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Houses in Oakland and Log cabins – Holiday Lettings - Holiday Rentals Oakland

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520 Holiday homes

Holiday condo in Oakland

Oakland condo

3 bedrooms / 3 bathrooms / sleeps 10

from £118 / night

£824 / week

Holiday home in Oakland

Oakland house

4 bedrooms / 3 bathrooms / sleeps 10

4

from £131 / night

£916 / week

Holiday log cabin in Oakland

Oakland log cabin

2 bedrooms / 2 bathrooms / sleeps 8

from £203 / night

£1,417 / week

Holiday home in Oakland

Oakland house

3 bedrooms / 2 bathrooms / sleeps 10

5

from £122 / night

£850 / week

Holiday home in Oakland

Oakland house

6 bedrooms / 5 bathrooms / sleeps 14

from £239 / night

£1,667 / week

Log cabin rental in Oakland

Oakland log cabin

2 bedrooms / 2 bathrooms / sleeps 6

from £138 / night

£962 / week

Log cabin rental in Oakland

Oakland log cabin

3 bedrooms / 3 bathrooms / sleeps 12

from £186 / night

£1,298 / week

Holiday home letting

Oakland house

3 bedrooms / 2 bathrooms / sleeps 8

7

from £122 / night

£850 / week

Holiday home in Oakland

Oakland house

6 bedrooms / 4 bathrooms / sleeps 16

“Great property!” We did a 4 day 3 night rental for the New Year holiday. When they say to use caution on the driveway in winter conditions they aren't kidding. In addition to the snow we received the week before, we got an additional 6 inches while we were there which made it impossible to use the gravel steep drive without 4 wheel and even then we had some problems. This really is a great property and has some great lake front access. It is located only like 5 or 7 minutes from the rental office, not the 15 or 20 they instructed us when we arrived. All of the furniture is very modern. A better television is needed in the upstairs living room though.

9

from £338 / night

£2,366 / week

Holiday condo rental

Oakland condo

5 bedrooms / 5 bathrooms / sleeps 14

from £255 / night

£1,786 / week

Oakland holiday home rental

Oakland house

2 bedrooms / 3 bathrooms / sleeps 6

4

from £108 / night

£752 / week

Holiday home rental

Oakland house

4 bedrooms / 4 bathrooms / sleeps 10

1

from £108 / night

£752 / week

Holiday home in Oakland

Oakland house

4 bedrooms / 3 bathrooms / sleeps 12

“Great time” We were celebrating our 15th wedding anniv. We having been vacationing in Deep Creek for the past 6 or 7 years by far this was the best place we stayed it was a beautiful home we had such a wonderful time we will return soon.

5

from £131 / night

£916 / week

Oakland holiday home rental

Oakland house

4 bedrooms / 2 bathrooms / sleeps 11

from £163 / night

£1,140 / week

Oakland holiday home rental

Oakland house

5 bedrooms / 3 bathrooms / sleeps 12

“Great Location, warrants better service” Great Location. Found enormous number of leaves on deck - clearly no one had serviced the unit prior to our arrival. Counter tops and kitchen appliances had gummy feel. Having to bring your own toilet paper made this a pedestrian rental - given the amount of money charged.

13

from £167 / night

£1,167 / week

Home rental in Oakland

Oakland house

3 bedrooms / 3 bathrooms / sleeps 8

from £131 / night

£916 / week

Holiday home letting

Oakland house

4 bedrooms / 3 bathrooms / sleeps 14

1

from £239 / night

£1,667 / week

Holiday home in Oakland

Oakland house

4 bedrooms / 3 bathrooms / sleeps 12

6

from £183 / night

£1,279 / week

Holiday log cabin in Oakland

Oakland log cabin

2 bedrooms / 1 bathroom / sleeps 6

from £152 / night

£1,061 / week

Holiday home in Oakland

Oakland house

5 bedrooms / 4 bathrooms / sleeps 14

from £187 / night

£1,305 / week

Holiday log cabin rental

Oakland log cabin

3 bedrooms / 3 bathrooms / sleeps 10

from £171 / night

£1,193 / week

Holiday home rental

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

“This home is perfect for those that want a private, quiet and se” This home is in perfect condition and is the perfect retreat for a large group. With 5 children under the age of 6 we needed a home that was secluded, safe, private and offered a large yard. This was it! The beds very super comfortable, the hot tub was perfect, and it is a nice short distance to the lake. The gameroom was a great area for the children and due to the safe and secluded neighborhood we felt completely comfortable letting them play outside with minimal supervision. The staff at Railey was helpful and responsive to the minor issues that we had. It's 5 O'Clock Somewhere is a must stay. We would go back in a heartbeat!

18

from £145 / night

£1,015 / week

Oakland holiday home rental

Oakland house

4 bedrooms / 3 bathrooms / sleeps 10

“Very nice weekend.” Some minor cleaning and repairs to lights in the bathroom. Master bed needs a step to get into the bed. The house is very cozy. Second time we have stayed there. Unfortunately it was cold and rainy most of the time we were there this year. Would love to come back again.

15

from £179 / night

£1,252 / week

Holiday home accommodation

Oakland house

5 bedrooms / 4 bathrooms / sleeps 10

“Great time” The only drawback we had was trying to get someone out to plow the road after the ice storm. This was finally resolved, but we did lose some ski time on our weekend lift tickets. The house was lovely and very comfortable, our dog even had a great time.

