A river flowing through a forest with a waterfall.

Oakland Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Oakland vacation rentals

A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

1. Suites at Silver Tree: A115 One Bedroom Lake View

Suites at Silver Tree: A115 One Bedroom Lake View
Oakland
10.0 out of 10, Exceptional, (1 review)
"Loved the location and Dutches Restaurant was top notch."
United States
Angela
The price is ￥35,691
￥45,527 total
includes taxes & fees
Oct 4 - Oct 5
Suites at Silver Tree: A115 One Bedroom Lake View
A wooden staircase leading to a covered porch with a view of the sky and clouds.

2. Enjoyable 2-bedroom apartment in lovely Oakland near local hotspots

Enjoyable 2-bedroom apartment in lovely Oakland near local hotspots
Oakland
9.0 out of 10, Wonderful, (2 reviews)
"The apartment is the main floor of an old home. It is located very close to downtown/historic Oakland. All the rooms are very spacious and minimalist aesthetic. It was a great base for our Garret County adventure. We were a party of 3. But a floor mattress makes it possible for a 4th. I only recommend bringing you own drinking water."
United States
Anne H.
The price is ￥26,606
￥46,058 total
includes taxes & fees
Oct 8 - Oct 9
Enjoyable 2-bedroom apartment in lovely Oakland near local hotspots
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

3. Suites at Silver Tree: A118 Studio Standard View

Suites at Silver Tree: A118 Studio Standard View
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"The hospitality was great."
United States
Mark
The price is ￥31,636
￥40,405 total
includes taxes & fees
Oct 8 - Oct 9
Suites at Silver Tree: A118 Studio Standard View
A log cabin interior with a wooden staircase, a living area with two sofas, a coffee table, and a dining area with a table and chairs.

4. The winter is coming !!!

The winter is coming !!!
Oakland
9.8 out of 10, Exceptional, (70 reviews)
"For those that like indoor entertainment and relaxation, this place is for you. There is air hockey, a video game machine, hot tub and tv in every room. The hot tub and air hockey is in an enclosed room off the living room so no worry about chlorine smells in the home. The video game Pac-Man is in the loft. You can relax by the fireplace place in the super comfy couches or sit on the porch swing and watch the deer or ground hogs walking by in the side yard."
United States
Shere
The price is ￥28,196
￥69,104 total
includes taxes & fees
Oct 5 - Oct 6
The winter is coming !!!
Exterior

5. Will O' The Wisp: 105A Efficiency/One Bath

Will O' The Wisp: 105A Efficiency/One Bath
Oakland
9.6 out of 10, Exceptional, (25 reviews)
"would stay again!"
United States
Patrick B.
The price is ￥35,203
￥45,304 total
includes taxes & fees
Oct 28 - Oct 29
Will O' The Wisp: 105A Efficiency/One Bath
A cabin with a deck and a fire pit in the foreground.

6. Deer Pass – Luxury Glamping Yurt Near Deep CreekMd

Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
Oakland
10.0 out of 10, Exceptional, (11 reviews)
"Great getaway"
United States
Holly M.
The price is ￥18,892
￥39,169 total
includes taxes & fees
Oct 4 - Oct 5
Deer Pass – Luxury Glamping Yurt Near Deep CreekMd
A cozy cabin interior with a stone fireplace, leather furniture, and large windows offering a view of the outdoors.

7. HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee

HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee
Oakland
10.0 out of 10, Exceptional, (48 reviews)
"The property and house were very inviting beautiful loved the area The house was very clean and the host was wonderful "
United States
Tessie R.
The price is ￥34,134
￥98,467 total
includes taxes & fees
Oct 4 - Oct 5
HotTub-FirePit-8MintoWisp-Arcade-4BD-NoCleaningFee
Exterior

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

Will O' The Wisp: 508G Two Bedroom/One Bath
Mountainside
8.8 out of 10, Excellent, (3 reviews)
"The unit had everything we needed for a weekend getaway. Kitchen was well stocked and clean. Comfortable beds. Lots of handy hooks and cubbies. Nice view. Two restaurants on site were very good. Very close to state park, wisp resort, stores, and restaurants."
United States
Carol
The price is ￥44,704
￥57,472 total
includes taxes & fees
Oct 2 - Oct 3
Will O' The Wisp: 508G Two Bedroom/One Bath
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

9. Suites at Silver Tree: A212 One Bedroom Standard View

Suites at Silver Tree: A212 One Bedroom Standard View
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"Would recommend!"
United States
Erin C.
The price is ￥33,438
￥42,958 total
includes taxes & fees
Oct 5 - Oct 6
Suites at Silver Tree: A212 One Bedroom Standard View
A spacious kitchen with a large island, white cabinets, and a stone backsplash.

10. Bray Run Vista | Dam View Retreat, Dam View Vista-Lake View-King Beds With Luxury Linens-Close to Sw...

Bray Run Vista | Dam View Retreat, Dam View Vista-Lake View-King Beds With Luxury Linens-Close to Sw...
Oakland
9.2 out of 10, Wonderful, (9 reviews)
"I give this rental 5 stars — 10/10! The host was very responsive and great to communicate with. I would definitely stay again."
United States
Ya’Digg C.
The price is ￥31,486
￥84,930 total
includes taxes & fees
Oct 4 - Oct 5
Bray Run Vista | Dam View Retreat, Dam View Vista-Lake View-King Beds With Luxury Linens-Close to Sw...
A balcony with a glass table and two chairs, overlooking a marina with boats and a lake.

