Oakland Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

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 ￥25,642
￥39,197 total
includes taxes & fees
Nov 11 - Nov 12
Ace Cabin Cozy Cabin - Hot Tub, Firepit, Views, Near Skiing, Trails & Lakes!
A hot tub in a backyard with a wooden deck, a metal shed, and a house with lights.

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 ￥25,642
￥39,197 total
includes taxes & fees
Nov 9 - Nov 10
Jack Cabin - Views, Hot Tub, Fire Pit & Outdoors!
A cozy cabin with wooden walls, a sofa, a desk with a computer, a refrigerator, and two windows.

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 ￥17,814
￥22,278 total
includes taxes & fees
Dec 4 - Dec 5
Fireside Cabin at Osborne Creek
A natural landscape with a pond, a wooden bridge, and a forested area.

4. Susquehanna Waterfall Haven

Susquehanna Waterfall Haven
Susquehanna
The price is ￥32,066
￥56,409 total
includes taxes & fees
Nov 9 - Nov 10
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.

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 ￥22,961
￥56,186 total
includes taxes & fees
Nov 9 - Nov 10
Waterfront Properties vacation rental
A two-story house with a front deck, a small garden, and a wooden swing set.

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 ￥37,229
￥57,568 total
includes taxes & fees
Nov 17 - Nov 18
Olivia House is a old farm house that has been updated!
A log cabin with a wooden door, a window, a bench, and a table.

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 ￥23,250
￥55,623 total
includes taxes & fees
Nov 9 - Nov 10
Handcrafted Riverfront Cabin on 10 acres
A cozy living room with a stone fireplace, wooden walls, a television, and a coffee table with decorative items.

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 ￥20,586
￥28,936 total
includes taxes & fees
Nov 9 - Nov 10
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.

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 ￥41,025
￥63,515 total
includes taxes & fees
Dec 1 - Dec 2
Spacious Winter Retreat w/ Hot Tub, Games, Fire Pit & Scenic Hilltop Views!
Living area

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 ￥63,340
￥93,518 total
includes taxes & fees
Nov 16 - Nov 17
Lakefront Home, Fast WiFi + Workspace, ideal for weeklong family friendly stays
A cozy living room with a sofa, a coffee table, and a lamp. There are large windows and a door leading to another room.

11. Hale Eddy

Hale Eddy
2.0 star property
Hancock
The price is ￥24,544
￥52,334 total
includes taxes & fees
Nov 8 - Nov 9
Hale Eddy
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, (31 reviews)
"This is really a beautiful place to stay, we definitely will return in summer. "
United States
Paul C.
The price is ￥22,517
￥47,413 total
includes taxes & fees
Nov 11 - Nov 12
Charming 120-year-old farmhouse by the creek
A rustic cabin with a stone wall and a wooden deck.

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 ￥37,371
￥59,074 total
includes taxes & fees
Nov 9 - Nov 10
Hilltop, relax and enjoy the Endless Mountains views
A wooden cabin interior with a staircase, leather sofa, and a coffee table.

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 ￥51,826
￥102,685 total
includes taxes & fees
Nov 9 - Nov 10
Modern Comforts Classic Cabin: Family/Fish Escape!
A wooden cabin with a porch, a swing, and a view of the surrounding forest.

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 ￥62,287
￥105,837 total
includes taxes & fees
Nov 9 - Nov 10
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.

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 ￥178,301
￥280,278 total
includes taxes & fees
Nov 12 - Nov 13
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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Find vacation rentals that suit your style

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Top Oakland Hotel Reviews

A modern lobby with a sofa, chairs, a coffee table, and a patterned rug.
Fairfield by Marriott Inn & Suites New Milford

Fairfield by Marriott Inn & Suites New Milford

Fairfield by Marriott Inn & Suites New Milford
New Milford

10/10 Excellent

The room was wonderful, the staff were kind and accommodating, the breakfast was excellent, and there was plenty of parking available.
United States
Tracey
Reviewed October 11, 2026
Fairfield by Marriott Inn & Suites New Milford

Find out more about Oakland

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Look no further and take a look at our great range of rental properties in Oakland!

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.