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Holiday Rentals in Oakland

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Bedrooms

Bathrooms

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5 km
141 rentals in Oakland.
OWLS NEST,Lakefront,Waterfront,Dock,HotTub,Kayaks,Paddleboards, Romantic Getaway, holiday rental in Oakland
OWLS NEST,Lakefront,Waterfront,Dock,HotTub,Kayaks,Paddleboards, Romantic Getaway, holiday rental in Oakland
OWLS NEST,Lakefront,Waterfront,Dock,HotTub,Kayaks,Paddleboards, Romantic Getaway, holiday rental in Oakland

OWLS NEST,Lakefront,Waterfront,Dock,HotTub,Kayaks,Paddleboards, Romantic Getaway

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Lakefront, dog friendly, dock slip, hot tub, and fire pit, holiday rental in Oakland
Lakefront, dog friendly, dock slip, hot tub, and fire pit, holiday rental in Oakland
Lakefront, dog friendly, dock slip, hot tub, and fire pit, holiday rental in Oakland

Lakefront, dog friendly, dock slip, hot tub, and fire pit

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Enchanting waterfront home with hot tub, game room, fireplace, & washer/dryer, holiday rental in Oakland
Enchanting waterfront home with hot tub, game room, fireplace, & washer/dryer, holiday rental in Oakland
Enchanting waterfront home with hot tub, game room, fireplace, & washer/dryer, holiday rental in Oakland

Enchanting waterfront home with hot tub, game room, fireplace, & washer/dryer

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Dog-friendly house on the lake with fireplace, kayak, central AC, & EV charger, holiday rental in Oakland
Dog-friendly house on the lake with fireplace, kayak, central AC, & EV charger, holiday rental in Oakland
Dog-friendly house on the lake with fireplace, kayak, central AC, & EV charger, holiday rental in Oakland

Dog-friendly house on the lake with fireplace, kayak, central AC, & EV charger

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Private cabin with hot tub, outdoor dining, and fireplace, holiday rental in Oakland
Private cabin with hot tub, outdoor dining, and fireplace, holiday rental in Oakland
Private cabin with hot tub, outdoor dining, and fireplace, holiday rental in Oakland

Private cabin with hot tub, outdoor dining, and fireplace

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Timroc II, FIVE STAR REVIEWS!  LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!, holiday rental in Oakland
Timroc II, FIVE STAR REVIEWS!  LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!, holiday rental in Oakland
Timroc II, FIVE STAR REVIEWS!  LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!, holiday rental in Oakland

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 13
Match: Sleeps
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Dog-friendly woodland cabin with hot tub, firepit, lawn games & great deck, holiday rental in Oakland
Dog-friendly woodland cabin with hot tub, firepit, lawn games & great deck, holiday rental in Oakland
Dog-friendly woodland cabin with hot tub, firepit, lawn games & great deck, holiday rental in Oakland

Dog-friendly woodland cabin with hot tub, firepit, lawn games & great deck

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Lakefront, Wooded, & Secluded Home - Family Dogs Welcome., holiday rental in Oakland
Lakefront, Wooded, & Secluded Home - Family Dogs Welcome., holiday rental in Oakland
Lakefront, Wooded, & Secluded Home - Family Dogs Welcome., holiday rental in Oakland

Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit, holiday rental in Oakland
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit, holiday rental in Oakland
Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit, holiday rental in Oakland

Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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New listing! Delightful cabin w/ firepit, full kitchen, & gas fireplace!, holiday rental in Oakland
New listing! Delightful cabin w/ firepit, full kitchen, & gas fireplace!, holiday rental in Oakland
New listing! Delightful cabin w/ firepit, full kitchen, & gas fireplace!, holiday rental in Oakland

New listing! Delightful cabin w/ firepit, full kitchen, & gas fireplace!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stockslager | House in Oakland, holiday rental in Oakland
Stockslager | House in Oakland, holiday rental in Oakland
Stockslager | House in Oakland, holiday rental in Oakland

Stockslager | House in Oakland

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
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
More info
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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
More info
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Choo Choo Rooster Scrapbook Retreat, holiday rental in Oakland
Choo Choo Rooster Scrapbook Retreat, holiday rental in Oakland
Choo Choo Rooster Scrapbook Retreat, holiday rental in Oakland

