Oakland Vacation Homes

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Our top choices for Oakland holiday homes

1. Rustic 3BR Cabin - HOT TUB - Oakland

Paradise Point

HK$3,841 total

includes taxes & fees

5 Aug - 6 Aug

2. Charming 3BR Condo - HOT TUB - Lake View

Oakland

HK$4,049 total

includes taxes & fees

12 Aug - 13 Aug

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

Oakland

HK$6,169 total

includes taxes & fees

12 Aug - 13 Aug

4. Luxor Mountaintop Cabin-Castle at Deep Creek Lake

Oakland

HK$8,483 total

includes taxes & fees

10 Aug - 11 Aug

5. Grand Victorian - Easy GAP Access, shops, and restaurants

Confluence

HK$5,033 total

includes taxes & fees

4 Aug - 5 Aug

6. Wisp View Retreat, Hot tub

Accident

HK$5,831 total

includes taxes & fees

1 Sept - 2 Sept

7. Lake Bear Lair | 4BR Lake View Home | Hot Tub

Garrett County

HK$7,746 total

includes taxes & fees

24 Aug - 25 Aug

8. Rustic 3BR Cabin - HOT TUB - McHenry

McHenry

Ashley C.

HK$4,611 total

includes taxes & fees

6 Aug - 7 Aug

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Top Oakland Hotel Reviews

Deep Creek Retreat | 5BR + Hot Tub + Game Room

10/10 Excellent

"Great property"

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

10/10 Excellent

"This place is well taken care of by the owners. It is nicer than advertised! We all loved it here! We played our yearly Deep Creek Pickle ball tournament in the parking area. This part of Deep Creek is no wake and fairly deep water. Location could not be better to everything."

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

10/10 Excellent

"Both the house and the host deserve their exceptional rating. The hot tub, fire pit and dock added to our stay, and this is the most well stocked house I have ever stayed in. Terri was so welcoming and responsive. She did everything she could to make sure we had a great stay. Wonderful experience!"

Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing

10/10 Excellent

"David was great! The check in process and house information were easy to follow. He was always available when needing to communicate and responded within reason. The house was clean and it was the perfect set up to celebrate my friend’s bachelorette! We had a great time and recommend staying with them!"

Spacious 5-bedroom house in Deep Creek, MD with Boat Dock

10/10 Excellent

"The amenities were excellent, and the great room quite spacious. The back patio was very comfortable and the hot tub a nice feature. The master bedroom was spacious. The kitchen was well equipped. Bedroom three with the bunkbeds was a bit dark and the upper bunkbeds rather low, making it impossible for a short adult to sit on the lower beds. There was a large temperature difference between the two house levels. The listing saying “with a dock” was misleading. I never considered the dock would be half a mile away."

Lakefront/Dock/Amazing views HotTub

10/10 Excellent

"We had a great stay this past week. It was great being right on the lake and having our own boat dock and right next to a boat rental marina. Everything in the house was as advertised and the very communicative and responsive experience with the host. With plenty of room for everyone to come together and plenty of space to find private down time, our extended family had wonderful vacation here."

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