The Best Airbnb Deals in
Oakland, Maryland

Save money on your trip by finding the biggest discounts for top-rated Airbnb rentals in Oakland, Maryland. Enter your travel dates to find the best deals!

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AirDNA Score: 93
$144/night

Molly

1 bed
1 bath
2 guests
Average Price:  
$144
0% Cheaper
than normal
AirDNA Score: 88
$189/night

Incredible Cozy Cabin Immersed in Nature

3 beds
1 bath
6 guests
Average Price:  
$293
35% Cheaper
than normal
AirDNA Score: 86
$145/night

The Original Hob

1 bed
1 bath
2 guests
Average Price:  
$146
1% Cheaper
than normal
AirDNA Score: 80
$150/night

SUGARBUSH - Sweet Serenity Tiny House

1 bed
1 bath
2 guests
Average Price:  
$150
0% Cheaper
than normal
AirDNA Score: 77
$94/night

Large estate, miles of trails, cozy glamping hut C

1 bed
6 baths
4 guests
Average Price:  
$98
4% Cheaper
than normal
AirDNA Score: 77
$86/night

Large estate, miles of trails, cozy glamping hut D

studio
6 baths
4 guests
Average Price:  
$95
9% Cheaper
than normal
AirDNA Score: 77
$231/night

Dancing Bears

3 beds
1 bath
6 guests
Average Price:  
$279
17% Cheaper
than normal
AirDNA Score: 73
$290/night

Hobbitat Home Place

2 beds
1 bath
4 guests
Average Price:  
$298
3% Cheaper
than normal
AirDNA Score: 71
$95/night

Large estate, miles of trails, cozy glamping hut U

1 bed
6 baths
4 guests
Average Price:  
$98
3% Cheaper
than normal
AirDNA Score: 70
$284/night

Mountain Escape @ Deep Creek Lake

4 beds
2 baths
10 guests
Average Price:  
$303
6% Cheaper
than normal
AirDNA Score: 69
$95/night

Large estate, miles of trails, cozy glamping hut S

1 bed
6 baths
6 guests
Average Price:  
$93
2% More
than normal
AirDNA Score: 69
$370/night

Dock Holiday-Lake access with a boat slip

3 beds
2.5 baths
8 guests
Average Price:  
$432
14% Cheaper
than normal
AirDNA Score: 67
$95/night

Large estate, miles of trails, cozy glamping hut A

1 bed
6 baths
4 guests
Average Price:  
$100
5% Cheaper
than normal
AirDNA Score: 66
$150/night

SUGARBUSH - Sweet Serenity Tiny House

1 bed
1 bath
4 guests
Average Price:  
$150
0% Cheaper
than normal
AirDNA Score: 65
$149/night

General Kelly Guesthouse

5 beds
2 baths
12 guests
Average Price:  
$174
14% Cheaper
than normal
AirDNA Score: 64
$125/night

Casa Cossick

2 beds
1 bath
6 guests
Average Price:  
$127
2% Cheaper
than normal
AirDNA Score: 64
$495/night

Private|LAKE&Waterfalls|PoolAccess|Firewood|HotTub

5 beds
3.5 baths
13 guests
Average Price:  
$642
23% Cheaper
than normal
AirDNA Score: 59
$195/night

Little Piece of Heaven

1 bed
1 bath
4 guests
Average Price:  
$197
1% Cheaper
than normal
AirDNA Score: 58
$595/night

Fancy Free | Lakefront, Hot Tub, Quiet Community

4 beds
4 baths
16 guests
Average Price:  
$971
39% Cheaper
than normal
AirDNA Score: 57
$275/night

Hidden Treasure | Quiet Location Near Activities

4 beds
3.5 baths
10 guests
Average Price:  
$478
42% Cheaper
than normal
AirDNA Score: 57
$723/night

Stylish Townhome with Hot Tub conveniently

3 beds
3 baths
10 guests
Average Price:  
$411
76% More
than normal
AirDNA Score: 57
$239/night

Paradise at Penn Cove | Walk to the Dock Slip!

3 beds
2 baths
7 guests
Average Price:  
$508
53% Cheaper
than normal
AirDNA Score: 57
$350/night

Mountain House | Pet Friendly, Dock, Great Views!

5 beds
3 baths
14 guests
Average Price:  
$577
39% Cheaper
than normal
AirDNA Score: 57
$302/night

Home Sweet Cabin | Peaceful, Multiple Game Tables!

