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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, (18 reviews)
"This is the perfect place for you to come and relax. "
United States
Anabel P.
The price is CA $226
CA $362 total
includes taxes & fees
Nov 12 - Nov 13
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!

2. 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)
"Diamond in the rough!!! Excellent "
United States
Tasha M.
The price is CA $226
CA $362 total
includes taxes & fees
Nov 12 - Nov 13
Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!

3. Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
9.8 out of 10, Exceptional, (21 reviews)
"Great location, great host, and great property. "
United States
Matthew A.
The price is CA $157
CA $197 total
includes taxes & fees
Nov 17 - Nov 18
Fireside Cabin at Osborne Creek

4. Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
The price is CA $283
CA $499 total
includes taxes & fees
Nov 12 - Nov 13
Susquehanna Waterfall Haven

5. Waterfront Properties vacation rental

Waterfront Properties vacation rental
Windsor
10.0 out of 10, Exceptional, (76 reviews)
"My family and I had a perfect weekend getaway at this beautiful property. Amy and her husband were extremely nice and helpful. We would definitely stay there again."
United States
KURT N.
The price is CA $203
CA $497 total
includes taxes & fees
Nov 12 - Nov 13
Waterfront Properties vacation rental

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

Olivia House is a old farm house that has been updated!
Susquehanna
10.0 out of 10, Exceptional, (54 reviews)
"We have now stayed a few times here. Every time has been nothing short of perfect!!"
United States
Anna E.
The price is CA $328
CA $512 total
includes taxes & fees
Nov 17 - Nov 18
Olivia House is a old farm house that has been updated!

7. Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres
Starlight
9.8 out of 10, Exceptional, (230 reviews)
"Awesome little cabin. Great river access and just the feeling of being remote and away without being too out of touch with amenities if needed."
United States
Joe M.
The price is CA $205
CA $492 total
includes taxes & fees
Nov 9 - Nov 10
Handcrafted Riverfront Cabin on 10 acres

8. Quiet Lakefront Retreat nestled in the woods.

Quiet Lakefront Retreat nestled in the woods.
Montrose
10.0 out of 10, Exceptional, (110 reviews)
"It was very clean great area and the hosts were so nice!!"
United States
Grace D.
The price is CA $182
CA $255 total
includes taxes & fees
Nov 12 - Nov 13
Quiet Lakefront Retreat nestled in the woods.

9. 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.
The price is CA $362
CA $565 total
includes taxes & fees
Nov 12 - Nov 13
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!

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

Lakefront Home, Fast WiFi + Workspace, ideal for weeklong family friendly stays
New Milford
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful setting"
United States
Gerald L.
The price is CA $559
CA $788 total
includes taxes & fees
Nov 30 - Dec 1
Lakefront Home, Fast WiFi + Workspace, ideal for weeklong family friendly stays

11. Hale Eddy

Hale Eddy
2.0 star property
Hancock
The price is CA $217
CA $462 total
includes taxes & fees
Nov 10 - Nov 11
Hale Eddy

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

Charming 120-year-old farmhouse by the creek
Hancock
9.0 out of 10, Wonderful, (31 reviews)
"This is really a beautiful place to stay, we definitely will return in summer. "
United States
Paul C.
The price is CA $199
CA $418 total
includes taxes & fees
Nov 12 - Nov 13
Charming 120-year-old farmhouse by the creek

13. Hilltop, relax and enjoy the Endless Mountains views

Hilltop, relax and enjoy the Endless Mountains views
Hallstead
9.2 out of 10, Wonderful, (15 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 $330
CA $521 total
includes taxes & fees
Nov 6 - Nov 7
Hilltop, relax and enjoy the Endless Mountains views

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

Modern Comforts Classic Cabin: Family/Fish Escape!
Deposit
10.0 out of 10, Exceptional, (3 reviews)
"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...
United States
Kristin G.
The price is CA $457
CA $905 total
includes taxes & fees
Nov 17 - Nov 18
Modern Comforts Classic Cabin: Family/Fish Escape!

15. 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
The price is CA $549
CA $933 total
includes taxes & fees
Nov 10 - Nov 11
Modern Comforts Classic Cabin: Family/fish Escape!

16. 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, (37 reviews)
"Beautiful home with kind, communicative hosts. This is a very quiet community with strict lake rules, be mindful of booking with a rowdy or loud group. House had really nice amenities and was easy to find."
United States
Kaitlyn B.
The price is CA $1,572
CA $2,471 total
includes taxes & fees
Nov 17 - Nov 18
12 Bedroom Lake House, 150 ft Lakefront, 1 Acre, Beach, Ski Elk Mountain Poconos
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?

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.