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

Will O' The Wisp: 302B One Bedroom/One Bath
Oakland
10.0 out of 10, Exceptional, (1 review)
"Everything was very clean and comfortable."
United States
Cheryl W.
The price is ￥36,233
￥46,645 total
includes taxes & fees
Oct 28 - Oct 29
Will O' The Wisp: 302B One Bedroom/One Bath
A spacious cabin with a large living area, wooden floors, and a kitchen with stone accents.

12. Log chalet w/ hot tub & BBQ grill

Log chalet w/ hot tub & BBQ grill
Oakland
9.4 out of 10, Exceptional, (3 reviews)
"Thank you SO MUCH for hosting us! The house was beautiful!! It was very convenient to everything we needed! We found the kitchen to be well stocked to cook in! The gameroom kept the kids very entertained, and the hot tub was well maintained and clean! Tony was great at communication and was very quick to reply! We would definitely stay here again!!!"
United States
Jennifer M.
The price is ￥47,350
￥114,903 total
includes taxes & fees
Oct 4 - Oct 5
Log chalet w/ hot tub & BBQ grill
A spacious living area with a stone fireplace, wooden beams, a staircase, and a view of a lake.

13. Suites at Silver Tree: A124 Studio Standard View

Suites at Silver Tree: A124 Studio Standard View
Oakland
8.0 out of 10, Very good, (2 reviews)
"The room was perfect!! No complaints here! Will definitely come back and stay"
United States
Lisa G.
The price is ￥31,815
￥40,609 total
includes taxes & fees
Oct 4 - Oct 5
Suites at Silver Tree: A124 Studio Standard View
A log cabin interior with a fireplace, wooden walls, a sofa, a coffee table, and a dining area.

14. Luxury Deep Creek Lake Cabin • Sauna • Hot Tub • Arcade • Fire Pit •Pet Friendly

Luxury Deep Creek Lake Cabin • Sauna • Hot Tub • Arcade • Fire Pit •Pet Friendly
Oakland
10.0 out of 10, Exceptional, (4 reviews)
"Wonderful host!!"
United States
Alex M.
The price is ￥53,558
￥126,160 total
includes taxes & fees
Oct 8 - Oct 9
Luxury Deep Creek Lake Cabin • Sauna • Hot Tub • Arcade • Fire Pit •Pet Friendly
A deck with a table and chairs, overlooking a lake and autumn foliage.

15. Private Lodge sleeps 25 guests Spectacular Views

Private Lodge sleeps 25 guests Spectacular Views
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"Our group had a wonderful time - the home is beautiful and perfect for a large group. The setting and view is perfect. The home was very clean and the host was quick to get maintenance to fix the hot tub. We hope to be back!"
United States
Jocelyn M.
The price is ￥158,611
￥306,468 total
includes taxes & fees
Oct 4 - Oct 5
Private Lodge sleeps 25 guests Spectacular Views
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

16. Suites at Silver Tree: A114 One Bedroom Standard View

Suites at Silver Tree: A114 One Bedroom Standard View
Oakland
10.0 out of 10, Exceptional, (1 review)
"Clean, friendly, beautiful."
United States
Cristian
The price is ￥32,446
￥41,495 total
includes taxes & fees
Oct 4 - Oct 5
Suites at Silver Tree: A114 One Bedroom Standard View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

17. Suites at Silver Tree: A210 Studio Standard View

Suites at Silver Tree: A210 Studio Standard View
Oakland
9.6 out of 10, Exceptional, (5 reviews)
"We loved everything about this property. The only thing I would make diferent is to have a breakfast menu available for your guest."
United States
Darlene
The price is ￥31,815
￥40,609 total
includes taxes & fees
Oct 3 - Oct 4
Suites at Silver Tree: A210 Studio Standard View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

18. 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, (6 reviews)
"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 ￥33,438
￥42,624 total
includes taxes & fees
Oct 4 - Oct 5
Suites at Silver Tree: A218 One Bedroom Standard View
A spacious lobby with a stone fireplace, wooden beams, and a high ceiling.

19. Suites at Silver Tree: A309 Studio & Loft Lake View

Suites at Silver Tree: A309 Studio & Loft Lake View
Oakland
10.0 out of 10, Exceptional, (1 review)
The price is ￥41,640
￥53,143 total
includes taxes & fees
Oct 4 - Oct 5
Suites at Silver Tree: A309 Studio & Loft Lake View
A spacious living room with a large sectional sofa, a round coffee table with a plant, and a sliding glass door leading to a deck.

20. Swings, Lakeview A-frame + Hot Tub, 120” screen

Swings, Lakeview A-frame + Hot Tub, 120” screen
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"Place was very clean and tidy upon arrival! Would rent here again "
United States
Tyrone C.
The price is ￥51,829
￥124,692 total
includes taxes & fees
Oct 26 - Oct 27
Swings, Lakeview A-frame + Hot Tub, 120” screen
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oakland Hotel Reviews

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

10/10 Excellent
"Perfect location- close to hiking, pizza, and ice cream but privatly nestled into the woods. The house was very comfortable and the spiral staircase was so charming. The hot tub was, by far, the nicest and best of any place I have rented. We are already talking about coming back to this area and will 100% see if this house is available when we do. The host was fantastic- we had 1 very minor glitch with the porch light and she responded immediately and got it working."
Angie B. 2-night trip
Posted 1 day ago
Dog Friendly Cabin in the Woods, Hot Tub & Firepit

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?

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,: This highly rated vacation home rental in Oakland offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other top choices in Oakland are Lakefront/Dock/Amazing views HotTub and Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp.

How many vacation rentals are there in Oakland?

With 465 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.