Top Chalets in Oakland in 2026

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Our top choices for Oakland chalets

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

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

Oakland

Abby H.

includes taxes & fees

16 Nov - 17 Nov

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

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

Oakland

Tyrone C.

includes taxes & fees

26 Oct - 27 Oct

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.

includes taxes & fees

26 Oct - 27 Oct

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

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

Timberline

Martin R.

includes taxes & fees

2 Nov - 3 Nov

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

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

Davis

includes taxes & fees

26 Oct - 27 Oct

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Top Oakland Hotel Reviews

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

8/10 Good

"We had a good time, weather was perfect, dogs had fun too!"

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!"

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

10/10 Excellent

"This place is exceptional! Very cozy, the beds are comfy, and that's including the sofa bed. Plenty of linens, towels and essentials. The fire pit was perfect, although we did not use the hot tub. Loved everything about this place, centrally located, it's clean and tidy, a lot of little extras, including vinyl records, a turntable, and games to play. We had a wonderful anniversary weekend getaway! Jeff is an ideal host. I HIGHLY recommend this place. Give it a try. You won't be disappointed!!"

Find out more about Oakland

Oakland Chalets information

Number of reviews	451
Accommodation	10 Chalets
Lowest Price	£352
Highest Price	£636

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakland chalets

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

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

3. Log chalet w/ hot tub & BBQ grill

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

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

Find holiday rentals that suit your style

Top Oakland Hotel Reviews

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

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

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

Find out more about Oakland

Oakland Chalets information

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Search Chalets in Oakland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Oakland chalets

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

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

3. Log chalet w/ hot tub & BBQ grill

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

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

Find holiday rentals that suit your style

Top Oakland Hotel Reviews

Dog Friendly Cabin in the Woods, Hot Tub & Firepit

Find out more about Oakland

Oakland Chalets information

Explore a world of travel with Expedia