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Holiday Homes in Oakland

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300 rentals in Oakland.
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Red Run Cabin, holiday rental in Oakland

Red Run Cabin

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Shiver Me Timbers, holiday rental in Oakland

Shiver Me Timbers

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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The Love Shack--  The BEST Couples and Small Family Retreat at Deep Creek Lake!, holiday rental in Oakland

The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Grizzly Den, holiday rental in Oakland

The Grizzly Den

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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FIVE STAR REVIEWS!  LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!, holiday rental in Oakland

FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village, holiday rental in Oakland

Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tucked Away, holiday rental in Oakland

Tucked Away

3 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 in Oakland

OWLS NEST,Premiere Lake Waterfront,Cabin w HotTub,private dock,Cozy Romantic,

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful, charming lakefront Cabin with stunning views, private dock, kayaks!, holiday rental in Oakland

Beautiful, charming lakefront Cabin with stunning views, private dock, kayaks!

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Lake Access Chalet-NO “OWNER FEES”, Indoor Pool, Home Theater, BoatDock, Firepit, holiday rental in Oakland

Lake Access Chalet-NO “OWNER FEES”, Indoor Pool, Home Theater, BoatDock, Firepit

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek, holiday rental in Oakland

Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Peaceful Lakefront !/Free WIFI/Wonderful Hot Tub!, holiday rental in Oakland

Peaceful Lakefront !/Free WIFI/Wonderful Hot Tub!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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DOGS WELCOME! Lake Access Home w/Hot Tub, Fire Pit, Pool Table, & 2 Fireplaces!, holiday rental in Oakland

DOGS WELCOME! Lake Access Home w/Hot Tub, Fire Pit, Pool Table, & 2 Fireplaces!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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5 bedroom 5 full bathroom suites, minutes from WISP mountain and Deep Creek Lake, holiday rental in Oakland

5 bedroom 5 full bathroom suites, minutes from WISP mountain and Deep Creek Lake

5 bedrooms
7 bathrooms
Sleeps 15
Match: Sleeps
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Lakefront Log Home w/Private Dock, Hot Tub, Pool Table, & Fire Pit!, holiday rental in Oakland

Lakefront Log Home w/Private Dock, Hot Tub, Pool Table, & Fire Pit!

2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lake Front 4 Bedroom Home With A Dock Centrally Located 5 Minutes To Wisp & Unos, holiday rental in Oakland

Lake Front 4 Bedroom Home With A Dock Centrally Located 5 Minutes To Wisp & Unos

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautifully renovated lake front cottage, holiday rental in Oakland

Beautifully renovated lake front cottage

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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DOGS WELCOME! Lake Area Cabin w/Hot Tub, Wood Fireplace, & Charcoal Grill!, holiday rental in Oakland

DOGS WELCOME! Lake Area Cabin w/Hot Tub, Wood Fireplace, & Charcoal Grill!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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DOGS WELCOME! Lake Area Cabin w/Hot Tub & Wood Fireplace!, holiday rental in Oakland

DOGS WELCOME! Lake Area Cabin w/Hot Tub & Wood Fireplace!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakefront, dog-friendly home w/ hot tubs, game room, dock & space for 25!, holiday rental in Oakland

Lakefront, dog-friendly home w/ hot tubs, game room, dock & space for 25!

6 bedrooms
7 bathrooms
Sleeps 25
Match: Sleeps
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DOGS WELCOME! Lake Area Home w/Hot Tub, Pool Table, & Jetted Tub!, holiday rental in Oakland

DOGS WELCOME! Lake Area Home w/Hot Tub, Pool Table, & Jetted Tub!

5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Dog-friendly country cabin w/ deck, firepit & air hockey - close to Yough River!, holiday rental in Oakland

Dog-friendly country cabin w/ deck, firepit & air hockey - close to Yough River!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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DOGS WELCOME! Lake Area Home w/Hot Tub!, holiday rental in Oakland

DOGS WELCOME! Lake Area Home w/Hot Tub!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lake Area Home w/Fire Pit, Wood Fireplace, & Gas Grill!, holiday rental in Oakland

Lake Area Home w/Fire Pit, Wood Fireplace, & Gas Grill!

4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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DOGS WELCOME! Lake Area Home w/Indoor Hot Tub, Sun Room, & 2 Fireplaces!, holiday rental in Oakland

DOGS WELCOME! Lake Area Home w/Indoor Hot Tub, Sun Room, & 2 Fireplaces!

3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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DOGS WELCOME! Lakefront Home w/Private Dock, Hot Tub, & Wood Fireplace!, holiday rental in Oakland

DOGS WELCOME! Lakefront Home w/Private Dock, Hot Tub, & Wood Fireplace!

