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Condos and vacation rentals in Oakland, MD

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All 230 Rentals in Oakland
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From
$125
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
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22 photos Details
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$220
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
13 photos Details
Reviews (7) Make Inquiry
From
$125
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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26 photos Details
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Also consider
Turtle Cove
3 Bedrooms, sleeps 6
$212 - $357 / night
Home Sweet Cabin
4 Bedrooms, sleeps 10
$247 - $337 / night
Five Diamonds
4 Bedrooms, sleeps 15
$1,410 - $2,055 / week
Hemlock Chalet
3 Bedrooms, sleeps 12
$1,026 - $1,731 / week
From
$175
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 14
24 photos Details
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$200
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 10
22 photos Details
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From
$225
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 12
26 photos Details
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From
$125
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
17 photos Details
Reviews (2) Make Inquiry
From
$255
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
23 photos Details
Reviews (26) Make Inquiry
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From
$215
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (28) Make Inquiry
From
$503
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 14
34 photos Details
Reviews (16) Make Inquiry
From
$245
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
23 photos Details
Reviews (13) Make Inquiry
From
$237
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 11
28 photos Details
Reviews (33) Make Inquiry
From
$250
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 11
28 photos Details
Reviews (5) Make Inquiry
From
$248
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
30 photos Details
Reviews (24) Make Inquiry
From
$245
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 10
20 photos Details
Reviews (34) Make Inquiry
From
$245
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (2) Make Inquiry
From
$245
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 8
30 photos Details
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From
$265
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 12
17 photos Details
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From
$200
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 4
24 photos Details
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From
$305
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 12
30 photos Details
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From
$302
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 13
43 photos Details
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From
$79
Per Night
Studio, 1 Bathroom, Sleeps 4
50 photos Details
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From
$238
Per Night
4 Bedrooms, 2 Bathrooms, Sleeps 8
10 photos Details
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From
$194
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details
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From
$325
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 12
17 photos Details
Reviews (2) Make Inquiry
From
$347
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
12 photos Details
Reviews (1) Make Inquiry
From
$347
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
18 photos Details
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From
$240
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
7 photos Details
Reviews (5) Make Inquiry
From
$1,474
Per Week
5 Bedrooms, 5 Bathrooms, Sleeps 14
11 photos Details
Reviews (11) Make Inquiry
From
$1,352
Per Week
5 Bedrooms, 5 Bathrooms, Sleeps 14
12 photos Details
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$1,574
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 12
12 photos Details
Reviews (5) Make Inquiry
From
$1,505
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 12
14 photos Details
Reviews (14) Make Inquiry
From
$1,134
Per Week
5 Bedrooms, 4 Bathrooms, Sleeps 10
13 photos Details
Reviews (8) Make Inquiry
From
$711
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
10 photos Details
Reviews (15) Make Inquiry
From
$1,385
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
14 photos Details
Reviews (4) Make Inquiry
From
$1,225
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 10
9 photos Details
Reviews (13) Make Inquiry
From
$806
Per Week
2 Bedrooms, 1 Bathroom, Sleeps 4
8 photos Details
Reviews (14) Make Inquiry
From
$1,083
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
11 photos Details
Reviews (1) Make Inquiry
From
$1,028
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 12
9 photos Details
Reviews (7) Make Inquiry
From
$7,579
Per Week
9 Bedrooms, 9 Bathrooms, Sleeps 26
21 photos Details
Reviews (9) Make Inquiry
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Book Online(6)
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Suitability

  • Wheelchair access (1)
  • Elder access (11)
  • Suitable for children (15)
  • Pet friendly (76)
  • Smoking allowed (0)

Amenities

  • Fireplace (210)
  • Hot Tub (183)
  • Air Conditioning (167)
  • Internet (128)
  • Grill (84)
  • View all amenities
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Book Online(6)

Suitability

  • Wheelchair access (1)
  • Elder access (11)
  • Suitable for children (15)
  • Pet friendly (76)
  • Smoking allowed (0)

Amenities

  • Fireplace (210)
  • Hot Tub (183)
  • Air Conditioning (167)
  • Internet (128)
  • Grill (84)
  • View all amenities