A river flowing through a forest with a waterfall.

Search Vacation Homes in Oakland

  • 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 homes

A wooden deck with Adirondack chairs, a sign reading 'WELCOME TO OUR PORT,' and a forested background.

1. Charming 4BR Home - HOT TUB - Oakland

Charming 4BR Home - HOT TUB - Oakland
Oakland
9.8 out of 10, Exceptional, (16 reviews)
"Property was great. The kids loved the layout outside. The fireplace was awesome. Great place to stay."
United States
Steven P.
The price is ￥21,322
￥85,977 total
includes taxes & fees
Oct 29 - Oct 30
Charming 4BR Home - HOT TUB - Oakland
A wooden deck with a railing overlooking a lake, with chairs and cushions.

2. Serene 3BR Lodge - THE Lake View - Oakland

Serene 3BR Lodge - THE Lake View - Oakland
Oakland
10.0 out of 10, Exceptional, (3 reviews)
"We thoroughly enjoyed our stay. Everything was comfortable and relaxing. My only suggestion would be to label the lights. Especially in the kitchen. Other than that, we loved it and would love to come back."
United States
Patti R.
The price is ￥31,737
￥94,643 total
includes taxes & fees
Oct 7 - Oct 8
Serene 3BR Lodge - THE Lake View - Oakland
A deck with a table and chairs, overlooking a lake and autumn foliage.

3. Private Lodge sleeps 31 guests Spectacular Views

Private Lodge sleeps 31 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 ￥159,034
￥304,273 total
includes taxes & fees
Oct 5 - Oct 6
Private Lodge sleeps 31 guests Spectacular Views
89886548 2aec 4dd9 870a 57edd6aad0b5

4. *Millstone Cottage w/Lake & Pool access, Wi-Fi

*Millstone Cottage w/Lake & Pool access, Wi-Fi
Preston County
8.8 out of 10, Excellent, (3 reviews)
"My husband and I loved our stay here for our 20th wedding anniversary! Would absolutely stay again "
United States
Melissa P.
The price is ￥27,802
￥34,987 total
includes taxes & fees
Oct 12 - Oct 13
*Millstone Cottage w/Lake & Pool access, Wi-Fi
A foosball table in a room with a patterned curtain and various boxes and items in the background.

5. Glendale Getaway: Nostalgic not Fancy

Glendale Getaway: Nostalgic not Fancy
Swanton
The price is ￥17,048
￥38,651 total
includes taxes & fees
Oct 5 - Oct 6
Glendale Getaway: Nostalgic not Fancy
A covered porch with wooden chairs and a table, overlooking a forested area.

6. Rustic 3BR Cabin - HOT TUB - McHenry

Rustic 3BR Cabin - HOT TUB - McHenry
McHenry
9.8 out of 10, Exceptional, (61 reviews)
"Great place and comfortable beds. We would definitely book again!"
United States
Ashley C.
The price is ￥27,232
￥89,829 total
includes taxes & fees
Oct 15 - Oct 16
Rustic 3BR Cabin - HOT TUB - McHenry
An indoor swimming pool with clear lanes, a lifeguard chair, and a high ceiling with visible structural beams.

7. Wisp View Retreat, Hot tub

Wisp View Retreat, Hot tub
Accident
The price is ￥23,993
￥114,125 total
includes taxes & fees
Oct 5 - Oct 6
Wisp View Retreat, Hot tub
A spacious living room with a fireplace, comfortable seating, and large windows.

8. Hot Tub Lakehouse! Game Room + Fire Pit! Walk to Lake! 15 Min to Wisp!

Hot Tub Lakehouse! Game Room + Fire Pit! Walk to Lake! 15 Min to Wisp!
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 ￥33,925
￥112,176 total
includes taxes & fees
Oct 12 - Oct 13
Hot Tub Lakehouse! Game Room + Fire Pit! Walk to Lake! 15 Min to Wisp!
A spacious living area with a stone fireplace, wooden ceiling, and a dining table with chairs.

9. Cozy Lake Access Home with Hot Tub

Cozy Lake Access Home with Hot Tub
McHenry
10.0 out of 10, Exceptional, (21 reviews)
"Location and floorspace was perfect for our ski trip "
United States
Todd M.
The price is ￥23,520
￥78,641 total
includes taxes & fees
Oct 26 - Oct 27
Cozy Lake Access Home with Hot Tub
A wooden dining area with a large table and chairs, large windows, and hanging pendant lights.

10. 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.
Splash Mountain 6 bedrooms with indoor pool & mountain and filtered lake view
A wooden cabin with a balcony, surrounded by a lush green forest.

