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Find vacation rentals that suit your style

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Chalets

Villas
Our top choices for Oakland chalets




1. Swings, Lakeview A-frame + Hot Tub, 120” screen
Swings, Lakeview A-frame + Hot Tub, 120” screenOakland
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)
"Place was very clean and tidy upon arrival! Would rent here again "
"Place was very clean and tidy upon arrival! Would rent here again "Tyrone C.
$685 nightly
The price is $726
$726 total
Dec 1 - Dec 2
Total with taxes and fees




2. Log chalet w/ hot tub & BBQ grill
Log chalet w/ hot tub & BBQ grillOakland
9.0 out of 10, Wonderful, (4 reviews)
9.0/10
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!!!"
"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!!!"Jennifer M.
$747 nightly
The price is $827
$827 total
Nov 12 - Nov 13
Total with taxes and fees




3. 3BR - Cozy Log Cabin - Hot Tub
3BR - Cozy Log Cabin - Hot TubSky Valley
9.2 out of 10, Wonderful, (5 reviews)
9.2/10
Wonderful
(5 reviews)




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




5. 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)
10/10
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"
"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"lisette
$504 nightly
The price is $570
$570 total
Nov 16 - Nov 17
Total with taxes and fees




6. Step Inside the Yellow Door – Your Mountain Chalet Escape Awaits
Step Inside the Yellow Door – Your Mountain Chalet Escape AwaitsDavis
10.0 out of 10, Exceptional, (1 review)
10/10
Exceptional
(1 review)
$370 nightly
The price is $420
$420 total
Nov 12 - Nov 13
Total with taxes and fees
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.
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.

Top reviews in Oakland




The Garrett Inn
The Garrett InnOakland
10/10 Excellent
This place was great for our family. Nice country feel, clean, and great location. Best of all was the staff working there were so friendly and courteous. We will be staying there again next trip around the area.
This place was great for our family. Nice country feel, clean, and great location. Best of all was the staff working there were so friendly and courteous. We will be staying there again next trip around the area.
Mo




Lake Pointe Inn
Lake Pointe InnMcHenry
10/10 Excellent
Lakefront
incredibly friendly
Lakefront
incredibly friendly
James




The Lodges at Sunset Village
The Lodges at Sunset VillageMcHenry
10/10 Excellent
We were very pleased with room on two day stay last weekend for ski trip at Wisp.
We were very pleased with room on two day stay last weekend for ski trip at Wisp.
Anonymous traveler




River House Lodge
River House LodgeRowlesburg
10/10 Excellent
Lovely place to stay if you prefer unique experiences and not the chain hotels that all look and feel alike. This is a very nicely restored historical building, full of fascinating details. We got a very nice room, where the only negative point could be the bathroom door that didn't want to stay closed. There was no TV in the room, which was big plus in our eyes. Be prepared for trains passing the town (and making some noise). However, it's part of this historical place. If you rely on local...
Lovely place to stay if you prefer unique experiences and not the chain hotels that all look and feel alike. This is a very nicely restored historical building, full of fascinating details. We got a very nice room, where the only negative point could be the bathroom door that didn't want to stay closed. There was no TV in the room, which was big plus in our eyes. Be prepared for trains passing the town (and making some noise). However, it's part of this historical place. If you rely on local...
Indrek




Baja Motel
Baja MotelOakland
10/10 Excellent
Enjoyed our stay, the room was quite clean and in order.
Riverside Suites is considering changing the theme of
the Hotel. But my buddy and I like the naming of the rooms
for wild west characters. We stayed in the Wyatt Earp
room next to Wild Bill Hickok. We think Riverside should
keep the theme. Enjoyed the Riverside Grill as well.
Enjoyed our stay, the room was quite clean and in order.
Riverside Suites is considering changing the theme of
the Hotel. But my buddy and I like the naming of the rooms
for wild west characters. We stayed in the Wyatt Earp
room next to Wild Bill Hickok. We think Riverside should
keep the theme. Enjoyed the Riverside Grill as well.
Anonymous traveler




