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Condos and vacation rentals in Oakland, MD

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 232 Rentals in Oakland
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$125
Per Night
Response Rate: 100%
2 Bedrooms, 2 Bathrooms, Sleeps 7
22 photos Details
Reviews (1) Make Inquiry
From
$220
Per Night
Response Rate: 100%
3 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details
Reviews (7) Make Inquiry
From
$125
Per Night
Response Rate: 100%
2 Bedrooms, 2 Bathrooms, Sleeps 4
26 photos Details
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Also consider
St. Bart's Retreat
7 Bedrooms, sleeps 18
$3,032 - $5,463 / week
The McHenry
2 Bedrooms, sleeps 8
$240 - $287 / night
All Seasons
4 Bedrooms, sleeps 12
$217 - $345 / night
Grande Villa
5 Bedrooms, sleeps 12
$297 - $397 / night
From
$165
Per Night
Response Rate: 100%
4 Bedrooms, 4 Bathrooms, Sleeps 11
24 photos Details
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From
$200
Per Night
Response Rate: 100%
3 Bedrooms, 2 Bathrooms, Sleeps 10
22 photos Details
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From
$125
Per Night
Response Rate: 100%
2 Bedrooms, 1 Bathroom, Sleeps 6
17 photos Details
Reviews (2) Make Inquiry
From
$1,375
Per Week
Response Rate: 10%
3 Bedrooms, 3 Bathrooms, Sleeps 10
34 photos Details
Reviews (3) Make Inquiry
From
$3,360
Per Week
Response Rate: 10%
4 Bedrooms, 4 Bathrooms, Sleeps 14
9 photos Details
Reviews (8) Make Inquiry
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From
$1,558
Per Week
Response Rate: 10%
3 Bedrooms, 3 Bathrooms, Sleeps 10
11 photos Details
Reviews (2) Make Inquiry
From
$960
Per Week
Response Rate: 10%
3 Bedrooms, 2 Bathrooms, Sleeps 6
6 photos Details
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From
$2,117
Per Week
Response Rate: 10%
4 Bedrooms, 5 Bathrooms, Sleeps 12
14 photos Details
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From
$1,615
Per Week
Response Rate: 10%
5 Bedrooms, 3 Bathrooms, Sleeps 13
10 photos Details
Reviews (6) Make Inquiry
From
$1,315
Per Week
Response Rate: 10%
3 Bedrooms, 4 Bathrooms, Sleeps 12
11 photos Details
Reviews (7) Make Inquiry
From
$1,868
Per Week
Response Rate: 10%
4 Bedrooms, 3 Bathrooms, Sleeps 10
13 photos Details
Reviews (3) Make Inquiry
From
$2,395
Per Week
Response Rate: 10%
3 Bedrooms, 4 Bathrooms, Sleeps 10
23 photos Details
Reviews (10) Make Inquiry
From
$945
Per Week
Response Rate: 10%
3 Bedrooms, 3 Bathrooms, Sleeps 8
7 photos Details
Reviews (5) Make Inquiry
From
$2,095
Per Week
Response Rate: 10%
4 Bedrooms, 3 Bathrooms, Sleeps 12
29 photos Details
Reviews (16) Make Inquiry
From
$1,940
Per Week
Response Rate: 10%
5 Bedrooms, 5 Bathrooms, Sleeps 10
9 photos Details
Reviews (7) Make Inquiry
From
$3,670
Per Week
Response Rate: 10%
6 Bedrooms, 5 Bathrooms, Sleeps 20
8 photos Details
Reviews (4) Make Inquiry
From
$2,295
Per Week
Response Rate: 10%
3 Bedrooms, 4 Bathrooms, Sleeps 10
13 photos Details
Reviews (7) Make Inquiry
From
$6,000
Per Week
Response Rate: 10%
6 Bedrooms, 7 Bathrooms, Sleeps 25
15 photos Details
Reviews (21) Make Inquiry
From
$1,585
Per Week
Response Rate: 10%
4 Bedrooms, 3 Bathrooms, Sleeps 12
16 photos Details
Reviews (3) Make Inquiry
From
$1,320
Per Week
Response Rate: 10%
3 Bedrooms, 2 Bathrooms, Sleeps 7
10 photos Details
Reviews (4) Make Inquiry
From
$905
Per Week
Response Rate: 10%
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
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From
$855
Per Week
Response Rate: 10%
3 Bedrooms, 4 Bathrooms, Sleeps 6
18 photos Details
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From
$968
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 14
34 photos Details
Reviews (16) Make Inquiry
From
$318
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
20 photos Details
Reviews (12) Make Inquiry
From
$297
Per Night
5 Bedrooms, 6 Bathrooms, Sleeps 12
11 photos Details
Reviews (1) Make Inquiry
From
$212
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
10 photos Details
Reviews (2) Make Inquiry
From
$3,367
Per Week
7 Bedrooms, 7 Bathrooms, Sleeps 18
23 photos Details
Reviews (9) Make Inquiry
From
$265
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (28) Make Inquiry
From
$1,288
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 10
19 photos Details
Reviews (1) Make Inquiry
From
$305
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 10
12 photos Details
Reviews (10) Make Inquiry
From
$1,669
Per Week
5 Bedrooms, 3 Bathrooms, Sleeps 12
16 photos Details
Reviews (13) Make Inquiry
From
$5,004
Per Week
8 Bedrooms, 9 Bathrooms, Sleeps 24
18 photos Details
Reviews (12) Make Inquiry
From
$2,173
Per Week
3 Bedrooms, 4 Bathrooms, Sleeps 10
15 photos Details
Reviews (6) Make Inquiry
From
$1,278
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 11
12 photos Details
Reviews (4) Make Inquiry
From
$5,985
Per Week
9 Bedrooms, 9 Bathrooms, Sleeps 26
21 photos Details
Reviews (9) Make Inquiry
From
$1,315
Per Week
3 Bedrooms, 4 Bathrooms, Sleeps 11
19 photos Details
Reviews (12) Make Inquiry
From
$1,288
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
13 photos Details
Reviews (15) Make Inquiry
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Suitability

  • Wheelchair access (0)
  • Elder access (11)
  • Suitable for children (13)
  • Pet friendly (75)
  • Smoking allowed (0)

Amenities

  • Fireplace (206)
  • Hot Tub (179)
  • Air Conditioning (167)
  • Internet (130)
  • Grill (80)
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Book Online(5)

Suitability

  • Wheelchair access (0)
  • Elder access (11)
  • Suitable for children (13)
  • Pet friendly (75)
  • Smoking allowed (0)

Amenities

  • Fireplace (206)
  • Hot Tub (179)
  • Air Conditioning (167)
  • Internet (130)
  • Grill (80)
  • View all amenities