Photo by KM Moore

Search Holiday Rentals in Oakland

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Top Holiday Rentals in Oakland

Dog-friendly cabin with private hot tub, Ping-Pong & lake views
Property grounds
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
8.8 out of 10, Excellent, 67 reviews
"Overall the property was great. Nice location. Pictures were accurate. Very clean property. Fully stocked kitchen. Minor things didn't work."
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
Cozy, family-friendly, lakeview condo with gas grill & firepit
Aerial view
Cozy, family-friendly, lakeview condo with gas grill & firepit
7.6 out of 10, Good, 30 reviews
"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
The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!
2 bedrooms, iron/ironing board, WiFi, bed sheets
The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!
10.0 out of 10, Exceptional, 259 reviews
"The Love Shack is perfect for a couple or a small family. It was clean and well maintained. The hot tub was very relaxing. We liked that all the appliances and equipment worked perfectly. The front porch was nice for sitting by the fire pit in the evening. Overall, we had a wonderful stay and will be returning."
The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!
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Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi
TV, fireplace
Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi
9.0 out of 10, Wonderful, 17 reviews
"Property has all you need for a comfortable stay"
Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi
Mountain view retreat with a hot tub, grill, & firepit - shared athletic courts
TV, fireplace
Mountain view retreat with a hot tub, grill, & firepit - shared athletic courts
9.0 out of 10, Wonderful, 2 reviews
"Excellent location to enjoy the restaurants, state parks, and entertainment that the Deep Creek area has to offer! Very close to the coffee shop and grocery shopping. Nice neighborhood for taking walks, and the kids loved the hot tub and pool table. Comfortable sleeping accommodations."
Mountain view retreat with a hot tub, grill, & firepit - shared athletic courts
Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
Exterior
Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
10.0 out of 10, Exceptional, 400 reviews
"Was a great stay for Mother’s Day"
Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
Deep Creek Lake Townhome w/Deck & Water Views
Fridge, microwave, stovetop, dishwasher
Deep Creek Lake Townhome w/Deck & Water Views
9.4 out of 10, Exceptional, 25 reviews
"Very clean and cozy! Thank you!"
Deep Creek Lake Townhome w/Deck & Water Views
New Construction! Modern Lakefront A-Frame with Hot Tub + Fire Pit
Smart TV, fireplace, DVD player, ping pong
New Construction! Modern Lakefront A-Frame with Hot Tub + Fire Pit
10.0 out of 10, Exceptional, 4 reviews
"The communication from the hosts was professional and frequent. The home was absolutely gorgeous and just newly renovated so very new all around. It fit our family of 9 very comfortably with 6 kids. The kids loved the view of the lake and the amenities were great."
New Construction! Modern Lakefront A-Frame with Hot Tub + Fire Pit
5BR lakefront retreat with hot tub, sauna, & dock
TV, fireplace, books
5BR lakefront retreat with hot tub, sauna, & dock
8.8 out of 10, Excellent, 3 reviews
"Perfect stay! We will be back for sure!"
5BR lakefront retreat with hot tub, sauna, & dock
Will O' The Wisp 709H: Lakefront Penthouse Studio Condo with Breathtaking Lake V
Beach
Will O' The Wisp 709H: Lakefront Penthouse Studio Condo with Breathtaking Lake V
9.4 out of 10, Exceptional, 10 reviews
"This place is nice and cozy. You got the view of the lake. Access to the condo and the lake is very convenient, elevator is very slow though. Overall, we had a great stay. Will recommend this place to my friends. Ciao!"
The price is €378
per night
16 Jun - 17 Jun
Will O' The Wisp 709H: Lakefront Penthouse Studio Condo with Breathtaking Lake V
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Fridge, microwave, oven, stovetop
Lakefront, dog friendly, dock slip, hot tub, and fire pit
10.0 out of 10, Exceptional, 14 reviews
"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
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
Property grounds
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,
8.8 out of 10, Excellent, 28 reviews
"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,
Dog-friendly home in a great, central location w/ private hot tub & golf nearby
Property grounds
Dog-friendly home in a great, central location w/ private hot tub & golf nearby
9.0 out of 10, Wonderful, 47 reviews
"We loved the features of the cabin. Comfy!"
Dog-friendly home in a great, central location w/ private hot tub & golf nearby
Modern house on the lake with private dock, hot tub, air hockey & central AC
Exterior
Modern house on the lake with private dock, hot tub, air hockey & central AC
6.8 out of 10, 9 reviews
"The property was not cleaned when we checked in. But the cleaning staff was there within 30 minutes and did a very thorough job. There were cobwebs outside and the rain gutters were clogged (and still are). Windows were dirty (and still are). The traffic noise made it hard to sleep. Part of the baseboard are missing in the bathroom upstairs and there is pink mold growing in the bathtub area. The fire pit could not be lit. There are 2 dirty, rusty lounge chairs by the propane tank on the patio....
Modern house on the lake with private dock, hot tub, air hockey & central AC
Dog-friendly secluded cabin with hot tub, firepit, lawn games, & great deck
Property grounds
Dog-friendly secluded cabin with hot tub, firepit, lawn games, & great deck
10.0 out of 10, Exceptional, 11 reviews
"Awesome property and very comfortable. We had a wonderful time and reccomend your stay at this cabin!"
Dog-friendly secluded cabin with hot tub, firepit, lawn games, & great deck
Charming home with furnished deck & lake view - walking distance to shops
Property grounds
Charming home with furnished deck & lake view - walking distance to shops
9.0 out of 10, Wonderful, 32 reviews
"We had a lovely weekend stay at this property, which has a view of the lake and forest, a full kitchen, and hot tub to enjoy. It was very clean on arrival. We would definitely stay again!"
Charming home with furnished deck & lake view - walking distance to shops
Gorgeous cabin on 2.3 acres with private hot tub & game room with pool table
Interior
Gorgeous cabin on 2.3 acres with private hot tub & game room with pool table
8.8 out of 10, Excellent, 10 reviews
"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
Lake view condo with wood fireplace
Property grounds
Lake view condo with wood fireplace
10.0 out of 10, Exceptional, 1 review
"Super close to wisp and great restaurants. The owners were great and quick to answer if you had a question. Such a cozy and cute place to stay"
Lake view condo with wood fireplace
Spacious home with convenient location & hot tub - near lake & dining
Aerial view
Spacious home with convenient location & hot tub - near lake & dining
9.0 out of 10, Wonderful, 43 reviews
"This house was nice however it could use some TLC. The positives were that it was close to Wisp, it was very clean, the hot tub was amazing. The negatives were the furniture, beds, it was not stocked well for a house that size with bakeware or utensils. I would rent the house again, but will come a bit more prepared."
Spacious home with convenient location & hot tub - near lake & dining
Quaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard
Property grounds
Quaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard
9.2 out of 10, Wonderful, 34 reviews
"House was perfect for our weekend get away with children and grandchild. Close proximity to good, shopping and activities."
Quaint dog-friendly retreat near the lake w/ wood stove, gas grill, & large yard
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 types of properties in Oakland you may be interested in

