A forested landscape with a waterfall.

Holiday Homes in Oakland

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Oakland holiday 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.
Charming 4BR Home - HOT TUB - 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 AU$2,432
includes taxes & fees
21 Oct - 22 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 AU$321
includes taxes & fees
16 Oct - 17 Oct
*Millstone Cottage w/Lake & Pool access, Wi-Fi
Exterior detail

4. Lake & Ski- Pets & Kids - Secluded

Lake & Ski- Pets & Kids - Secluded
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 AU$525
includes taxes & fees
26 Oct - 27 Oct
Lake & Ski- Pets & Kids - Secluded
A living room with a fireplace, a television, and a sofa.

5. Lakeside & Slopeside

Lakeside & Slopeside
McHenry
9.2 out of 10, Wonderful, (7 reviews)
The price is AU$679
includes taxes & fees
16 Oct - 17 Oct
Lakeside & Slopeside
A foosball table in a room with a patterned curtain and various boxes and items in the background.

6. Glendale Getaway: Nostalgic not Fancy

Glendale Getaway: Nostalgic not Fancy
Swanton
The price is AU$352
includes taxes & fees
22 Oct - 23 Oct
Glendale Getaway: Nostalgic not Fancy
A stone building with a wooden deck and a chimney.

7. Rustic 3BR Cabin - HOT TUB - Lake View - Oakland

Rustic 3BR Cabin - HOT TUB - Lake View - Oakland
Oakland
10.0 out of 10, Exceptional, (1 review)
"Nice quiet location near the water! Would stay here again."
United States
Katy D.
Rustic 3BR Cabin - HOT TUB - Lake View - Oakland
A spacious living room with a wooden ceiling, a fireplace, a large window overlooking Deep Creek Lake, and a television.

8. 5BR - Chalet - Hot Tub

5BR - Chalet - Hot Tub
McHenry
5BR - Chalet - Hot Tub
A dock with boats, a clear sky, and a forested hill in the background.

9. 2BR - Cozy - Lakefront - Hot Tub

2BR - Cozy - Lakefront - Hot Tub
McHenry
The price is AU$546
includes taxes & fees
19 Oct - 20 Oct
2BR - Cozy - Lakefront - Hot Tub
A campsite with a fire pit, benches, and a grassy area with trees in the background.

10. Charming 4BR Lodge - HOT TUB - Swanton

Charming 4BR Lodge - HOT TUB - Swanton
Swanton
The price is AU$799
includes taxes & fees
26 Oct - 27 Oct
Charming 4BR Lodge - HOT TUB - Swanton
An indoor swimming pool with clear lanes, a lifeguard chair, and a high ceiling with visible structural beams.

11. Wisp View Retreat, Hot tub

Wisp View Retreat, Hot tub
Accident
The price is AU$998
includes taxes & fees
28 Oct - 29 Oct
Wisp View Retreat, Hot tub
A spacious living area with a stone fireplace, wooden ceiling, and a dining table with chairs.

12. Cozy Lake Access Home with Hot Tub

Cozy Lake Access Home with Hot Tub
McHenry
10.0 out of 10, Exceptional, (22 reviews)
"A very nice place to stay. The area is also very beautiful. Could definitely see us coming back for an extended stay."
United States
Cody S.
The price is AU$689
includes taxes & fees
21 Oct - 22 Oct
Cozy Lake Access Home with Hot Tub
A road curving to the right with a sign for 'The Pinnacle' hotel.

13. 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 AU$1,027
includes taxes & fees
19 Oct - 20 Oct
Deep Creek Lakehouse: Hot Tub, Game Room, Fire Pit
A cozy living room with a stone fireplace, a television, and a large window overlooking greenery.

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

Lake House: Lake View, Hot Tub, Dock, Wisp
Garrett County
The price is AU$1,082
includes taxes & fees
25 Oct - 26 Oct
Lake House: Lake View, Hot Tub, Dock, Wisp
A small house with a wooden exterior, a dark roof, and a lit front door.

15. 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, (64 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 AU$372
includes taxes & fees
21 Oct - 22 Oct
Cozy Sunlit Mountain Loft near Blackwater Falls and Canaan Valley in Davis, WV
A spacious living room with a large sectional sofa, a fireplace, and a balcony with a view of the outdoors.

16. 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 AU$952
includes taxes & fees
5 Nov - 6 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.

17. 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 AU$2,455
includes taxes & fees
27 Oct - 28 Oct
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.

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

Renovated 2bd 1ba Waterfront, Hottub, Trails!
Friendsville
The price is AU$675
includes taxes & fees
19 Oct - 20 Oct
Renovated 2bd 1ba Waterfront, Hottub, Trails!
A covered porch with a wooden deck, two wicker chairs, and a decorative fence.

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

New Private 2bd 1 ba, Hot tub, Trails, Waterfront!
Friendsville
The price is AU$689
includes taxes & fees
18 Oct - 19 Oct
New Private 2bd 1 ba, Hot tub, Trails, Waterfront!
A bunk bed room with a wooden floor, a small bedside table, and a window with blinds.

20. Cozy family friendly hilltop chalet in Thomas

Cozy family friendly hilltop chalet in Thomas
Thomas
The price is AU$530
includes taxes & fees
22 Oct - 23 Oct
Cozy family friendly hilltop chalet in Thomas
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

Baja Motel

Baja Motel

10/10 Excellent
"Only stayed for a couple nights, but it was a really lovely spot."
Faelyn 2-night trip
Posted 2 days ago
Baja Motel

Find out more about Oakland

Oakland Holiday Homes information

Number of reviews
144
Accommodation
483 Holiday Homes
Lowest Price
AU$321
Highest Price
AU$2,455