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Oakland Vacation Rentals

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Nov 15 - Nov 16
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Vacation Rentals in Oakland

Exterior
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.

Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.

Oakland
10.0 out of 10, Exceptional, (4)
"The hosts were very communicative when we had a couple of issues they resolved them immediately The place is actually very clean, although there were a couple of areas that needed improvement and we reported that to the host It's very spacious and we would come back again"
United States
Juliann D.
The price is ￥16,524
￥55,568 total
includes taxes & fees
Nov 16 - Nov 17
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
Terrace/patio
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

Oakland
10.0 out of 10, Exceptional, (9)
"We had an awesome stay here! The yurt was absolutely beautiful, and the location was perfect. We would 100% stay again"
United States
Tyler S.
The price is ￥17,001
￥36,527 total
includes taxes & fees
Nov 16 - Nov 17
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Property grounds
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

2.0 star property
Oakland
10.0 out of 10, Exceptional, (10)
"This is an incredible house in a beautiful location. Shawn was more than helpful and an incredible host. We will definitely be returning renters. "
United States
chris s.
The price is ￥34,619
￥111,943 total
includes taxes & fees
Dec 3 - Dec 4
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
Terrace/patio
Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!

Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!

Oakland
10.0 out of 10, Exceptional, (17)
"Had a great time with friends during our fantasy football draft weekend, highly recommend this place!"
United States
Luke T.
The price is ￥27,680
￥106,666 total
includes taxes & fees
Nov 25 - Nov 26
Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!
Fridge, microwave, oven, dishwasher
Cubs Den - Hot Tub- Walk to Lake-Fire Pit -Kayaks

Cubs Den - Hot Tub- Walk to Lake-Fire Pit -Kayaks

Oakland
9.0 out of 10, Wonderful, (9)
"The house was absolutely adorable with all the little touches that helped make our stay very pleasant and fun. The upstairs was so cute and perfect for the kids. They loved it!"
United States
Mark H.
The price is ￥17,619
￥86,459 total
includes taxes & fees
Dec 15 - Dec 16
Cubs Den - Hot Tub- Walk to Lake-Fire Pit -Kayaks
Fridge, microwave, oven, stovetop
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna

Wooded Retreat w Hot Tub, Loft, Game Room & Sauna

Oakland
10.0 out of 10, Exceptional, (1)
"Wonderful place for the perfect getaway! Just like the photos definitely worth every penny. Just have in mind that you are in the woods so the bugs are inevitable but the inside of the place was very clean.Me and my family took advantage of all the amenities from the grill, hot tub, fire place. Don't think twice and book this place!"
United States
Bonny S.
The price is ￥36,384
￥90,090 total
includes taxes & fees
Dec 9 - Dec 10
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna
Exterior
The winter is coming !!!

The winter is coming !!!

Oakland
9.8 out of 10, Exceptional, (46)
"Check-in was extremely easy and the cabin was immaculate. There was more than enough room, everything was updated and well maintained, and the sun room with the hot tub was amazing. We would definitely love to visit this cabin again, perhaps in the fall or winter to get an even different experience!"
United States
Kevin M.
The price is ￥23,519
￥62,302 total
includes taxes & fees
Nov 16 - Nov 17
The winter is coming !!!
Interior
Suites at Silver Tree: A310 Studio & Loft Standard View

Suites at Silver Tree: A310 Studio & Loft Standard View

Oakland
10.0 out of 10, Exceptional, (4)
"First time at Deep Lake and the condo. Loved our time there. Highly recommended. We will be back!!"
United States
Phuong M.
The price is ￥48,402
￥62,222 total
includes taxes & fees
Dec 7 - Dec 8
Suites at Silver Tree: A310 Studio & Loft Standard View
Smart TV, video games
In the heart of Deep Creek Lake! - "Shamrock Inn"

In the heart of Deep Creek Lake! - "Shamrock Inn"

Mountainside
9.6 out of 10, Exceptional, (5)
"Awesome "
United States
Mariam H.
The price is ￥29,071
￥71,772 total
includes taxes & fees
Nov 16 - Nov 17
In the heart of Deep Creek Lake! - "Shamrock Inn"
Fridge, microwave, oven, stovetop
That Special Place

That Special Place

Oakland
10.0 out of 10, Exceptional, (26)
"Excellent place, very comfortable, we had a great time during my birthday week, I would rent it again in the future, good view, very good area."
United States
Jorge Daniel F.
The price is ￥27,680
￥66,038 total
includes taxes & fees
Nov 30 - Dec 1
That Special Place
Beach
Will O' The Wisp: 102B One Bedroom/One Bath

Will O' The Wisp: 102B One Bedroom/One Bath

Oakland
10.0 out of 10, Exceptional, (4)
"Wonderful restful stay."
United States
Rose J.
The price is ￥45,707
￥58,987 total
includes taxes & fees
Dec 16 - Dec 17
Will O' The Wisp: 102B One Bedroom/One Bath
Beach
Will O' The Wisp: 107B One Bedroom/One Bath

Will O' The Wisp: 107B One Bedroom/One Bath

Mountainside
10.0 out of 10, Exceptional, (2)
"Very clean. Great location. "
United States
Tom B.
The price is ￥52,847
￥68,109 total
includes taxes & fees
Dec 15 - Dec 16
Will O' The Wisp: 107B One Bedroom/One Bath
Interior
Suites at Silver Tree: A123 Studio Lake View