Choo Choo Rooster Scrapbook Retreat

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough, holiday rental in Oakland
Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough, holiday rental in Oakland
Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough, holiday rental in Oakland

Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Dog-friendly Lakefront Log Home on a Quiet Cove with Front Deck & Private Dock, holiday rental in Oakland
Dog-friendly Lakefront Log Home on a Quiet Cove with Front Deck & Private Dock, holiday rental in Oakland
Dog-friendly Lakefront Log Home on a Quiet Cove with Front Deck & Private Dock, holiday rental in Oakland

Dog-friendly Lakefront Log Home on a Quiet Cove with Front Deck & Private Dock

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
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Oakland Retreat ~ 13 Mi to Deep Creek Lake!, holiday rental in Oakland
Oakland Retreat ~ 13 Mi to Deep Creek Lake!, holiday rental in Oakland
Oakland Retreat ~ 13 Mi to Deep Creek Lake!, holiday rental in Oakland

Oakland Retreat ~ 13 Mi to Deep Creek Lake!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful Lake Front Cottage, holiday rental in Oakland
Beautiful Lake Front Cottage, holiday rental in Oakland
Beautiful Lake Front Cottage, holiday rental in Oakland

Beautiful Lake Front Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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New listing! Cute cabin w/ a full kitchen & firepit - near rivers, parks, & lake, holiday rental in Oakland
New listing! Cute cabin w/ a full kitchen & firepit - near rivers, parks, & lake, holiday rental in Oakland
New listing! Cute cabin w/ a full kitchen & firepit - near rivers, parks, & lake, holiday rental in Oakland

New listing! Cute cabin w/ a full kitchen & firepit - near rivers, parks, & lake

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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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 3
Match: Sleeps
More info
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Meant to Be: Dog Friendly, Minutes from Swallow Falls & Lake Activities, holiday rental in Oakland
Meant to Be: Dog Friendly, Minutes from Swallow Falls & Lake Activities, holiday rental in Oakland
Meant to Be: Dog Friendly, Minutes from Swallow Falls & Lake Activities, holiday rental in Oakland

Meant to Be: Dog Friendly, Minutes from Swallow Falls & Lake Activities

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Hideaway: Dog Friendly, Lake Access Chalet w/ Hot Tub, holiday rental in Oakland
Hideaway: Dog Friendly, Lake Access Chalet w/ Hot Tub, holiday rental in Oakland
Hideaway: Dog Friendly, Lake Access Chalet w/ Hot Tub, holiday rental in Oakland

Hideaway: Dog Friendly, Lake Access Chalet w/ Hot Tub

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Cabin in the Woods, holiday rental in Oakland
Cabin in the Woods, holiday rental in Oakland
Cabin in the Woods, holiday rental in Oakland

Cabin in the Woods

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Bear Foot Cove: Split Lakefront, Dock Slip, Fire Pit, Hot Tub!, holiday rental in Oakland
Bear Foot Cove: Split Lakefront, Dock Slip, Fire Pit, Hot Tub!, holiday rental in Oakland
Bear Foot Cove: Split Lakefront, Dock Slip, Fire Pit, Hot Tub!, holiday rental in Oakland

Bear Foot Cove: Split Lakefront, Dock Slip, Fire Pit, Hot Tub!

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
More info
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Water in the Sky: Lakefront, Dogs Welcome, Private Dock, Hot Tub!, holiday rental in Oakland
Water in the Sky: Lakefront, Dogs Welcome, Private Dock, Hot Tub!, holiday rental in Oakland
Water in the Sky: Lakefront, Dogs Welcome, Private Dock, Hot Tub!, holiday rental in Oakland

Water in the Sky: Lakefront, Dogs Welcome, Private Dock, Hot Tub!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Double Martini: Charming Cabin w/in 5 Minutes from Activities, Restaurants, &, holiday rental in Oakland
Double Martini: Charming Cabin w/in 5 Minutes from Activities, Restaurants, &, holiday rental in Oakland
Double Martini: Charming Cabin w/in 5 Minutes from Activities, Restaurants, &, holiday rental in Oakland

