeous property and very responsive answers to questions etc "
United States
Christie L.
Breathtaking 44+ Acre Country Estate
Endless Mountain Resort
4.0 star property
8.6 out of 10, Excellent, (34)
"Pool was amazing. However the pilot in our place would not light for wood stove or down stairs. "
United States
Ashley
Endless Mountain Resort
Riverfront Cabin West Branch Delaware River
9.8 out of 10, Exceptional, (116)
"Great lil place, great host, will stay again when visiting family who live in town. "
United States
Traci B.
Riverfront Cabin West Branch Delaware River
Waterfront house on the upper most portion of the West Branch Delaware.
10.0 out of 10, Exceptional, (34)
"Nice family style place to stay. "
United States
Joe Z.
Waterfront house on the upper most portion of the West Branch Delaware.
Cabin on the Lake • Deck, Dock & Woods
9.4 out of 10, Exceptional, (3)
"Nice place tucked away in the woods. Great place to read and watch nature."
United States
Travis M.
Cabin on the Lake • Deck, Dock & Woods
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing
10.0 out of 10, Exceptional, (48)
"The house and property were gorgeous - well maintained, clean, quiet, great views and very comfortable. We'll be back to visit! "
United States
GK Z.
Tranquil River cottage w/hot tub, firepit , mins to a 18-holes golfing & fishing
Private Heated POOL• Lakeview• HotTub• Movie Theater• Games
10.0 out of 10, Exceptional, (11)
"Beautiful home with lots of little extras provided. Loved everything about it - pool, hot tub, fire pit stocked with plenty of wood, the view, large family space inside and out. Absolutely would recommend this house!"
United States
Pat M.
Private Heated POOL• Lakeview• HotTub• Movie Theater• Games
Charming & Private Delaware Riverfront Home near Callicoon NY
9.8 out of 10, Exceptional, (186)
"Beautiful stay "
United States
Lisa H.
Charming & Private Delaware Riverfront Home near Callicoon NY
Indoor Pool,Largest Game Lodge,Sleeps 39
10.0 out of 10, Exceptional, (56)
"Love the place! Plenty of space both inside and out. Beautiful log cabins. Would highly recommend! "
United States
Zachary M.
Indoor Pool,Largest Game Lodge,Sleeps 39
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

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 $295 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?

12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos: 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. It has 12 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself 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.