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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
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$125
Per Night
Response Rate: 100%
2 Bedrooms, 2 Bathrooms, Sleeps 4
26 photos Details
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Also consider
Bear Foot Cove
5 Bedrooms, sleeps 14
$2,158 - $2,708 / week
Harmony
4 Bedrooms, sleeps 12
$1,568 - $3,887 / week
Vista on the Lake
2 Bedrooms, sleeps 7
$1,102 - $1,957 / week
Deck on the Lake - walk to Honi-Honi. Lakefront
2 Bedrooms, sleeps 8
$258 - $318 / 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
$968
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 14
34 photos Details
Reviews (16) Make Inquiry
From
$212
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
10 photos Details
Reviews (2) Make Inquiry
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From
$4,682
Per Week
8 Bedrooms, 8 Bathrooms, Sleeps 26
19 photos Details
Reviews (14) Make Inquiry
From
$1,288
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 10
19 photos Details
Reviews (1) Make Inquiry
From
$298
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 11
28 photos Details
Reviews (5) Make Inquiry
From
$297
Per Night
5 Bedrooms, 6 Bathrooms, Sleeps 12
11 photos Details
Reviews (1) Make Inquiry
From
$1,375
Per Week
Response Rate: 30%
3 Bedrooms, 3 Bathrooms, Sleeps 10
34 photos Details
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From
$2,117
Per Week
Response Rate: 30%
4 Bedrooms, 5 Bathrooms, Sleeps 12
14 photos Details
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From
$5,985
Per Week
9 Bedrooms, 9 Bathrooms, Sleeps 26
21 photos Details
Reviews (9) Make Inquiry
From
$3,367
Per Week
7 Bedrooms, 7 Bathrooms, Sleeps 18
23 photos Details
Reviews (9) Make Inquiry
From
$318
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
20 photos Details
Reviews (12) Make Inquiry
From
$5,004
Per Week
8 Bedrooms, 9 Bathrooms, Sleeps 24
18 photos Details
Reviews (12) Make Inquiry
From
$1,075
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
10 photos Details
Reviews (9) Make Inquiry
From
$283
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 11
28 photos Details
Reviews (33) Make Inquiry
From
$265
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (28) Make Inquiry
From
$1,146
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
12 photos Details
Reviews (1) Make Inquiry
From
$1,558
Per Week
Response Rate: 30%
3 Bedrooms, 3 Bathrooms, Sleeps 10
11 photos Details
Reviews (2) 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
$3,032
Per Week
7 Bedrooms, 7 Bathrooms, Sleeps 18
21 photos Details
Reviews (8) Make Inquiry
From
$3,360
Per Week
Response Rate: 30%
4 Bedrooms, 4 Bathrooms, Sleeps 14
9 photos Details
Reviews (8) Make Inquiry
From
$2,173
Per Week
3 Bedrooms, 4 Bathrooms, Sleeps 10
15 photos Details
Reviews (6) Make Inquiry
From
$497
Per Night
5 Bedrooms, 5 Bathrooms, Sleeps 14
23 photos Details
Reviews (1) Make Inquiry
From
$297
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 12
11 photos Details
Reviews (6) Make Inquiry
From
$1,410
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 15
13 photos Details
Reviews (9) Make Inquiry
From
$310
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
30 photos Details
Reviews (24) Make Inquiry
From
$1,288
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
13 photos Details
Reviews (15) Make Inquiry
From
$332
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 12
15 photos Details
Reviews (6) Make Inquiry
From
$347
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
12 photos Details
Reviews (1) Make Inquiry
From
$299
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 12
15 photos Details
Reviews (17) Make Inquiry
From
$1,278
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 11
12 photos Details
Reviews (4) Make Inquiry
From
$240
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 8
8 photos Details
Reviews (1) Make Inquiry
From
$1,225
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 10
9 photos Details
Reviews (13) Make Inquiry
From
$1,456
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 12
10 photos Details
Reviews (5) 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)
  • View all amenities
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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