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Oakland
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Luxury Rentals and Vacation Rentals in Oakland, MD
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388 rentals
in Oakland.
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The Love Shack-- The BEST Couples and Small Family Retreat at Deep Creek Lake!
183 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match:
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Quaint and So Cozy Deep Creek Lake Log Cabin in Sought After Yellowstone Village
13,057 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match:
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OWLS NEST, Premiere Lake Waterfront, Cabin w HotTub, Private Dock, Cozy Romantic
182 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match:
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Lake Access Chalet-NO “OWNER FEES”, Indoor Pool, Home Theater, BoatDock, Firepit
98 reviews
Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
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Level lakefront, family-friendly, low fees, private dock
53 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match:
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Cozy WISP/LAKE area Private & Tranquil Luxury DECK FIREPLACE & HOT TUB / 5 STAR!
95 reviews
Rental Home
5 bedrooms
4 bathrooms
Sleeps 13
Match:
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Beautiful Lake Front Cottage
62 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match:
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Peaceful Lakefront !/Free WIFI/Wonderful Hot Tub!
75 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match:
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Stunning 7 Bedroom 6.5 Bath Lakefront Home with Dock
56 reviews
Rental Home
7 bedrooms
7 bathrooms
Sleeps 20
Match:
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Secluded Lakefront Log Home w/ Hot Tub and Private Dock!
80 reviews
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match:
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FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!
60 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match:
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Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.
40 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match:
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Sparks To Stars: Lake Access, Dogs Welcome, Hot Tub, Fire Pit!
68 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match:
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The Grizzly Den: Lake Area, Dogs Welcome, Hot Tub, Fireplace!
146 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match:
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The Evergreen: Lake Area, Dogs Welcome, Hot Tub, Fireplace, Grill!
76 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match:
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Red Run Cabin
30 reviews
Cabin
3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Reflections: Lakefront, Private Dock, Hot Tub, Pool table, Fire Pit!
61 reviews
Rental Home
2 bedrooms
3 bathrooms
Sleeps 8
Match:
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Divided Sky: Lake Area, Dogs Welcome, Hot Tub, Pool Table!
57 reviews
Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match:
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Water in the Sky: Lakefront, Dogs Welcome, Private Dock, Hot Tub!
45 reviews
Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match:
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Premier chalet w/ private hot tub, pool table, firepit, & tranquil wooded views
42 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match:
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The Deep Creek: Lake Area, Hot Tub, Fireplace, Grill!
156 reviews
Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match:
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No Worries: Lake Area, Dogs Welcome, Hot Tub!
194 reviews
Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match:
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A Winter View: Lake Area, Hot Tub, Fire Pit, Fireplace, Gas Grill!
31 reviews
Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match:
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Dog-Friendly Home with Deck, Forest View - Close to Lake & Ski Slopes
75 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match:
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Amazing Lake Views & Upscale Decor in the Heart of Deep Creek
16 reviews
Rental Home
5 bedrooms
6 bathrooms
Sleeps 14
Match:
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Serenity Summit: Centrally located townhome with hot tub
95 reviews
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match:
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5 BR Immaculate Chalet, Dog Friendly, Dock Slip, Hot Tub, Community Pool
164 reviews
Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match:
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Man Haus: Lakefront w/ Private Dock & Hot Tub, Walk to Restaurants
30 reviews
Rental Home
4 bedrooms
6 bathrooms
Sleeps 12
Match:
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Delightful 3 Bedroom home within walking distance to your dock slip!
28 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match:
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4 Bedroom Lakefront Home with hot tub in quiet neighborhood!
78 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match:
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Spacious townhome - 5 minutes from favorite activities & restaurants!
48 reviews
Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match:
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Spacious 4 bedroom home with phenomenal lakefront!
35 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match:
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Woodland Cabin w/ Private Hot Tub, Firepit, Foosball Fable & Free WiFi!
18 reviews
Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match:
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Centrally located Craftsman home close to DCL state park!
37 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match:
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Walking distance to restaurants, 5 minutes from DCL State Park!
19 reviews
Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match:
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Conveniently located cabin with fire pit & dock slip - close to state parks!
26 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match:
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The Lake's The Limit: Lakefront, Dock Slip, 2 Fire Pits, Hot Tub!
27 reviews
Rental Home
5 bedrooms
5 bathrooms
Sleeps 14
Match:
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Centrally located, tastefully decorated townhome!
32 reviews
Rental Home
5 bedrooms
4 bathrooms
Sleeps 11
Match:
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Charming cottage w/ large yard & entertainment room - near everything, 2 dogs OK
29 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Dog-Friendly Lakefront Home with Hot Tubs, Game Room, Dock & Space for 25
93 reviews
Rental Home
6 bedrooms
7 bathrooms
Sleeps 25
Match:
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Whitewater Lodge: Lake Area, Dogs Welcome, Indoor Hot Tub, Sun Room!
33 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match:
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Unique and charming cottage by the sea
18 reviews
Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match:
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Lake access with dock slip, close to favorite lake activities!
18 reviews
Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match:
Sleeps
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Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough
66 reviews
Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps
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All About the View: Lakefront Home with Awe-Inspiring Views!
46 reviews
Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match:
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Log home with private hot tub, air hockey, pool table & media room
38 reviews
Rental Home
5 bedrooms
4 bathrooms
Sleeps 14
Match:
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Three Bedroom Cabin On Wooded Lot Near Lake. Secluded, Family And Pet Friendly.
82 reviews
Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match:
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The Mountain Airy: Great Location, Indoor Hot Tub & 2 Fireplaces
25 reviews
Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match:
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5BR lakefront Cottage. Almost Heaven offers a true family retreat at Deep Creek
24 reviews
Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match:
Sleeps
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Lovin Life Deep Creek 5 Bedroom Luxury Log Home w/ Pool Table & Hot Tub
36 reviews
Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match:
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