Suites at Silver Tree: A123 Studio Lake View

2.0 star property
Oakland
The price is ￥38,605
￥49,907 total
includes taxes & fees
Nov 16 - Nov 17
Suites at Silver Tree: A123 Studio Lake View
Indoor pool, a heated pool
Will O' The Wisp: 302B One Bedroom/One Bath

Will O' The Wisp: 302B One Bedroom/One Bath

2.0 star property
Oakland
The price is ￥50,750
￥64,082 total
includes taxes & fees
Nov 16 - Nov 17
Will O' The Wisp: 302B One Bedroom/One Bath
Interior
Suites at Silver Tree: A318 One Bedroom & Loft Standard View

Suites at Silver Tree: A318 One Bedroom & Loft Standard View

Oakland
10.0 out of 10, Exceptional, (2)
"We were comfortable and enjoyed our time at the suite with a loft. The only suggestion I would make is there needs to be more light/light fixtures in the main bedroom. There is only one bedside lamp. We hope to have the opportunity to stay here again in the future."
United States
Karen B.
The price is ￥45,466
￥58,387 total
includes taxes & fees
Dec 7 - Dec 8
Suites at Silver Tree: A318 One Bedroom & Loft Standard View
Interior
Suites at Silver Tree: A118 Studio Standard View

Suites at Silver Tree: A118 Studio Standard View

Oakland
10.0 out of 10, Exceptional, (1)
"Great place for a quick getaway ski trip to Wisp"
United States
William A.
The price is ￥32,326
￥41,602 total
includes taxes & fees
Nov 25 - Nov 26
Suites at Silver Tree: A118 Studio Standard View
Interior
Suites at Silver Tree: A126 One Bedroom Standard View

Suites at Silver Tree: A126 One Bedroom Standard View

Oakland
10.0 out of 10, Exceptional, (3)
"Very well maintained and managed. Right on the water with a wide variety of things to do@"
United States
Joe S.
The price is ￥32,134
￥41,385 total
includes taxes & fees
Nov 24 - Nov 25
Suites at Silver Tree: A126 One Bedroom Standard View
Interior
Suites at Silver Tree: A218 One Bedroom Standard View

Suites at Silver Tree: A218 One Bedroom Standard View

Oakland
10.0 out of 10, Exceptional, (2)
"Our one bedroom suite was clean and comfortably appointed, The lobby was beautiful and a lovely place to congregate. Staff were friendly."
United States
Ann Mahling
The price is ￥32,134
￥41,058 total
includes taxes & fees
Nov 16 - Nov 17
Suites at Silver Tree: A218 One Bedroom Standard View
Beach
Will O' The Wisp: 710H Studio Loft/One Bath

Will O' The Wisp: 710H Studio Loft/One Bath

Oakland
8.4 out of 10, Very Good, (6)
"Spiral staircase not for seniors. Difficult to come down spiral staircase at night to use bathroom. had to leave lights on downstairs to find way to bathroom at night as furniture on lower level placed too close to staircase to avoid possible hitting head when walking by or near staircase. Hallways narrow, hot and dark. Entry with code difficult at night and too many digits to enter in dark hallways without using phone flashlight. WiFi reception terrible. Could not make phone calls while in the...
United States
Jim M.
The price is ￥42,050
￥53,672 total
includes taxes & fees
Nov 16 - Nov 17
Will O' The Wisp: 710H Studio Loft/One Bath
Beach
Will O' The Wisp: 208B One Bedroom/One Bath

Will O' The Wisp: 208B One Bedroom/One Bath

Oakland
10.0 out of 10, Exceptional, (1)
"The property was spotless and had everything needed! View from the patio was relaxing and proximity to restaurants was so convenient!"
United States
Rebecca T.
The price is ￥47,122
￥60,764 total
includes taxes & fees
Dec 15 - Dec 16
Will O' The Wisp: 208B One Bedroom/One Bath
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

Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

10/10 Excellent
"Great with communication "
Lamar S. 3-night trip
Posted 11 days ago
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

Find out more about Oakland

Search for holiday rentals in Oakland on Expedia! You can easily find your home rentals, villas, holiday apartments in Oakland using one of the methods below:

  • View our selection of featured holiday rentals in Oakland
  • Use the map to find apartments and other holiday homes in the Oakland neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Oakland while they last

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

Frequently asked questions

Can I find vacation rentals in Oakland?

Yes, there are vacation rentals close to top points of interest in Oakland, or you can choose a more remote option if you'd like a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Oakland. Make sure you have time to check out the ski areas and ecotours during your trip.

What's the top vacation rental that Oakland has to offer?

Level lakefront, family-friendly, hot tub, low fees, private dock: This highly rated vacation home rental in Oakland 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 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. Our travelers also rate 3-bed, charming modernized cottage tucked into wooded hillside in Deep Creek, MD as a favorite home for rent in Oakland.

How many vacation rentals are there in Oakland?

With 517 Expedia vacation rentals, you're sure to find just the right place for your Oakland stay.

What’s there to see and do in Oakland?

Deep Creek Lake and Youghiogheny River are a couple of lovely local spots to get outside and enjoy nature. Herrington Manor State Park and Swallow Falls State Park are other places to visit while you're in town.

What’s a vacation rental in Oakland like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Oakland. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for family gatherings.