Photo by KM Moore

Oakland Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Oakland

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

10.0 out of 10, Exceptional, (440)
"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

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

8.4 out of 10, Very good, (52)
"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,

Charming Dog Friendly Cottage w/ Dock & Fire Pit

9.6 out of 10, Exceptional, (19)
"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

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

8.8 out of 10, Excellent, (10)
"Perfect stay! We will be back for sure!"
The price is AU$1,884
includes taxes & fees
17 Aug - 18 Aug
5BR lakefront retreat with hot tub, sauna, & dock

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

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

10.0 out of 10, Exceptional, (12)
"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

Deep Creek Lake views from the elevated deck & deluxe suite - near golf

9.6 out of 10, Exceptional, (5)
"I took the family of 6 to the lake. It was chilly outside but this property was perfect. Plenty of space for us all, each couple had a bathroom. The living room open concept with kitchen was perfect for us being able to enjoy the tv, games, food and beverages together. "
Deep Creek Lake views from the elevated deck & deluxe suite - near golf

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

9.8 out of 10, Exceptional, (254)
"Communication was excellent (the most thorough welcome email I've ever received!)Very thoughtfully stocked (books, videos, marshmallows, etc)Lighting and decor created a very cozy ambianceClose to every place we wanted to go to (Wisp, Deep Creek State Park, Firewater, etc)"
Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

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!

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

2.0 star property
9.2 out of 10, Wonderful, (38)
"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 Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

10.0 out of 10, Exceptional, (26)
"Enjoyed our stay at this big-tiny house."
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

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

10.0 out of 10, Exceptional, (299)
"While in the area to look to purchase some property my fiance and I stayed here, the host pointed us to an amazing dinner at Dutch’s and we found we wished we could stay at this cozy cabin longer. "
The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!

Sisters Treehouse

9.6 out of 10, Exceptional, (99)
"Property was wonderful. Location was great. Enjoyed our stay at this property. Thank you for letting us use your place."
Sisters Treehouse

Cabin in the Woods

10.0 out of 10, Exceptional, (15)
"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

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

8.6 out of 10, Excellent, (9)
"Location was great , house was just missing bed linens"
Wandering Woods- Dog-friendly 3 bedroom home with lake access and hot tub!

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

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

10.0 out of 10, Exceptional, (6)
EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

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

10.0 out of 10, Exceptional, (29)
"We LOVED the house! Clean, cozy, great little town. Couldn’t ask for better hosts!"
The price is AU$1,010
includes taxes & fees
21 Aug - 22 Aug
Jamesons Cabin! 8 Minutes to Wisp! Hot Tub! Fire Pit! Arcade! Pets! EV Charger!

Cozy Lake Area Townhome w/ Lake Views, A/C & Grill

8.6 out of 10, Excellent, (4)
"Nice place in the middle of deep creek. Short walk from lake, nice view."
Cozy Lake Area Townhome w/ Lake Views, A/C & Grill

A quiet little town

2.0 out of 10, (1)
"Property host never sent check in information nor did they answer any questions. The phone number listed was for someone who wasn’t even associated with the property so you couldn’t even talk anyone. Needless to say we weren’t able to actually stay there due to no communication from the host. Vrbo was useless in getting us a place to stay. Their guarantee turned out to be the biggest joke. They did nothing to find us a place to stay but we’re going to give us credit for future stays. So we were...
A quiet little town
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Oakland Hotel Reviews

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 560 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.