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Oakland Holiday Apartments

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263 rentals in Oakland.
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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, holiday rental in Oakland
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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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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!, holiday rental in Oakland
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!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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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,, holiday rental in Oakland
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,

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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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, holiday rental in Oakland
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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Beautifully renovated lake front cottage, holiday rental in Oakland
Beautifully renovated lake front cottage, holiday rental in Oakland
Beautifully renovated lake front cottage, holiday rental in Oakland

Beautifully renovated lake front cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
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Peaceful Lakefront !/Free WIFI/Wonderful Hot Tub!, holiday rental in Oakland
Peaceful Lakefront !/Free WIFI/Wonderful Hot Tub!, holiday rental in Oakland
Peaceful Lakefront !/Free WIFI/Wonderful Hot Tub!, holiday rental in Oakland

Peaceful Lakefront !/Free WIFI/Wonderful Hot Tub!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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, holiday rental in Oakland
Charming, Eco-Friendly Cabin Retreat, Heart of Deep Creek, holiday rental in Oakland

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Luxury *SECLUDED*Tranquil FOREST Cabin By LAKE-Deck FIREPLACE, Hot Tub/Pool Tbl, holiday rental in Oakland
Luxury *SECLUDED*Tranquil FOREST Cabin By LAKE-Deck FIREPLACE, Hot Tub/Pool Tbl, holiday rental in Oakland
Luxury *SECLUDED*Tranquil FOREST Cabin By LAKE-Deck FIREPLACE, Hot Tub/Pool Tbl, holiday rental in Oakland

Luxury *SECLUDED*Tranquil FOREST Cabin By LAKE-Deck FIREPLACE, Hot Tub/Pool Tbl

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 13
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Level lakefront, family-friendly, low fees, private dock, holiday rental in Oakland
Level lakefront, family-friendly, low fees, private dock, holiday rental in Oakland
Level lakefront, family-friendly, low fees, private dock, holiday rental in Oakland

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 in Oakland
Stunning 7 Bedroom  6.5 Bath Lakefront Home with Dock, holiday rental in Oakland
Stunning 7 Bedroom  6.5 Bath Lakefront Home with Dock, holiday rental in Oakland

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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FIVE STAR REVIEWS!  LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!, holiday rental in Oakland
FIVE STAR REVIEWS!  LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!, holiday rental in Oakland
FIVE STAR REVIEWS!  LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!, holiday rental in Oakland

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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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, holiday rental in Oakland
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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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Secluded Lakefront Log Home w/ Hot Tub and Private Dock!, holiday rental in Oakland
Secluded Lakefront Log Home w/ Hot Tub and Private Dock!, holiday rental in Oakland
Secluded Lakefront Log Home w/ Hot Tub and Private Dock!, holiday rental in Oakland

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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5 BR Immaculate Chalet, Dog Friendly, Dock Slip, Hot Tub, Community Pool, holiday rental in Oakland
5 BR Immaculate Chalet, Dog Friendly, Dock Slip, Hot Tub, Community Pool, holiday rental in Oakland
5 BR Immaculate Chalet, Dog Friendly, Dock Slip, Hot Tub, Community Pool, holiday rental in Oakland

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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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!, holiday rental in Oakland
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!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Red Run Cabin, holiday rental in Oakland
Red Run Cabin, holiday rental in Oakland
Red Run Cabin, holiday rental in Oakland

Red Run Cabin

Cabin Holiday Rental
3 bedrooms
2 bathrooms
Sleeps 6
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!, holiday rental in Oakland
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!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
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!, holiday rental in Oakland
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!

Holiday Rental House
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!, holiday rental in Oakland
DOGS WELCOME! Lake Area Cabin w/Hot Tub & Wood Fireplace!, holiday rental in Oakland

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Sisters Treehouse, holiday rental in Oakland
Sisters Treehouse, holiday rental in Oakland
Sisters Treehouse, holiday rental in Oakland

Sisters Treehouse

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 7
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!, holiday rental in Oakland
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!

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 25
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!, holiday rental in Oakland
Lake Area Home w/Fire Pit, Wood Fireplace, & Gas Grill!, holiday rental in Oakland

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
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!, holiday rental in Oakland
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!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
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!, holiday rental in Oakland
DOGS WELCOME! Lake Area Home w/Hot Tub!, holiday rental in Oakland

DOGS WELCOME! Lake Area Home w/Hot Tub!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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!, holiday rental in Oakland
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!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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, holiday rental in Oakland
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

Holiday Rental House
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!, holiday rental in Oakland
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!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
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!, holiday rental in Oakland
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!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Spacious townhome - 5 minutes from favorite activities & restaurants!, holiday rental in Oakland
Spacious townhome - 5 minutes from favorite activities & restaurants!, holiday rental in Oakland
Spacious townhome - 5 minutes from favorite activities & restaurants!, holiday rental in Oakland

Spacious townhome - 5 minutes from favorite activities & restaurants!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Walking distance to restaurants, 5 minutes from DCL State Park!, holiday rental in Oakland
Walking distance to restaurants, 5 minutes from DCL State Park!, holiday rental in Oakland
Walking distance to restaurants, 5 minutes from DCL State Park!, holiday rental in Oakland

