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Our top choices for Oakland vacation homes

1. Captain's Quarters Deep Creek Log Cabin Oasis

Captain's Quarters Deep Creek Log Cabin Oasis
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was clean and comfortable. Keith was very responsive to messages and incredibly helpful. We especially enjoyed the massage chairs and the hot tub Looking forward to visiting again.."
United States
Brendan P.
The price is ¥24,984
¥54,968 total
includes taxes & fees
Nov 16 - Nov 17
Captain's Quarters Deep Creek Log Cabin Oasis

2. Dar's Deep Creek Log Cabin Timber Hideaway

Dar's Deep Creek Log Cabin Timber Hideaway
Oakland
The price is ¥34,412
¥70,472 total
includes taxes & fees
Nov 16 - Nov 17
Dar's Deep Creek Log Cabin Timber Hideaway

3. Pine Trees, Hot Tub & Game Room

Pine Trees, Hot Tub & Game Room
Oakland
10.0 out of 10, Exceptional, (49 reviews)
"My family loved the cabin! Perfect setting for a family weekend."
United States
Michael D.
The price is ¥32,566
¥79,748 total
includes taxes & fees
Nov 22 - Nov 23
Pine Trees, Hot Tub & Game Room

4. Pine Loom Lodge | Dog-Friendly | Hot Tub + TV | Game Room | Near Ski, Lake &Golf

Pine Loom Lodge | Dog-Friendly | Hot Tub + TV | Game Room | Near Ski, Lake &Golf
Oakland
10.0 out of 10, Exceptional, (9 reviews)
"The lodge was very cozy and had everything we could need during our stay. The beds were very comfortable "
United States
Paula P.
The price is ¥47,616
¥112,285 total
includes taxes & fees
Nov 30 - Dec 1
Pine Loom Lodge | Dog-Friendly | Hot Tub + TV | Game Room | Near Ski, Lake &Golf

5. Lakefront, Level Yard, Hot Tub & Dock

Lakefront, Level Yard, Hot Tub & Dock
Paradise Point
9.8 out of 10, Exceptional, (127 reviews)
"Cozy comfortable & clean house , super convenient to Wisp, yet private and quiet. "
United States
Tricia S.
The price is ¥42,283
¥95,389 total
includes taxes & fees
Nov 15 - Nov 16
Lakefront, Level Yard, Hot Tub & Dock

6. Newly Renovated Lakefront Home with Private Dock, Hot Tub & Beautiful Lake Views

Newly Renovated Lakefront Home with Private Dock, Hot Tub & Beautiful Lake Views
Oakland
The price is ¥59,614
¥147,654 total
includes taxes & fees
Nov 16 - Nov 17
Newly Renovated Lakefront Home with Private Dock, Hot Tub & Beautiful Lake Views

7. Gorgeous LakeFront: All-Seasons w/hottub

Gorgeous LakeFront: All-Seasons w/hottub
Oakland
9.4 out of 10, Exceptional, (3 reviews)
"EZ walk to lake, fenced yard for dog, master bed was firm, garage fun was awesome!"
United States
Mary W.
The price is ¥93,486
¥161,093 total
includes taxes & fees
Nov 22 - Nov 23
Gorgeous LakeFront: All-Seasons w/hottub

8. Hot Tub • Near Wisp & Lake • Private • Fire Pit • Pets & Kids

Hot Tub • Near Wisp & Lake • Private • Fire Pit • Pets & Kids
McHenry
9.8 out of 10, Exceptional, (6 reviews)
"The property was excellent. Clean and nicely decorated. Very pet-friendly. Warm and cozy "
United States
Jessica O.
The price is ¥16,285
¥64,011 total
includes taxes & fees
Nov 12 - Nov 13
Hot Tub • Near Wisp & Lake • Private • Fire Pit • Pets & Kids

9. Splash Mountain 6 bedrooms with indoor pool & mountain and filtered lake view

Splash Mountain 6 bedrooms with indoor pool & mountain and filtered lake view
Garrett County
10.0 out of 10, Exceptional, (1 review)
"The listing is accurate and complete"
United States
chuck w.
The price is ¥19,530
¥128,317 total
includes taxes & fees
Nov 16 - Nov 17
Splash Mountain 6 bedrooms with indoor pool & mountain and filtered lake view

10. Cozy Lake Access Home with Hot Tub

Cozy Lake Access Home with Hot Tub
McHenry
10.0 out of 10, Exceptional, (25 reviews)
"The property was perfect for three old guys wanting a place to stay for a few days of golfing."
United States
mark f.
The price is ¥21,284
¥72,362 total
includes taxes & fees
Nov 13 - Nov 14
Cozy Lake Access Home with Hot Tub

11. Wisp View Retreat, Hot tub

Wisp View Retreat, Hot tub
Accident
The price is ¥24,221
¥109,306 total
includes taxes & fees
Nov 15 - Nov 16
Wisp View Retreat, Hot tub

