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Top Holiday Rentals in Oakland

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

9.8 out of 10, Exceptional, (10)
"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

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

8.4 out of 10, Very good, (55)
"This was my first time staying with VRBO. It was a million dollar view. There were just a few minor things that were mentioned before on other reviews that were not taken care of such as the hole in the master bedroom door, the smell of sewage in the kitchen the garbage disposal area, and also the stairs down to the dock area didn't seem too stable. I would have liked to have seen the fountain on but I do realize it's earlier in the year. The owners may want to change the curtains because not...
Dog-friendly house on the lake, central AC, & EV charger

EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

10.0 out of 10, Exceptional, (3)
"Loved the location of this beautiful cabin - while the weather wasn’t always ideal for outdoor activities during our time in Deep Creek, we enjoyed spending time in the cabin!"
EverGreenGrove-Hemlock2BR/1 BA/Dog Friendly/Hottub

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

8.0 out of 10, Very good, (20)
"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

Lake Loft at Deep Creek Lake

2.0 star property
10.0 out of 10, Exceptional, (3)
"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!"
The price is £271
includes taxes & fees
13 Jul - 14 Jul
Lake Loft at Deep Creek Lake

Bright condo with Deep Creek Lake views, wood fireplace

8.2 out of 10, Very good, (79)
"The property was clean, comfortable and well stocked."
Bright condo with Deep Creek Lake views, wood fireplace

Cabin in the Woods

10.0 out of 10, Exceptional, (10)
"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

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

10.0 out of 10, Exceptional, (23)
"We had such a nice stay at the tiny house! The inside was adorable and the location is perfect. The views were beautiful and there were lots of hiking trails and delicious food nearby. We definitely plan to come back for another stay soon!"
The Tiny House @ Deep Creek Lake - centrally located to everything Deep Creek

Deep Creek Lake Townhome w/ Deck & Water Views

9.6 out of 10, Exceptional, (39)
"Host had great communication and was very friendly. Space was clean and welcoming. We loved the view, as well as how close it is to Wisp. We would stay again! "
Deep Creek Lake Townhome w/ Deck & Water Views

New Construction! Modern Lakefront A-Frame with Hot Tub + Fire Pit

9.6 out of 10, Exceptional, (14)
"Nice place for a weekend getaway"
New Construction! Modern Lakefront A-Frame with Hot Tub + Fire Pit

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

9.8 out of 10, Exceptional, (251)
"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

Charming Dog Friendly Cottage w/ Dock & Fire Pit

9.6 out of 10, Exceptional, (18)
"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 home with furnished deck & lake view - walking distance to shops

8.8 out of 10, Excellent, (43)
"The property was exactly as advertised and just what we wanted from our weekend!"
Charming home with furnished deck & lake view - walking distance to shops

Huge, Beautiful and Quiet Home with Amazing Amenities

9.4 out of 10, Exceptional, (8)
"Great family place. House is as described. User friendly appliances, tv’s and hot tub! All 14 of us enjoyed our stay."
Huge, Beautiful and Quiet Home with Amazing Amenities

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

10.0 out of 10, Exceptional, (294)
"I absolutely loved staying at the Love Shack! It was really cozy and cute. It’s dog friendly which was great! The hot tub was a great little add on to the property and the cabin is close to a lot of great places. We would definitely stay here again!"
The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!

Sisters Treehouse

9.6 out of 10, Exceptional, (97)
"Property was wonderful. Location was great. Enjoyed our stay at this property. Thank you for letting us use your place."
Sisters Treehouse

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

8.4 out of 10, Very good, (49)
"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,

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

8.2 out of 10, Very good, (30)
"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

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

10.0 out of 10, Exceptional, (42)
"We enjoyed our stay and the peace of this lovely home very much!"
Lakefront, dog friendly, dock slip, hot tub, and fire pit

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

10.0 out of 10, Exceptional, (6)
"Great stay, beautiful home and location which met all of our needs. Would highly recommend. Only complaint was grass was over a foot high when we arrived, looked like it hadn't been cut this year and made the yard unusable. However, after calling to report the yard condition a crew came out and got everything mowed. They were very nice and apologetic about the yard condition and had the property mowed and we were able to then use the yard."
Log Retreat: Lake Access, Dogs Welcome, Dock Slip, 2 Hot Tubs!
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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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?

Bon Vivant-Pet Friendly, Lake Front, Minutes to HoniHoni, Uno, Brenda's, Wisp: This highly rated holiday home rental in Oakland offers a fireplace, a selection of games and a BBQ 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. You and your friends and family can relax into your holiday with amenities such as 1 hot tub. Some other top choices in Oakland are Dog-friendly house on the lake, central AC, & EV charger and Modern house on the lake with private dock, hot tub, air hockey & central AC.

How many holiday rentals are there in Oakland?

With 561 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.