Walking distance to restaurants, 5 minutes from DCL State Park!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Child-friendly luxurious lodge one block from the lake, holiday rental in Oakland
Child-friendly luxurious lodge one block from the lake, holiday rental in Oakland
Child-friendly luxurious lodge one block from the lake, holiday rental in Oakland

Child-friendly luxurious lodge one block from the lake

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Three Bedroom Cabin On Wooded Lot Near Lake. Secluded, Family And Pet Friendly., holiday rental in Oakland
Three Bedroom Cabin On Wooded Lot Near Lake. Secluded, Family And Pet Friendly., holiday rental in Oakland
Three Bedroom Cabin On Wooded Lot Near Lake. Secluded, Family And Pet Friendly., holiday rental in Oakland

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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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!, holiday rental in Oakland
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!

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 in Oakland
Lake Area Cabin w/Hot Tub, Wood Fireplace, & Charcoal Grill!, holiday rental in Oakland
Lake Area Cabin w/Hot Tub, Wood Fireplace, & Charcoal Grill!, holiday rental in Oakland

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Quiet, cozy, comfortable home at Deep Creek, Maryland, holiday rental in Oakland
Quiet, cozy, comfortable home at Deep Creek, Maryland, holiday rental in Oakland
Quiet, cozy, comfortable home at Deep Creek, Maryland, holiday rental in Oakland

Quiet, cozy, comfortable home at Deep Creek, Maryland

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Lake access with dock slip, close to favorite lake activities!, holiday rental in Oakland
Lake access with dock slip, close to favorite lake activities!, holiday rental in Oakland
Lake access with dock slip, close to favorite lake activities!, holiday rental in Oakland

Lake access with dock slip, close to favorite lake activities!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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All About the View: Lakefront Home with Awe-Inspiring Views!, holiday rental in Oakland
All About the View: Lakefront Home with Awe-Inspiring Views!, holiday rental in Oakland
All About the View: Lakefront Home with Awe-Inspiring Views!, holiday rental in Oakland

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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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!, holiday rental in Oakland
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!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Centrally located, tastefully decorated townhome!, holiday rental in Oakland
Centrally located, tastefully decorated townhome!, holiday rental in Oakland
Centrally located, tastefully decorated townhome!, holiday rental in Oakland

Centrally located, tastefully decorated townhome!

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
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Family-friendly lakefront home w/ lake view, dock, fireplace - dogs OK!, holiday rental in Oakland
Family-friendly lakefront home w/ lake view, dock, fireplace - dogs OK!, holiday rental in Oakland
Family-friendly lakefront home w/ lake view, dock, fireplace - dogs OK!, holiday rental in Oakland

Family-friendly lakefront home w/ lake view, dock, fireplace - dogs OK!

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
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, holiday rental in Oakland
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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Astounding & secluded mountain chalet with lake views!, holiday rental in Oakland
Astounding & secluded mountain chalet with lake views!, holiday rental in Oakland
Astounding & secluded mountain chalet with lake views!, holiday rental in Oakland

Astounding & secluded mountain chalet with lake views!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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The Mountain Airy: Great Location, Indoor Hot Tub & 2 Fireplaces, holiday rental in Oakland
The Mountain Airy: Great Location, Indoor Hot Tub & 2 Fireplaces, holiday rental in Oakland
The Mountain Airy: Great Location, Indoor Hot Tub & 2 Fireplaces, holiday rental in Oakland

The Mountain Airy: Great Location, Indoor Hot Tub & 2 Fireplaces

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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, holiday rental in Oakland
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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Unique and Charming Cabin at the Lake, holiday rental in Oakland
Unique and Charming Cabin at the Lake, holiday rental in Oakland
Unique and Charming Cabin at the Lake, holiday rental in Oakland

Unique and Charming Cabin at the Lake

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Cross the River: Charming cottage w/ hot tub & river access!, holiday rental in Oakland
Cross the River: Charming cottage w/ hot tub & river access!, holiday rental in Oakland
Cross the River: Charming cottage w/ hot tub & river access!, holiday rental in Oakland

Cross the River: Charming cottage w/ hot tub & river access!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxury log home in a central location!, holiday rental in Oakland
Luxury log home in a central location!, holiday rental in Oakland
Luxury log home in a central location!, holiday rental in Oakland

Luxury log home in a central location!

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Woodland cabin w/ private hot tub, firepit, foosball table & nearby lake access!, holiday rental in Oakland
Woodland cabin w/ private hot tub, firepit, foosball table & nearby lake access!, holiday rental in Oakland
Woodland cabin w/ private hot tub, firepit, foosball table & nearby lake access!, holiday rental in Oakland

Woodland cabin w/ private hot tub, firepit, foosball table & nearby lake access!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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, holiday rental in Oakland
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Lakefront Home w/ Private Indoor Pool, holiday rental in Oakland
Beautiful Lakefront Home w/ Private Indoor Pool, holiday rental in Oakland
Beautiful Lakefront Home w/ Private Indoor Pool, holiday rental in Oakland

Beautiful Lakefront Home w/ Private Indoor Pool

Holiday Rental House
8 bedrooms
8 bathrooms
Sleeps 22
Match: Sleeps
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