The Best Airbnb Deals in
Annapolis, Maryland

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

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AirDNA Score: 93
$150/night

Wright’s Cottage, Pets Welcome!

1 bed
1 bath
2 guests
Average Price:  
$149
1% More
than normal
AirDNA Score: 93
$215/night

Old Orchard Cottage

2 beds
1 bath
4 guests
Average Price:  
$231
7% Cheaper
than normal
AirDNA Score: 86
$119/night

Wall to Wall Cool- Filled with Original Art and Sculpture

1 bed
1 bath
4 guests
Average Price:  
$143
17% Cheaper
than normal
AirDNA Score: 85
$50/night

Annapolis Studio Apartment for longer stays - Pool

1 bed
1 bath
1 guest
Average Price:  
$82
39% Cheaper
than normal
AirDNA Score: 83
$399/night

Crab Cakes and Football Historic District

2 beds
1.5 baths
4 guests
Average Price:  
$446
11% Cheaper
than normal
AirDNA Score: 83
$220/night

3BR/2BA Annapolis Cottage

3 beds
2 baths
6 guests
Average Price:  
$324
32% Cheaper
than normal
AirDNA Score: 82
$511/night

Beautiful Home in Quiet Private Setting near Annapolis

4 beds
3 baths
8 guests
Average Price:  
$533
4% Cheaper
than normal
AirDNA Score: 81
$235/night

Private Art-Filled Guesthouse near Naval Academy

studio
1 bath
2 guests
Average Price:  
$259
9% Cheaper
than normal
AirDNA Score: 80
$935/night

Modern Waterfront: Quiet but close to Everything.

5 beds
4 baths
12 guests
Average Price:  
$1107
16% Cheaper
than normal
AirDNA Score: 79
$153/night

Chesapeake Birdhouse Studio

1 bed
1 bath
2 guests
Average Price:  
$182
16% Cheaper
than normal
AirDNA Score: 79
$395/night

Charming Annapolis Water View Home

4 beds
4 baths
14 guests
Average Price:  
$421
6% Cheaper
than normal
AirDNA Score: 77
$239/night

Spacious Home in Private Neighborhood with Beach

4 beds
3.5 baths
8 guests
Average Price:  
$403
41% Cheaper
than normal
AirDNA Score: 74
$450/night

Annapolis home near all the main attractions.

4 beds
3.5 baths
8 guests
Average Price:  
$488
8% Cheaper
than normal
AirDNA Score: 73
$300/night

Old. Don’t usw

1 bed
1 bath
2 guests
Average Price:  
$550
45% Cheaper
than normal
AirDNA Score: 73
$180/night

Soak up the Soothing Vibe at a Grayscale Annapolis Loft

studio
1 bath
2 guests
Average Price:  
$199
10% Cheaper
than normal
AirDNA Score: 71
$407/night

Across from stadium - walk to downtown Annapolis!

4 beds
3 baths
10 guests
Average Price:  
$465
12% Cheaper
than normal
AirDNA Score: 71
$281/night

Eastport Bungalow

3 beds
1 bath
6 guests
Average Price:  
$334
16% Cheaper
than normal
AirDNA Score: 71
$495/night

You''ll Never Want to Leave

5 beds
2.5 baths
13 guests
Average Price:  
$622
20% Cheaper
than normal
AirDNA Score: 71
$105/night

Our Annapolis Penthouse

1 bed
1 bath
3 guests
Average Price:  
$110
5% Cheaper
than normal
AirDNA Score: 71
$185/night

Charming Renovated Historic Home Downtown wparking

3 beds
2 baths
6 guests
Average Price:  
$372
50% Cheaper
than normal
AirDNA Score: 71
$701/night

Relax on the peninsula in Eastport Annapolis!