4 beds
2 baths
10 guests
Average Price:  
$482
37% Cheaper
than normal
AirDNA Score: 57
$621/night

Lake Goers: Lake Views, Boat Slip, 5 Minutes to

4 beds
2 baths
10 guests
Average Price:  
$491
26% More
than normal
AirDNA Score: 57
$214/night

Loft of Luxury | Lake Views, Walk to Food + Shops

2 beds
1 bath
6 guests
Average Price:  
$424
50% Cheaper
than normal
AirDNA Score: 57
$636/night

Spacious Chalet with Sunset Lake Views

5 beds
4.5 baths
16 guests
Average Price:  
$809
21% Cheaper
than normal
AirDNA Score: 56
$468/night

3BR | Dogs OK | Fireplace | Hot Tub whitewat]

3 beds
3 baths
9 guests
Average Price:  
$463
1% More
than normal
AirDNA Score: 56
$656/night

5BR | A/C | Fireplace | Hot Tub [bluskies]

5 beds
4.5 baths
14 guests
Average Price:  
$822
20% Cheaper
than normal
AirDNA Score: 56
$1132/night

9BR | Dock | Dogs OK | Hot Tub | Fire Pit [logret]

9 beds
5.5 baths
16 guests
Average Price:  
$1277
11% Cheaper
than normal
AirDNA Score: 56
$434/night

5BR | Fireplace | Hot Tub | Pool Table [onlaketi]

5 beds
4.5 baths
12 guests
Average Price:  
$553
22% Cheaper
than normal
AirDNA Score: 56
$513/night

5BR | A/C | Dogs OK | Fireplace | Hot Tub [divide]

5 beds
3 baths
14 guests
Average Price:  
$661
22% Cheaper
than normal
AirDNA Score: 56
$438/night

2BR | A/C | Fireplace | Hot Tub | Fire Pit [owlc]

2 beds
2 baths
8 guests
Average Price:  
$344
27% More
than normal
AirDNA Score: 55
$133/night

Country 3BR Dog Friendly | Deck | Firepit

3 beds
1 bath
6 guests
Average Price:  
$211
37% Cheaper
than normal
AirDNA Score: 51
$400/night

Spectacular Chalet, Timroc II, close to lake, Wisp

5 beds
3.5 baths
14 guests
Average Price:  
$432
7% Cheaper
than normal
AirDNA Score: 50
$160/night

Private Unit on Farm with Kitchen & Balcony

1 bed
1 bath
2 guests
Average Price:  
$174
8% Cheaper
than normal
AirDNA Score: 50
$700/night

The Farmhouse at Lucas Farm

4 beds
2 baths
12 guests
Average Price:  
$700
0% Cheaper
than normal
AirDNA Score: 47
$362/night

Big Rock Candy Mountain Lodge - Deep Creek Lake

5 beds
4 baths
14 guests
Average Price:  
$398
9% Cheaper
than normal
AirDNA Score: 45
$116/night

Prime 2BR Lakeview | Deck | Fireplace

2 beds
1 bath
6 guests
Average Price:  
$193
40% Cheaper
than normal
AirDNA Score: 40
$1019/night

6BR Lakefront Dog Friendly | Hot Tub | Dock

6 beds
6.5 baths
16 guests
Average Price:  
$1136
10% Cheaper
than normal
AirDNA Score: 37
$165/night

Bear Necessities @ Deep Creek Lake

1 bed
1 bath
2 guests
Average Price:  
$182
9% Cheaper
than normal
AirDNA Score: 36
$560/night

4BR | Dogs OK | Hot Tub | Fire Pit [parvw]

4 beds
3.5 baths
12 guests
Average Price:  
$463
21% More
than normal
AirDNA Score: 35
$460/night

Laurel Grove

4 beds
3 baths
12 guests
Average Price:  
$478
4% Cheaper
than normal
AirDNA Score: 35
$299/night

Vintage Oakland @ Oakland Maryland

4 beds
3 baths
10 guests
Average Price:  
$308
3% Cheaper
than normal
AirDNA Score: 34
$213/night

Spacious 4BR | Hot Tub | Fireplace | Deck

4 beds
3.5 baths
10 guests
Average Price:  
$312
32% Cheaper
than normal
AirDNA Score: 33
$431/night

4BR Lakefront | Hot Tub | Dock | Fireplace

4 beds
0 bath
12 guests
Average Price:  
$489
12% Cheaper
than normal
AirDNA Score: 32
$455/night

Mountain Meadow | Large Yard, Gazebo + Hot Tub!

