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
$226/night
Old Orchard Cottage
2 beds
1 bath
4 guests
Average Price:
$229
1% Cheaper
than normal
AirDNA Score: 93
$155/night
Wright’s Cottage, Pets Welcome!
1 bed
1 bath
2 guests
Average Price:
$158
2% Cheaper
than normal
AirDNA Score: 93
$425/night
Renovated Annapolis Row House a Minute''s Walk to USNA
2 beds
2.5 baths
6 guests
Average Price:
$299
42% More
than normal
AirDNA Score: 91
$169/night
Private 2B Apt--less than 1 mi to Downtown
2 beds
1 bath
6 guests
Average Price:
$190
11% Cheaper
than normal
AirDNA Score: 86
$165/night
Annapolis Guesthouse - Completely Separate Space
2 beds
1 bath
5 guests
Average Price:
$191
14% Cheaper
than normal
AirDNA Score: 86
$100/night
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bed
1 bath
4 guests
Average Price:
$146
32% Cheaper
than normal
AirDNA Score: 86
$425/night
Charming Row House in Historic District
2 beds
1 bath
6 guests
Average Price:
$259
64% More
than normal
AirDNA Score: 83
$451/night
Crab Cakes and Football Historic District
2 beds
1.5 baths
4 guests
Average Price:
$431
5% More
than normal
AirDNA Score: 83
$247/night
3BR/2BA Annapolis Cottage
3 beds
2 baths
6 guests
Average Price:
$321
23% Cheaper
than normal
AirDNA Score: 82
$566/night
Beautiful Home in Quiet Private Setting near Annapolis
4 beds
3 baths
8 guests
Average Price:
$533
6% More
than normal
AirDNA Score: 81
$251/night
Private Art-Filled Guesthouse near Naval Academy
studio
1 bath
2 guests
Average Price:
$263
5% Cheaper
than normal
AirDNA Score: 79
$145/night
Chesapeake Birdhouse Studio
1 bed
1 bath
2 guests
Average Price:
$170
15% Cheaper
than normal
AirDNA Score: 79
$141/night
Brand New Reno in Historic Dist w 2 Parking spots
2 beds
1 bath
4 guests
Average Price:
$208
32% Cheaper
than normal
AirDNA Score: 79
$400/night
Charming Annapolis Water View Home
4 beds
4 baths
14 guests
Average Price:
$456
12% Cheaper
than normal
AirDNA Score: 78
$107/night
Step Out to Main Street From a Chic Loft
1 bed
1 bath
4 guests
Average Price:
$182
41% Cheaper
than normal
AirDNA Score: 73
$325/night
Perfect Eastport location
2 beds
1 bath
4 guests
Average Price:
$315
3% More
than normal
AirDNA Score: 72
$240/night
AirDNA Score: 71
$278/night
Eastport Bungalow
3 beds
1 bath
6 guests
Average Price:
$334
17% Cheaper
than normal
AirDNA Score: 71
$146/night
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 beds
1 bath
4 guests
Average Price:
$205
29% Cheaper
than normal
AirDNA Score: 71
$295/night
Charming Renovated Historic Home Downtown wparking
3 beds
2 baths
6 guests
Average Price:
$352
16% Cheaper
than normal
AirDNA Score: 71
$231/night
Large 1st flr Annapolis/Eastport 3 room Flat
1 bed
1 bath
2 guests
Average Price:
$260
11% Cheaper
than normal
AirDNA Score: 71
$495/night
You'll Never Want to Leave
5 beds
2.5 baths
13 guests
Average Price:
$569
13% Cheaper
than normal
AirDNA Score: 71
$266/night
Historic Downtown Property
3 beds
2.5 baths
6 guests
Average Price:
$297
10% Cheaper
than normal
AirDNA Score: 71
$500/night
Sophisticated & Spacious Historic Home w/ Parking!
3 beds
2.5 baths
6 guests
Average Price:
$614
19% Cheaper
than normal
AirDNA Score: 71
$260/night
Hideaway in the Middle of Everything AYC 2+BR apt
2 beds
1 bath
6 guests
Average Price:
$345
25% Cheaper
than normal
AirDNA Score: 71
$107/night
Private Annapolis Inlaw Apartment
1 bed
1 bath
4 guests
Average Price:
$137
22% Cheaper
than normal
AirDNA Score: 71
$299/night
Across from stadium - walk to downtown Annapolis!
4 beds
3 baths
10 guests
Average Price:
$441
32% Cheaper
than normal
AirDNA Score: 71
$678/night
Relax on the peninsula in Eastport Annapolis!
