Updating...

Enter dates for more accurate prices

Oakland Rentals

Filter

Bedrooms

  • Any
  • 1+ Bedrooms
  • 2+ Bedrooms
  • 3+ Bedrooms
  • 4+ Bedrooms
  • 5+ Bedrooms
  • 6+ Bedrooms
  • 7+ Bedrooms
  • 8+ Bedrooms
  • 9+ Bedrooms
  • 10+ Bedrooms
  • 11+ Bedrooms
  • 12+ Bedrooms
  • 13+ Bedrooms
  • 14+ Bedrooms
  • 15+ Bedrooms

Price range

Per night

$10 - $500

Oakland Rentals

About Oakland

446 Houses

Triple-T Lodge

Oakland house

4 bedrooms / 3 bathrooms / sleeps 12

“First class all the way” Beautiful home, great location, near to everything! Railey Vacation Rentals is on top of their game. From arrival to departure everything was absolutely perfect. If something was needed, it was handled by Railey immediately. Top notch accommodations and everything was clean and I mean clean. We'll definitely return in the near future.

Price per night from

$45

1 / 10

Diamond on the Lake

Oakland house

5 bedrooms / 6 bathrooms / sleeps 14

“The Diamond Still Sparkles!” This is a beautiful place to stay - stunning sunsets - the house has everything you need (except a 2nd refrigerator and a chaise or more comfortable porch furniture). The screened in gazebo is delightful

Price per night from

$100

1 / 13

Tree house

Oakland log cabin

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$104

1 / 25

Absolute Delight

Oakland house

8 bedrooms / 7 bathrooms / sleeps 25

“Great Time, Great Friends, and Great House” We had very good service, we booked Absolute Delight again for 2009, and we also stayed there in 2007. The house met all of our needs. Having 2 refrigerators was a plus for that size of a house. Also, we chose Absolute Delight because of the extra beds in a few of the bedrooms. Having 2 master bedrooms upstairs with the extra beds was something we looked at when first choosing Absoulute Delight. The kids can sleep in the Parent's room in their own beds and also be upstairs away from the noise. The location was also a huge advantage. We really enjoyed staying at Absolute Delight. I think this is our 15th year in a row renting from Railey's over the New Year holiday.

Price per night from

$321

1 / 25

Swallow Falls Inn Cabin 3

Oakland house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$124

1 / 10

The Herrington

Oakland house

10 bedrooms / 15 bathrooms / sleeps 34

Price per night from

$1,174

1 / 77

Bear Cove

Oakland house

3 bedrooms / 4 bathrooms / sleeps 10

“Great value” A group of us rented Bear Cove rented this for a bachelorette weekend. Spacious, clean, quiet and beautiful lake front property! This is great for a quiet get away!

Price per night from

$100

1 / 12

Making Memories

Oakland house

4 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$258

1 / 16

Unreel

Oakland house

5 bedrooms / 4 bathrooms / sleeps 13

“Christmas Skiing” The best part were the heated floors. It was always a warm morning at Unreel in the winter.

Price per night from

$201

1 / 55

Price per night from

$89

1 / 45

Willow Point

Oakland house

2 bedrooms / 2 bathrooms / sleeps 6

“Willow Point is One of The Best” My wife and I have rented several cottages around the lake and Willow Point is by far the best. Everything from the cottage itself to the location on the lake is perfect. We travel with 2 dogs and don't need a house that sleeps 20. Willow Point is located on a quiet road where we have a safe place to walk and it's only a short boat ride to the Honi Honi for food and spirits! You won't be disappointed.

Price per night from

$61

1 / 14

At Last

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$100

1 / 60

Morning Breeze

Oakland house

4 bedrooms / 3 bathrooms / sleeps 10

“Great place to stay,” Lakefront home with private doc. Well appointed home. Although not needed during this stay, home does not have a/C. It is a little older but well maintained. It was a great location on the lake, secluded yet close to conveniences. The location of the lake was great, well protected. The one leg of the dock need to be stabilized, but overall worked well

Price per night from

$100

1 / 21

Lost Bearadise

Oakland house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$89

1 / 18

Swallow Falls Inn Cabin 4

Oakland house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$165

1 / 10

Magnificent View Point

Oakland house

4 bedrooms / 5 bathrooms / sleeps 12

“Magnificent” Magnificent View Point lives up to it's name. This was our 2nd stay at this beautiful lake front home. The home is beautifully decorated, bright & cheery. The kitchen is well equipped with everything you could possibly need. The large lot is conducive to playing games with a short walk to your private dock. Swimming is great there because there isn't any lake grass. It is located at the end of a quiet cove which is so relaxing & peaceful. The owners have done everything possible to make one's stay a great memory.

