Photo by KM Moore

Search Holiday Rentals in Oakland

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Top Holiday Rentals 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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
Property grounds
Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek
9.8 out of 10, Exceptional, (225)
"We enjoyed our stay here! It was a cute property, and Communication was great."
Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek
Fridge, microwave, oven, stovetop
Bright condo with Deep Creek Lake views, wood fireplace & access to pool/hot tub
8.4 out of 10, Very good, (59)
"very nice for a quick trip away. It’s near everything you need!"
Bright condo with Deep Creek Lake views, wood fireplace & access to pool/hot tub
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
TV, fireplace
Modern house on the lake with private dock, hot tub, air hockey & central AC
6.8 out of 10, (9)
"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
Exterior
Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
10.0 out of 10, Exceptional, (399)
"The Nirvana cabin is in a wonderfully quiet little subdivision that is easy access to restaurants and parks. Clean and just a delight to visit."
Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
Property grounds
Charming home with furnished deck & lake view - walking distance to shops
9.0 out of 10, Wonderful, (31)
"Property was nice. Hot tub was amazing. Didn't find the keys at first for the hot tub. Called the property management company and they never followed up but we ended up finding them on the fridge. When we arrived the emails and texts didn't list the door access so we had to call about that. Otherwise very nice and more affordable on fees than other places I looked at. There were dishes left in the dishwasher that weren't precleaned properly but we only stayed for 2 nights so I just hand washed...
Charming home with furnished deck & lake view - walking distance to shops
Flat-screen TV, fireplace, video games, DVD player
Suites at Silver Tree A314: Studio and Loft Suite with Free WIFI and Fireplace!
10.0 out of 10, Exceptional, (5)
"Unique, fun architecture near many recreational activities "
The price is €232
includes taxes & fees
3 Jun - 4 Jun
Suites at Silver Tree A314: Studio and Loft Suite with Free WIFI and Fireplace!
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
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
Pool
Dog-friendly house on the lake with fireplace, kayak, central AC, & EV charger
8.8 out of 10, Excellent, (39)
"House had a great view! Directly on the water. Good location close to all the main attractions. Kitchen was very spacious too. Areas of opportunity: The WiFi internet connection wasn’t good. Also it felt like every time we were outside we were being watched & recorded by the Ring cameras. Overall, we had a good experience."
Dog-friendly house on the lake with fireplace, kayak, central AC, & EV charger
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
Fridge, microwave, oven, stovetop
Modern, centrally located, lake views, hot tub + fire pit in Deep Creek
The price is €345
includes taxes & fees
28 May - 29 May
Modern, centrally located, lake views, hot tub + fire pit in Deep Creek
Fridge, microwave, oven, stovetop
That Special Place
10.0 out of 10, Exceptional, (16)
"The home was a perfect size for us. Plenty of room. We all enjoyed our stay and hope to return during the Fall. The owner is exceptional and always responded to our questions. His suggestions for restaurants were excellent! Thank you for having us!"
The price is €393
includes taxes & fees
18 Jun - 19 Jun
That Special Place
Exterior
The winter is coming !!!
9.8 out of 10, Exceptional, (32)
"We decided to get away for a long weekend and this was the perfect place! Our kiddos had a blast, as did we! The cabin was in such a great location and our host was extremely helpful and communicative to our questions and needs! Highly recommend!"
The price is €393
includes taxes & fees
12 Jun - 13 Jun
The winter is coming !!!
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
New: Lakefront Luxury Home with Private Indoor Heated Pool!
10.0 out of 10, Exceptional, (2)
"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!
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

Front of property
The Garrett Inn
2.5 star property
9.6 out of 10, Exceptional, (319)
"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 €104
includes taxes & fees
23 May - 24 May
The Garrett Inn
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
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,
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

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 3 days ago
The Garrett Inn