Oakland Vacation Homes

A river flowing through a forest with a waterfall.

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Our top choices for Oakland holiday homes

A wooden deck with a railing overlooking a lake, with chairs and cushions.

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

Oakland

Patti R.

HK$4,567 total

includes taxes & fees

7 Oct - 8 Oct

A deck with a table and chairs, overlooking a lake and autumn foliage.

2. Private Lodge sleeps 25 guests Spectacular Views

Oakland

Jocelyn M.

HK$14,397 total

includes taxes & fees

28 Sept - 29 Sept

A bedroom with wooden paneling, a dresser with drawers, a mirror, and a television on a stand.

3. Glendale Getaway: Nostalgic not Fancy

Swanton

HK$1,896 total

includes taxes & fees

30 Sept - 1 Oct

A covered porch with wooden chairs and a table, overlooking a forested area.

4. Rustic 3BR Cabin - HOT TUB - McHenry

McHenry

Ashley C.

HK$4,231 total

includes taxes & fees

15 Oct - 16 Oct

A small house with a wooden exterior, a dark roof, and a lit front door.

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

Davis

Patti

HK$1,627 total

includes taxes & fees

28 Sept - 29 Sept

A spacious living room with a fireplace, comfortable seating, and large windows.

6. Hot Tub Lakehouse! Game Room + Fire Pit! Walk to Lake! 5 Min to Wisp!

Swanton

Harsh S.

HK$5,283 total

includes taxes & fees

28 Sept - 29 Sept

A spacious living area with a stone fireplace, wooden ceiling, and a dining table with chairs.

7. Cozy Lake Access Home with Hot Tub

McHenry

Todd M.

HK$3,579 total

includes taxes & fees

28 Sept - 29 Sept

A spacious room with a large bathtub, wooden ceiling, stone wall, and a view of greenery outside.

8. Rustic 3BR Farmhouse - MOUNTAIN VIEW - McHenry

McHenry

Celeste

HK$3,379 total

includes taxes & fees

18 Oct - 19 Oct

An indoor swimming pool with clear lanes, a lifeguard chair, and a high ceiling with visible structural beams.

9. Wisp View Retreat, Hot tub

Accident

HK$5,364 total

includes taxes & fees

4 Oct - 5 Oct

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.

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

Thomas

Jonathan P.

HK$2,189 total

includes taxes & fees

1 Oct - 2 Oct

A living room with a blue sofa, red cushions, a TV, and a small staircase.

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

Garrett County

HK$5,929 total

includes taxes & fees

29 Sept - 30 Sept

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

Confluence

Pedro R.

HK$1,209 total

includes taxes & fees

28 Sept - 29 Sept

A wooden cabin with a balcony, surrounded by a lush green forest.

13. Rustic 4BR Cabin - HOT TUB - McHenry

McHenry

Jerome and Adrienne H.

HK$4,584 total

includes taxes & fees

12 Oct - 13 Oct

A wooden cabin with a porch, steps, and potted plants.

14. Charming bungalow in marvelous Parsons with AC

Parsons

Donna M.

HK$1,582 total

includes taxes & fees

1 Oct - 2 Oct

A spacious living room with a large sectional sofa, a fireplace, and a balcony with a view of the outdoors.

15. 4BR Mountain Retreat on 2+ Private Acres • Near Lake • Hot Tub • Mountain Views

McHenry

Rebekah G.

HK$4,623 total

includes taxes & fees

28 Sept - 29 Sept

A riverside view with two Adirondack chairs and a small building with a red roof.

16. Parsons Riverside Retreat: Steps away from a rolling mountain stream and trails

Parsons

Randall

HK$2,442 total

includes taxes & fees

29 Sept - 30 Sept

A compact kitchen with a stove, microwave, sink, and a refrigerator.

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

Davis

Chanda

HK$3,057 total

includes taxes & fees

18 Oct - 19 Oct

A modern kitchen with granite countertops, green cabinets, a stainless steel refrigerator, and a bar area with white chairs.

18. Highwater Hideaway

Bruceton Mills

Jose Ariel

HK$2,011 total

includes taxes & fees

14 Oct - 15 Oct

A deck with outdoor seating and a barbecue grill, surrounded by trees with autumn leaves.

19. 2 bd 2bth, Thomas, WV, near Canaan and Davis, WV skiing, trails, State Parks

Thomas

Richard F.

HK$2,534 total

includes taxes & fees

28 Sept - 29 Sept

20. 8BR Water View - Huge Gameroom - Hot Tub 6 acres

Waterfront Greens

"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!"

Annie

HK$12,418 total

includes taxes & fees

28 Sept - 29 Sept

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Top Oakland Hotel Reviews

Baja Motel

10/10 Excellent

"Super clean, friendly staff, well maintained. Quiet environment. Very relaxing"

The winter is coming !!!

8/10 Good

"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."

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

10/10 Excellent

"Great communication and super easy access with modern entrance keypad, Hot tub worked great and it was very clean. Cabin is secluded, but only a 2-3 miles from many unique shops and restaurants, Modern appliances with all utensils, dishes, glasses, pots pans, everything you need, even marshmallow roasting sticks, there was plenty of Dry-wood supply for our three night visit using fire pit.. The host communicated very well throughout our whole stay, we loved His and hers full bathrooms-The girlfriend took the downstairs full bath with a larger counter for her make up and I claimed the upstairs full bath, Plus, there is another half bath!!! The Internet was fast and the large TV’s in the LR and bedroom with king size bed worked great (as there was only my girlfriend and I, we didn’t use the other 2 bedrooms or the loft). We both highly recommend this cabin for it’s decor, atmosphere and space with super easy check in process as compared to other cabins we have rented"

Amazing Central Location! Lakefront! Hot tub/dock!

10/10 Excellent

"Beautiful house with a great location. We had a reunion with 10 old friends. There was plenty of space to cook and prepare food, comfy beds, and plenty of bathrooms. Dock and fire pit are nice and convenient. Lots to do nearby. The Arrowhead store is 3 minutes away. Overall, great experience!"

Sisters Treehouse

10/10 Excellent

"I was pleasantly surprised. The unit was very clean and spacious. It could easily accommodate a large family or two couples. Instructions were well labeled and clear. There was plenty of lighting and outlets. The owner responded quickly to any questions. The location was close to activities near the lake. It overlooks the lake, and I think will be much better view when the leaves fall."

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