5 beds
4 baths
16 guests
Average Price:  
$590
23% Cheaper
than normal
AirDNA Score: 30
$598/night

Centrally located getaway with hot tub & pool

4 beds
3 baths
12 guests
Average Price:  
$494
21% More
than normal
AirDNA Score: 30
$97/night

Large 3BR Dog Friendly | Deck | W/D

3 beds
2 baths
8 guests
Average Price:  
$162
40% Cheaper
than normal
AirDNA Score: 29
$275/night

Valhalla on Mystic Creek | Deck, Great Location!

3 beds
3.5 baths
7 guests
Average Price:  
$486
43% Cheaper
than normal
AirDNA Score: 29
$140/night

Large 3BR Lakeview Dog Friendly | Dock | Deck

3 beds
2.5 baths
6 guests
Average Price:  
$217
35% Cheaper
than normal
AirDNA Score: 29
$459/night

Waves N' Moguls | Hot Tub, Great Views!

5 beds
4.5 baths
10 guests
Average Price:  
$680
32% Cheaper
than normal
AirDNA Score: 29
$526/night

LakeStar Chalet | Hot Tub, Minutes from Activities

5 beds
3 baths
12 guests
Average Price:  
$657
20% Cheaper
than normal
AirDNA Score: 29
$350/night

Some Kind of Wonderful | Near State Park!

4 beds
3 baths
12 guests
Average Price:  
$576
39% Cheaper
than normal
AirDNA Score: 29
$645/night

Fir Shore | Spacious Cabin, Hot Tub + Dock Slip

6 beds
5 baths
14 guests
Average Price:  
$1119
42% Cheaper
than normal
AirDNA Score: 29
$373/night

2BR | Dogs OK | Fireplace | Hot Tub [thewhita]

2 beds
1 bath
6 guests
Average Price:  
$384
3% Cheaper
than normal
AirDNA Score: 28
$311/night

Tranquil 5BR | Hot Tub | Fireplace | Deck

5 beds
3 baths
11 guests
Average Price:  
$410
24% Cheaper
than normal
AirDNA Score: 28
$277/night

Quiet 2BR Lakefront Dog Friendly | Dock

2 beds
2 baths
10 guests
Average Price:  
$326
15% Cheaper
than normal
AirDNA Score: 28
$470/night

4BR | Fireplace | Hot Tub | Fire Pit [loghev]

4 beds
3.5 baths
10 guests
Average Price:  
$400
18% More
than normal
AirDNA Score: 27
$118/night

Renovated 1BR Lakeview | Balcony

1 bed
1 bath
4 guests
Average Price:  
$157
25% Cheaper
than normal
AirDNA Score: 26
$257/night

3BR Lakeview Dog Friendly | Hot Tub

3 beds
2.5 baths
6 guests
Average Price:  
$306
16% Cheaper
than normal
AirDNA Score: 26
$188/night

Charming 3BR | Hot Tub | Dock | Fireplace

3 beds
1 bath
8 guests
Average Price:  
$256
27% Cheaper
than normal
AirDNA Score: 22
$367/night

Wooded 4BR | Hot Tub | Fireplace | Deck

4 beds
3.5 baths
12 guests
Average Price:  
$476
23% Cheaper
than normal
AirDNA Score: 21
$623/night

Mountaintop Chalet with Spacious Deck & Central

4 beds
3 baths
10 guests
Average Price:  
$576
8% More
than normal
AirDNA Score: 21
$471/night

Trailside Tranquility | Central Location, Views!

4 beds
3 baths
10 guests
Average Price:  
$611
23% Cheaper
than normal
AirDNA Score: 21
$702/night

Conveniently located log cabin with outdoor hot

2 beds
2 baths
8 guests
Average Price:  
$391
80% More
than normal
AirDNA Score: 21
$543/night

Delightful 3 Bedroom Mountain home with hot tub

3 beds
2 baths
10 guests
Average Price:  
$432
26% More
than normal
AirDNA Score: 21
$436/night

Paradise Found | Amazing Lake Views, Private Dock!