2 beds
1.5 baths
6 guests
Average Price:
$718
6% Cheaper
than normal
AirDNA Score: 71
$650/night
2003 Craftsman; Heart of Eastport!
3 beds
2.5 baths
6 guests
Average Price:
$551
18% More
than normal
AirDNA Score: 71
$355/night
West Annapolis Gem for Boat Show
3 beds
1.5 baths
6 guests
Average Price:
$370
4% Cheaper
than normal
AirDNA Score: 70
$135/night
Charming lower-level apartment in Annapolis
1 bed
1 bath
2 guests
Average Price:
$161
16% Cheaper
than normal
AirDNA Score: 69
$405/night
Carriage House near Navy Stadium, parking, pets
2 beds
1 bath
6 guests
Average Price:
$419
3% Cheaper
than normal
AirDNA Score: 69
$370/night
Eastport Haven House
4 beds
4 baths
9 guests
Average Price:
$542
32% Cheaper
than normal
AirDNA Score: 69
$900/night
Burley on the Bay
5 beds
4.5 baths
12 guests
Average Price:
$865
4% More
than normal
AirDNA Score: 68
$400/night
Light, Bright and Comfortable! No cleaning fee!
3 beds
2 baths
6 guests
Average Price:
$323
24% More
than normal
AirDNA Score: 67
$900/night
Newly renovated minutes to downtown
5 beds
3.5 baths
8 guests
Average Price:
$907
1% Cheaper
than normal
AirDNA Score: 66
$800/night
Full home just blocks from downtown Annapolis
4 beds
2.5 baths
8 guests
Average Price:
$851
6% Cheaper
than normal
AirDNA Score: 65
$388/night
Moon Tub Cottage. Chic Cozy Charm. Pubs, Shops
3 beds
2 baths
6 guests
Average Price:
$346
12% More
than normal
AirDNA Score: 65
$622/night
Beautiful Home-Steps to Navy Stadium & Downtown!
4 beds
3 baths
8 guests
Average Price:
$691
10% Cheaper
than normal
AirDNA Score: 65
$774/night
Lovely & Spacious Severn River Waterfront
4 beds
4 baths
8 guests
Average Price:
$937
17% Cheaper
than normal
AirDNA Score: 65
$865/night
Spacious Commissioning or Induction week home!
4 beds
4.5 baths
10 guests
Average Price:
$953
9% Cheaper
than normal
AirDNA Score: 65
$418/night
Historic Annapolis Getaway - 45 steps to Downtown!
4 beds
3 baths
8 guests
Average Price:
$727
43% Cheaper
than normal
AirDNA Score: 65
$510/night
1920s House in Presidents Hill
3 beds
1.5 baths
5 guests
Average Price:
$539
5% Cheaper
than normal
AirDNA Score: 64
$289/night
AirDNA Score: 64
$175/night
Independent Access Garage Apartment, Near Downtown
1 bed
1 bath
2 guests
Average Price:
$196
11% Cheaper
than normal
AirDNA Score: 64
$170/night
Cozy Apt. +beach playground-15mins to Annapolis DT
2 beds
1 bath
4 guests
Average Price:
$294
42% 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
$325/night
Heart of Eastport 4 bedroom Modern Craftsman!
4 beds
3.5 baths
10 guests
Average Price:
$626
48% Cheaper
than normal
AirDNA Score: 60
$600/night
Beautiful Large Glass Contemporary Wooded Privacy.
7 beds
3.5 baths
12 guests
Average Price:
$719
17% Cheaper
than normal
AirDNA Score: 58
$300/night
2. 20ac wtrfrnt estate - Studio apt
studio
1.5 baths
2 guests
Average Price:
$396
24% 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
$1350/night
Beautiful 5 bdrm - minutes from downtown & USNA!
5 beds
4.5 baths
12 guests
Average Price:
$1513
11% Cheaper
than normal
AirDNA Score: 57
$190/night
"Jode's Retreat" Your Home Away From Home
3 beds
1 bath
6 guests
Average Price:
$264
28% Cheaper
than normal
AirDNA Score: 57
$249/night
Red Brick Inn, Apt. #1 - Downtown Annapolis
3 beds
1 bath
8 guests
Average Price:
$425
41% Cheaper
than normal
AirDNA Score: 56
$185/night
GREAT LOCATION ON SPA CREEK
1 bed
1 bath
4 guests
Average Price:
$211
12% Cheaper
than normal
AirDNA Score: 55
$584/night
Waterfront home in Annapolis MD with private pier
3 beds
3 baths
10 guests
Average Price:
$645
9% Cheaper
than normal
AirDNA Score: 55
$726/night
Excellent Location, Super Clean, Super Spacious !
7 beds
4.5 baths
15 guests
Average Price:
$899
19% 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
$525/night
Nautical Touches to This Beautiful Eastport Home
2 beds
2.5 baths
6 guests
Average Price:
$539
3% Cheaper
than normal
AirDNA Score: 53
$169/night
Charming Detached Studio w/ easy walk to Downtown.
1 bed
1 bath
2 guests
Average Price:
$275
39% Cheaper
than normal
AirDNA Score: 52
$179/night
Tranquil apartment in the woods
1 bed
1 bath
4 guests
Average Price:
$165
8% More
than normal
AirDNA Score: 52
$235/night
The Apartment ...relax and enjoy Annapolis.
