The Best Oakland, MD Chalets from $437

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In two weeks

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In three months

In four months

Our top choices for Oakland chalets

A two-story house with a deck and outdoor seating area.

1. Everwoods @ Deep Creek Lake - Speakeasy, hot tub, bunk room on private acreage

Oakland

A wooden cabin with a deck, large windows, and a staircase.

2. Swings, Lakeview A-frame + Hot Tub, 120” screen

Oakland

Tyrone C.

$716 nightly

Nov 16 - Nov 17

Total with taxes and fees

A wooden deck with a fire pit, red outdoor furniture, and a view of the surrounding forest.

3. Log chalet w/ hot tub & BBQ grill

Oakland

Jennifer M.

$824 nightly

Oct 28 - Oct 29

Total with taxes and fees

A two-story house with a balcony and a deck.

4. Lake Views! HOT TUB! Walk to Lake Rentals, Coffee & Eats. Minutes to Everything!

Oakland

Abby H.

$635 nightly

Nov 16 - Nov 17

Total with taxes and fees

A log cabin interior with a large wooden ceiling, a fireplace, a sofa, and a dining area.

5. Spacious 6BR Chalet - HOT TUB - McHenry

McHenry

"First the host Justin was absolutely amazing, his staff was wonderful and helped us get in the property quickly, the entire house was immaculate; the rooms, the bathrooms, the dining area, the kitchen very well equipped, the living room, the game room, the jacuzzi and even the sun room/balcony this home felt like a home away from home and it was so beautiful the art on the walls all told a story. You can tell this home means a lot to the family and it's very beautiful, my family was very happy...

Mamie W.

$746 nightly

Nov 12 - Nov 13

Total with taxes and fees

A cabin with a stone exterior, surrounded by dense forest.

6. Luxurious, rustic, private vacation home with great view.

Timberline

lisette

$504 nightly

Nov 2 - Nov 3

Total with taxes and fees

A two-story cabin with a wooden deck and a metal roof.

7. Step Inside the Yellow Door – Your Mountain Chalet Escape Awaits

Davis

$386 nightly

Nov 23 - Nov 24

Total with taxes and fees

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Top Oakland Hotel Reviews

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!"

Find out more about Oakland

Oakland Chalets information

Number of reviews	452
Accommodation	10 Chalets
Lowest Price	$437
Highest Price	$908

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Check prices for these dates

Our top choices for Oakland chalets

1. Everwoods @ Deep Creek Lake - Speakeasy, hot tub, bunk room on private acreage

2. Swings, Lakeview A-frame + Hot Tub, 120” screen

3. Log chalet w/ hot tub & BBQ grill

4. Lake Views! HOT TUB! Walk to Lake Rentals, Coffee & Eats. Minutes to Everything!

5. Spacious 6BR Chalet - HOT TUB - McHenry

6. Luxurious, rustic, private vacation home with great view.

7. Step Inside the Yellow Door – Your Mountain Chalet Escape Awaits

Find vacation rentals that suit your style

Top Oakland Hotel Reviews

Baja Motel

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

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

Charming Dog Friendly Cottage w/ Dock & Fire Pit

The Garrett Inn

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

That Special Place

Lakefront/Dock/Amazing views HotTub

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

Find out more about Oakland

Oakland Chalets information

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