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: 80
$150/night

SUGARBUSH - Sweet Serenity Tiny House

1 bed
1 bath
2 guests
Average Price:  
$150
0% Cheaper
than normal
AirDNA Score: 79
$199/night

Winter is Coming

3 beds
3 baths
10 guests
Average Price:  
$330
40% Cheaper
than normal
AirDNA Score: 77
$230/night

Dancing Bears

3 beds
1 bath
6 guests
Average Price:  
$277
17% Cheaper
than normal
AirDNA Score: 74
$253/night

Deep Creek Lake Cozy Cottage (Dog Friendly)

3 beds
1 bath
5 guests
Average Price:  
$368
31% Cheaper
than normal
AirDNA Score: 71
$469/night

Dolce Vita @ Deep Creek Lake

4 beds
3 baths
10 guests
Average Price:  
$499
6% Cheaper
than normal
AirDNA Score: 70
$385/night

Cozy Cabin @ Deep Creek Lake

3 beds
1.5 baths
8 guests
Average Price:  
$380
1% More
than normal
AirDNA Score: 70
$330/night

Mountain Escape @ Deep Creek Lake

4 beds
2 baths
10 guests
Average Price:  
$311
6% More
than normal
AirDNA Score: 69
$295/night

Dock Holiday-Lake access with a boat slip

3 beds
2.5 baths
8 guests
Average Price:  
$429
31% 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: 64
$453/night

Private-HotTub-Firewood-CARC-Essentials-Cozy-Sleds

5 beds
3.5 baths
13 guests
Average Price:  
$665
32% 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
$310/night

Lovin'' Life - Luxury home w/ lake views 5 STAR

5 beds
3 baths
14 guests
Average Price:  
$361
14% Cheaper
than normal
AirDNA Score: 59
$195/night

Little Piece of Heaven

1 bed
1 bath
4 guests
Average Price:  
$196
1% Cheaper
than normal
AirDNA Score: 58
$843/night

La Bella Vita | Amazing Lake Views, Upscale Decor

5 beds
5.5 baths
14 guests
Average Price:  
$859
2% Cheaper
than normal
AirDNA Score: 58
$365/night

Lake House | Close to Swallow Falls State Park

4 beds
3.5 baths
12 guests
Average Price:  
$703
48% Cheaper
than normal
AirDNA Score: 58
$712/night

St. Bart''s Retreat | Pet Friendly, Lakefront Home!

7 beds
6.5 baths
16 guests
Average Price:  
$1345
47% Cheaper
than normal
AirDNA Score: 58
$358/night

Log Home with Indoor Hot Tub & Central Location

3 beds
3 baths
8 guests
Average Price:  
$444
19% Cheaper
than normal
AirDNA Score: 58
$517/night

Windsor House | Pet Friendly, Hot Tub, Lake Access

4 beds
5 baths
12 guests
Average Price:  
$619
16% Cheaper
than normal
AirDNA Score: 58
$384/night

Grande Villa | Lake Views + Near Activities

5 beds
5.5 baths
12 guests
Average Price:  
$680
44% Cheaper
than normal
AirDNA Score: 57
$273/night

Life is Good Today | Lake Views + Boat Slip

3 beds
3.5 baths
8 guests
Average Price:  
$510
46% Cheaper
than normal
AirDNA Score: 57
$1406/night

Grand Chestnut Lodge | Lakefront, Sunset Views!

9 beds
7.5 baths
16 guests
Average Price:  
$1565
10% Cheaper
than normal
AirDNA Score: 57
$305/night

Hidden Treasure | Quiet Location Near Activities

4 beds
3.5 baths
8 guests
Average Price:  
$546
44% Cheaper
than normal
AirDNA Score: 57
$284/night

Picture Perfect | Centrally Located, Hot Tub!

4 beds
3.5 baths
12 guests
Average Price:  
$748
62% Cheaper
than normal
AirDNA Score: 57
$576/night

Whisked Away | Lakefront Home, Private Dock!

5 beds
4.5 baths
14 guests
Average Price:  
$1042
45% Cheaper
than normal
AirDNA Score: 57
$211/night

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

2 beds
1 bath
6 guests
Average Price:  
$415
49% Cheaper
than normal
AirDNA Score: 57
$363/night

2BR | Fireplace | Grill | Hot Tub [deepcrk]

2 beds
2 baths
4 guests
Average Price:  
$355
2% More
than normal
AirDNA Score: 57
$338/night

Lake View | Centrally Located with Lake Views!

3 beds
2 baths
8 guests
Average Price:  
$589
43% Cheaper
than normal
AirDNA Score: 57
$433/night

Boxer Overlook | Lake Views, Hot Tub, Mountainside

5 beds
3 baths
14 guests
Average Price:  
$668
35% Cheaper
than normal
AirDNA Score: 57
$543/night

Deja Blue | Lake Access, Hot Tub, Near Activities!