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Premier chalet w/ private hot tub, pool table, firepit, & tranquil wooded views, holiday rental in Oakland

Premier chalet w/ private hot tub, pool table, firepit, & tranquil wooded views

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Lake Area Cabin w/Hot Tub, Wood Fireplace, & Charcoal Grill!, holiday rental in Oakland

Lake Area Cabin w/Hot Tub, Wood Fireplace, & Charcoal Grill!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Breath Taking Views, Lake Access, Modern Chalet, holiday rental in Oakland

Breath Taking Views, Lake Access, Modern Chalet

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Log home w/ private hot tub, air hockey/pool tables & media room!, holiday rental in Oakland

Log home w/ private hot tub, air hockey/pool tables & media room!

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Lake Access Home w/Hot Tub, Pool Table, Fire Pit, & Gas Grill!, holiday rental in Oakland

Lake Access Home w/Hot Tub, Pool Table, Fire Pit, & Gas Grill!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Lovin Life Deep Creek 5 Bedroom Luxury Log Home w/ Pool Table & Hot Tub, holiday rental in Oakland

Lovin Life Deep Creek 5 Bedroom Luxury Log Home w/ Pool Table & Hot Tub

5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Home w/mountain views, hot tub, pool table, wet bar - Close to Lake activities!, holiday rental in Oakland

Home w/mountain views, hot tub, pool table, wet bar - Close to Lake activities!

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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The Evergreen, holiday rental in Oakland

The Evergreen

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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It's 5 O'Clock Somewhere, holiday rental in Oakland

It's 5 O'Clock Somewhere

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Family- and dog-friendly home w/ deck, forest view - close to lake & ski slopes, holiday rental in Oakland

Family- and dog-friendly home w/ deck, forest view - close to lake & ski slopes

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New listing! Adorable cabin in the woods w/ full kitchen, firepit, & porch!, holiday rental in Oakland

New listing! Adorable cabin in the woods w/ full kitchen, firepit, & porch!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Dog-friendly lakefront home w/ hot tub, dock, shared tennis - near the slopes!, holiday rental in Oakland

Dog-friendly lakefront home w/ hot tub, dock, shared tennis - near the slopes!

3 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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NEW! Lake Access Home w/Dock Slip, Hot Tub, Fire Pit & MANY Community Amenities!, holiday rental in Oakland

NEW! Lake Access Home w/Dock Slip, Hot Tub, Fire Pit & MANY Community Amenities!

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Blue Spruce, holiday rental in Oakland

Blue Spruce

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Quaint retreat w/ firepit, fully equipped kitchen, & easy access to trails!, holiday rental in Oakland

Quaint retreat w/ firepit, fully equipped kitchen, & easy access to trails!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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DOGS WELCOME! Lake Access Home w/Hot Tub, Fire Pit & Gas Fireplace!, holiday rental in Oakland

DOGS WELCOME! Lake Access Home w/Hot Tub, Fire Pit & Gas Fireplace!

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Timberlodge, holiday rental in Oakland

Timberlodge

9 bedrooms
7 bathrooms
Sleeps 28
Match: Sleeps
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Charming cottage w/ large yard & entertainment room - near everything, 2 dogs OK, holiday rental in Oakland

Charming cottage w/ large yard & entertainment room - near everything, 2 dogs OK

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Looking for a picture-perfect cabin retreat? Designed with relaxation in mind,, holiday rental in Oakland

Looking for a picture-perfect cabin retreat? Designed with relaxation in mind,

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sundance, holiday rental in Oakland

Sundance

7 bedrooms
7 bathrooms
Sleeps 22
Match: Sleeps
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DOGS WELCOME! Lake Area Home w/Hot Tub, Pool Table, Fire Pit, & Gas Fireplace!, holiday rental in Oakland

DOGS WELCOME! Lake Area Home w/Hot Tub, Pool Table, Fire Pit, & Gas Fireplace!

5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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* $1000 off Early Summer NOW! (Weeks beginning June 10th and 17th) This gorgeou, holiday rental in Oakland

* $1000 off Early Summer NOW! (Weeks beginning June 10th and 17th) This gorgeou

9 bedrooms
7 bathrooms
Sleeps 28
Match: Sleeps
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Looking for a picture perfect mountain retreat? Journey’s End is the one!  Brig, holiday rental in Oakland

Looking for a picture perfect mountain retreat? Journey’s End is the one! Brig

8 bedrooms
10 bathrooms
Sleeps 26
Match: Sleeps
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Lakefront Townhouse #08 w/Dock Slip, Wood Fireplace, & Community Fire Pit!, holiday rental in Oakland

Lakefront Townhouse #08 w/Dock Slip, Wood Fireplace, & Community Fire Pit!

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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