Compare Oakland Chalets

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Featured Chalets in Oakland

Timroc II, FIVE STAR REVIEWS! 15 MINUTES FROM WISP! HOT TUB! PRIVATE 2 ACRES!

Timroc II, FIVE STAR REVIEWS! 15 MINUTES FROM WISP! HOT TUB! PRIVATE 2 ACRES!

Oakland MD
Guests of this chalet enjoy a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly chalet include barbecue grills and a garden.
Hot Tub
Kitchen
Bearly Believable By The Lake & WISP hot-tub/pets

Bearly Believable By The Lake & WISP hot-tub/pets

McHenry MD
Guests of this chalet enjoy features like a gym, a hot tub, and an arcade/game room. Additional amenities include laundry facilities and barbecue grills.
Hot Tub
Kitchen
Lake View Chalet with Hot Tub and Fire Pit

Lake View Chalet with Hot Tub and Fire Pit

Oakland MD
At this chalet, guests have access to a hot tub, an arcade/game room, and laundry facilities. This family-friendly chalet also has barbecue grills.
Hot Tub
Kitchen
Lakefront A-Frame - Hot Tub, Dock, Near Wisp – Deep Creek

Lakefront A-Frame - Hot Tub, Dock, Near Wisp – Deep Creek

Oakland MD
Guests of this chalet enjoy a hot tub, an arcade/game room, and laundry facilities. This family-friendly chalet also has barbecue grills.
Hot Tub
Kitchen
Spacious family-friendly chalet w/fenced dog run & large deck near the lake/Wisp

Spacious family-friendly chalet w/fenced dog run & large deck near the lake/Wisp

Oakland MD
Guests staying at this chalet have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.

Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats.

Oakland MD
$403 nightly
The price is $455 total per night
$455 total
Apr 24 - Apr 25
Total with taxes and fees
At this chalet, guests have access to a hot tub, an arcade/game room, and laundry facilities. This family-friendly chalet also has barbecue grills.
Hot Tub
Kitchen
Lakeview Chalet in Deep Creek Lake + Hot Tub

Lakeview Chalet in Deep Creek Lake + Hot Tub

Oakland MD
$608 nightly
The price is $644 total per night
$644 total
Apr 14 - Apr 15
Total with taxes and fees
Guests of this chalet enjoy features like a gym, a hot tub, and laundry facilities. Additional amenities include a garden and barbecue grills.
Hot Tub
Kitchen
Dizzy's Den--A Log Cabin in the Woods near the lake --formerly the "Love Shack"

Dizzy's Den--A Log Cabin in the Woods near the lake --formerly the "Love Shack"

Oakland MD
Guests staying at this chalet enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free chalet also has a garden.
Hot Tub
Kitchen
Wooded Retreat w Hot Tub, Loft, Game Room & Sauna

Wooded Retreat w Hot Tub, Loft, Game Room & Sauna

Oakland MD
At this chalet, guests have access to a sauna, a hot tub, and laundry facilities. This smoke-free chalet also has barbecue grills.
Hot Tub
Kitchen
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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.

Hotel Options in Oakland

    The Garrett Inn

    The Garrett Inn

    17848 Garrett Highway Oakland MD
    $108 nightly
    The price is $123 total per night from Apr 15 to Apr 16
    $123 total
    Apr 15 - Apr 16
    Total with taxes and fees
    9.6/10 Exceptional! (425 reviews)
    In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

    In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

    Oakland MD
    Baja Motel

    Baja Motel

    1501 Maryland Hwy Oakland MD
    $122 nightly
    The price is $139 total per night from Apr 20 to Apr 21
    $139 total
    Apr 20 - Apr 21
    Total with taxes and fees
    9/10 Wonderful! (92 reviews)

Chalets

Book the best chalets in Oakland
Take a break from reality and kick back in a Oakland chalet on your next vacation. Stay right in the middle of all the action, but feel like you’re miles away. Be as active or as relaxed as you want. Your chalet is truly yours. No one can tell you what to do on your chalet stay—and it’s the best way to enjoy a getaway.

Get the most from your chalet stay
You’ll make incredible new memories at chalets in Oakland. They look great in your photos, with sunning backdrops and cozy touches like fireplaces and exposed beam ceilings. Wake up to light streaming through your big picture window and admire your incredible view. Don’t just look at the great outdoors, though. Get out there and experience all that Oakland has to offer.

Bring the whole group, because you’ll find plenty of space to spread out at Oakland chalet houses. Whether you use all those bedrooms for the kids or for your crazy crew, you can settle in quickly thanks to chalets’ convenient amenities. Whip up a meal in no time in the kitchen or kitchenette, or whip out your phone to call for delivery. Cozy up to the fire, or fire up the blender for some drinks. When you’ve got a chalet, it’s going to be good day.

Oakland Chalets essential information

Accommodation
10 Chalets
Lowest Price
$123
Highest Price
$644
Popular accommodation
Timroc II, FIVE STAR REVIEWS! 15 MINUTES FROM WISP! HOT TUB! PRIVATE 2 ACRES!, Bearly Believable By The Lake & WISP hot-tub/pets, Lake View Chalet with Hot Tub and Fire Pit, Lakefront A-Frame - Hot Tub, Dock, Near Wisp – Deep Creek, Spacious family-friendly chalet w/fenced dog run & large deck near the lake/Wisp, Lake Views! HOT TUB! 8 min to WISP ski. Central Location. Walk to Coffee & Eats., Lakeview Chalet in Deep Creek Lake + Hot Tub, Dizzy's Den--A Log Cabin in the Woods near the lake --formerly the "Love Shack", Wooded Retreat w Hot Tub, Loft, Game Room & Sauna