4 beds
3 baths
8 guests
Average Price:  
$883
51% Cheaper
than normal
AirDNA Score: 21
$176/night

Central location 3BR Dog Friendly | Hot Tub

3 beds
2 baths
8 guests
Average Price:  
$246
28% Cheaper
than normal
AirDNA Score: 21
$421/night

Serenity Summit | Pet Friendly, Hot Tub, Views!

5 beds
4 baths
10 guests
Average Price:  
$673
37% Cheaper
than normal
AirDNA Score: 21
$367/night

Blue Waters | Community Indoor Pool + Dock Slip!

3 beds
2 baths
8 guests
Average Price:  
$539
32% Cheaper
than normal
AirDNA Score: 21
$572/night

All About the View | Lakefront, Awe-Inspiring View

4 beds
4 baths
10 guests
Average Price:  
$850
33% Cheaper
than normal
AirDNA Score: 21
$558/night

Wright Off the Lake | Pet Friendly, Great Location

5 beds
3 baths
11 guests
Average Price:  
$653
15% Cheaper
than normal
AirDNA Score: 21
$750/night

Stone Crest | Centrally Located, Fire Pit!

6 beds
5 baths
16 guests
Average Price:  
$981
24% Cheaper
than normal
AirDNA Score: 21
$423/night

Whispering Pines | Spacious Townhome, Attractions!

5 beds
4.5 baths
10 guests
Average Price:  
$583
27% Cheaper
than normal
AirDNA Score: 21
$269/night

Kare Bear Cabin | Walk to Restaurants, Remodeled

3 beds
2 baths
8 guests
Average Price:  
$481
44% Cheaper
than normal
AirDNA Score: 21
$391/night

Easy Like Sunday Morning | 5 Min to DCL State Park

4 beds
3.5 baths
12 guests
Average Price:  
$607
36% Cheaper
than normal
AirDNA Score: 21
$564/night

Canoe Cottage | In the Heart of Deep Creek Lake!

5 beds
3 baths
10 guests
Average Price:  
$763
26% Cheaper
than normal
AirDNA Score: 21
$596/night

Centrally located chalet within minutes from lake

3 beds
2 baths
10 guests
Average Price:  
$516
16% More
than normal
AirDNA Score: 21
$236/night

Arrowhead Village 15 | Near Restaurants + Market

3 beds
3 baths
8 guests
Average Price:  
$448
47% Cheaper
than normal
AirDNA Score: 21
$532/night

The Quarterdeck | Pet Friendly, Mountain Views!

4 beds
4 baths
12 guests
Average Price:  
$702
24% Cheaper
than normal
AirDNA Score: 21
$601/night

Bearfoot Lodge: Lakefront charmer with private

3 beds
3 baths
8 guests
Average Price:  
$611
2% Cheaper
than normal
AirDNA Score: 21
$294/night

The Mountain Airy | Great Location, Hot Tub!

3 beds
3 baths
8 guests
Average Price:  
$526
44% Cheaper
than normal
AirDNA Score: 21
$336/night

Knotty Pines | Dock Slip + Near State Parks

3 beds
2 baths
10 guests
Average Price:  
$523
36% Cheaper
than normal
AirDNA Score: 20
$1994/night

10BR | Theater | Hot Tub | Pool [theherr]

10 beds
10.5 baths
16 guests
Average Price:  
$2578
23% Cheaper
than normal
AirDNA Score: 20
$127/night

3BR | A/C | Dogs OK | Hot Tub | Fire Pit [lovemem]

3 beds
3 baths
10 guests
Average Price:  
$555
77% Cheaper
than normal
AirDNA Score: 20
$443/night

4BR | Fireplace | Hot Tub | Fire Pit [cozycab]

4 beds
2.5 baths
12 guests
Average Price:  
$372
19% More
than normal
AirDNA Score: 20
$423/night

3BR | A/C | Fireplace | Grill | Hot Tub [lucky]

3 beds
3 baths
8 guests
Average Price:  
$364
16% More
than normal
AirDNA Score: 20
$474/night

5BR | Fireplace | Hot Tub | Pool Table [dreamon]

5 beds
4.5 baths
10 guests
Average Price:  
$476
0% Cheaper
than normal
AirDNA Score: 20
$748/night

5BR | Fireplace | Hot Tub | Fire Pit [sumside]

5 beds
4 baths
14 guests
Average Price:  
$633
18% More
than normal