Photo by Jenn Charbonneau

Oakland Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday 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 place was so clean and fully stocked. We had a wonderful stay. Five stars!! "
United States
Lori S.
The price is HK$723
HK$2,682 total
includes taxes & fees
8 Dec - 9 Dec
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.
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)
"We were very pleased with our"
United States
Inna D.
The price is HK$887
HK$4,362 total
includes taxes & fees
14 Dec - 15 Dec
Cubs Den - Hot Tub- Walk to Lake-Fire Pit -Kayaks
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)
"The owner was awesome and made it so stress free and easy. There is lots to do nearby or the cabin is the perfect place to just relax and do nothing!"
United States
Melissa G.
Logged & Loaded Cabin! 9Min to WISP! Hot tub, fire pit! Pets! EV charger!
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 HK$856
HK$1,840 total
includes taxes & fees
30 Nov - 1 Dec
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, (11)
"Nothing negative to say. Beautiful place and friendly owner. Owner is accessible and very accommodating. "
United States
Sean
The price is HK$1,743
HK$5,671 total
includes taxes & fees
3 Dec - 4 Dec
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!
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)
"Place was absolutely gorgeous host was very accommodating. Can't say enough good things about it"
United States
Michael M.
The price is HK$1,464
HK$3,648 total
includes taxes & fees
25 Nov - 26 Nov
In the heart of Deep Creek Lake! - "Shamrock Inn"
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 HK$1,994
HK$4,741 total
includes taxes & fees
9 Dec - 10 Dec
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna
Fridge, microwave, oven, stovetop
That Special Place

That Special Place

Oakland
10.0 out of 10, Exceptional, (26)
"We enjoyed our stay, beautiful cabin with a lake view.Would highly recommend this place, the host was super responsive to any questions we had. Easy check in and out. Kitchen well equipped, overall great experience."
United States
Rosemary C.
The price is HK$1,394
HK$3,293 total
includes taxes & fees
30 Nov - 1 Dec
That Special Place
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 HK$1,600
HK$2,063 total
includes taxes & fees
25 Nov - 26 Nov
Suites at Silver Tree: A118 Studio Standard View
Interior
Suites at Silver Tree: A212 One Bedroom Standard View

Suites at Silver Tree: A212 One Bedroom Standard View

2.0 star property
Oakland
The price is HK$1,609
HK$2,074 total
includes taxes & fees
8 Dec - 9 Dec
Suites at Silver Tree: A212 One Bedroom Standard View
Beach
Will O' The Wisp: 306C One Bedroom/One Bath

Will O' The Wisp: 306C One Bedroom/One Bath

Oakland
9.8 out of 10, Exceptional, (14)
"Great condo for a quick weekend getaway!"
United States
Karen L.
The price is HK$1,922
HK$2,455 total
includes taxes & fees
28 Nov - 29 Nov
Will O' The Wisp: 306C One Bedroom/One Bath
Beach
Will O' The Wisp: 508G Two Bedroom/One Bath

Will O' The Wisp: 508G Two Bedroom/One Bath

Mountainside
8.0 out of 10, Very good, (1)
The price is HK$2,385
HK$3,040 total
includes taxes & fees
25 Nov - 26 Nov
Will O' The Wisp: 508G Two Bedroom/One Bath
Exterior
The winter is coming !!!

The winter is coming !!!

Oakland
9.8 out of 10, Exceptional, (47)
"Very easy to check in and out! Thank you! "
United States
Edward
The price is HK$1,394
HK$3,285 total
includes taxes & fees
15 Dec - 16 Dec
The winter is coming !!!
Terrace/patio
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!

Oakland
10.0 out of 10, Exceptional, (34)
"Great property, loved our stay here! We will definitely stay here again! "
United States
Shawnnelle H.
The price is HK$3,993
HK$8,282 total
includes taxes & fees
22 Dec - 23 Dec
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!
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 HK$1,940
HK$2,451 total
includes taxes & fees
25 Nov - 26 Nov
Will O' The Wisp: 302B One Bedroom/One Bath
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)
"Beautiful, clean and quiet"
United States
Howard L.
The price is HK$1,609
HK$2,074 total
includes taxes & fees
8 Dec - 9 Dec
Suites at Silver Tree: A126 One Bedroom Standard View
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 can’t wait to come back! It was a great stay!"
United States
Kari H.
The price is HK$2,028
HK$2,584 total
includes taxes & fees
30 Nov - 1 Dec
Suites at Silver Tree: A318 One Bedroom & Loft Standard View
Interior
Suites at Silver Tree: A124 Studio Standard View

Suites at Silver Tree: A124 Studio Standard View

2.0 star property
Oakland
The price is HK$1,609
HK$2,024 total
includes taxes & fees
8 Dec - 9 Dec
Suites at Silver Tree: A124 Studio 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 HK$1,609
HK$2,074 total
includes taxes & fees
8 Dec - 9 Dec
Suites at Silver Tree: A218 One Bedroom Standard View
Flat-screen TV, fireplace, video games, DVD player
Suites at Silver Tree: A204 Studio Standard View

Suites at Silver Tree: A204 Studio Standard View

Oakland
The price is HK$1,609
HK$2,074 total
includes taxes & fees
8 Dec - 9 Dec
Suites at Silver Tree: A204 Studio Standard View
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

The winter is coming !!!

The winter is coming !!!

10/10 Excellent
"Very easy to check in and out! Thank you! "
Edward 1-night trip
Posted 6 days ago
The winter is coming !!!

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 holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing 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 are some of the best holiday rentals that Oakland has to offer?

Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing : This highly rated holiday home rental in Oakland is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Our travellers also rate Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip as a favourite home for rent in Oakland.

How many holiday rentals are there in Oakland?

With 468 Expedia holiday rentals, you're guaranteed 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 holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.