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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 231 Rentals in Oakland
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From
$125
Per Night
Response Rate: 100%
2 Bedrooms, 2 Bathrooms, Sleeps 7
15 photos Details
Reviews (1) Make Inquiry
From
$130
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, 1 Bathroom, Sleeps 4
17 photos Details
Reviews (2) Make Inquiry
Also consider
Hilltop Happy Hour
4 Bedrooms, sleeps 12
$1,139 - $1,541 / week
Haley's Carriage House
2 Bedrooms, sleeps 4
$1,083 - $1,458 / week
All Seasons
4 Bedrooms, sleeps 12
$217 - $345 / night
Deck on the Lake - walk to Honi-Honi. Lakefront
2 Bedrooms, sleeps 8
$122 - $318 / night
From
$1,129
Per Week
3 Bedrooms, 4 Bathrooms, Sleeps 8
9 photos Details
Reviews (6) Make Inquiry
From
$1,055
Per Week
3 Bedrooms, 4 Bathrooms, Sleeps 10
12 photos Details
Reviews (7) Make Inquiry
From
$137
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 8
15 photos Details
Reviews (24) Make Inquiry
From
$1,278
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 11
12 photos Details
Reviews (4) Make Inquiry
From
$925
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 10
34 photos Details
Reviews (3) Make Inquiry
Get the List
From
$139
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
12 photos Details
Reviews (25) Make Inquiry
From
$297
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 12
11 photos Details
Reviews (6) Make Inquiry
From
$399
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 10
18 photos Details
Reviews (1) Make Inquiry
From
$1,364
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
8 photos Details
Reviews (9) Make Inquiry
From
$129
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 10
9 photos Details
Reviews (32) Make Inquiry
From
$119
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 11
16 photos Details
Reviews (32) Make Inquiry
From
$1,010
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 8
10 photos Details
Reviews (4) Make Inquiry
From
$1,489
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
12 photos Details
Reviews (3) Make Inquiry
From
$1,005
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 10
11 photos Details
Reviews (2) Make Inquiry
From
$123
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 11
17 photos Details
Reviews (5) Make Inquiry
From
$1,746
Per Week
3 Bedrooms, 4 Bathrooms, Sleeps 10
12 photos Details
Reviews (2) Make Inquiry
From
$1,146
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
12 photos Details
Reviews (1) Make Inquiry
From
$1,322
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 11
11 photos Details
Reviews (18) Make Inquiry
From
$347
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 12
15 photos Details
Reviews (19) Make Inquiry
From
$397
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 8
17 photos Details
Reviews (15) Make Inquiry
From
$1,352
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
9 photos Details
Reviews (2) Make Inquiry
From
$1,736
Per Week
4 Bedrooms, 5 Bathrooms, Sleeps 10
12 photos Details
Reviews (3) Make Inquiry
From
$710
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 6
4 photos Details
Reviews (3) Make Inquiry
From
$1,225
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 10
9 photos Details
Reviews (13) Make Inquiry
From
$1,245
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 9
11 photos Details
Reviews (3) Make Inquiry
From
$494
Per Night
4 Bedrooms, 4 Bathrooms, Sleeps 10
23 photos Details
Reviews (5) Make Inquiry
From
$1,631
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 11
10 photos Details
Reviews (10) Make Inquiry
From
$347
Per Night
4 Bedrooms, 5 Bathrooms, Sleeps 12
18 photos Details
Reviews (17) Make Inquiry
From
$299
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 12
15 photos Details
Reviews (17) Make Inquiry
From
$1,458
Per Week
4 Bedrooms, 5 Bathrooms, Sleeps 11
11 photos Details
Reviews (11) Make Inquiry
From
$1,410
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 15
13 photos Details
Reviews (9) Make Inquiry
From
$1,607
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 10
13 photos Details
Reviews (8) Make Inquiry
From
$240
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 8
8 photos Details
Reviews (1) Make Inquiry
From
$337
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 10
12 photos Details
Reviews (1) Make Inquiry
From
$1,649
Per Week
6 Bedrooms, 4 Bathrooms, Sleeps 16
15 photos Details
Reviews (20) Make Inquiry
From
$1,083
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
11 photos Details
Reviews (1) Make Inquiry
From
$1,845
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 14
9 photos Details
Reviews (8) Make Inquiry
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Book Online(2)

Suitability

  • Wheelchair access (0)
  • Elder access (11)
  • Suitable for children (13)
  • Pet friendly (63)
  • Smoking allowed (0)

Amenities

  • Fireplace (189)
  • Hot Tub (162)
  • Air Conditioning (149)
  • Internet (128)
  • Grill (58)
  • View all amenities
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Book Online(2)

Suitability

  • Wheelchair access (0)
  • Elder access (11)
  • Suitable for children (13)
  • Pet friendly (63)
  • Smoking allowed (0)

Amenities

  • Fireplace (189)
  • Hot Tub (162)
  • Air Conditioning (149)
  • Internet (128)
  • Grill (58)
  • View all amenities