Photo by KM Moore

Holiday Rentals in Oakland

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Holiday Rentals in Oakland

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

7.6 out of 10, Good, (15)
"Look every person and home has a few things we want to change but this place had everything we need to make our stay most enjoyable"
Modern house on the lake with private dock, hot tub, air hockey & central AC

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

10.0 out of 10, Exceptional, (276)
"We loved the cabin! In the perfect quiet location. Very clean and the host was amazing with communication. Definitely recommend this place! "
The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!

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

8.8 out of 10, Excellent, (38)
"Had a relaxing time at the property. Close to stores and restaurants."
In the Heart of Deep Creek, Wood Fire, steps Lake, Coffee, Pizza, minutes Whisp,

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

9.8 out of 10, Exceptional, (237)
"This property does not disappoint!! What you see in the photos is exactly how this tastefully decorated cabin will look on arrival. Dale was a wonderful host. She emailed us helpful information ahead of our visit and answered our questions quickly. "
Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

10.0 out of 10, Exceptional, (13)
"We rented the Gathering Place for a long weekend during a beautiful Fall weekend. The location was great, close to the water and only about 15 minutes to Swallow Falls. The house was very welcoming and cozy, but larger than what it appears online. The bed was comfortable and the hot tub and fireplace were so nice to come home to! Communication was great with the host and they were very helpful and quick with their responses. If you're looking for a Deep Creek home to rent, this is the place! "
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

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

8.6 out of 10, Excellent, (7)
"Perfect stay! We will be back for sure!"
5BR lakefront retreat with hot tub, sauna, & dock

Raccoon Lagoon Deep Creek Lake Front Rental Minutes from Wisp Ski Resort!!

10.0 out of 10, Exceptional, (36)
"Had the BEST stay at Raccoon Lagoon. 10000/10 would recommend to anyone looking for a place to stay at deep creek! "
Raccoon Lagoon Deep Creek Lake Front Rental Minutes from Wisp Ski Resort!!

Dog-friendly cabin with private hot tub, Ping-Pong & lake views

8.6 out of 10, Excellent, (77)
"A beautifully furnished cabin so close to the amenities and state parks of Deep Creek Lake. So well stocked with everything you need "
Dog-friendly cabin with private hot tub, Ping-Pong & lake views

Bright condo with Deep Creek Lake views, wood fireplace

8.2 out of 10, Very good, (71)
"The property was clean, comfortable and well stocked."
Bright condo with Deep Creek Lake views, wood fireplace

Cozy, family-friendly, lakeview condo with gas grill & firepit

7.6 out of 10, Good, (41)
"Very clean. Great location and view of the lake. Loved having a fire pit and grill. Hosts were very communicative. Note that one of the bedrooms has a queen bed and the other one now has a bunk bed (twin on top, double on bottom). Would definitely stay here again!"
Cozy, family-friendly, lakeview condo with gas grill & firepit

Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough River

9.6 out of 10, Exceptional, (76)
"Great place and close to Wisp. Really enjoyed our stay! Will book there again. Great location with fire pit and yard! Just one small issue - there were dozens of lady bugs in the upstairs bedroom. It was fine but thought you all should know."
Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough River

Good Vibrations: Lake Access, Log Chalet, Hot Tub, Fire Pit, Grill!

9.6 out of 10, Exceptional, (7)
"Perfect home loved every part, can’t wait to return "
Good Vibrations: Lake Access, Log Chalet, Hot Tub, Fire Pit, Grill!

Spacious family-friendly chalet w/fenced dog run & large deck near the lake/Wisp

9.6 out of 10, Exceptional, (18)
"Really enjoyed our stay. My husband and I celebrated our 12 year anniversary with our pups. Loved the fenced yard and closed deck. The place was spacious and clean. It was a wonderful stay!"
Spacious family-friendly chalet w/fenced dog run & large deck near the lake/Wisp

Amazing Central Location! Lakefront! Hot tub/dock!

9.4 out of 10, Exceptional, (40)
"Great accommodation, perfect location directly on the lake. The house had two stoves , two dishwashers, and two fridges. Amble parking and wonderful hot tub. I should also add that compared to other rentals on the lake, this house was within our budget. Well done all."
Amazing Central Location! Lakefront! Hot tub/dock!

New! Serenity Shores: Lake Area, Dogs OK, Hot Tub, Fireplace, Fire Pit, A/C!

9.2 out of 10, Wonderful, (16)
"We love the fire pit making s’mores with family and friends! Loved the hot tub! Very quiet wooded area, saw a black bear at the end of the property! We loved our stay! "
New! Serenity Shores: Lake Area, Dogs OK, Hot Tub, Fireplace, Fire Pit, A/C!

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

10.0 out of 10, Exceptional, (30)
"This home provided all that we could need. Lots of space for the family to be together. We would consider this home again when back in the area!"
Lakefront, dog friendly, dock slip, hot tub, and fire pit

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

8.4 out of 10, Very good, (26)
"Enjoyed our stay..location is great..close to restaurants and entertainment. "
Rural, Dog-Friendly Home Tucked Into the Woods with Gas Fireplace and Free WiFi

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

8.6 out of 10, Excellent, (48)
"My sister, daughter and I were in wow mode from the moment we walked in the door. The pictures on line did not do justice to the "Million Dollar View" description. The place was very clean, inviting, accommodating and beautiful! Appliances were very updated and snacks and treats were also left on the counter for us. Owner thought of everything to make this as pleasant as it was for us. We will definitely return again. Thank you"
Dog-friendly house on the lake, central AC, & EV charger

Deep Creek Lake Townhome w/ Deck & Water Views

9.6 out of 10, Exceptional, (32)
"Very clean and well maintained. Decor includes interesting items from around the world. Master bed was comfy, and owner was friendly on the phone. When she learned we were coming for my husband's birthday, she left a fun card for him with all the check-in info. We went in October and enjoyed the cozy gas fireplace and beautiful lake view. A busy road stands between the condo and the lake, but it's not a huge issue in cold weather when windows are closed. If you're looking for remote mountain...
Deep Creek Lake Townhome w/ Deck & Water Views

New: Lakefront Luxury Home with Private Indoor Heated Pool!

9.6 out of 10, Exceptional, (4)
"We had a full house for the weekend and still had plenty of room to move around. The layout was absolutely perfect for us, a mix of family and friends. Location was great! Close to Wisp, food options, market. Also not in a heavily trafficked part of the lake, we were able to jump off the dock to swim, paddle board and kayak out. Will definitely book again!"
New: Lakefront Luxury Home with Private Indoor Heated Pool!
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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Other types of properties in Oakland you may be interested in

The Garrett Inn

2.5 star property
9.6 out of 10, Exceptional, (351)
"A very quaint place- loved it!"
The price is €118
includes taxes & fees
26 Nov - 27 Nov
The Garrett Inn

Riverside Suites

2.0 star property
9.0 out of 10, Wonderful, (48)
"All the comforts and amazingly clean!!"
The price is €155
includes taxes & fees
26 Nov - 27 Nov
Riverside Suites

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

7.6 out of 10, Good, (15)
"Look every person and home has a few things we want to change but this place had everything we need to make our stay most enjoyable"
Modern house on the lake with private dock, hot tub, air hockey & central AC
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.

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.