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Oakland Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Oakland vacation rentals

A log cabin with a wooden deck, a cozy bedroom with a bed and a sofa, and a dining area with a table and chairs.

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 AED 411
AED 764 total
includes taxes & fees
12 Oct - 13 Oct
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
A natural landscape with a pond, a wooden bridge, and a forested area.

2. Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
The price is AED 744
AED 1,363 total
includes taxes & fees
6 Oct - 7 Oct
Susquehanna Waterfall Haven
A round table with a red umbrella, two white chairs, and a grassy area near a body of water with trees in the background.

3. Waterfront Properties vacation rental

Waterfront Properties vacation rental
Windsor
10.0 out of 10, Exceptional, (74 reviews)
"We enjoyed our stay. The accommodations were great!"
United States
Terri R.
The price is AED 459
AED 1,170 total
includes taxes & fees
5 Oct - 6 Oct
Waterfront Properties vacation rental
An outdoor seating area with a fire pit, chairs, and a table.

4. Rustic 3-bedroom cottage in Windsor.

Rustic 3-bedroom cottage in Windsor.
Windsor
The price is AED 489
AED 1,034 total
includes taxes & fees
19 Oct - 20 Oct
Rustic 3-bedroom cottage in Windsor.
An outdoor bar area with a rustic wooden structure, a grill, and a sign that reads 'BAR-B-Q'.

5. 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 AED 459
AED 835 total
includes taxes & fees
4 Oct - 5 Oct
Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!
A cozy living room with a stone fireplace, wooden walls, a television, and a coffee table with decorative items.

6. Quiet Lakefront Retreat nestled in the woods.

Quiet Lakefront Retreat nestled in the woods.
Montrose
10.0 out of 10, Exceptional, (107 reviews)
"It was very clean great area and the hosts were so nice!!"
United States
Grace D.
The price is AED 477
AED 698 total
includes taxes & fees
5 Oct - 6 Oct
Quiet Lakefront Retreat nestled in the woods.
An open patio with a wooden pergola, two chairs, a small table with a bottle and glasses, and a view of a grassy yard with trees and a house in the distance.

7. 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 AED 735
AED 1,276 total
includes taxes & fees
5 Oct - 6 Oct
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
A cozy cabin with wooden walls, a sofa, a desk with a computer, a refrigerator, and two windows.

8. Fireside Cabin at Osborne Creek

Fireside Cabin at Osborne Creek
Port Crane
10.0 out of 10, Exceptional, (18 reviews)
"Great location, great host, and great property. "
United States
Matthew A.
The price is AED 459
AED 602 total
includes taxes & fees
5 Oct - 6 Oct
Fireside Cabin at Osborne Creek
A log cabin with a wooden door, a window, a bench, and a table.

9. Handcrafted Riverfront Cabin on 10 acres

Handcrafted Riverfront Cabin on 10 acres
Starlight
9.8 out of 10, Exceptional, (227 reviews)
"Great little cabin in a great location. "
United States
Michael M.
The price is AED 522
AED 1,333 total
includes taxes & fees
7 Oct - 8 Oct
Handcrafted Riverfront Cabin on 10 acres
A cozy living room with a sofa, a coffee table, and a lamp. There are large windows and a door leading to another room.

10. Hale Eddy

Hale Eddy
2.0 star property
Hancock
The price is AED 635
AED 1,287 total
includes taxes & fees
27 Oct - 28 Oct
Hale Eddy
A rustic cabin with a stone wall and a wooden deck.

11. Hilltop, relax and enjoy the Endless Mountains views

Hilltop, relax and enjoy the Endless Mountains views
Hallstead
9.2 out of 10, Wonderful, (14 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 AED 826
AED 1,392 total
includes taxes & fees
19 Oct - 20 Oct
Hilltop, relax and enjoy the Endless Mountains views
A room with wooden ceiling beams, a skylight, a framed picture, and a window with a snowy forest view.

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

Charming 120-year-old farmhouse by the creek
Hancock
9.0 out of 10, Wonderful, (28 reviews)
"This is really a beautiful place to stay, we definitely will return in summer. "
United States
Paul C.
The price is AED 555
AED 1,249 total
includes taxes & fees
4 Oct - 5 Oct
Charming 120-year-old farmhouse by the creek
Property grounds

13. 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 AED 735
AED 938 total
includes taxes & fees
5 Oct - 6 Oct
Ska'no'ne-Peaceful escape; Sunrise coffee on the covered porch, sun set Fire pit
Living area

14. 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 AED 2,277
AED 3,284 total
includes taxes & fees
6 Oct - 7 Oct
Lakefront Home, Fast WiFi + Workspace, ideal for weeklong family friendly stays
A wooden cabin interior with a staircase, leather sofa, and a coffee table.

15. 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 AED 1,201
AED 2,481 total
includes taxes & fees
5 Oct - 6 Oct
Modern Comforts Classic Cabin: Family/Fish Escape!
A wooden cabin with a porch, a swing, and a view of the surrounding forest.

16. 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 AED 1,443
AED 2,453 total
includes taxes & fees
5 Oct - 6 Oct
Modern Comforts Classic Cabin: Family/fish Escape!
A two-story house with a well-lit front porch and a dock extending into a body of water.

17. 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, (36 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 AED 4,132
AED 6,495 total
includes taxes & fees
12 Oct - 13 Oct
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

DoubleTree by Hilton Hotel Binghamton

DoubleTree by Hilton Hotel Binghamton

10/10 Excellent
"Parking was easy and room was fine and clean ."
Martina 1-night trip
Posted 2 hours ago
DoubleTree by Hilton Hotel Binghamton

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.