Price per night from

$289

1 / 19

Hemlock Chalet

Oakland house

3 bedrooms / 2 bathrooms / sleeps 12

“Great cabin, clean and beautiful!” The Hemlock Chalet was a wonderful place to relax and enjoy Deep Creek. Though it is a bit of drive to the mountain, the cabin was clean, beautifully decorated, and spacious. My friends and I had a blast.

Price per night from

$52

1 / 15

Sylvan Sweet

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$110

1 / 19

Hilltop Happy Hour

Oakland house

4 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$69

1 / 23

Blue Spruce

Oakland house

4 bedrooms / 3 bathrooms / sleeps 10

“A truly wonderful week!” It's refreshing these days when everything a business tells you they will do...they actually do. Everything went so smoothly and was just as Railey said it would be.

Price per night from

$89

1 / 23

AAH Chalet

Oakland house

5 bedrooms / 3 bathrooms / sleeps 12

“Ahh Chalet” Raileys Mountain Lake Rental was great as usual. Very easy check in and check out process. We had two issues at the begining of the week and all it took was one phone call and they were resolved that same day aAH Chalet was a great lakefront home located close to all activities. The house was furnished beautifully and the kitchen was very well stocked. There were plenty of extra pillows and blankets. The outdoor fire pit, private dock and hot tub were all big hits with all three families that stayed. Renting our boat from Bill Marina was an extremly easy process because aHH Chalet was in walking distance to pick up and drop off the boat. The location was great. Some may not like being directly in the middle of everything but it worked out great considering we had five teenage girls with us. They were able to walk to the Lakeside Creamery and Popcorn Factory every evening and we made morning walks to arrowhead market. It was in close driving distance to the Wisp, Funland and restaurants. There were three families that stayed at aHH Chalet and we all enjoyed it. Staying lakefront and near everything was great. I highly recommend aHH Chalet!

Price per night from

$101

1 / 23

Crosswinds

Oakland house

5 bedrooms / 4 bathrooms / sleeps 14

“Big House, Big Fun” The house was large and spacious. Especially the large parking pad, which made it very easy to park 4 vehicles with bass boats in tow! Did not even have to unhitch the trailers. The hot tub was a nice added amenity, as was the large master bath with cathedral ceilings. Our group thuroughly enjoyed the pool table too. My only complaint was that the queen sleeper sofa was out of commission the entire 3 days we stayed, thus forcing 2 gentleman to sleep on horrible portable beds, and 2 even slept on the floor. Railey Realty was pleasant and convenient, but could have handled the bed situation a little better in my opinion. All in all, I give our experience a 9 out of 10. We would rent this house again in the future.

Price per night from

$83

1 / 12

Wispering Ridge

Oakland house

2 bedrooms / 3 bathrooms / sleeps 6

“Great location, great view” The townhome was spotless. We love to cook and the kitchen was well equipped. Linens were provided and that was a great help. Location just off 219 but we had a great view of Deep Creek Lake. Only problem for elderly guest were the steps from the parking lot to reach the front door.

Price per night from

$59

1 / 24

Creature Comforts

Oakland house

6 bedrooms / 4 bathrooms / sleeps 16

“Spectacularly awesome!” It's not often when an entire family can get away during the holidays for some R & R! A last minute decision was made and Railey Mountain Vacation, specifically "Creature Comforts" vacation home provided the venue for our family to obtain the holiday vacation that we sought! We had an awsome time, the amenities and activities were superb!

