Holiday Rentals in Oakland
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
355 rentals 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
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
2 bathrooms
Sleeps 6
Match: Sleeps
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OWLS NEST, Deep Lake Waterfront, Private Dock, HotTub, Kayaks,Canoe,Paddleboards
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
2 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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Private Luxury LAKE & WISP area DECK FIREPLACE & Hot Tub / PREMIER HOST / 5 STAR
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 13
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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Timroc II, FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Secluded Lakefront Log Home w/ Hot Tub & Private Dock!
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Sparks To Stars: Lake Access, Dogs Welcome, Hot Tub, Fire Pit!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Dog-Friendly Lakefront Home with Hot Tubs, Game Room, Dock & Space for 25
Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 25
Match: Sleeps
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The Grizzly Den: Lake Area, Dogs Welcome, Hot Tub, Fireplace!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Reflections: Lakefront, Private Dock, Hot Tub, Pool table, Fire Pit!
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Red Run Cabin
Cabin Holiday Rental
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Payment Protection
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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Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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No Worries: Lake Area, Dogs Welcome, Hot Tub!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Divided Sky: Lake Area, Dogs Welcome, Hot Tub, Pool Table!
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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Water in the Sky: Lakefront, Dogs Welcome, Private Dock, Hot Tub!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Whitewater Lodge: Lake Area, Dogs Welcome, Indoor Hot Tub, Sun Room!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
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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The Deep Creek: Lake Area, Hot Tub, Fireplace, Grill!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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A Winter View: Lake Area, Hot Tub, Fire Pit, Fireplace, Gas Grill!
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
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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Serenity Summit: Centrally located townhome with hot tub
Holiday Rental House
5 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
2 bathrooms
Sleeps 6
Match: Sleeps
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Changes in Attitude: Lakefront home with private dock & hot tub!
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Spacious 4 bedroom home with phenomenal lakefront!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Premier chalet with private hot tub, pool table, firepit & tranquil wooded views
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
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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Blue Sky Lodge: Lake Access, Hot Tub, Pool table, 2 Fire Pits, Grill!
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 14
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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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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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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Centrally located with 2 master suites and a fire pit!
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Love and Memories: Lake Access, Dogs Welcome, Hot Tub, Fire Pit!
Holiday Rental House
3 bedrooms
3 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
1 bathroom
Sleeps 4
Match: Sleeps
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Dog-friendly cabin with private hot tub, Ping-Pong, free WiFi, lake views
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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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New listing! Cute cabin w/ a full kitchen & firepit - near rivers, parks, & lake
Holiday Rental House
1 bedroom
1 bathroom
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
2 bathrooms
Sleeps 10
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
3 bathrooms
Sleeps 14
Match: Sleeps
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Beautiful Lakefront Home w/ Private Indoor Pool
Holiday Rental House
8 bedrooms
8 bathrooms
Sleeps 22
Match: Sleeps
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Centrally located, tastefully decorated townhome!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Centrally located Craftsman home close to DCL state park!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Showing results 1-50 of 355
Frequently Asked Questions about Oakland
- Yes, here are some popular holiday rentals in Oakland that have internet access:
- Red Run Cabin
- Mystic Haven: Lake Area, Hot Tub, Fire Pit, Pool Table, Fireplace!
- For sun or for snow, this home is “Always in Season!” There’s no better perch t
- Some of the most popular kid friendly rentals in Oakland are:
- Red Run Cabin
- Mystic Haven: Lake Area, Hot Tub, Fire Pit, Pool Table, Fireplace!
- For sun or for snow, this home is “Always in Season!” There’s no better perch t