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Top Holiday Rentals in Oakland

In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

8.4 out of 10, Very good, (53)
"We had a great time, the location was great and the place was clean"
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village

10.0 out of 10, Exceptional, (443)
"Very welcoming. Quite yet still close enough to all the food and recreation. Would definitely stay there again !!!"
Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village

Charming Dog Friendly Cottage w/ Dock & Fire Pit

9.6 out of 10, Exceptional, (21)
"My family and I had a great time at the Red Cottage. We would definitely stay here again."
Charming Dog Friendly Cottage w/ Dock & Fire Pit

Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

9.8 out of 10, Exceptional, (254)
"Impressed by this charming cabin! It’s clean, private, and well stocked with basics. Would stay there again."
Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

Swallow Falls Cabin 1- Cozy 1-Bedroom Perfect for a Romantic Getaway!

2.0 star property
9.2 out of 10, Wonderful, (40)
"The rooms are nice and has a very clean atmosphere great for 2 people will deff be going back soon!"
Swallow Falls Cabin 1- Cozy 1-Bedroom Perfect for a Romantic Getaway!

The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!

10.0 out of 10, Exceptional, (301)
"What a fantastic cabin in a great location, close to everything but nice and secluded and quiet. Perfect for our family of 4 and our doggo. "
The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!

Swallow Falls Cabin 1

2.0 star property
9.2 out of 10, Wonderful, (29)
"Nice place nice places to visit."
Swallow Falls Cabin 1

Lake Loft at Deep Creek Lake

2.0 star property
9.8 out of 10, Exceptional, (8)
"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

Modern house on the lake with private dock, hot tub, air hockey & central AC

7.6 out of 10, Good, (24)
"Other than a hell of a lot of mosquitos being inside the home everything else was perfect after about an hour or 2 they were gone or maybe after a few drinks but I will be booking again the home was amazing"
Modern house on the lake with private dock, hot tub, air hockey & central AC

Amazing Central Location! Lakefront! Hot tub/dock!

9.4 out of 10, Exceptional, (49)
"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!

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

10.0 out of 10, Exceptional, (6)
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

Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

10.0 out of 10, Exceptional, (30)
"We LOVED the house! Clean, cozy, great little town. Couldn’t ask for better hosts!"
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

Wandering Woods- Dog-friendly 3 bedroom home with lake access and hot tub!

9.0 out of 10, Wonderful, (12)
"Location was great , house was just missing bed linens"
Wandering Woods- Dog-friendly 3 bedroom home with lake access and hot tub!

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!

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

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

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

10.0 out of 10, Exceptional, (108)
"Great weekend getaway"
Level lakefront, family-friendly, hot tub, low fees, private dock

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

8.0 out of 10, Very good, (32)
"Was a very nice home to spend a weekend at"
Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

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
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, 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 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?

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. Our travellers also rate Charming Dog Friendly Cottage w/ Dock & Fire Pit as a favourite home for rent in Oakland.

How many holiday rentals are there in Oakland?

With 556 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.