2 beds
1.5 baths
6 guests
Average Price:  
$751
7% Cheaper
than normal
AirDNA Score: 71
$419/night

2003 Craftsman; Heart of Eastport!

3 beds
2.5 baths
6 guests
Average Price:  
$587
29% Cheaper
than normal
AirDNA Score: 71
$295/night

SuperHost Prime Stadium Location

3 beds
1.5 baths
6 guests
Average Price:  
$420
30% Cheaper
than normal
AirDNA Score: 70
$135/night

Charming lower-level apartment in Annapolis

1 bed
1 bath
2 guests
Average Price:  
$151
11% Cheaper
than normal
AirDNA Score: 70
$178/night

Eastport-Annapolis Private Bsmt. Apt 1 mile -DTA

1 bed
1 bath
4 guests
Average Price:  
$165
8% More
than normal
AirDNA Score: 69
$355/night

Carriage House near Navy Stadium, parking, pets

2 beds
1 bath
6 guests
Average Price:  
$438
19% Cheaper
than normal
AirDNA Score: 69
$315/night

Eastport Haven House

4 beds
4 baths
9 guests
Average Price:  
$528
40% Cheaper
than normal
AirDNA Score: 69
$798/night

Burley on the Bay

5 beds
4.5 baths
12 guests
Average Price:  
$902
12% Cheaper
than normal
AirDNA Score: 67
$900/night

Newly renovated minutes to downtown

5 beds
3.5 baths
8 guests
Average Price:  
$950
5% Cheaper
than normal
AirDNA Score: 66
$800/night

Full home just blocks from downtown Annapolis

4 beds
2.5 baths
8 guests
Average Price:  
$845
5% Cheaper
than normal
AirDNA Score: 66
$960/night

Wedding Reception, Commissioning Week, & Crafters

4 beds
3.5 baths
10 guests
Average Price:  
$1012
5% Cheaper
than normal
AirDNA Score: 65
$865/night

Spacious Commissioning or Induction week home!

4 beds
4.5 baths
10 guests
Average Price:  
$942
8% Cheaper
than normal
AirDNA Score: 65
$200/night

Lovely family home just minutes from Annapolis

4 beds
2.5 baths
8 guests
Average Price:  
$297
33% Cheaper
than normal
AirDNA Score: 65
$510/night

1920s House in Presidents Hill

3 beds
1.5 baths
5 guests
Average Price:  
$529
4% Cheaper
than normal
AirDNA Score: 65
$2000/night

Four Blocks to Downtown--Luxurious & Convenient!

4 beds
3.5 baths
8 guests
Average Price:  
$2000
0% Cheaper
than normal
AirDNA Score: 64
$400/night

Waterfront Vacation Home

3 beds
3.5 baths
11 guests
Average Price:  
$556
28% Cheaper
than normal
AirDNA Score: 64
$190/night

Cozy Apt. +beach playground-15mins to Annapolis DT

2 beds
1 bath
4 guests
Average Price:  
$307
38% Cheaper
than normal
AirDNA Score: 64
$119/night

Charming Eastport

1 bed
1 bath
2 guests
Average Price:  
$168
29% Cheaper
than normal
AirDNA Score: 64
$174/night

Independent Access Garage Apartment, Near Downtown

1 bed
1 bath
2 guests
Average Price:  
$189
8% Cheaper
than normal
AirDNA Score: 64
$650/night

4 Bed & 3 Bath Contemporary in Heart of Eastport!

4 beds
3.5 baths
12 guests
Average Price:  
$575
13% More
than normal
AirDNA Score: 64
$434/night

Heart of Eastport 4 bedroom Modern Craftsman!

4 beds
3.5 baths
10 guests
Average Price:  
$642
32% Cheaper
than normal
AirDNA Score: 60
$600/night

Beautiful Large Glass Contemporary Wooded Privacy.

7 beds
3.5 baths
12 guests
Average Price:  
$698
14% Cheaper
than normal
AirDNA Score: 59
$500/night

Beautiful Home in the Heart of Downtown, w/Parking

4 beds
3 baths
9 guests
Average Price:  
$530
6% Cheaper
than normal
AirDNA Score: 58
$75/night

2. 20ac wtrfrnt estate - Studio apt

studio
1.5 baths
2 guests
Average Price:  
$400
81% Cheaper
than normal
AirDNA Score: 57
$1350/night

Annapolis Elegance! Minutes from downtown & USNA!