11. Rustic 4BR Cabin - HOT TUB - McHenry

Rustic 4BR Cabin - HOT TUB - McHenry
McHenry
9.6 out of 10, Exceptional, (77 reviews)
"Place is great! Family loved it! Great location close enough to eveeyrhing there is to do."
United States
Jerome and Adrienne H.
The price is ￥31,971
￥99,457 total
includes taxes & fees
Oct 12 - Oct 13
Rustic 4BR Cabin - HOT TUB - McHenry
A small house with a wooden exterior, a dark roof, and a lit front door.

12. 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, (61 reviews)
"Very cozy . Parking right in front of property.Just perfect for two adults. Very close to Blackwater Fall State Park."
United States
Patti
The price is ￥12,628
￥36,132 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Sunlit Mountain Loft near Blackwater Falls and Canaan Valley in Davis, WV
A cozy living room with a stone fireplace, a television, and a large window overlooking greenery.

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

Lake House: Lake View, Hot Tub, Dock, Wisp
Garrett County
The price is ￥52,976
￥123,282 total
includes taxes & fees
Oct 7 - Oct 8
Lake House: Lake View, Hot Tub, Dock, Wisp
A modern living room with a black sectional sofa, a dining area with white chairs, and a kitchen with white cabinets and stainless steel appliances.

14. The Fox Den, 2 bdrm, walk to Purple Fiddle, near Canaan, Davis, Blackwater Falls

The Fox Den, 2 bdrm, walk to Purple Fiddle, near Canaan, Davis, Blackwater Falls
Thomas
10.0 out of 10, Exceptional, (45 reviews)
"Beautiful property tucked in town. Parking was easy and the place was brand new and extremely clean."
United States
Jonathan P.
The price is ￥20,315
￥45,596 total
includes taxes & fees
Oct 12 - Oct 13
The Fox Den, 2 bdrm, walk to Purple Fiddle, near Canaan, Davis, Blackwater Falls
MBR with queen and full bath. Balcony.

15. Davis, WV 2BR full kitchen NR Stumptown Ales

Davis, WV 2BR full kitchen NR Stumptown Ales
Davis
10.0 out of 10, Exceptional, (135 reviews)
"Great place to stay while visiting the Davis WV area. Plenty of room, clean and comfortable, and well stocked kitchen. Very close to shops and restaurants and grocery store. Would definitely stay at this property again while visiting the area."
United States
Karen E.
The price is ￥25,730
￥54,318 total
includes taxes & fees
Nov 2 - Nov 3
Davis, WV 2BR full kitchen NR Stumptown Ales
A row of colorful brick buildings with various storefronts, including a shop named 'Riverfront Antiques'.

16. 2BR/1BA Cozy Retreat near Timberline slopes

2BR/1BA Cozy Retreat near Timberline slopes
Davis
10.0 out of 10, Exceptional, (46 reviews)
"Very nice stay. Overall very clean. Close to the town and walkable distance to restaurants."
United States
Emily
2BR/1BA Cozy Retreat near Timberline slopes
A spacious living room with a large sectional sofa, a fireplace, and a balcony with a view of the outdoors.

17. 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 ￥45,934
￥103,404 total
includes taxes & fees
Oct 5 - Oct 6
4BR Mountain Retreat on 2+ Private Acres • Near Lake • Hot Tub • Mountain Views
A modern kitchen with white cabinets, a stainless steel refrigerator, and two white chairs.

18. 1BR Tiny Home in Thomas, NR Purple Fiddle

1BR Tiny Home in Thomas, NR Purple Fiddle
Thomas
9.6 out of 10, Exceptional, (79 reviews)
"Thanks for a great stay!"
United States
Tom R.
1BR Tiny Home in Thomas, NR Purple Fiddle
A spa area with a hot tub, a waterfall feature, and a stone wall with greenery.

19. New! Epic lakefront home with indoor pool!

New! Epic lakefront home with indoor pool!
McHenry
9.8 out of 10, Exceptional, (13 reviews)
"Welcoming and fantastic amenities!"
United States
Vincent M.
The price is ￥120,755
￥308,764 total
includes taxes & fees
Oct 5 - Oct 6
New! Epic lakefront home with indoor pool!
A modern kitchen with white cabinets, a dishwasher, and a dining area with a round table and chairs.

20. Renovated 2bd 1ba Waterfront, Hottub, Trails!

Renovated 2bd 1ba Waterfront, Hottub, Trails!
Friendsville
The price is ￥26,835
￥75,724 total
includes taxes & fees
Oct 5 - Oct 6
Renovated 2bd 1ba Waterfront, Hottub, Trails!
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 4 days ago
Dog Friendly Cabin in the Woods, Hot Tub & Firepit

Find out more about Oakland

Oakland Vacation Homes information

Number of reviews
573
Accommodation
491 Vacation Homes
Lowest Price
￥34,987
Highest Price
￥308,764