Double Martini: Charming Cabin w/in 5 Minutes from Activities, Restaurants, &

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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 2
Match: Sleeps
More info
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Delightful 3 Bedroom home within walking distance to your dock slip!, holiday rental in Oakland
Delightful 3 Bedroom home within walking distance to your dock slip!, holiday rental in Oakland
Delightful 3 Bedroom home within walking distance to your dock slip!, holiday rental in Oakland

Delightful 3 Bedroom home within walking distance to your dock slip!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Convenient Cabin 3BR 1.5 BA, King Bed, Grill, more, holiday rental in Oakland
Convenient Cabin 3BR 1.5 BA, King Bed, Grill, more, holiday rental in Oakland
Convenient Cabin 3BR 1.5 BA, King Bed, Grill, more, holiday rental in Oakland

Convenient Cabin 3BR 1.5 BA, King Bed, Grill, more

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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A quiet little town, holiday rental in Oakland
A quiet little town, holiday rental in Oakland
A quiet little town, holiday rental in Oakland

A quiet little town

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Escape Inn: Lake Area, A/C, Fire Pit!, holiday rental in Oakland
Escape Inn: Lake Area, A/C, Fire Pit!, holiday rental in Oakland
Escape Inn: Lake Area, A/C, Fire Pit!, holiday rental in Oakland

Escape Inn: Lake Area, A/C, Fire Pit!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Conveniently located log cabin with outdoor hot tub!, holiday rental in Oakland
Conveniently located log cabin with outdoor hot tub!, holiday rental in Oakland
Conveniently located log cabin with outdoor hot tub!, holiday rental in Oakland

Conveniently located log cabin with outdoor hot tub!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Quiet 3 bedroom home with fire pit, holiday rental in Oakland
Quiet 3 bedroom home with fire pit, holiday rental in Oakland
Quiet 3 bedroom home with fire pit, holiday rental in Oakland

Quiet 3 bedroom home with fire pit

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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New! Lakeview Oasis: Lakefront, Hot Tub!, holiday rental in Oakland
New! Lakeview Oasis: Lakefront, Hot Tub!, holiday rental in Oakland
New! Lakeview Oasis: Lakefront, Hot Tub!, holiday rental in Oakland

New! Lakeview Oasis: Lakefront, Hot Tub!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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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
More info
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Willow Point: Lakefront, Dogs Welcome, Hot Tub, Private Dock, Lake Views!, holiday rental in Oakland
Willow Point: Lakefront, Dogs Welcome, Hot Tub, Private Dock, Lake Views!, holiday rental in Oakland
Willow Point: Lakefront, Dogs Welcome, Hot Tub, Private Dock, Lake Views!, holiday rental in Oakland

Willow Point: Lakefront, Dogs Welcome, Hot Tub, Private Dock, Lake Views!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Secluded Home on 20 Acres with Hot Tub, Horse Barn, and Private Mountain Stream, holiday rental in Oakland
Secluded Home on 20 Acres with Hot Tub, Horse Barn, and Private Mountain Stream, holiday rental in Oakland
Secluded Home on 20 Acres with Hot Tub, Horse Barn, and Private Mountain Stream, holiday rental in Oakland

Secluded Home on 20 Acres with Hot Tub, Horse Barn, and Private Mountain Stream

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming cabin on 3 wooded acres, close to skiing, state parks, lake activities, holiday rental in Oakland
Charming cabin on 3 wooded acres, close to skiing, state parks, lake activities, holiday rental in Oakland
Charming cabin on 3 wooded acres, close to skiing, state parks, lake activities, holiday rental in Oakland

Charming cabin on 3 wooded acres, close to skiing, state parks, lake activities

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Clawson Cabin: Lake Access with Dock Slip, Close to Swallow Falls and Favorite A, holiday rental in Oakland
Clawson Cabin: Lake Access with Dock Slip, Close to Swallow Falls and Favorite A, holiday rental in Oakland
Clawson Cabin: Lake Access with Dock Slip, Close to Swallow Falls and Favorite A, holiday rental in Oakland

