Holiday Rentals in Oakland
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384 rentals in Oakland.
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The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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OWLS NEST, Premiere Lake Waterfront, Cabin w HotTub, Private Dock, Cozy Romantic
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Lake Access Chalet-NO “OWNER FEES”, Indoor Pool, Home Theater, BoatDock, Firepit
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Beautiful Lake Front Cottage
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Peaceful Lakefront !/Free WIFI/Wonderful Hot Tub!
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Level lakefront, family-friendly, low fees, private dock
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock
Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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Luxury*LAKE area*PRIVATE*Tranquil COZY Cabin*HOT TUB by DECK FIREPLACE*Pool Tbl
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Secluded Lakefront Log Home w/ Hot Tub and Private Dock!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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DOGS WELCOME! Lake Access Home w/Hot Tub, Fire Pit, Pool Table, & 2 Fireplaces!
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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DOGS WELCOME! Lake Area Cabin w/Hot Tub, Wood Fireplace, & Charcoal Grill!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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DOGS WELCOME! Lake Area Cabin w/Hot Tub & Wood Fireplace!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Red Run Cabin
Cabin Holiday Rental
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront Log Home w/Private Dock, Hot Tub, Pool Table, & Fire Pit!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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DOGS WELCOME! Lake Area Home w/Indoor Hot Tub, Sun Room, & 2 Fireplaces!
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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DOGS WELCOME! Lake Area Home w/Hot Tub, Pool Table, & Jetted Tub!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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DOGS WELCOME! Lake Area Home w/Hot Tub!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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5 BR Immaculate Chalet, Dog Friendly, Dock Slip, Hot Tub, Community Pool
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Three Bedroom Cabin On Wooded Lot Near Lake. Secluded, Family And Pet Friendly.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake Area Cabin w/Hot Tub, Wood Fireplace, & Charcoal Grill!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Premier chalet w/ private hot tub, pool table, firepit, & tranquil wooded views
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Lake Area Home w/Hot Tub, Fire Pit, Wood Fireplace, & Gas Grill!
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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All About the View: Lakefront Home with Awe-Inspiring Views!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Lakefront, dog-friendly home w/ hot tubs, game room, dock & space for 25!
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 25
Match: Sleeps
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Walking distance to restaurants, 5 minutes from DCL State Park!
Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Quaint retreat w/ firepit, fully equipped kitchen, & easy access to trails!
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Lovin Life Deep Creek 5 Bedroom Luxury Log Home w/ Pool Table & Hot Tub
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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DOGS WELCOME! Lakefront Home w/Private Dock, Hot Tub, & Wood Fireplace!
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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Spacious townhome - 5 minutes from favorite activities & restaurants!
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Lake access with dock slip, close to favorite lake activities!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Changes in Attitude: Lakefront home with private dock & hot tub!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
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Lake Access Home w/Hot Tub, Pool Table, 2 Fire Pits, & Gas Grill!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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4 Bedroom Lakefront Home with hot tub in quiet neighborhood!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Amazing Lake Views & Upscale Decor in the Heart of Deep Creek
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Quiet, cozy, comfortable home at Deep Creek, Maryland
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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New listing! Adorable cabin in the woods w/ full kitchen, firepit, & porch!
Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Unique and charming cottage by the sea
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Conveniently located cabin with fire pit & dock slip - close to state parks!
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Delightful 3 Bedroom home within walking distance to your dock slip!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Centrally located, tastefully decorated townhome!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps
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Beautiful Lakefront Home w/ Private Indoor Pool
Holiday Rental House
8 bedrooms
9 bathrooms
Sleeps 22
Match: Sleeps
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The Mountain Airy: Great Location, Indoor Hot Tub & 2 Fireplaces
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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DOGS WELCOME! Lake Access Home w/Hot Tub, Fire Pit & Gas Fireplace!
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Log home with private hot tub, air hockey, pool table & media room
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
More info
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Charming cottage w/ large yard & entertainment room - near everything, 2 dogs OK
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Combines a central location with stylish decor!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Frequently Asked Questions about Oakland
- Yes, here are some popular holiday rentals in Oakland that have a pool:\n
- \n
- Lakefront Home w/Private Dock, Hot Tub, Pool Table, & Wood Fireplace! \n
- DOGS WELCOME! Lake Access Home w/Dock Slip & TONS of Community Amenities! \n
- Lake Area Home w/Hot Tub, Fire Pit, Pool Table, & Wood Fireplace! \n
- Yes, here are some popular holiday rentals in Oakland that have internet access:\n
- \n
- Red Run Cabin \n
- Lake Area Home w/Hot Tub, Fire Pit, Pool Table, & Gas Fireplace! \n
- For sun or for snow, this home is “Always in Season!” There’s no better perch t \n
- The best pet friendly rentals in Oakland are:\n
- \n
- Red Run Cabin \n
- DOGS WELCOME! Lake Access Home w/Dock Slip & TONS of Community Amenities! \n
- DOGS WELCOME! Lake Area Home w/Hot Tub, Fire Pit, & Wood Fireplace! \n
- Some of the most popular kid friendly rentals in Oakland are:\n
- \n
- Red Run Cabin \n
- Lake Area Home w/Hot Tub, Fire Pit, Pool Table, & Gas Fireplace! \n
- For sun or for snow, this home is “Always in Season!” There’s no better perch t \n