Oakland Vacation Homes

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Our top choices for Oakland holiday homes

1. Captain's Quarters Deep Creek Log Cabin Oasis

Oakland

Brendan P.

HK$2,703 total

includes taxes & fees

29 Oct - 30 Oct

2. Dar's Deep Creek Log Cabin Timber Hideaway

Oakland

HK$4,370 total

includes taxes & fees

11 Nov - 12 Nov

3. Newly Renovated Lakefront Home with Private Dock, Hot Tub & Beautiful Lake Views

Oakland

HK$7,373 total

includes taxes & fees

2 Nov - 3 Nov

A covered outdoor patio with tables and chairs, a wooden deck, and a view of the surrounding greenery.

4. Private Lodge sleeps 31 guests Spectacular Views

Oakland

Jocelyn M.

A wooden deck with railings and string lights, leading to a house with a porch and a window.

5. Near Wisp & Lake• Private • Fire Pit • Pets & Kids

McHenry

Jessica O.

HK$3,055 total

includes taxes & fees

11 Nov - 12 Nov

6. Splash Mountain 6 bedrooms with indoor pool & mountain and filtered lake view

Garrett County

chuck w.

HK$6,673 total

includes taxes & fees

4 Nov - 5 Nov

A kitchen with a central island, a dining table, and a refrigerator.

7. Glendale Getaway: Nostalgic not Fancy

Swanton

Jason M.

HK$1,913 total

includes taxes & fees

11 Nov - 12 Nov

A cabin with a porch, a grill, and a deck.

8. 3BR - Cozy Cabin - Hot Tub

McHenry

HK$3,098 total

includes taxes & fees

31 Oct - 1 Nov

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Top Oakland Hotel Reviews

The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

10/10 Excellent

"We loved the Tiny House, it had everything we needed and was a relaxing weekend away!"

Baja Motel

8/10 Good

"I never did find an ice machine; not sure if there's one there. This operation has apparently experienced a change in ownership, and the new owners, Raul and Josie, are trying hard. While we were there, there was a leak from the bathtub that got to the unit below us, and we had to temporarily locate to the unit next door, then back after they finished repairs by next day noon. Expedia really should include phone numbers to the operators when booking because it will better facilitate emergency contacting when needed (such as this). The rooms are all named after "old west" characters (such as Wyatt Erp Room) and are individually different. I may have to try them all!"

Charming Dog Friendly Cottage w/ Dock & Fire Pit

8/10 Good

"The Red Cottage was a nice place to stay on our four night vacation away with our dog. The house was clean and did not smell of pets at all. Our dog adjusted well to the change of scenery and being in the mountains with new smells. The house was clean and well-stocked with kitchen supplies. Even with the request to bring paper products, there was a bag left for us with a roll of paper towels, two rolls of toilet paper, and mini dish and laundry soap, which was a nice surprise. The sleep number bed was super comfortable and we slept amazingly well. The proximity to downtown McHenry and Oakland is perfect, with lots of places to stop and explore within a short distance of the house. This was the perfect time of year to visit with Autumn Glory in full swing at Deep Creek. Our only complaint is the highway noise at the edge of the property was too much and made it hard to sit outside to enjoy the view. We enjoyed the hot tub very much, yet the last night we were there, the hot tub temp dropped to 95 degrees and the bubble stopped working. Given everything was so well maintained, this is sure to be quickly repaired."

The Garrett Inn

8/10 Good

"When we arrived to the Garrett Inn, we were able to check in, and were given a key to the room, and told where to park (each room's number was plainly painted on the space for each room, however, due to the configuration of the parking lot vs the way the room's were situated, the parking spaces were off-set from the individual rooms, so when parked for the room assigned, the space was two spaces offset. The room was well appointed, two full beds, a bathroom with a pocket door, a small table with two chairs. There was a microwave and room size refrigerator in the corner of the room, with coffee fixings and a coffee pot. The beds were firm but slept good. However, there was a bit of car noise from the busy highway (Rt 219), but it calmed down after about 11 pm. There was a great restaurant across the street, and also about a quarter of a mile down the road from the motel, both served great food. This motel was perfect for those who were exploring the local area and require a base to work from, this motel is perfect. It's not a chain motel, but it's quaint and fills all the basic needs of a motel."

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

10/10 Excellent

"Great, open property. Very clean. Fire pit was awesome! Lake access was perfect. Bill was amazing. If we needed anything, he was there in less than 5 minutes. We will definitely re-book!"

Lakefront/Dock/Amazing views HotTub

10/10 Excellent

"The guest house was absolutely beautiful. The space was exactly what we needed. We had room to gather and do things as a larger group but also had the space to be alone if we wanted to. The views are amazing, the house was clean, the bedrooms and bathrooms were wonderful as well. We thoroughly enjoyed our stay. I appreciated the quick response when I had questions both before and during our stay. I would absolutely recommend this property to anyone and would also stay again!"

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