The Garrett Inn
Front of property
The Garrett Inn
2.5 star property
9.6 out of 10, Exceptional, 321 reviews
"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. "
The price is €119
per night
11 Jun - 12 Jun
The Garrett Inn
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
Property grounds
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
8.8 out of 10, Excellent, 67 reviews
"Overall the property was great. Nice location. Pictures were accurate. Very clean property. Fully stocked kitchen. Minor things didn't work."
Dog-friendly cabin with private hot tub, Ping-Pong & lake views
Riverside Suites
Pillow-top beds, laptop workspace, free WiFi
Riverside Suites
2.0 star property
9.2 out of 10, Wonderful, 19 reviews
"i must say, this is one of the cleanest hotels that i have ever stayed! there is a bar/restaurant on the premise that was very convenient! good food, bands on saturday night! the bed was very comfortable, and the room was extremely clean! i would definitely recommend this place!"
The price is €141
per night
10 Jun - 11 Jun
Riverside Suites
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.

Frequently asked questions

Can I find holiday rentals in Oakland?

Yes, there are holiday rentals close to the most popular sights in Oakland, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Oakland. Make sure you have time to check out the ski areas and ecotours during your trip.

How many holiday rentals are there in Oakland?

With 629 Expedia holiday rentals, you're guaranteed to find just the right place for your Oakland stay.

What’s there to see and do in Oakland?

Deep Creek Lake and Swallow Falls State Park are a couple of lovely local spots to get outside and enjoy nature. Youghiogheny River and Herrington Manor State Park are other places to visit while you're in town.

What’s a holiday rental in Oakland like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Oakland. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.

Recent reviews of Oakland properties
Expedia verified reviews

Riverside Suites

Riverside Suites

5/5 Excellent
our stay riverside suites
"i must say, this is one of the cleanest hotels that i have ever stayed! there is a bar/restaurant on the premise that was very convenient! good food, bands on saturday night! the bed was very comfortable, and the room was extremely clean! i would definitely recommend this place!"
A verified traveller stayed at Riverside Suites
Posted 2 days ago
Riverside Suites