Oakland, MD Vacation Homes from ￥24,528

A river flowing through a forest with a waterfall.

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Our top choices for Oakland vacation homes

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

Oakland

2. Charming 4BR Home - HOT TUB - Oakland

Oakland

Steven P.

￥89,021 total

includes taxes & fees

Sep 17 - Sep 18

3. Welcome to Lakeski Lodge! Lake and Mountain View! Lake access and dock!

Oakland

"We stayed at this lakeside home during the winter, and it was a cozy and memorable getaway. The snowy setting made the views especially beautiful, and the lake looked peaceful and picturesque surrounded by fresh snow. Once inside, the house felt warm, comfortable, and welcoming—perfect for escaping the cold.The home was clean and well laid out, with comfortable beds and a kitchen that had almost everything we needed. It was a great place to relax, unwind, and enjoy time together while staying...

Kelly S.

￥86,739 total

includes taxes & fees

Sep 14 - Sep 15

4. Lakefront, Private Dock, Hot Tub, IndoorSoccer

Oakland

Mary W.

5. 2BR - Slope Access - Fireplace

McHenry

Michael P.

￥75,633 total

includes taxes & fees

Aug 27 - Aug 28

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

Swanton

Harsh S.

￥107,473 total

includes taxes & fees

Sep 21 - Sep 22

7. Cozy Lake Access Home with Hot Tub

McHenry

Todd M.

￥76,969 total

includes taxes & fees

Sep 2 - Sep 3

8. Rustic 3BR Cabin - HOT TUB - McHenry

McHenry

Ashley C.

￥92,739 total

includes taxes & fees

Sep 25 - Sep 26

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Top Oakland Hotel Reviews

Baja Motel

10/10 Excellent

"c"

Will O' The Wisp: 103A Efficiency/One Bath

10/10 Excellent

"A perfect unit for this solo traveler. Will O' Wisp is beautiful and everyone there is friendly and helpful. There's lots to do whether it's sunny or rainy. After staying previous years at an inn with no dining service except breakfast, and nothing nearby to walk to, it was good to have 2 onsite choices and plenty more nearby. I ate at Aces Run twice, very comfortable vibe. Also appreciated the pool and hot tub. I'll be going back."

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

10/10 Excellent

"The house was perfect for our family group of adults, 2 children and one labradoodle. There was plenty to entertain everyone, including a hot tub, firepit, use of kayaks, a heated swimming pool and a full size pacman console.The kitchen was lovely snd well stocked.Beds were comfortable.The hostess responded quickly to all questions."

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

10/10 Excellent

"I’d love to start off by saying thank you to the host for the great weekend. My favorite part of staying in this cabin was the beautiful nights by the fire. The atmosphere of the house along with the serine woods is amazing. The host kindly provided roasting forks along with a smores station, but that’s not the best part. SHE PROVIDES THE WOOD FOR THE FIRE! Other than the fire pit, the hot tub is so relaxing, very clearly well maintained and clean and it even overlooks the fire pit and a tranquil wooded backyard. The interior of the home is very cozy. Big bedrooms, very nice bathrooms, and a very nice vaulted ceiling over the living room. Now as stated in the description there is no A/C so it can get warm at times, but with the windows open and the fan blowing it stayed roughly 5-7 degrees cooler inside than the outside temp. Just plan your trip accordingly. There was a small issue, but the host said they were getting the problem resolved after we checked out so I don’t want to put that against her. Over all a very relaxing experience."

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

10/10 Excellent

"We had a great week. The home is well cared for and comfortable. The bedrooms were a nice size. We relaxed in the hot tub, while enjoying a view of the lake. The location allowed us to explore Deep Creek, Accident, Oakland, Frostburgh and West Virginia. The owner responded promptly to all of our questions and was pleasant to work with."

Find out more about Oakland

Oakland Vacation Homes information

Number of reviews	303
Accommodation	491 Vacation Homes
Lowest Price	￥24,528
Highest Price	￥148,833

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakland vacation homes

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

2. Charming 4BR Home - HOT TUB - Oakland

3. Welcome to Lakeski Lodge! Lake and Mountain View! Lake access and dock!

4. Lakefront, Private Dock, Hot Tub, IndoorSoccer

5. 2BR - Slope Access - Fireplace

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

7. Cozy Lake Access Home with Hot Tub

8. Rustic 3BR Cabin - HOT TUB - McHenry

9. Wisp View Retreat, Hot tub

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

11. Minutes from LAKE - Ranch - Pets & Kids welcome - Secluded

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

13. Highwater Hideaway

14. 2 bd 2bth, Thomas, WV, near Canaan and Davis, WV skiing, trails, State Parks

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

16. Base Camp, 3-bedroom house, sleeps 7 in charming Thomas WV

17. Charming bungalow in marvelous Parsons with AC

18. Lake Bear Lair|4BR Lake View Home|Hot Tub|Dock

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

20. Luxury Lodge with Hot Tub, Arcade & Lake Access

Find vacation rentals that suit your style

Top Oakland Hotel Reviews

Baja Motel

Cove Creek Lodge: 201 Poolside Double Queen Fireplace Room

Will O' The Wisp: 103A Efficiency/One Bath

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

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

Prime Location w Hot tub & Firepit

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Lakefront/Dock/Amazing views HotTub

Find out more about Oakland

Oakland Vacation Homes information

Explore a world of travel with Expedia

Search Vacation Homes in Oakland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakland vacation homes

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

2. Charming 4BR Home - HOT TUB - Oakland

3. Welcome to Lakeski Lodge! Lake and Mountain View! Lake access and dock!

4. Lakefront, Private Dock, Hot Tub, IndoorSoccer

5. 2BR - Slope Access - Fireplace

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

7. Cozy Lake Access Home with Hot Tub

8. Rustic 3BR Cabin - HOT TUB - McHenry

9. Wisp View Retreat, Hot tub

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

11. Minutes from LAKE - Ranch - Pets & Kids welcome - Secluded

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

13. Highwater Hideaway

14. 2 bd 2bth, Thomas, WV, near Canaan and Davis, WV skiing, trails, State Parks

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

16. Base Camp, 3-bedroom house, sleeps 7 in charming Thomas WV

17. Charming bungalow in marvelous Parsons with AC

18. Lake Bear Lair|4BR Lake View Home|Hot Tub|Dock

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

20. Luxury Lodge with Hot Tub, Arcade & Lake Access

Find vacation rentals that suit your style

Top Oakland Hotel Reviews

Baja Motel

Find out more about Oakland

Oakland Vacation Homes information

Explore a world of travel with Expedia