Price per night from

$196

1 / 20

Home on the Ridge

Oakland house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$70

1 / 15

Pine Oasis

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

“great place” This was the perfect place for us in terms of size, location. We loved that it was on the water. If we could ad anything, it would be a fire pit outside.

Price per night from

$152

1 / 75

It's 5 O'Clock Somewhere

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

“beautiful weekend” our group has rented this home several times and it is always very clean. we rent this home because we look for 5 couples to have their own private bedroom & bath & it is difficult to find very many homes that met our needs w/ queen &/or king beds for five couples. the locate is nice & the hot tub is under the deck for cover in bad weather.the view is nice & we would rent again.

Price per night from

$105

1 / 12

Red Run Cabin

Oakland log cabin

3 bedrooms / 2 bathrooms / sleeps 6

“One fine package!” John was most helpful and the house is quite nice. Not brand new but very well kept. Been coming to this area for over 45 years and now I have a place I want to go back to! Not the Ritz but just fine by me & my wife and I feel this is one of the best deals in the area. This place is perfect for a group or a family. Very quiet this time of year ( seems it might be in summer also). Easy to get to. Has everything you could ask for, albeit not the "top of the line", but again how much does one need when going skiing? Far cry better than any Holiday or Comfort Inn, that for sure! We expect to return with our next trip and have told all of our friends. A suggestion is to be prepaired to get a fire going right away as the electric baseboard heaters take a while if the house has cooled down to 45 or so degrees. They work just fine and keep the house toasty once they have a chance - but that's hours, not minutes. I expected this and is not a complaint what so ever.

Responds fast! avg. 1 hour 58 minutes

Price per night from

$200

1 / 22

Telstar.gon

Oakland house

6 bedrooms / 5 bathrooms / sleeps 15

“Fabulous Home!!” Beautifully decorated home equipped with everything we could possible need!! It easily accommodated our group of 15 adults. The large dining area meant all of us could sit down around the large table for a meal at the same time. The kitchen has tons of large pots and pans. The bed and bath linens were clean. The home is located at the end of a cul-de-sac which offers lots of privacy. We will definitely book this home next year!!

Price per night from

$195

1 / 16

Crowd Pleaser

Oakland house

4 bedrooms / 5 bathrooms / sleeps 11

“This rental was a Crowd Pleaser” This was a very comfortable rental. Clean and well stock with everything necessary for a quiet getaway. There are a lot of steps and being 70+ it makes us think about returning. If we were younger we would definitely come back. The views are wonderful and there are 3 balconies to sit and enjoy the sites. It was a sunny weekend so we really enjoyed the outside.

Price per night from

$84

1 / 14

Ritz on the Lake

Oakland house

8 bedrooms / 8 bathrooms / sleeps 26

“We had an awesome time!!” We stayed at the Ritz on the Lake in Oct...it was very nice!! The house is well kept, clean and supplied with lots of useful pots, pans, utensils, etc. The only problem was that I believe something is wrong with the refridgerators. We brought alot of food so it was imperative that they work properly and although a maintainance man came out on our 2nd day, he claimed they were working fine, but they weren't. It was a good thing that we had plenty of coolers with ice that kept our meats and other perishables cold. Other than that, it was really a great time. The house is really nice, warm and "home-like" which was exactly what we were looking for!!

Price per night from

$577

1 / 19

LinLaurAl

Oakland house

5 bedrooms / 3 bathrooms / sleeps 12

“had an enjoyable time” First floor bedrooms were uncomfortable because of poor ventilation. This could have been remedied with either more efficient air circulation or the presence of the smallest BTU air conditioners. Master bedroom was also rather stuffy until I positioned the two floor fans to draw outside air into the room. The only problem with this is that there are no properly working patio door screens in the entire house.