Clawson Cabin: Lake Access with Dock Slip, Close to Swallow Falls and Favorite A

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Private Family Home w/ Deck, Porch + Forest Views!, holiday rental in Oakland
Private Family Home w/ Deck, Porch + Forest Views!, holiday rental in Oakland
Private Family Home w/ Deck, Porch + Forest Views!, holiday rental in Oakland

Private Family Home w/ Deck, Porch + Forest Views!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Secluded Oakland House w/ On-Site Hiking!, holiday rental in Oakland
Secluded Oakland House w/ On-Site Hiking!, holiday rental in Oakland
Secluded Oakland House w/ On-Site Hiking!, holiday rental in Oakland

Secluded Oakland House w/ On-Site Hiking!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Serenity Chalet: Dog Friendly Getaway Close to Activities, holiday rental in Oakland
Serenity Chalet: Dog Friendly Getaway Close to Activities, holiday rental in Oakland
Serenity Chalet: Dog Friendly Getaway Close to Activities, holiday rental in Oakland

Serenity Chalet: Dog Friendly Getaway Close to Activities

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Minutes From:
Deep Creek Lake, Wisp Ski Resort, Swallow Falls, Restaurants, holiday rental in Oakland
Minutes From:
Deep Creek Lake, Wisp Ski Resort, Swallow Falls, Restaurants, holiday rental in Oakland
Minutes From:
Deep Creek Lake, Wisp Ski Resort, Swallow Falls, Restaurants, holiday rental in Oakland

Minutes From: Deep Creek Lake, Wisp Ski Resort, Swallow Falls, Restaurants

Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Wooded Bliss: Spacious Lake Access Chalet w/ Boat Slip & Fire Pit, holiday rental in Oakland
Wooded Bliss: Spacious Lake Access Chalet w/ Boat Slip & Fire Pit, holiday rental in Oakland
Wooded Bliss: Spacious Lake Access Chalet w/ Boat Slip & Fire Pit, holiday rental in Oakland

Wooded Bliss: Spacious Lake Access Chalet w/ Boat Slip & Fire Pit

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Conveniently located cabin with fire pit & dock slip - close to state parks!, holiday rental in Oakland
Conveniently located cabin with fire pit & dock slip - close to state parks!, holiday rental in Oakland
Conveniently located cabin with fire pit & dock slip - close to state parks!, holiday rental in Oakland

Conveniently located cabin with fire pit & dock slip - close to state parks!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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New! Pop-a-Top Inn: Lake Access, Hot Tub, Wood Fireplace!, holiday rental in Oakland
New! Pop-a-Top Inn: Lake Access, Hot Tub, Wood Fireplace!, holiday rental in Oakland
New! Pop-a-Top Inn: Lake Access, Hot Tub, Wood Fireplace!, holiday rental in Oakland

New! Pop-a-Top Inn: Lake Access, Hot Tub, Wood Fireplace!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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New! Pier Pressure: Lakefront, Dock Slip, Hot Tub,  Wood Fireplace!, holiday rental in Oakland
New! Pier Pressure: Lakefront, Dock Slip, Hot Tub,  Wood Fireplace!, holiday rental in Oakland
New! Pier Pressure: Lakefront, Dock Slip, Hot Tub,  Wood Fireplace!, holiday rental in Oakland

New! Pier Pressure: Lakefront, Dock Slip, Hot Tub, Wood Fireplace!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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New! Howie's Landing: Dogs Welcome, Lake Area, Hot Tub!, holiday rental in Oakland
New! Howie's Landing: Dogs Welcome, Lake Area, Hot Tub!, holiday rental in Oakland
New! Howie's Landing: Dogs Welcome, Lake Area, Hot Tub!, holiday rental in Oakland

New! Howie's Landing: Dogs Welcome, Lake Area, Hot Tub!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
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
More info
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Free canoe and kayaks use! Super cute lake house with hot tub and fire pit, holiday rental in Oakland
Free canoe and kayaks use! Super cute lake house with hot tub and fire pit, holiday rental in Oakland
Free canoe and kayaks use! Super cute lake house with hot tub and fire pit, holiday rental in Oakland

Free canoe and kayaks use! Super cute lake house with hot tub and fire pit

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 141
Frequently Asked Questions about Oakland