5 beds
4.5 baths
12 guests
Average Price:  
$1552
13% Cheaper
than normal
AirDNA Score: 57
$200/night

One bedroom apartment in Annapolis

1 bed
1 bath
4 guests
Average Price:  
$195
3% More
than normal
AirDNA Score: 57
$190/night

"Jode''s Retreat" Your Home Away From Home

3 beds
1 bath
6 guests
Average Price:  
$262
27% Cheaper
than normal
AirDNA Score: 57
$110/night

RECENTLY RENOVATED Cottage Near Downtown Annapolis

1 bed
1 bath
2 guests
Average Price:  
$124
11% Cheaper
than normal
AirDNA Score: 57
$249/night

Red Brick Inn, Apt. #1 - Downtown Annapolis

3 beds
1 bath
8 guests
Average Price:  
$382
35% Cheaper
than normal
AirDNA Score: 56
$175/night

GREAT LOCATION ON SPA CREEK

1 bed
1 bath
4 guests
Average Price:  
$211
17% Cheaper
than normal
AirDNA Score: 55
$490/night

Annapolis Nautical Cottage EASTPORT NAVY BOAT SHOW

2 beds
1.5 baths
8 guests
Average Price:  
$571
14% Cheaper
than normal
AirDNA Score: 55
$625/night

Eastport Peninsula Charm

4 beds
2.5 baths
8 guests
Average Price:  
$655
5% Cheaper
than normal
AirDNA Score: 55
$180/night

Country House on the Bay

5 beds
3 baths
10 guests
Average Price:  
$221
19% Cheaper
than normal
AirDNA Score: 55
$315/night

Downtown Annapolis Home

3 beds
2.5 baths
6 guests
Average Price:  
$540
42% Cheaper
than normal
AirDNA Score: 55
$800/night

Excellent Location, Super Clean, Super Spacious !

7 beds
4.5 baths
15 guests
Average Price:  
$984
19% Cheaper
than normal
AirDNA Score: 55
$600/night

Waterfront home in Annapolis MD with private pier

3 beds
3 baths
10 guests
Average Price:  
$648
7% Cheaper
than normal
AirDNA Score: 54
$550/night

Contemporary in Heart of Eastport w 2 car garage!

3 beds
2.5 baths
6 guests
Average Price:  
$483
14% More
than normal
AirDNA Score: 53
$385/night

Nautical Touches to This Beautiful Eastport Home

2 beds
2.5 baths
6 guests
Average Price:  
$481
20% Cheaper
than normal
AirDNA Score: 53
$202/night

Charming Detached Studio w/ easy walk to Downtown.

1 bed
1 bath
2 guests
Average Price:  
$230
12% Cheaper
than normal
AirDNA Score: 53
$950/night

Annapolis USNA Family Rental

5 beds
3.5 baths
10 guests
Average Price:  
$997
5% Cheaper
than normal
AirDNA Score: 52
$149/night

Tranquil apartment in the woods

1 bed
1 bath
4 guests
Average Price:  
$158
6% Cheaper
than normal
AirDNA Score: 52
$425/night

Downtown Annapolis Apartment

2 beds
2 baths
6 guests
Average Price:  
$473
10% Cheaper
than normal
AirDNA Score: 52
$235/night

The Apartment ...relax and enjoy Annapolis.

1 bed
1.5 baths
4 guests
Average Price:  
$259
9% Cheaper
than normal
AirDNA Score: 51
$1000/night

5 BDR across from USNA Stadium

5 beds
5.5 baths
12 guests
Average Price:  
$1000
0% Cheaper
than normal
AirDNA Score: 51
$1000/night

Perfect home for Annapolis Boat Shows!

4 beds
3 baths
10 guests
Average Price:  
$1092
8% Cheaper
than normal
AirDNA Score: 50
$500/night

Annapolis Waterfront Cottage

4 beds
2 baths
8 guests
Average Price:  
$693
28% Cheaper
than normal
AirDNA Score: 50
$875/night

Class of 2023 Grad Week house w/ room for a crowd

4 beds
2.5 baths
10 guests
Average Price:  
$989
12% Cheaper
than normal
AirDNA Score: 48
$1000/night

Eastport in Annapolis

4 beds
3 baths
8 guests
Average Price:  
$1028
3% Cheaper
than normal
AirDNA Score: 48
$801/night