Price per night from

$103

1 / 13

Glistening Waters

Oakland house

4 bedrooms / 4 bathrooms / sleeps 12

“Railey's Deep Creek Lake property - Glistening Waters” Railey has excellent service from identifying a rental property that fits my needs through check in on the day I arrived. Friendly, competent people. The Glistening Waters property offers wooded seclusion perfect for unwinding and relaxing. Located at the end of a private road, the grassy well-maintained garden is level. Ideal for playing yard games like croquet and bocce ball. The surrounding large oak trees and fern covered ground offer a tranquil view as they meet the lake. A private dock conveniently located beside Glisten Waters allows docking of a rental boat or jet ski and a short 2 minute walk to the house for a mid-afternoon snack. The house's interior is immaculately clean and modern. The hot tub is icing on the cake to have social time with your family. I highly recommend Glistening Waters. And

Price per night from

$66

1 / 14

Arctic Retreat

Oakland house

3 bedrooms / 2 bathrooms / sleeps 8

“our stay felt like we was at home” My overall review is the place was actualy better than deepvillage when we came june 25,2010

Price per night from

$68

1 / 13

Cedar Lodge

Oakland house

4 bedrooms / 3 bathrooms / sleeps 12

“Lovely stay at Cedar Lodge” Our group truly enjoyed our extended weekend at Cedar Lodge. It was a very cozy home with room enough for everyone to find couch for reading. Really enjoyed the front porch. We really appreciated being allowed to bring our dogs, they loved going on walks on the quiet streets and going to the lake.

Price per night from

$65

1 / 20

Papa Bear

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

“beautiful” papa bear is a beautiful home my family and I was there on march 29th for the weekend ...we had such a great time the house is convenient to everything...It had everything we needed their..plenty of space!!! we will be coming back in june!!!

Price per night from

$44

1 / 11

Harmony

Oakland house

4 bedrooms / 3 bathrooms / sleeps 12

“Great views of deep creek” Excellent location. Cleanliness of home was not very good. In need of thorough cleaning, especially carpet in pool room. To much dust on tables and drawers.

Price per night from

$54

1 / 35

Tamaqua Lodge

Oakland house

6 bedrooms / 5 bathrooms / sleeps 15

“Wonderful” The house was great. Very clean, except for mouse droppings in a couple draws. Kitchen stocked with all utensils, winter view was beautiful. Difficult to get home at comfortable temp, too warm upstairs and downstairs too cold.

Price per night from

$171

1 / 21
Viewing 38 of 446

About Oakland

×

Located in the beautiful mountains of western Maryland, Oakland is the perfect woodland escape. Be the first to see the sun hit the green hills from your vacation home's bedroom balcony, then walk just minutes to Deep Creek Lake, perfect for boating, tubing, hiking, and swimming. Feel free to bring the water skis and kayak as there is plenty of space inside your vacation rental to store your equipment. While you are here, spend a day at Swallow Falls State Park, home to some of Maryland's most beautiful natural scenery. Hike along trails with panoramic views of rocky gorges, flowing rapids, and Muddy Creek Falls, a thrashing 53-foot waterfall. The park offers a large picnic area with a pavilion and playground, as well as nature programs, boat rentals, and a beach for swimming during the summer.

Here are a few additional suggestions of things to do in the area:

  • Visit Maryland's Historic B&O Train Station: This authentic 1884 train station has been restored to its original Queen Anne condition. The train speaks to Oakland's old, small town feel and adjoins a shop that sells baked goods, candles and maple syrup.
  • See a show at Our Town Theatre: This little production company offers great local and imported talent. Be sure to check the current schedule while visiting, and catch great comedies, dramas, and more.
  • Visit the county's Historical Society Museum: Like the train station, the historical museum is a great place to learn about the area's history and get a feel for small town life in another era.
  • Play golf: Champion caliber Deep Creek golf courses offer some of the best greens in the state. After a day of golf, spend an afternoon indulging in a pedicure at a luxury Deep Creek spa.
  • Go horseback riding: Several private stables in the state park area offer one-on-one lessons or trail rides with a friendly knowledgeable guide.
  • Experience Deep Creek skiing: In the winter, Deep Creek offers pristine, powdery trails perfect for both cross country and downhill skiing.

Experience the best of Oakland and the Deep Creek Lake area by staying in your own private luxury vacation rental. A trendy winter condo or summer apartment rental may be perfect for a long weekend getaway with friends. You may also decide to host your family and friends for a barbeque at your lakeside vacation home or mountain cabin. While you're visiting Oakland, make the most of your stay by scheduling a visit to nearby Swanton or McHenry.

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more