5 beds
4.5 baths
12 guests
Average Price:  
$687
21% Cheaper
than normal
AirDNA Score: 57
$400/night

Mountain House | Pet Friendly, Dock, Great Views!

5 beds
3 baths
14 guests
Average Price:  
$627
36% Cheaper
than normal
AirDNA Score: 57
$432/night

Paradise at Penn Cove | Walk to the Dock Slip!

2 beds
2 baths
7 guests
Average Price:  
$509
15% Cheaper
than normal
AirDNA Score: 57
$716/night

Bear Hollow Lodge | 5 Minutes to Lake Activities

5 beds
4.5 baths
14 guests
Average Price:  
$1116
36% Cheaper
than normal
AirDNA Score: 57
$268/night

Home Sweet Cabin | Peaceful, Multiple Game Tables!

4 beds
2 baths
10 guests
Average Price:  
$521
49% Cheaper
than normal
AirDNA Score: 57
$235/night

Wine Down | Centrally Located, Hot Tub, Pool Table

4 beds
3 baths
12 guests
Average Price:  
$684
66% 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: 57
$723/night

Stylish Townhome with Hot Tub conveniently

3 beds
3 baths
10 guests
Average Price:  
$411
76% More
than normal
AirDNA Score: 56
$771/night

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

5 beds
4.5 baths
14 guests
Average Price:  
$863
11% Cheaper
than normal
AirDNA Score: 56
$546/night

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

3 beds
3 baths
9 guests
Average Price:  
$470
16% More
than normal
AirDNA Score: 56
$1163/night

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

9 beds
5.5 baths
16 guests
Average Price:  
$1338
13% Cheaper
than normal
AirDNA Score: 56
$480/night

4BR | A/C | Fireplace | Hot Tub | WIFI [shiver]

4 beds
4 baths
12 guests
Average Price:  
$422
14% More
than normal
AirDNA Score: 56
$318/night

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

2 beds
1 bath
6 guests
Average Price:  
$388
18% Cheaper
than normal
AirDNA Score: 56
$562/night

5BR | Hot Tub | Fire Pit | Sauna | WIFI [eaglen]

5 beds
4 baths
14 guests
Average Price:  
$606
7% Cheaper
than normal
AirDNA Score: 56
$550/night

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

5 beds
3 baths
14 guests
Average Price:  
$664
17% Cheaper
than normal
AirDNA Score: 56
$1236/night

8BR | Private Dock | Fireplace | Hot Tub [enchant]

8 beds
7.5 baths
16 guests
Average Price:  
$1420
13% Cheaper
than normal
AirDNA Score: 56
$865/night

7BR | A/C | Dock | Hot Tub | Pool Table [aspen]

7 beds
6.5 baths
16 guests
Average Price:  
$1256
31% Cheaper
than normal
AirDNA Score: 56
$411/night

3BR | Dock | Dogs OK | Fire Pit [lwood]

3 beds
2 baths
8 guests
Average Price:  
$379
8% More
than normal
AirDNA Score: 56
$685/night

5BR | Dock | Dogs OK | Hot Tub | Fire Pit [logmah]

5 beds
3.5 baths
14 guests
Average Price:  
$812
16% Cheaper
than normal
AirDNA Score: 56
$437/night

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

2 beds
2 baths
8 guests
Average Price:  
$373
17% More
than normal
AirDNA Score: 56
$446/night

3BR | A/C | Fireplace | Hot Tub | WIFI [lostbear]

3 beds
3 baths
8 guests
Average Price:  
$365
22% More
than normal
AirDNA Score: 56
$680/night

5BR | Fireplace | Fire Pit | Pool Table [alvie]

6 beds
5.5 baths
14 guests
Average Price:  
$1020
33% Cheaper
than normal
AirDNA Score: 56
$320/night

3BR | Dock | Dogs OK | Fireplace [hlcha]

3 beds
2 baths
10 guests
Average Price:  
$351
9% Cheaper
than normal
AirDNA Score: 56
$549/night

5BR | A/C | Private Dock | Hot Tub [tradlk]

5 beds
3.5 baths
14 guests
Average Price:  
$774
29% Cheaper
than normal
AirDNA Score: 56
$1029/night

8BR | Dock | Dogs OK | Hot Tub [lakehouse]

8 beds
6.5 baths
16 guests
Average Price:  
$1221
16% Cheaper
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
$320/night

Spectacular Chalet, Timroc II, close to lake, Wisp

5 beds
3.5 baths
14 guests
Average Price:  
$431
26% 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
$356/night