1 bed
1.5 baths
4 guests
Average Price:
$258
9% Cheaper
than normal
AirDNA Score: 51
$800/night
Entire home just blocks from downtown Annapolis
4 beds
2.5 baths
8 guests
Average Price:
$781
2% More
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
$349/night
AirDNA Score: 51
$216/night
AirDNA Score: 51
$1000/night
Perfect home for Annapolis Boat Shows!
4 beds
3 baths
10 guests
Average Price:
$1086
8% Cheaper
than normal
AirDNA Score: 51
$818/night
Spacious Murray Hill - 6 BR walk downtown & Navy
6 beds
4.5 baths
12 guests
Average Price:
$878
7% Cheaper
than normal
AirDNA Score: 50
$875/night
Class of 2025 Grad Week house w/ room for a crowd
4 beds
2.5 baths
10 guests
Average Price:
$943
7% Cheaper
than normal
AirDNA Score: 50
$475/night
Annapolis Waterfront Cottage
4 beds
2 baths
8 guests
Average Price:
$702
32% Cheaper
than normal
AirDNA Score: 50
$550/night
Townhouse at Naval Academy & Dock
3 beds
1.5 baths
8 guests
Average Price:
$598
8% Cheaper
than normal
AirDNA Score: 48
$1000/night
An Eastport beauty in Annapolis.
4 beds
3 baths
8 guests
Average Price:
$1035
3% Cheaper
than normal
AirDNA Score: 48
$295/night
The Very Best location- 50 Steps from Main Street
3 beds
2 baths
6 guests
Average Price:
$409
28% Cheaper
than normal
AirDNA Score: 48
$751/night
Gorgeous Historic Downtown Annapolis House
5 beds
3.5 baths
12 guests
Average Price:
$1108
32% Cheaper
than normal
AirDNA Score: 47
$650/night
Waterfront Oasis in Eastport-Easy Walk to Downtown
5 beds
3.5 baths
10 guests
Average Price:
$734
11% Cheaper
than normal
AirDNA Score: 47
$295/night
Amazing Views from Spa Creek 2BD Condo with Pool
2 beds
1 bath
6 guests
Average Price:
$392
25% Cheaper
than normal
AirDNA Score: 45
$249/night
Historic Home Steps from City Center & Waterfront
2 beds
2 baths
6 guests
Average Price:
$344
28% Cheaper
than normal
AirDNA Score: 45
$249/night
Historic District - One block from Main street
2 beds
1.5 baths
4 guests
Average Price:
$475
48% Cheaper
than normal
AirDNA Score: 45
$530/night
Charming Townhouse in Murray Hill
3 beds
3.5 baths
8 guests
Average Price:
$567
7% Cheaper
than normal
AirDNA Score: 44
$1600/night
Garden House next to USNA & Harbor
3 beds
3.5 baths
6 guests
Average Price:
$1430
12% More
than normal
AirDNA Score: 43
$175/night
1B Annapolis Apartment
1 bed
1 bath
4 guests
Average Price:
$199
12% Cheaper
than normal
AirDNA Score: 38
$199/night
Red Brick Inn, Apt. #B - Downtown Annapolis
2 beds
1 bath
6 guests
Average Price:
$295
33% Cheaper
than normal
AirDNA Score: 38
$195/night
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
$500/night
Beautiful Waterfront Home Sleeps 12
5 beds
3 baths
13 guests
Average Price:
$500
0% Cheaper
than normal
AirDNA Score: 36
$165/night
1A Annapolis Apartment
1 bed
1 bath
4 guests
Average Price:
$185
11% Cheaper
than normal
AirDNA Score: 36
$165/night
2B One Bedroom Annapolis Apartment
2 beds
1 bath
4 guests
Average Price:
$186
11% Cheaper
than normal
AirDNA Score: 33
$375/night
Brick Georgian w Pool, Pet Friendly 1 mile to all!
3 beds
2.5 baths
7 guests
Average Price:
$445
16% 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
$173/night
Check yourself in! 3-Br House near Annapolis Mall
3 beds
2.5 baths
8 guests
Average Price:
$289
40% 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: 21
$1250/night
Craftsman Home in Eastport
3 beds
2.5 baths
6 guests
Average Price:
$1450
14% Cheaper
than normal
AirDNA Score: 14
$301/night
Restful and Charming Home in Eastport
3 beds
1.5 baths
6 guests
Average Price:
$346
13% Cheaper
than normal
AirDNA Score: 14
$1000/night
Annapolis/USNA Commissioning Week Rental
5 beds
3.5 baths
12 guests
Average Price:
$1036
3% Cheaper
than normal
AirDNA Score: 13
$280/night
Upscale Waterfront Condo Annapolis
1 bed
1 bath
2 guests
Average Price:
$297
6% Cheaper
than normal
AirDNA Score: 12
$300/night
A Waterfront Upscale Annapolis Condo
1 bed
1 bath
2 guests
Average Price:
$316
5% Cheaper
than normal