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Oakland Rentals

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524 Houses

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

$272

Tranquil Dreams

Oakland house

4 bedrooms / 3 bathrooms / sleeps 10

“Fun Stay” Many amenities (toilet paper, cleaning supplies, grilling materials, camping gear) were already provided when we arrived, making for a nice, care-free vacation. Beautiful location. Wonderful living space. Billiards table, fire pit, and hot-tub a great addition. Some of the beds were a little uncomfortable.

Price per night from

$160

Arrowhead #26

Oakland condo

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$144

Deer Pass

Oakland house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$290

Hemlock Chalet

Oakland house

3 bedrooms / 2 bathrooms / sleeps 10

“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

$148

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

$131

Owl Cabin

Oakland log cabin

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$247

Linwood

Oakland house

3 bedrooms / 2 bathrooms / sleeps 8

“Rental for wedding party” Plenty of space, nice locations, big patio and deck

Price per night from

$148

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

$215

Home on the Ridge

Oakland house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$160

Windy Acres

Oakland log cabin

3 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$226

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

$244

A Winter View

Oakland house

4 bedrooms / 2 bathrooms / sleeps 11

Price per night from

$198

Almost Heaven

Oakland condo

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$160

Log Heaven

Oakland house

4 bedrooms / 4 bathrooms / sleeps 10

“Weekend Getaway with friends” We had a very nice stay at Log Heaven. It must have been newly renovated because it was just beautiful. Fun times with friends. We recommend a stay at this cabin and we will surely be back. The only thing is that it did not have air conditioning but plenty of cieling fans. Luckily we stayed when the weather was just gorgeous.

Price per night from

$131

Paradise Chalet

Oakland log cabin

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$208

Simply Cozy

Oakland condo

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$311

Lake It Easy

Oakland house

3 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$131

Tree house

Oakland log cabin

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$168

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

$215

At Last

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$477

Sunset Dream

Oakland house

4 bedrooms / 3 bathrooms / sleeps 14

“Nice layout and beauutiful location.” This was a nice house that seems to be undergoing some renovation. We were there during a virtually snowless ski vacation - but the house provided a great home base for reconnecting with family and enjoying the area. The layout with the bulk of the sleeping areas in an area removed from the activity in the large family room/kitchen was perfect for letting everyone get together while still providing an ability for finding your own space. We had problems with the heater and the dishwasher, but Railey responded quickly and hopefully this will not be an issue for future renters. Given its location right on the lake, it looks like it would be perfect for a summer stay.

Price per night from

$296

Dream On

Oakland house

5 bedrooms / 4 bathrooms / sleeps 10

“Tons of room for family fun!” Dream on is a great property with many upgrades you may have at home. The kitchen was fully stocked with the essentials needed for cooking a big meal. The open layout allows the whole family to gather in one place. The parking only allows for 3 cars because of the mounds of snow. I do think the cleaning service could have done a better job. Overall, a beautiful house.

Price per night from

$162

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

$409

The Whitetail

Oakland log cabin

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$185

Just Perfect

Oakland house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$160

The Evergreen

Oakland log cabin

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$231

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

$131

Summerside

Oakland house

5 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$226

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

$177

Bare Necessities

Oakland house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$188

Always in Season

Oakland house

6 bedrooms / 5 bathrooms / sleeps 14

“One of our Best Vacations” This house offered something for everyone. A pool table, videomachine, hot tub, fire pit, short sloping walk to dock, and a hammock to relax. There were six bedrooms, and 4 of them had their own bathrooms. The house was close to Herrington Manor and Swallow Falls, plus a quick drive to Oakland. My favorite part was roasting marshmallows.

Price per night from

$366

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

$160

Glistening Waters

Oakland house

4 bedrooms / 4 bathrooms / sleeps 12

“comfort” Thank you for your service and all the help! Everything worked out great!

Price per night from

$244

Whitewater Lodge

Oakland log cabin

3 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$177

Peregrine's Perch

Oakland house

8 bedrooms / 9 bathrooms / sleeps 24

“Another amazing trip” Weve stayed at this property multiple times and it still amazes us how much of a great time we have with a house full of amenities. You almost never have to leave with all the things to do.

Price per night from

$1,243

Mountaineer

Oakland house

3 bedrooms / 4 bathrooms / sleeps 8

“Great house, good value, Pet Friendly!” Our recent stay at Moutaineer was excellent as was the rental process through Railey Mountain Vacations. We arrived after check-in and the drop box system worked very well. I would advise those choosing Mountaineer during the winter season that the driveway is very steep and although the driveway had been plowed at some point, only the vehicles with 4WD capability made it up to the house. We left the other cars parked at the base of the driveway. Not a big deal, just something to mention. The amentities were excellent and the house had a very warm and cozy vibe. Last word of caution would be the cover for the hot tub. It was damaged in such a way that it made it very difficult to open it up (very heavy). But we managed eventually and were very happy to have a great way to warm up after a day of skiing! Thanks again Railey and Mountaineer! All and all an awesome weekend!

Price per night from

$160

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

$160

Viewing 38 of 524
rentals in Oakland

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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.

Top Destination reviews

Almost Aspen
Almost aspen - try almost Heaven!

We stayed in this gorgeous house for our annual New Years Eve Trip with 15 of our close friends. Not only is the house very modern, but has extra perks like flat screen Tv's, awesome sound system that plays throughout the whole house, 2 refrigerators and dishwashers, and an amazing fireplace. We were all able to sit and eat together, which most houses make you spread out a bit with big groups due to space. The property provided firewood for us so we saved a lot of money on firewood. Check in was easy as well. We will definitely make a return trip to this house! Do yourself a favor and check this house out if you have a large group!see more
Emerald Bay
Just Perect

There was 10 adults. Plenty of space to be together playing cards or seperate for a break from one another. This place is very clean inside. Very pleased to go on vacation and not have to clean the bathroom before using it. The only complaint was the computer room bed is very hard, but that is personal because there may be someone in your group that needs that. If you don't, do not plan on using this bed for someone. take a blow up mattress. Very peaceful and enjoyable time.see more
Glistening Waters
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. Andsee more
Magnificent View Point
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.see more
Telstar.gon
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!!see more
Red Run Cabin
Awesome! It was so beautiful & peaceful.

I enjoyed everything about our visit. The property was well kept and we felt like we were at home. The environment was very comfortable. It was convenient to travel to the grocery store and to find places to eat. It was nice having the state park pass. We visited 2 state parks while we were there (Oct. 27-30). We want to visit again next year! We were wondering about summer rentals & noticed that there wasn't AC. We can't imagine sleeping on a hot summer night without it.see more

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