10

from £131 / night

£916 / week

Holiday home in Oakland

Oakland house

4 bedrooms / 3 bathrooms / sleeps 12

from £131 / night

£916 / week

Holiday condo in Oakland

Oakland condo

5 bedrooms / 5 bathrooms / sleeps 14

from £131 / night

£916 / week

Holiday home letting

Oakland house

3 bedrooms / 4 bathrooms / sleeps 10

from £108 / night

£752 / week

Holiday home in Oakland

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

5

from £396 / night

£2,768 / week

Log cabin rental in Oakland

Oakland log cabin

3 bedrooms / 3 bathrooms / sleeps 9

from £147 / night

£1,028 / week

Oakland holiday home rental

Oakland house

5 bedrooms / 5 bathrooms / sleeps 14

“Papa Bear was a lovely home in a great location.” Beautifully decorated and spacious. It easily accomodated our family of 14. The view of the lake was spectacular. There were a few issues,though. The hot tub was not in working order which was disappointing. Some of the beds were uncomfortable. One of the bedrooms on the top floor was noisy and very warm when the fireplace was on. The pullout couch in the basement master was broken (fine for kids but certainly not for adults). Despite these issues we enjoyed our stay. We appreciated the good customer service that Railey provided.

11

from £131 / night

£916 / week

Holiday home in Oakland

Oakland house

5 bedrooms / 3 bathrooms / sleeps 12

5

from £142 / night

£989 / week

Home rental in Oakland

Oakland house

8 bedrooms / 9 bathrooms / sleeps 24

“A Little Piece of Heaven at Deep Creek” Our whole family was there to celebrate our 50th wedding anniversary and we all enjoyed our whole stay. The view is beautiful, the home was all we could ask for and more and of course the Deep Creek area has much to offer all ages. The only problem we had was the bears getting into the trash even though we took precautions to try to see that they did not. We understood that the lady next door feeds them...not a good thing.

12

from £1,022 / night

£7,149 / week

Holiday home in Oakland

Oakland house

3 bedrooms / 3 bathrooms / sleeps 8

from £155 / night

£1,081 / week

Holiday home in Oakland

Oakland house

4 bedrooms / 5 bathrooms / sleeps 14

“Magnificent View Point” Probably one of our best vacations at Deep Creek Lake, largely as result of the house and its location on the lake. The house was everything we hoped it would be and it provided good value for the money spent to lease it. Well equipped and well furnished. Of the six houses we have rented in last six years, it is probably second best. Position on the point made for beautiful setting on the lake. Swiming and fishing were great for all of the family. Only set back was the aproach to the house. Tree in front obscured the mailbox and the house number and there was no Railey's sign to be seen anywhere. On our first approach to the house, we turned around and left because nothing matched what we were told to expect and there was a vacant car parked in the parking lot. On second approach to the house, we found the house number on the mailbox underneath the tree. Next trick was to get into the house. Neither set of keys worked on the front doors. Seems the keys were newly cut so didn't work well. After some serious twisting and multiple tries, was able to open one of the doors. Later, I put some lubricant in the keyhole. Problem solved.

6

from £437 / night

£3,058 / week

Holiday home in Oakland

Oakland house

9 bedrooms / 9 bathrooms / sleeps 26

“Family stay at Under the Stars - Annual Kadar Reunion” Our stay was delightful in every respect. This was our 11thfamily reunion and the accomodation met every expectation at Deep Creek. Minor problem was with the pool alarm which kept malfunctioning and needed several service calls, which were courteous and prompt. All other amenities that come with a facility that houses 26 were immaculate and worked properly. LaDonna is a definite asset to the Railey organization as she followed up on all our needs for this year and next year's reunion rental. Thank you for having her on your staff!

10

from £1,111 / night

£7,775 / week

Holiday home in Oakland

Oakland house

3 bedrooms / 3 bathrooms / sleeps 8

from £131 / night

£916 / week

Holiday home in Oakland

Oakland house

3 bedrooms / 2 bathrooms / sleeps 8

5

from £108 / night

£752 / week

Holiday log cabin in Oakland

Oakland log cabin

2 bedrooms / 1 bathroom / sleeps 6

from £163 / night

£1,140 / week

Oakland holiday home rental

Oakland house

2 bedrooms / 2 bathrooms / sleeps 6

“very nice house” This was a warm, cozy, spotless winter getaway spot for myself, my girlfriend and our chocolate lab. All necessary amenities were available including a very ample supply of dry firewood, a clean well functioning hottub with a great view and a spacious well supplied kitchen. The fireplace, decent TV, cooking and eating utensils and bedroom view all exceeded expectations. The only downside was the difficult driveway entrance and unusable upstairs shower. The main bathroom however was excellent.

11

from £145 / night

£1,015 / week

Holiday home in Oakland

Oakland house

3 bedrooms / 4 bathrooms / sleeps 8

6

from £131 / night

£916 / week

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rentals in Oakland

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Oakland holidays

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 holiday 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 holiday 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 programmes, 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 cheque 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 calibre 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 holiday 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 holiday home or mountain cabin. While you're visiting Oakland, make the most of your stay by scheduling a visit to nearby Swanton or McHenry.

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