Oakland Rentals
From $455 per night (USD)VRBO
Dog Friendly Deep Creek Chalet w/ Hot Tub & Deck
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Name: Divided Sky | Bedrooms: 5 | Bathrooms: 3 | Sleeps: 13 | Access: Lake Area | Dogs Welcome Max. 2 | MUST BE 24+ YEAR ...
From $455 per night (USD)VRBO
From $371 per night (USD)Expedia
Lost Bearadise: Lake Area, Indoor Hot Tub, Fireplaces, Foosball, A/C!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Name: Lost Bearadise | Bedrooms: 3 | Bathrooms: 3 | Sleeps: 8 | Access: Lake Area | Pets Not Permitted | MUST BE 24+ YEA ...
From $371 per night (USD)Expedia
From $522 per night (USD)VRBO
Historic Family 6-bedroom home on delightful 2nd Street in Oakland, MD
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Welcome to this historic 1880s home on Second Street in downtown Oakland, Maryland. Furnished with antiques yet comforta ...
From $522 per night (USD)VRBO
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Broadford Park View
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to this 5 bedroom/3 1/2 Bsth home with Modern kitchen on main level that opens to Living room and Dining area. W ...
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From $237 per night (USD)VRBO
Windy Acres | Dog Friendly + Hot Tub & Great Views!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 11
Get ready to escape to a destination like no other at Windy Acres. This stunning chalet-style log cabin located in Herri ...
From $237 per night (USD)VRBO
From $465 per night (USD)Expedia
Elegant Home Away: Hot Tub, Game Room, Kid Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
The perfect location for your Deep Creek escape! Enjoy a quiet retreat in this custom-built oasis near the golf course! ...
From $465 per night (USD)Expedia