The Casselman Inn
The Casselman InnGrantsville
10/10 Excellent
Clean rooms. great housekeeping , friendly people, the resteraunt had awesome food ansd super nice waitresses
Clean rooms. great housekeeping , friendly people, the resteraunt had awesome food ansd super nice waitresses
TrinaF




Keyser Inn
Keyser InnKeyser
10/10 Excellent
The staff at Keyser Inn, helpful, friendly and very professional.
The staff at Keyser Inn, helpful, friendly and very professional.
Nancy




Modern Homestead Guest House
Modern Homestead Guest HouseReedsville
10/10 Excellent
This is a very nice little place. I was moving my daughter into her dorm and needed a place to stay for one night. This was perfect. The cafe next door was perfect for coffee in the morning. I'll be back.
This is a very nice little place. I was moving my daughter into her dorm and needed a place to stay for one night. This was perfect. The cafe next door was perfect for coffee in the morning. I'll be back.
Shaun




Cozy Anchors Away Cabin Hideaway w/ Fire Pit!
Cozy Anchors Away Cabin Hideaway w/ Fire Pit!Parsons
10/10 Excellent
This little cabin was the perfect getaway for me and my husband!! It is beautiful!!
This little cabin was the perfect getaway for me and my husband!! It is beautiful!!
Jerlyn




SureStay Plus Hotel by Best Western Keyser
SureStay Plus Hotel by Best Western KeyserKeyser
10/10 Excellent
Parking was very close and all the snow was removed. Desk person was most helpful in a number of ways. Room was super clean as was the whole facility. Checking in and out was a breeze. Room, even on the first floor, as I requested, was very quiet. Room rate was very reasonable too. Will stay there again!
Parking was very close and all the snow was removed. Desk person was most helpful in a number of ways. Room was super clean as was the whole facility. Checking in and out was a breeze. Room, even on the first floor, as I requested, was very quiet. Room rate was very reasonable too. Will stay there again!
Anonymous traveler




The Inn at Canaan
The Inn at CanaanDavis
10/10 Excellent
Very Clean room, super nice front desk, convenient location, gas station, and a store just cross street. The inn is also very close to the ski area at timberline and Canaan Valley state park.
Very Clean room, super nice front desk, convenient location, gas station, and a store just cross street. The inn is also very close to the ski area at timberline and Canaan Valley state park.
Q




Alpine Lake Resort
Alpine Lake ResortTerra Alta
10/10 Excellent
Love everything about Alpine
Love everything about Alpine
Daniel




Comfort Inn Grantsville-Deep Creek Lake
Comfort Inn Grantsville-Deep Creek LakeGrantsville
10/10 Excellent
It was a great stay!
It was a great stay!
tara




Microtel Inn & Suites by Wyndham Hazelton/Bruceton Mills
Microtel Inn & Suites by Wyndham Hazelton/Bruceton MillsBruceton Mills
10/10 Excellent
A one night stay that was very pleasant.
A one night stay that was very pleasant.
Billy




Parsons Semper Fi Cabin w/ Fire Pit!
Parsons Semper Fi Cabin w/ Fire Pit!Parsons
10/10 Excellent
I would highly recommend it
I would highly recommend it
Philip




Abrams Creek Center
Abrams Creek CenterElk Garden
10/10 Excellent
Booked a cabin last minute during a snow storm for me and my two Border Collies. The owner actually called me to make sure that I knew it was a camping cabin - which I thought was super nice. He brought down a second heater in case the first one didn’t warm the cabin up enough.
It was a camping cabin so rustic. No WiFi or cabin itself so I skied up closer to the main house to pick it up when needed.
Gorgeous and peaceful surroundings!
Will definitely return in warmer weather to check out the...
Booked a cabin last minute during a snow storm for me and my two Border Collies. The owner actually called me to make sure that I knew it was a camping cabin - which I thought was super nice. He brought down a second heater in case the first one didn’t warm the cabin up enough.
It was a camping cabin so rustic. No WiFi or cabin itself so I skied up closer to the main house to pick it up when needed.
Gorgeous and peaceful surroundings!
Will definitely return in warmer weather to check out the...
Kathy




