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Oakland Holiday Rentals

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Holiday Rentals in Oakland

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
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
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,
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Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
10.0 out of 10, Exceptional, (400)
"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
9.4 out of 10, Exceptional, (24)
"Condo is very spacious and the view of the lake is magnificent. Condo is centrally located. There is a small smart tv in the living room but no tv in the bedrooms."
Deep Creek Lake Townhome w/Deck & Water Views
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 NZ$401
per night
3 Jun - 4 Jun
Suites at Silver Tree A314: Studio and Loft Suite with Free WIFI and Fireplace!
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
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
Dog-friendly secluded cabin with hot tub, firepit, lawn games, & great deck
10.0 out of 10, Exceptional, (10)
"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
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
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
New Construction! Modern Lakefront A-Frame with Hot Tub + Fire Pit
10.0 out of 10, Exceptional, (4)
"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
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
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
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
Mountain view retreat with a hot tub, grill, & firepit - shared athletic courts
9.0 out of 10, Wonderful, (2)
"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
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!!!"
The price is NZ$1,724
per night
3 Jun - 4 Jun
Lakefront/Dock/Amazing views HotTub
Modern, centrally located, lake views, hot tub + fire pit in Deep Creek
The price is NZ$740
per night
2 Jun - 3 Jun
Modern, centrally located, lake views, hot tub + fire pit in Deep Creek
Adorable adventure cabin in the woods with full kitchen, firepit, & porch
9.2 out of 10, Wonderful, (35)
"If you are looking for a quite away from everything area, this is the spot. We really enjoyed the quieteness but 15 minutes drive to everything."
Adorable adventure cabin in the woods with full kitchen, firepit, & porch
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
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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.

Other types of properties in Oakland you may be interested in

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Oakland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Oakland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Oakland. Seeing all the best attractions is bound to make you fall in love with Oakland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Oakland short-term rentals, that won’t be hard to do.

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.

What are some of the best holiday rentals that Oakland has to offer?

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,: This highly rated holiday home rental in Oakland offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Some other top choices in Oakland are Deep Creek Lake Townhome w/Deck & Water Views and Modern house on the lake with private dock, hot tub, air hockey & central AC.

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.

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