Gorgeous Historic Downtown Annapolis House

5 beds
3.5 baths
12 guests
Average Price:  
$1214
34% Cheaper
than normal
AirDNA Score: 47
$238/night

Charming Guest House-Annapolis

1 bed
1 bath
2 guests
Average Price:  
$269
12% Cheaper
than normal
AirDNA Score: 47
$507/night

Waterfront Oasis in Eastport-Easy Walk to Downtown

5 beds
3.5 baths
10 guests
Average Price:  
$734
31% Cheaper
than normal
AirDNA Score: 45
$535/night

Charming Townhouse in Murray Hill

3 beds
3.5 baths
8 guests
Average Price:  
$558
4% Cheaper
than normal
AirDNA Score: 45
$250/night

Historic Home Steps from City Center & Waterfront

2 beds
2 baths
6 guests
Average Price:  
$356
30% Cheaper
than normal
AirDNA Score: 44
$350/night

All Things ANNAPOLIS...

2 beds
2 baths
4 guests
Average Price:  
$450
22% Cheaper
than normal
AirDNA Score: 44
$1441/night

Garden House next to USNA & Harbor

3 beds
3.5 baths
6 guests
Average Price:  
$1329
8% More
than normal
AirDNA Score: 43
$141/night

2A One Bedroom Annapolis Apartment

1 bed
1 bath
4 guests
Average Price:  
$180
22% Cheaper
than normal
AirDNA Score: 38
$199/night

Red Brick Inn, Apt. #B - Downtown Annapolis

2 beds
1 bath
6 guests
Average Price:  
$275
28% Cheaper
than normal
AirDNA Score: 38
$195/night

The Lobster Loft

2 beds
1 bath
6 guests
Average Price:  
$196
1% Cheaper
than normal
AirDNA Score: 36
$450/night

Annapolis Condo - minutes from downtown/Academy

3 beds
2 baths
6 guests
Average Price:  
$442
2% More
than normal
AirDNA Score: 36
$118/night

1A Annapolis Apartment

1 bed
1 bath
4 guests
Average Price:  
$181
35% Cheaper
than normal
AirDNA Score: 36
$118/night

2B One Bedroom Annapolis Apartment

2 beds
1 bath
4 guests
Average Price:  
$182
35% Cheaper
than normal
AirDNA Score: 36
$500/night

Beautiful Waterfront Home Sleeps 11

5 beds
3 baths
13 guests
Average Price:  
$500
0% Cheaper
than normal
AirDNA Score: 33
$565/night

2 blocks from Stadium and walking distance to Town

4 beds
3 baths
10 guests
Average Price:  
$595
5% Cheaper
than normal
AirDNA Score: 31
$345/night

Families & Friends gather here to enjoy

5 beds
2.5 baths
10 guests
Average Price:  
$373
8% Cheaper
than normal
AirDNA Score: 31
$185/night

Check yourself in! 3-Br House near Annapolis Mall

3 beds
2.5 baths
8 guests
Average Price:  
$291
36% Cheaper
than normal
AirDNA Score: 29
$240/night

Charming Downtown Home - 3 Blocks Off Main

2 beds
1.5 baths
5 guests
Average Price:  
$408
41% Cheaper
than normal
AirDNA Score: 23
$275/night

Downtown Annapolis Historic Home!

2 beds
1.5 baths
4 guests
Average Price:  
$338
19% Cheaper
than normal
AirDNA Score: 22
$241/night

22 Fleet St. - History & Charm Near the Annapolis

3 beds
2.5 baths
6 guests
Average Price:  
$1043
77% Cheaper
than normal
AirDNA Score: 21
$1250/night

Craftsman Home in Eastport

3 beds
2.5 baths
6 guests
Average Price:  
$1450
14% Cheaper
than normal
AirDNA Score: 13
$275/night

Upscale Waterfront Condo Annapolis

1 bed
1 bath
2 guests
Average Price:  
$292
6% Cheaper
than normal
AirDNA Score: 12
$285/night

A Waterfront Upscale Annapolis Condo

1 bed
1 bath
2 guests
Average Price:  
$324
12% Cheaper
than normal