Big Rock Candy Mountain Lodge - Deep Creek Lake

5 beds
4 baths
14 guests
Average Price:  
$393
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
$154/night

Deep Creek Lake Townhome w/Deck & Water Views

2 beds
2.5 baths
6 guests
Average Price:  
$231
33% Cheaper
than normal
AirDNA Score: 37
$165/night

Bear Necessities @ Deep Creek Lake

studio
1 bath
2 guests
Average Price:  
$181
9% Cheaper
than normal
AirDNA Score: 36
$561/night

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

4 beds
3.5 baths
12 guests
Average Price:  
$454
24% More
than normal
AirDNA Score: 35
$299/night

Vintage Oakland @ Oakland Maryland

4 beds
3 baths
10 guests
Average Price:  
$314
5% Cheaper
than normal
AirDNA Score: 35
$410/night

Laurel Grove

4 beds
3 baths
12 guests
Average Price:  
$484
15% 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
$757/night

Mountain Meadow | Large Yard, Gazebo + Hot Tub!

5 beds
4 baths
16 guests
Average Price:  
$618
22% 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
$655/night

Nature''s Retreat | Private Dock, Community Pool!

5 beds
4.5 baths
14 guests
Average Price:  
$1023
36% Cheaper
than normal
AirDNA Score: 29
$376/night

Just About Paradise | Seasonal Lake Views + Deck

5 beds
3.5 baths
14 guests
Average Price:  
$707
47% Cheaper
than normal
AirDNA Score: 29
$297/night

Happy Trails | Lake Access + Dock Slip, Near Wisp!

3 beds
2.5 baths
10 guests
Average Price:  
$599
50% Cheaper
than normal
AirDNA Score: 29
$259/night

Valhalla on Mystic Creek | Deck, Great Location!

3 beds
3.5 baths
10 guests
Average Price:  
$519
50% 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
$234/night

Cross the River | Hot Tub + River Access!

2 beds
1 bath
6 guests
Average Price:  
$413
43% Cheaper
than normal
AirDNA Score: 29
$635/night

Fir Shore | Spacious Cabin, Hot Tub + Dock Slip

6 beds
5 baths
14 guests
Average Price:  
$1093
42% Cheaper
than normal
AirDNA Score: 29
$384/night

Waves N'' Moguls | Hot Tub, Great Views!

5 beds
4.5 baths
10 guests
Average Price:  
$684
44% Cheaper
than normal
AirDNA Score: 29
$335/night

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

2 beds
1 bath
6 guests
Average Price:  
$387
13% Cheaper
than normal
AirDNA Score: 29
$451/night

LakeStar Chalet | Hot Tub, Minutes from Activities

5 beds
3 baths
12 guests
Average Price:  
$722
38% Cheaper
than normal
AirDNA Score: 29
$468/night

Some Kind of Wonderful | Near State Park!

4 beds
3 baths
12 guests
Average Price:  
$592
21% 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
$271/night

2BR | Private Dock | Dogs OK | Hot Tub [tolson]

2 beds
1 bath
6 guests
Average Price:  
$431
37% Cheaper
than normal
AirDNA Score: 28
$439/night

4BR | Dock | Hot Tub | Fire Pit [outoff]

4 beds
4 baths
12 guests
Average Price:  
$516
15% 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
$488/night

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

4 beds
3.5 baths
10 guests
Average Price:  
$410
19% 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
$284/night

Strawberry Fields | Hot Tub, Amazing Location!

3 beds
3.5 baths
8 guests
Average Price:  
$443
36% Cheaper
than normal
AirDNA Score: 22
$586/night

Lakeside Vista | Lakefront, Private Dock + Views

4 beds
3 baths
10 guests
Average Price:  
$874
33% 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
$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
$321/night

Trailside Tranquility | Central Location, Views!

4 beds
3 baths
10 guests
Average Price:  
$643
50% 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
$623/night

Mountaintop Chalet with Spacious Deck & Central

4 beds
3 baths
10 guests
Average Price:  
$576
8% More
than normal
AirDNA Score: 21
$540/night

Paradise Found | Amazing Lake Views, Private Dock!

4 beds
3 baths
10 guests
Average Price:  
$904
40% Cheaper
than normal
AirDNA Score: 21
$743/night

Stone Crest | Centrally Located, Fire Pit!

6 beds
5 baths
16 guests
Average Price:  
$1092
32% Cheaper
than normal
AirDNA Score: 21
$392/night

Whispering Pines | Spacious Townhome, Attractions!

5 beds
4.5 baths
10 guests
Average Price:  
$631
38% 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
$395/night

Serenity Summit | Pet Friendly, Hot Tub, Views!

5 beds
4 baths
10 guests
Average Price:  
$688
43% Cheaper
than normal