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Homes in Oakland, MD

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All 208 Rentals in Oakland
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$147
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1 / 13
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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$142
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1 / 22
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2 Bedrooms, 2 Bathrooms, Sleeps 7
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$255
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1 / 26
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5 Bedrooms, 5 Bathrooms, Sleeps 14
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Also consider
Crystal Lake
5 Bedrooms, sleeps 14
$1,595 - $3,492 / week
Wynsome Run Lodge
7 Bedrooms, sleeps 18
$822 - $1,345 / night
407-Buxton Cottage
3 Bedrooms, sleeps 7
$479 - $543 / night
Awesome View
8 Bedrooms, sleeps 24
$6,294 - $10,145 / week
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$255
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1 / 26
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4 Bedrooms, 3 Bathrooms, Sleeps 12
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$142
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1 / 26
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$198
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1 / 24
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5 Bedrooms, 3 Bathrooms, Sleeps 14
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$227
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1 / 22
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3 Bedrooms, 2 Bathrooms, Sleeps 10
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$2,186
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1 / 12
5 Bedrooms, 4 Bathrooms, Sleeps 13
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$536
Per Night
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1 / 9
4 Bedrooms, 4 Bathrooms, Sleeps 14
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4 of 5 stars Reviewed 6 September 2011
We stayed here with our adult children and our 4 young grandchildren, and it was a great home for this 3-generation group. There were plenty of bathrooms (3.5), and the game room...
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$282
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1 / 5
2 Bedrooms, 2 Bathrooms, Sleeps 4
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5 of 5 stars Reviewed 20 August 2014
The cabin was clean and ready for us when we arrived. Hot tub was clean and very private because of the patio around it. It was a genuine log cabin in a nice little community of...
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$280
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1 / 12
3 Bedrooms, 2 Bathrooms, Sleeps 10
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4 of 5 stars Reviewed 16 December 2011
Took a chance as we never rented from Taylor-Made. Our entire experience from finding the perfect property on their website to making the reservation to service during our stay...
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$1,063
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1 / 15
6 Bedrooms, 7 Bathrooms, Sleeps 25
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5 of 5 stars Reviewed 12 October 2014
We had a great long weekend skiing at Wisp and spending time together with our big group of friends at Laurel Cove. It was so convenient to stay under one roof, enjoy meals...
5 of 5 stars Reviewed 11 August 2014
Great house and location, 20 people including 10 grandkids ages 15 to 3. Plenty of room for all, highlights were the two hot tubs and the pool table. The swimming area for the...
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$1,706
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1 / 14
4 Bedrooms, 3 Bathrooms, Sleeps 12
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5 of 5 stars Reviewed 15 August 2014
Our family, 2 adults and 3 children (12, 15 and 17) plus Snow Lab, Luie enjoyed this spacious 4 bedroom home. Great hot tub. Saw many deer in the wooded backyard. Short walk to...
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$664
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1 / 6
1 Bedroom, 1 Bathroom, Sleeps 4
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$1,570
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1 / 14
4 Bedrooms, 3 Bathrooms, Sleeps 10
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$1,218
Per Week
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1 / 10
3 Bedrooms, 3 Bathrooms, Sleeps 8
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5 of 5 stars Reviewed 4 October 2014
We loved this place. It was all that we wanted and more. We took our dog with us and he loved being sooo... close to the lake - Right across the street. Things were really...
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$806
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1 / 6
2 Bedrooms, 1 Bathroom, Sleeps 6
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$1,541
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1 / 9
4 Bedrooms, 4 Bathrooms, Sleeps 12
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From
$1,299
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1 / 12
4 Bedrooms, 3 Bathrooms, Sleeps 10
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From
$1,460
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1 / 19
3 Bedrooms, 3 Bathrooms, Sleeps 10
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From
$664
Per Week
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1 / 6
1 Bedroom, 1 Bathroom, Sleeps 4
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From
$3,589
Per Week
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1 / 15
8 Bedrooms, 5 Bathrooms, Sleeps 24
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5 of 5 stars Reviewed 4 January 2012
When everyone walked in they were VERY pleased with this lake house. Beautifully decorated and very roomy. The view was great. We had 22 guests and we never seemed to be on top...
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$3,799
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1 / 16
7 Bedrooms, 7 Bathrooms, Sleeps 22
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5 of 5 stars Reviewed 9 July 2012
Just returned from a super-fantastic vacation at Deep Creek Lake. We stayed at a property called Sundance and it was perfect for our extended family of 17 people. The home is...
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$2,078
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1 / 14
4 Bedrooms, 4 Bathrooms, Sleeps 12
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From
$1,906
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1 / 11
4 Bedrooms, 5 Bathrooms, Sleeps 11
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From
$1,227
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1 / 11
3 Bedrooms, 3 Bathrooms, Sleeps 8
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From
$3,736
Per Week
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1 / 12
8 Bedrooms, 7 Bathrooms, Sleeps 22
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From
$3,497
Per Week
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1 / 27
5 Bedrooms, 5 Bathrooms, Sleeps 14
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5 of 5 stars Reviewed 13 May 2014
We had a great visit to Deep Creek Lake and loved At Last. Lake and waterfront were awesome! This property actually has a sand beach which is extremely unique at the Deep...
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$6,358
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1 / 19
8 Bedrooms, 8 Bathrooms, Sleeps 26
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From
$3,661
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1 / 16
8 Bedrooms, 7 Bathrooms, Sleeps 25
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From
$11,761
Per Week
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1 / 37
10 Bedrooms, 10 Bathrooms, Sleeps 34
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5 of 5 stars Reviewed 29 June 2014
I can't believe there are no reviews on this property. So feel inclined to make one. I've visited Deep Creek several times now, and absolutely love renting through Railey...
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$913
Per Week
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1 / 8
2 Bedrooms, 1 Bathroom, Sleeps 4
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4 of 5 stars Reviewed 3 November 2014
If you are looking for a modern, lavish cabin for a retreat this is not the place for you. If you are looking for a cabin with a lot of character and natural wood with enough...
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From
$1,215
Per Week
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1 / 10
3 Bedrooms, 4 Bathrooms, Sleeps 8
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From
$1,680
Per Week
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1 / 10
4 Bedrooms, 3 Bathrooms, Sleeps 10
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From
$1,227
Per Week
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1 / 10
3 Bedrooms, 2 Bathrooms, Sleeps 8
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From
$1,880
Per Week
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1 / 12
5 Bedrooms, 5 Bathrooms, Sleeps 14
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5 of 5 stars Reviewed 29 May 2014
I enjoyed the home 3 master bedrooms and two nice bedrooms in the basement with a full bath. 5 mins to grocery store and about 8mins to Funland and other activities. I would rent...
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From
$2,204
Per Week
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1 / 14
5 Bedrooms, 5 Bathrooms, Sleeps 14
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From
$1,448
Per Week
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1 / 12
4 Bedrooms, 3 Bathrooms, Sleeps 11
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From
$1,598
Per Week
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1 / 13
4 Bedrooms, 3 Bathrooms, Sleeps 15
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From
$1,490
Per Week
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1 / 19
3 Bedrooms, 4 Bathrooms, Sleeps 11
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Suitability

  • Wheelchair access (0)
  • Elder access (1)
  • Suitable for children (6)
  • Pet friendly (68)
  • Smoking allowed (0)

Amenities

  • Fireplace (194)
  • Hot Tub (171)
  • Air Conditioning (153)
  • Internet (110)
  • Grill (66)
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