Photo by KM Moore

Holiday Homes in Oakland

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Featured Holiday Homes in Oakland

Property grounds
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
8.8 out of 10, Excellent, (28)
"The place is pretty nice. Just perfect for us. Other than some very minor issues such as dated appliances, the place was very well maintained. We really enjoyed our stay. The host is always there to answer our questions. Definitely a great place to stay."
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Fridge, microwave, stovetop, dishwasher
Deep Creek Lake Townhome w/Deck & Water Views
9.4 out of 10, Exceptional, (23)
"Amazing views, great area."
Deep Creek Lake Townhome w/Deck & Water Views
Interior
Gorgeous cabin on 2.3 acres with private hot tub & game room with pool table
8.8 out of 10, Excellent, (10)
"It was a cozy birthday weekend with friends and family. The is located in a very quiet and beautiful area. The house had everything we needed and we had plenty of room for everyone to have their own space. I highly recommend this house!"
Gorgeous cabin on 2.3 acres with private hot tub & game room with pool table
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Fridge, microwave, oven, stovetop
Lakefront, dog friendly, dock slip, hot tub, and fire pit
10.0 out of 10, Exceptional, (14)
"We all really enjoyed our stay. The hosts were quick to reply. The house was beautiful and clean!"
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Property grounds
Lakefront/Dock/Amazing views HotTub
9.8 out of 10, Exceptional, (21)
"Our family of 10 had a great time on the lake. The house is comfortable to host a large group. Multiple King beds is a big plus. The lake views are stunning. Parking can be a bit tricky if you have multiple cars but after a few times pulling in and out we figured it out. We are looking forward to visiting again, hopefully in warmer months to take full advantage of the lake activities. Hima was amazing at answering all of our questions throughout our stay. I highly recommend Hygge Memories!!!"
Lakefront/Dock/Amazing views HotTub
Microwave, dishwasher, coffee/tea maker, toaster
Oakland Retreat ~ 13 Mi to Deep Creek Lake!
9.8 out of 10, Exceptional, (14)
"Our stay was very relaxing. The house was decorated beautifully, very comfortable, and close to everything we wanted visit. The only thing that I didn’t like was that you had to take your own trash, especially when you pay a cleaning fee, and the beds were uncomfortable. We appreciate the host letting us stay. We enjoyed our trip."
Oakland Retreat ~ 13 Mi to Deep Creek Lake!
Fridge, microwave, oven, stovetop
Elegant Home Away: Hot Tub, Game Room, Kid Friendly!
Elegant Home Away: Hot Tub, Game Room, Kid Friendly!
Property grounds
New! Serenity Shores: Lake Area, Hot Tub, Fireplace, Fire Pit, A/C!
9.2 out of 10, Wonderful, (12)
"This was perfect for us, very cozy and clean. Will come back for sure"
New! Serenity Shores: Lake Area, Hot Tub, Fireplace, Fire Pit, A/C!
TV, fireplace
Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi
9.0 out of 10, Wonderful, (17)
"Property has all you need for a comfortable stay"
Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi
Property grounds
Dog-friendly home in a great, central location w/ private hot tub & golf nearby
9.0 out of 10, Wonderful, (47)
"We loved the features of the cabin. Comfy!"
Dog-friendly home in a great, central location w/ private hot tub & golf nearby
Property grounds
New: Lakefront Luxury Home with Private Indoor Heated Pool!
9.4 out of 10, Exceptional, (3)
"This house is beautiful, huge, and perfect for any large group. The house was clean and check in and check out were easy. 10/10 recommend."
New: Lakefront Luxury Home with Private Indoor Heated Pool!
3 bedrooms, free WiFi, bed sheets
Lake It Easy: Lake Access, Fireplace, Wifi, Lake Views!
9.4 out of 10, Exceptional, (29)
"The property was so lovely and comfortable. Very clean and more than enough space. I cannot say enough about the property. The only negative I have to share is the noise of Garrett Highway. The property faces the road and the vehicular noise was non-stop day and night. My spouse was wakened up in the middle of the night several times due to the noise. That said, the actual property was fabulous!"
Lake It Easy: Lake Access, Fireplace, Wifi, Lake Views!
Property grounds
Central Lake House with Private Dock! Walk to Area Hot Spots!
9.8 out of 10, Exceptional, (18)
"I recently stayed on property and it was a lovely time. You can't ask for a better location if you want to be close to the nightlife of the area. Only issue was a broken piece of the basement stairway, but I wouldn't hold that against the houses rating as it was only a minor flaw."
Central Lake House with Private Dock! Walk to Area Hot Spots!
Outdoor spa tub
New! Howie's Landing: Dogs Welcome, Lake Area, Hot Tub!
10.0 out of 10, Exceptional, (2)
"The place is so cute! Its clean, decorated nicely, and has everything you shoudl need..and more. Alot of space in driveway. Nice view of the woods from the nice sized hottub. Quiet street. Tv in every bedroom, central air a bonus! Will def be staying here again"
New! Howie's Landing: Dogs Welcome, Lake Area, Hot Tub!
Smart TV, fireplace, DVD player, table football
Summerside: Lakefront, Dock Slip, Hot Tub, Fire Pit, Pool Table!
8.8 out of 10, Excellent, (13)
"This property was quiet and nice to stay at"
Summerside: Lakefront, Dock Slip, Hot Tub, Fire Pit, Pool Table!
Fridge, microwave, oven, stovetop
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
10.0 out of 10, Exceptional, (8)
"I had a bachelor party for a weekend at this property. The place is immaculate. The owners are friendly and accommodating. I will be bringing my family next."
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
Terrace/patio
Tranquil Home with Private Hot Tub & Game Room - Close to Lake Access
8.0 out of 10, Very good, (40)
"Great house, everything was nice and clean. working hot tub, kids enjoyed very much. only about 10 minutes from the ski resort and 10 minutes from walmart. very convenient for all needs and wants. only few cons, the dishwasher and the dryer weren't working, but we got around it."
Tranquil Home with Private Hot Tub & Game Room - Close to Lake Access
Marina
Mountain High: Lake Access, Hot Tub, Two Fireplaces, Fire Pit!
10.0 out of 10, Exceptional, (4)
"Mountain High is a beautiful property -- complete with deer and wild turkey wandering through the yard. We were a group of 8 adults and 1 infant, and everything worked as advertised. The only complaint was from a person occupying the downstairs bedroom -- that the ceiling squeaked occasionally when people were moving through the upstairs rooms. We used the hot tub, fire pit, upstairs fireplace, kitchen & laundry room. All worked as advertised."
Mountain High: Lake Access, Hot Tub, Two Fireplaces, Fire Pit!
Game room
Lake's End: Lakefront, Dock Slip, Pool Table, Fireplace, Hot Tub!
9.6 out of 10, Exceptional, (9)
"The house looks even better in person! Perfect for groups of friends to celebrate together"
Lake's End: Lakefront, Dock Slip, Pool Table, Fireplace, Hot Tub!
Property grounds
LakeAccess DeckSlide, 7PR HotTub, Games, OD Movies
10.0 out of 10, Exceptional, (4)
"Absolutely the most well maintained house that we stayed at in Deep Creek! Highly recommended!"
LakeAccess DeckSlide, 7PR HotTub, Games, OD Movies
Don't see what you're looking for?
See all available properties in Oakland
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.

