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Oakland, MD Holiday Rentals & Apartments
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Kid friendly (135)
Pet friendly (42)
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Holiday Rental House (135)
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Waterfront (59)
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5 km
Swallow Falls State Park
Deep Creek Lake State Park
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137 rentals
in Oakland.
OWLS NEST,Lakefront,Waterfront,Dock,HotTub,Kayaks,Paddleboards, Romantic Getaway
182 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Lakefront, dog friendly, dock slip, hot tub, and fire pit
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 14
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Enchanting waterfront home with hot tub, game room, fireplace, & washer/dryer
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5 bedrooms
5 bathrooms
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Dog-friendly house on the lake with fireplace, kayak, central AC, & EV charger
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3 bedrooms
4 bathrooms
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Private cabin with hot tub, outdoor dining, and fireplace
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
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Timroc II, FIVE STAR REVIEWS! LAKE ACCESS, GREAT SWIMMING, PRIVATE 2 ACRES!
4 reviews
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 13
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Dog-friendly woodland cabin with hot tub, firepit, lawn games & great deck
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2 bedrooms
2 bathrooms
Sleeps 9
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Lakefront, Wooded, & Secluded Home - Family Dogs Welcome.
14 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 10
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Gathering Place: Lakefront w. boat slip | Dog friendly | Hot tub | Fire pit
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 12
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New listing! Delightful cabin w/ firepit, full kitchen, & gas fireplace!
3 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
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Stockslager | House in Oakland
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 5
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New listing! Adorable cabin in the woods w/ full kitchen, firepit, & porch!
5 reviews
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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Peaceful Lakefront !/Free WIFI/Wonderful Hot Tub!
75 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Choo Choo Rooster Scrapbook Retreat
Holiday Rental House
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4 bedrooms
1 bathroom
Sleeps 4
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Dog-Friendly Country Cabin with Deck, Firepit & Air Hockey - Close to Yough
66 reviews
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Dog-friendly Lakefront Log Home on a Quiet Cove with Front Deck & Private Dock
5 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 10
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Oakland Retreat ~ 13 Mi to Deep Creek Lake!
2 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Beautiful Lake Front Cottage
62 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 7
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New listing! Cute cabin w/ a full kitchen & firepit - near rivers, parks, & lake
6 reviews
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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Three Bedroom Cabin On Wooded Lot Near Lake. Secluded, Family And Pet Friendly.
82 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Meant to Be: Dog Friendly, Minutes from Swallow Falls & Lake Activities
2 reviews
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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Hideaway: Dog Friendly, Lake Access Chalet w/ Hot Tub
82 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 8
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Cabin in the Woods
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Bear Foot Cove: Split Lakefront, Dock Slip, Fire Pit, Hot Tub!
3 reviews
Holiday Rental House
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5 bedrooms
7 bathrooms
Sleeps 14
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Water in the Sky: Lakefront, Dogs Welcome, Private Dock, Hot Tub!
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 5
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Double Martini: Charming Cabin w/in 5 Minutes from Activities, Restaurants, &
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Cross the River: Charming cottage w/ hot tub & river access!
137 reviews
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Delightful 3 Bedroom home within walking distance to your dock slip!
28 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 7
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Convenient Cabin 3BR 1.5 BA, King Bed, Grill, more
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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A quiet little town
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 9
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Escape Inn: Lake Area, A/C, Fire Pit!
2 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 8
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Conveniently located log cabin with outdoor hot tub!
22 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 8
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Quiet 3 bedroom home with fire pit
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 4
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New! Lakeview Oasis: Lakefront, Hot Tub!
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 8
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Quaint retreat w/ firepit, fully equipped kitchen, & easy access to trails!
9 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Willow Point: Lakefront, Dogs Welcome, Hot Tub, Private Dock, Lake Views!
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Secluded Home on 20 Acres with Hot Tub, Horse Barn, and Private Mountain Stream
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Charming cabin on 3 wooded acres, close to skiing, state parks, lake activities
1 review
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Clawson Cabin: Lake Access with Dock Slip, Close to Swallow Falls and Favorite A
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Private Family Home w/ Deck, Porch + Forest Views!
3 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Secluded Oakland House w/ On-Site Hiking!
4 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 9
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Serenity Chalet: Dog Friendly Getaway Close to Activities
5 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Minutes From: Deep Creek Lake, Wisp Ski Resort, Swallow Falls, Restaurants
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 7
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Wooded Bliss: Spacious Lake Access Chalet w/ Boat Slip & Fire Pit
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 10
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Conveniently located cabin with fire pit & dock slip - close to state parks!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 10
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New! Pop-a-Top Inn: Lake Access, Hot Tub, Wood Fireplace!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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New! Pier Pressure: Lakefront, Dock Slip, Hot Tub, Wood Fireplace!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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New! Howie's Landing: Dogs Welcome, Lake Area, Hot Tub!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Quiet, cozy, comfortable home at Deep Creek, Maryland
4 reviews
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 10
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Free canoe and kayaks use! Super cute lake house with hot tub and fire pit
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Showing results 1-50 of 137
Frequently Asked Questions about Oakland
Do any holiday rentals in Oakland have a pool?
Yes, here are some popular holiday rentals in Oakland that have a pool:
OWLS NEST,Lakefront,Waterfront,Dock,HotTub,Kayaks,Paddleboards, Romantic Getaway
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Enchanting waterfront home with hot tub, game room, fireplace, & washer/dryer
See all holiday rentals with a pool in Oakland on Tripadvisor
Do any holiday rentals in Oakland have internet access?
Yes, here are some popular holiday rentals in Oakland that have internet access:
OWLS NEST,Lakefront,Waterfront,Dock,HotTub,Kayaks,Paddleboards, Romantic Getaway
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Enchanting waterfront home with hot tub, game room, fireplace, & washer/dryer
See all holiday rentals in Oakland on Tripadvisor
What are the best pet friendly rentals in Oakland?
The best pet friendly rentals in Oakland are:
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Dog-friendly house on the lake with fireplace, kayak, central AC, & EV charger
Dog-friendly woodland cabin with hot tub, firepit, lawn games & great deck
See all pet friendly holiday rentals in Oakland on Tripadvisor
What are some great rentals in Oakland that are kid friendly?
Some of the most popular kid friendly rentals in Oakland are:
OWLS NEST,Lakefront,Waterfront,Dock,HotTub,Kayaks,Paddleboards, Romantic Getaway
Lakefront, dog friendly, dock slip, hot tub, and fire pit
Enchanting waterfront home with hot tub, game room, fireplace, & washer/dryer
See all kid friendly holiday rentals in Oakland on Tripadvisor