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Holiday Rentals in Oakland

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Holiday Rentals in Oakland

Holiday Home in Oakland

10.0 out of 10, Exceptional, (51)
"This house was actually as beautiful as the pictures! We had a great stay and hope to return in the future."
United States
Sandra R.
Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip

Holiday Home in Oakland

10.0 out of 10, Exceptional, (84)
"As advertised! Very comfortable. A wonderful getaway!"
United States
Joanna C.
Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing

Cabin in Oakland

2.0 star property
10.0 out of 10, Exceptional, (12)
"Nothing negative to say. Beautiful place and friendly owner. Owner is accessible and very accommodating. "
United States
Sean
The price is €640
includes taxes & fees
1 Dec - 2 Dec
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

Holiday Home in Oakland

10.0 out of 10, Exceptional, (41)
"The property was beautiful and we had a very relaxing stay"
United States
Courtney U.
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Holiday Home in Paradise Point

10.0 out of 10, Exceptional, (116)
"Relaxing lake home in a quiet cove. Conveniently located. Clean and comfortable."
United States
Mary M.
Level lakefront, family-friendly, hot tub, low fees, private dock

Cabin in Oakland

9.8 out of 10, Exceptional, (261)
"Very homey and great layout! Already planning on coming back!"
United States
Agnes H.
Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

Holiday Home in Oakland

9.6 out of 10, Exceptional, (54)
"A great backdrop for a mini family reunion."
United States
Nora V.
Amazing Central Location! Lakefront! Hot tub/dock!

Cabin in Oakland

9.8 out of 10, Exceptional, (47)
"Very easy to check in and out! Thank you! "
United States
Edward
The winter is coming !!!

Holiday Home in Oakland

10.0 out of 10, Exceptional, (2)
"Perfect location for our anniversary trip. "
United States
Natalie M.
3-bed, charming modernized cottage tucked into wooded hillside in Deep Creek, MD

Chalet in Oakland

10.0 out of 10, Exceptional, (109)
"Fantastic week at a fantastic cabin!"
United States
Karen H.
Timroc II, FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!

Holiday Home in Oakland

8.6 out of 10, Excellent, (12)
"In town to celebrate daughter Graduating from college! Great house, beds so comfy!!! House had all we needed & views are amazing! "
United States
B.J. B.
5BR lakefront retreat with hot tub, sauna, & dock

Cabin in Oakland

10.0 out of 10, Exceptional, (8)
"Super comfortable, clean, beautiful, thoughtful and stylish design, good location, nice size for a small family. It’s the best place I have ever stayed. We will definitely come back again!"
United States
Kaoru M.
EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

Holiday Home in Oakland

9.6 out of 10, Exceptional, (15)
"House was great! Large enough for our big group "
United States
Jodi P.
New: Lakefront Luxury Home with Private Indoor Heated Pool!

Holiday Home in Oakland

8.4 out of 10, Very good, (63)
"We had a great time and the place was exactly as advertised, it was perfect."
United States
John K.
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Holiday Home in Oakland

9.2 out of 10, Wonderful, (15)
"Our family had a wonderful time! Great spot, easy check in and out. Only downside is how close you are to the highway, there is some road noise. "
United States
Joanna Z.
Cozy Dog Friendly Cabin w/ Hot Tub & Lake Access

Holiday Home in Oakland

9.6 out of 10, Exceptional, (15)
"Great place to stay for a bachelor party weekend! Host was easy to contact, accommodating and made the check in process insanely easy. "
United States
Sean M.
Serene Mountain Escape: Hot Tub, Foosball, Views

Cabin in Oakland

10.0 out of 10, Exceptional, (34)
"Great property, loved our stay here! We will definitely stay here again! "
United States
Shawnnelle H.
The price is €942
includes taxes & fees
22 Dec - 23 Dec
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

Aparthotel in Oakland

10.0 out of 10, Exceptional, (1)
"Great place for a quick getaway ski trip to Wisp"
United States
William A.
The price is €231
includes taxes & fees
30 Nov - 1 Dec
Suites at Silver Tree: A118 Studio Standard View

Holiday Home in OAKLAND

7.6 out of 10, Good, (4)
"Property did not match pictures much repair needed over priced location great view not awesome! so easy to fix. rental co threw in last minute paperwork and confrontational on solving loved deep creek would choose other property and go thru local co directly as vrbo was no help and just added to cost"
United States
Terence M.
Lakefront Chalet w/ Pool, Private Dock, & Hot Tub

Cottage in Oakland

10.0 out of 10, Exceptional, (31)
"Had a great visit, perfect for 2 people dogs. Great location, we loved the fireplace and the record player! Host was very responsive before ending visit."
United States
Lauren W.
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek
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.
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Top Oakland Hotel Reviews

Find out more about Oakland

Everything you need to know about Oakland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oakland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oakland holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oakland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oakland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oakland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oakland holiday rentals we have selected for you start as low as €231 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oakland rentals

At Expedia, we put the best Oakland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oakland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oakland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oakland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing : This highly rated holiday home rental in Oakland is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday. Our travellers also rate Perfect Lake Escape | Dog Friendly Hot Tub, Fire Pit, Dock Slip as a favourite home for rent in Oakland.

How many holiday rentals are there in Oakland?

With 468 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 Youghiogheny River are a couple of lovely local spots to get outside and enjoy nature. Herrington Manor State Park and Swallow Falls 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.