Other property types in Oakland

Property grounds
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
8.8 out of 10, Excellent, (28)
"The place is pretty nice. Just perfect for us. Other than some very minor issues such as dated appliances, the place was very well maintained. We really enjoyed our stay. The host is always there to answer our questions. Definitely a great place to stay."
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Property grounds
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
8.8 out of 10, Excellent, (65)
"Family and dogs enjoyed stay in this well-equipped cabin with a beautifiul working wood fireplace."
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
Aerial view
Cozy, family-friendly, lakeview condo with gas grill & firepit
7.6 out of 10, Good, (30)
"Cute for 2 people, but if you have trouble with steps look for a different location. Bed in main bedroom was VERY tall off the ground and hard to get into for a 5 foot tall woman. Clean property, but although sleeps 6 is stated in rental, it was comfortable for myself and my friend on our girls weekend. Give local restaurant Black Bear Tavern a 5 star rating also. EXCELLENT service, selection, food was amazing and entertainment was spot on for what we were looking for. Location nearby...
Cozy, family-friendly, lakeview condo with gas grill & firepit
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.

Oakland Holiday Homes information

Number of reviews
256
Accommodation
471 Holiday Homes
Lowest Price
Highest Price

Recent Reviews in Oakland
Expedia verified reviews

The Garrett Inn

The Garrett Inn

5/5 Excellent
"Friendly staff , very clean , bathroom was small and sheets were a little rough. The room had a cozy farmhouse feel . I would definitely stay there again. "
A verified traveller stayed at The Garrett Inn
Posted 5 days ago
The Garrett Inn