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Oakland Holiday Rentals

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Holiday Rentals in Oakland

The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

10.0 out of 10, Exceptional, (29)
"Enjoyed our stay at this big-tiny house."
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

Timroc II, FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!

10.0 out of 10, Exceptional, (105)
"This place was fantastic. The host is very kind and generous! Would definitely stay again. "
Timroc II, FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!

Amazing Central Location! Lakefront! Hot tub/dock!

9.4 out of 10, Exceptional, (52)
"Our group of friends rented this property for a fun and relaxing weekend in Deep Creek. The house was clean, spacious, and accommodating, with something for everyone! Anyone interested in stay in this area should book this property!"
Amazing Central Location! Lakefront! Hot tub/dock!

Cozy Cabin with Hot Tub, Fire Pit, Game Room -near Deep Creek Lake

10.0 out of 10, Exceptional, (17)
"The property was excellent and exactly as described. The owner went out of his way to make sure we had everything we needed and then some."
Cozy Cabin with Hot Tub, Fire Pit, Game Room -near Deep Creek Lake

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

10.0 out of 10, Exceptional, (7)
"Perfect cabin for a romantic gateway, easily accessible, close to the lake. Would recommend."
EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

Cabin in the Woods

10.0 out of 10, Exceptional, (16)
"This was our favorite of all the vacation rentals we have done. The cabin is charming and the amenities outstanding. The hot tub and firepit in the yard are great. We really enjoyed our stay"
Cabin in the Woods

Bright condo with Deep Creek Lake views, wood fireplace

8.2 out of 10, Very good, (82)
"We stayed in the 6A condo last year and this one was even better. Omly complaint is that a lot of the plugs were loose and we couldn’t plug anything into them except a select few."
Bright condo with Deep Creek Lake views, wood fireplace

New: Lakefront Luxury Home with Private Indoor Heated Pool!

9.4 out of 10, Exceptional, (13)
"Great house for a large group with lots to do!"
New: Lakefront Luxury Home with Private Indoor Heated Pool!

Level lakefront, family-friendly, hot tub, low fees, private dock

10.0 out of 10, Exceptional, (110)
"Great weekend getaway"
Level lakefront, family-friendly, hot tub, low fees, private dock

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

10.0 out of 10, Exceptional, (13)
"This was perfect for our family’s ski weekend at Wisp with our teens. We loved the hot tub, fireplace, and close proximity to restaurants. We’ll come back again!"
Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp

Recreational Therapy- Private 2 Bedroom with Hot Tub and Firepit

9.6 out of 10, Exceptional, (41)
"Excellent "
Recreational Therapy- Private 2 Bedroom with Hot Tub and Firepit

New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

2.0 star property
10.0 out of 10, Exceptional, (7)
"My family and I had a great stay at this property this last weekend. Shawn was very responsive and flexible it made our stay a breeze. We loved the games downstairs and the proximity to Wisp Resort. Would recommend! "
The price is NZ$1,181
includes taxes & fees
11 Sept - 12 Sept
New Listing! New 7 Person HotTub & Grill FirePit 2 Arcades 9 Minutes to Wisp!

Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

8.0 out of 10, Very good, (33)
"Was a very nice home to spend a weekend at"
Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

5BR lakefront retreat with hot tub, sauna, & dock

8.8 out of 10, Excellent, (11)
"In town to celebrate daughter Graduating from college! Great house, beds so comfy!!! House had all we needed & views are amazing! "
5BR lakefront retreat with hot tub, sauna, & dock

Lake Loft at Deep Creek Lake

2.0 star property
9.8 out of 10, Exceptional, (9)
"We had a great stay! Thank goodness for the dryer to dry our snow gear to keep us out on the slopes! The place awesome! And the host is great to work with and very responsive to needs!! Would love to come back again in the summer! Definitely recommend to anyone!"
Lake Loft at Deep Creek Lake

Log Retreat: Lake Access, Dogs Welcome, Dock Slip, 2 Hot Tubs!

10.0 out of 10, Exceptional, (6)
"Perfect for our long weekend away! Very clean and well maintained property. Beautiful location with plenty of space for everyone. "
Log Retreat: Lake Access, Dogs Welcome, Dock Slip, 2 Hot Tubs!

Will O' The Wisp 203A: Lakefront Efficiency Condo, Access to Indoor Pool!

9.4 out of 10, Exceptional, (29)
"Perfect for our needs!"
Will O' The Wisp 203A: Lakefront Efficiency Condo, Access to Indoor Pool!

Dog-friendly house on the lake, central AC, & EV charger

8.4 out of 10, Very good, (57)
"the view."
Dog-friendly house on the lake, central AC, & EV charger

Lakefront, dog friendly, dock slip, hot tub, and fire pit

10.0 out of 10, Exceptional, (49)
"Great for groups! Clean, perfect location and comfortable for a group of 14 adults. "
Lakefront, dog friendly, dock slip, hot tub, and fire pit

Timberlodge: Lakefront, Indoor Pool, Private Dock, Hot Tub, Fire Pit!

9.4 out of 10, Exceptional, (15)
"We had a blast at this wooded oasis. Tons of space and cozy rooms for every guest. Would love to book again. "
Timberlodge: Lakefront, Indoor Pool, Private Dock, Hot Tub, Fire Pit!
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

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, 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 NZ$1,181 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?

Amazing Central Location! Lakefront! Hot tub/dock!: This highly rated holiday home rental in Oakland is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with 1 hot tub and table football. Some other top choices in Oakland are Level lakefront, family-friendly, hot tub, low fees, private dock and Lakefront, 3 Amazing Decks, Tennis/Pickle Ball, Boat Slip, Hot Tub, Bed Swing .

How many holiday rentals are there in Oakland?

With 521 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.