12. Dogs OK 5 Bedroom+2 Den Mansion w/ HOT TUB on top the mountain 7 min lake access

Dogs OK 5 Bedroom+2 Den Mansion w/ HOT TUB on top the mountain 7 min lake access
McHenry
10.0 out of 10, Exceptional, (14 reviews)
"This property was gorgeous and had everything that our large group needed!"
United States
Courtney V.
The price is ¥37,866
¥152,449 total
includes taxes & fees
Nov 29 - Nov 30
Dogs OK 5 Bedroom+2 Den Mansion w/ HOT TUB on top the mountain 7 min lake access

13. Lake Access, Hot Tub, Sleeps 12

Lake Access, Hot Tub, Sleeps 12
Swanton
10.0 out of 10, Exceptional, (25 reviews)
"Very neatly kept house….beautiful and cozy place to spend the vacation…Amazing property and amazing host. "
United States
Harsh S.
The price is ¥36,825
¥110,839 total
includes taxes & fees
Nov 30 - Dec 1
Lake Access, Hot Tub, Sleeps 12

14. 5BR | Fireplace | Deck | Game Room

5BR | Fireplace | Deck | Game Room
McHenry
10.0 out of 10, Exceptional, (13 reviews)
"Excellent location and property. Had everything we needed, and the owner was more than accommodating. Thank you "
United States
Derek D.
The price is ¥43,489
¥104,815 total
includes taxes & fees
Nov 12 - Nov 13
5BR | Fireplace | Deck | Game Room

15. #1 Cabin~Walk to WISP! Lake access & dock! HOT Tub~Game room~Fire Pit & DOGS OK!

#1 Cabin~Walk to WISP! Lake access & dock! HOT Tub~Game room~Fire Pit & DOGS OK!
McHenry
9.8 out of 10, Exceptional, (39 reviews)
"Our family of 4 stayed for 4 nights and we were very impressed with how clean the home was. Communication with the host was easy and quick. Would stay with this host again!"
United States
John K.
The price is ¥39,569
¥106,549 total
includes taxes & fees
Nov 16 - Nov 17
#1 Cabin~Walk to WISP! Lake access & dock! HOT Tub~Game room~Fire Pit & DOGS OK!

16. Lake House: Lake View, Hot Tub, Dock, Wisp

Lake House: Lake View, Hot Tub, Dock, Wisp
Garrett County
The price is ¥62,885
¥128,908 total
includes taxes & fees
Nov 24 - Nov 25
Lake House: Lake View, Hot Tub, Dock, Wisp

17. Cozy Sunlit Mountain Loft near Blackwater Falls and Canaan Valley in Davis, WV

Cozy Sunlit Mountain Loft near Blackwater Falls and Canaan Valley in Davis, WV
Davis
9.6 out of 10, Exceptional, (70 reviews)
"Great location - is within walking distance of the very cute downtown area."
United States
Laurie L.
The price is ¥14,285
¥36,769 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Sunlit Mountain Loft near Blackwater Falls and Canaan Valley in Davis, WV

18. Paddle Point Retreat - Mountain & Lake Views - Fire Pit

Paddle Point Retreat - Mountain & Lake Views - Fire Pit
McHenry
The price is ¥46,426
¥51,567 total
includes taxes & fees
Nov 12 - Nov 13
Paddle Point Retreat - Mountain & Lake Views - Fire Pit

19. 4BR Mountain Retreat on 2+ Private Acres • Near Lake • Hot Tub • Mountain Views

4BR Mountain Retreat on 2+ Private Acres • Near Lake • Hot Tub • Mountain Views
McHenry
8.0 out of 10, Very good, (1 review)
"Very nice and very quiet and private. Was very enjoyable. Some improvements needed are upstairs full bathroom, sink is clogged and other sink has no water. The dishwater doesn’t work real well or stove. I would recommend staying there. Also we ran out of gas for the barbecue grill"
United States
Rebekah G.
The price is ¥42,061
¥94,048 total
includes taxes & fees
Nov 16 - Nov 17
4BR Mountain Retreat on 2+ Private Acres • Near Lake • Hot Tub • Mountain Views

20. New Private 2bd 1 ba, Hot tub, Trails, Waterfront!

New Private 2bd 1 ba, Hot tub, Trails, Waterfront!
Friendsville
The price is ¥26,982
¥74,163 total
includes taxes & fees
Nov 12 - Nov 13
New Private 2bd 1 ba, Hot tub, Trails, Waterfront!
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.

Learn more about Oakland

Nestled beside Deep Creek Lake, this mountain town offers year-round adventures from skiing to kayaking. Explore the historic downtown where local shops and farm-to-table restaurants welcome you in hiking boots after a day outdoors.

A waterfall cascading over rocks in a forested area.

Top reviews in Oakland