Oakland Chalets

Find vacation rentals that suit your style

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Our top choices for Oakland chalets

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

Swings, Lakeview A-frame + Hot Tub, 120” screen
Oakland
10.0 out of 10, Exceptional, (2 reviews)
"Place was very clean and tidy upon arrival! Would rent here again "
United States
Tyrone C.
$678 nightly
The price is $718
Dec 1 - Dec 2
Total with taxes and fees
Swings, Lakeview A-frame + Hot Tub, 120” screen

2. Log chalet w/ hot tub & BBQ grill

Log chalet w/ hot tub & BBQ grill
Oakland
9.0 out of 10, Wonderful, (4 reviews)
"Thank you SO MUCH for hosting us! The house was beautiful!! It was very convenient to everything we needed! We found the kitchen to be well stocked to cook in! The gameroom kept the kids very entertained, and the hot tub was well maintained and clean! Tony was great at communication and was very quick to reply! We would definitely stay here again!!!"
United States
Jennifer M.
$783 nightly
The price is $865
Nov 15 - Nov 16
Total with taxes and fees
Log chalet w/ hot tub & BBQ grill

3. Serenity Sunsets! 2.8miles to WISP, hot-tub, pets

Serenity Sunsets! 2.8miles to WISP, hot-tub, pets
McHenry
10.0 out of 10, Exceptional, (3 reviews)
"This place is great and was very clean!"
United States
Galit B.
$554 nightly
The price is $609
Nov 22 - Nov 23
Total with taxes and fees
Serenity Sunsets! 2.8miles to WISP, hot-tub, pets

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

Luxurious, rustic, private vacation home with great view.
Timberline
10.0 out of 10, Exceptional, (440 reviews)
"The house was like a museum. The house was clean, and the kitchen well stocked. The views were amazing, deer in the yard every day. Centrally located from many beautiful hiking trails. One of the best rentals we have stayed at"
United States
lisette
$504 nightly
The price is $570
Nov 17 - Nov 18
Total with taxes and fees
Luxurious, rustic, private vacation home with great view.

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

Step Inside the Yellow Door – Your Mountain Chalet Escape Awaits
Davis
10.0 out of 10, Exceptional, (1 review)
$370 nightly
The price is $420
Nov 15 - Nov 16
Total with taxes and fees
Step Inside the Yellow Door – Your Mountain Chalet Escape Awaits
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Learn more about Oakland

Nestled beside Deep Creek Lake, this mountain town offers year-round adventures from skiing to kayaking. Explore the historic downtown where local shops and farm-to-table restaurants welcome you in hiking boots after a day outdoors.

A waterfall cascading over rocks in a forested area.

Top reviews in Oakland

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