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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Oakland holiday homes

A dock with boats, a clear sky, and a forested hill in the background.

1. Rustic 3BR Farmhouse - Fire Pit- Oakland

Rustic 3BR Farmhouse - Fire Pit- Oakland
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"Everything was excellent,but I would update the description because the house does have AC.(Which was a blessing on a hot,humid day in August!) Definitely will come back."
United States
Steve D.
Rustic 3BR Farmhouse - Fire Pit- Oakland
A deck with a table and chairs, overlooking a lake and autumn foliage.

2. 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 HK$7,907
HK$15,277 total
includes taxes & fees
13 Oct - 14 Oct
Private Lodge sleeps 31 guests Spectacular Views
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3. *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 HK$1,382
HK$1,748 total
includes taxes & fees
12 Oct - 13 Oct
*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.

4. Glendale Getaway: Nostalgic not Fancy

Glendale Getaway: Nostalgic not Fancy
Swanton
The price is HK$848
HK$1,922 total
includes taxes & fees
22 Oct - 23 Oct
Glendale Getaway: Nostalgic not Fancy
A dock with boats, a clear sky, and a forested hill in the background.

5. 2BR - Cozy - Lakefront - Hot Tub

2BR - Cozy - Lakefront - Hot Tub
McHenry
The price is HK$833
HK$3,064 total
includes taxes & fees
19 Oct - 20 Oct
2BR - Cozy - Lakefront - Hot Tub
An indoor swimming pool with clear lanes, a lifeguard chair, and a high ceiling with visible structural beams.

6. Wisp View Retreat, Hot tub

Wisp View Retreat, Hot tub
Accident
The price is HK$1,193
HK$5,674 total
includes taxes & fees
12 Oct - 13 Oct
Wisp View Retreat, Hot tub
A spacious living area with a stone fireplace, wooden ceiling, and a dining table with chairs.

7. Cozy Lake Access Home with Hot Tub

Cozy Lake Access Home with Hot Tub
McHenry
10.0 out of 10, Exceptional, (22 reviews)
The price is HK$1,130
HK$3,835 total
includes taxes & fees
14 Oct - 15 Oct
Cozy Lake Access Home with Hot Tub
A two-story house with a balcony, a stone chimney, and a bear statue in the yard.

8. Deep Creek Lakehouse: Hot Tub, Game Room, Fire Pit

Deep Creek Lakehouse: Hot Tub, Game Room, Fire Pit
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 HK$1,687
HK$5,577 total
includes taxes & fees
21 Oct - 22 Oct
Deep Creek Lakehouse: Hot Tub, Game Room, Fire Pit
A small house with a wooden exterior, a dark roof, and a lit front door.

9. 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, (63 reviews)
The price is HK$636
HK$1,805 total
includes taxes & fees
2 Nov - 3 Nov
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.

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

Lake House: Lake View, Hot Tub, Dock, Wisp
Garrett County
Lake House: Lake View, Hot Tub, Dock, Wisp
A spacious living room with a large sectional sofa, a fireplace, and a balcony with a view of the outdoors.

11. 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 HK$2,386
HK$5,266 total
includes taxes & fees
9 Nov - 10 Nov
4BR Mountain Retreat on 2+ Private Acres • Near Lake • Hot Tub • Mountain Views
A spa area with a hot tub, a waterfall feature, and a stone wall with greenery.

12. New! Epic lakefront home with indoor pool!

New! Epic lakefront home with indoor pool!
McHenry
9.8 out of 10, Exceptional, (13 reviews)
The price is HK$4,944
HK$13,977 total
includes taxes & fees
18 Oct - 19 Oct
New! Epic lakefront home with indoor pool!
A covered porch with a wooden deck, two wicker chairs, and a decorative fence.

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

New Private 2bd 1 ba, Hot tub, Trails, Waterfront!
Friendsville
The price is HK$1,334
HK$3,883 total
includes taxes & fees
12 Oct - 13 Oct
New Private 2bd 1 ba, Hot tub, Trails, Waterfront!
A modern kitchen with white cabinets, a dishwasher, and a dining area with a round table and chairs.

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

Renovated 2bd 1ba Waterfront, Hottub, Trails!
Friendsville
The price is HK$1,334
HK$3,790 total
includes taxes & fees
12 Oct - 13 Oct
Renovated 2bd 1ba Waterfront, Hottub, Trails!
A bunk bed room with a wooden floor, a small bedside table, and a window with blinds.

15. Cozy family friendly hilltop chalet in Thomas

Cozy family friendly hilltop chalet in Thomas
Thomas
The price is HK$1,099
HK$2,959 total
includes taxes & fees
19 Oct - 20 Oct
Cozy family friendly hilltop chalet in Thomas
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.

16. 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 HK$1,547
HK$2,978 total
includes taxes & fees
12 Oct - 13 Oct
The Fox Den, 2 bdrm, walk to Purple Fiddle, near Canaan, Davis, Blackwater Falls
Interior

17. Stone's Throw Cabin moments away from the best of the Laurel Highlands!

Stone's Throw Cabin moments away from the best of the Laurel Highlands!
Confluence
10.0 out of 10, Exceptional, (37 reviews)
"Great location and vibe!"
United States
Pedro R.
The price is HK$939
HK$1,209 total
includes taxes & fees
11 Oct - 12 Oct
Stone's Throw Cabin moments away from the best of the Laurel Highlands!
A compact kitchen with a stove, microwave, sink, and a refrigerator.

18. MOUNTAIN VIEW HOUSE, 2-minute walk to downtown

MOUNTAIN VIEW HOUSE, 2-minute walk to downtown
Davis
10.0 out of 10, Exceptional, (18 reviews)
"Clean, quaint, and the hosts are super hospitable!"
United States
Maggie M.
The price is HK$1,151
HK$3,028 total
includes taxes & fees
19 Oct - 20 Oct
MOUNTAIN VIEW HOUSE, 2-minute walk to downtown
Living area

19. 8BR Water View - Huge Gameroom - Hot Tub 6 acres

8BR Water View - Huge Gameroom - Hot Tub 6 acres
Waterfront Greens
9.4 out of 10, Exceptional, (3 reviews)
"What a wonderful time we had for a holiday family vacation at this home. Everything was immaculately clean and there were many things provided in the kitchen (plateware, cookware, etc.) and bathrooms (towels, shampoo, body wash). We had everything we needed and more. The rooms were each nicely decorated and cozy. We loved the open living room area and kitchen/dining space. It snowed on our last day and it truly felt magical. The host was responsive and easy to communicate with. Thank you!"
United States
Annie
The price is HK$7,990
HK$14,540 total
includes taxes & fees
17 Oct - 18 Oct
8BR Water View - Huge Gameroom - Hot Tub 6 acres
MBR with queen and full bath. Balcony.

20. 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)
"The property was well kept and had all of the amenities we needed including en suite bathrooms for both bedrooms. The location is wonderful and gives easy access to walking around Davis."
United States
Rachel M.
The price is HK$2,252
HK$3,982 total
includes taxes & fees
15 Oct - 16 Oct
Davis, WV 2BR full kitchen NR Stumptown Ales
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

AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table, NEW FIRE PIT

AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table, NEW FIRE PIT

10/10 Excellent
"Second time staying"
Kristin c. 4-night trip
Posted 4 days ago
AMAZING LAKE FRONT 7 BR Home, Hot Tub, Fire Pit, Dock, Pool Table, NEW FIRE PIT

Find out more about Oakland

Oakland Vacation Homes information

Number of reviews
366
Accommodation
491 Vacation Homes
Lowest Price
HK$1,209
Highest Price
HK$15,277

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