We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Oakland, MD

Use a credit card to book with our Peace of Mind Protection.
Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
All 231 Rentals in Oakland
loading...
Sort by
From
₹65,972
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
11 photos Details
Reviews (1) Make Enquiry
From
₹196,759
Per Week
8 Bedrooms, 7 Bathrooms, Sleeps 25
16 photos Details
Reviews (2) Make Enquiry
From
₹21,138
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
18 photos Details
Reviews (1) Make Enquiry
Also consider
Edgewater
5 Bedrooms, sleeps 14
₹95,151 - ₹167,154 / week
Making Memories
4 Bedrooms, sleeps 12
₹151,499 - ₹296,845 / week
Bearfoot Lodge
5 Bedrooms, sleeps 12
₹93,567 - ₹124,574 / week
Home on the Ridge
3 Bedrooms, sleeps 8
₹61,647 - ₹78,704 / week
From
₹21,138
Per Night
4 Bedrooms, 5 Bathrooms, Sleeps 12
17 photos Details
Reviews (18) Make Enquiry
From
₹14,620
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
7 photos Details
Reviews (5) Make Enquiry
From
₹15,046
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 10
12 photos Details
Reviews (14) Make Enquiry
From
₹13,097
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
22 photos Details
Reviews (28) Make Enquiry
From
₹30,641
Per Night
5 Bedrooms, 4 Bathrooms, Sleeps 14
34 photos Details
Reviews (16) Make Enquiry
Get the List
From
₹7,615
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
22 photos Details
Reviews (3) Make Enquiry
From
₹7,615
Per Night
2 Bedrooms, 1 Bathroom, Sleeps 6
17 photos Details
Reviews (2) Make Enquiry
From
₹13,402
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
13 photos Details
Reviews (7) Make Enquiry
From
₹144,250
Per Week
6 Bedrooms, 4 Bathrooms, Sleeps 16
14 photos Details
Reviews (3) Make Enquiry
From
₹89,790
Per Week
5 Bedrooms, 5 Bathrooms, Sleeps 14
11 photos Details
Reviews (11) Make Enquiry
From
₹200,841
Per Week
8 Bedrooms, 7 Bathrooms, Sleeps 22
12 photos Details
Reviews (7) Make Enquiry
From
₹111,720
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 12
14 photos Details
Reviews (3) Make Enquiry
From
₹192,922
Per Week
8 Bedrooms, 5 Bathrooms, Sleeps 24
15 photos Details
Reviews (8) Make Enquiry
From
₹62,500
Per Week
3 Bedrooms, 2 Bathrooms, Sleeps 12
7 photos Details
Reviews (5) Make Enquiry
From
₹193,957
Per Week
8 Bedrooms, 8 Bathrooms, Sleeps 26
19 photos Details
Reviews (14) Make Enquiry
From
₹65,302
Per Week
3 Bedrooms, 4 Bathrooms, Sleeps 8
10 photos Details
Reviews (6) Make Enquiry
From
₹187,683
Per Week
7 Bedrooms, 5 Bathrooms, Sleeps 18
15 photos Details
Reviews (13) Make Enquiry
From
₹393,031
Per Week
9 Bedrooms, 8 Bathrooms, Sleeps 28
16 photos Details
Reviews (14) Make Enquiry
From
₹289,108
Per Week
8 Bedrooms, 8 Bathrooms, Sleeps 26
15 photos Details
Reviews (8) Make Enquiry
From
₹62,622
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 12
9 photos Details
Reviews (7) Make Enquiry
From
₹26,925
Per Night
5 Bedrooms, 3 Bathrooms, Sleeps 13
10 photos Details
Reviews (6) Make Enquiry
From
₹82,846
Per Week
4 Bedrooms, 4 Bathrooms, Sleeps 12
9 photos Details
Reviews (9) Make Enquiry
From
₹49,098
Per Week
2 Bedrooms, 1 Bathroom, Sleeps 4
8 photos Details
Reviews (14) Make Enquiry
From
₹84,369
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
14 photos Details
Reviews (4) Make Enquiry
From
₹237,086
Per Week
7 Bedrooms, 7 Bathrooms, Sleeps 20
15 photos Details
Reviews (4) Make Enquiry
From
₹204,861
Per Week
7 Bedrooms, 6 Bathrooms, Sleeps 20
18 photos Details
Reviews (3) Make Enquiry
From
₹91,679
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 12
14 photos Details
Reviews (14) Make Enquiry
From
₹74,622
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 10
9 photos Details
Reviews (13) Make Enquiry
From
₹192,922
Per Week
8 Bedrooms, 6 Bathrooms, Sleeps 22
15 photos Details
Reviews (8) Make Enquiry
From
₹82,359
Per Week
5 Bedrooms, 5 Bathrooms, Sleeps 14
12 photos Details
Reviews (4) Make Enquiry
From
₹118,482
Per Week
5 Bedrooms, 5 Bathrooms, Sleeps 14
14 photos Details
Reviews (5) Make Enquiry
From
₹69,079
Per Week
5 Bedrooms, 4 Bathrooms, Sleeps 10
13 photos Details
Reviews (8) Make Enquiry
From
₹101,060
Per Week
5 Bedrooms, 5 Bathrooms, Sleeps 14
12 photos Details
Reviews (12) Make Enquiry
From
₹78,460
Per Week
4 Bedrooms, 3 Bathrooms, Sleeps 10
13 photos Details
Reviews (15) Make Enquiry
From
₹148,270
Per Week
6 Bedrooms, 6 Bathrooms, Sleeps 14
13 photos Details
Reviews (7) Make Enquiry
From
₹24,245
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 12
29 photos Details
Reviews (17) Make Enquiry
From
₹100,451
Per Week
6 Bedrooms, 4 Bathrooms, Sleeps 16
15 photos Details
Reviews (20) Make Enquiry
Go to map view
Book Online(6)
Use filters to find the best results!

Suitability

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

Amenities

  • Fireplace (211)
  • Hot Tub (184)
  • Air Conditioning (168)
  • Internet (128)
  • Grill (84)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities