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: 86
$89/night
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bed
1 bath
4 guests
Average Price:
$138
36% Cheaper
than normal
AirDNA Score: 86
$165/night
Annapolis Guesthouse - Completely Separate Space
2 beds
1 bath
5 guests
Average Price:
$200
17% Cheaper
than normal
AirDNA Score: 85
$446/night
Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*
3 beds
2 baths
8 guests
Average Price:
$487
8% Cheaper
than normal
AirDNA Score: 82
$562/night
Beautiful Home in Quiet Private Setting near Annapolis
4 beds
3 baths
8 guests
Average Price:
$533
5% More
than normal
AirDNA Score: 81
$235/night
Private Art-Filled Guesthouse near Naval Academy
studio
1 bath
2 guests
Average Price:
$265
11% Cheaper
than normal
AirDNA Score: 81
$124/night
AirDNA Score: 80
$935/night
Modern Waterfront: Quiet but close to Everything.
5 beds
4 baths
12 guests
Average Price:
$1186
21% Cheaper
than normal
AirDNA Score: 79
$110/night
Furnished Bright & Airy Condo 10 mins to downtown
2 beds
2 baths
4 guests
Average Price:
$325
66% Cheaper
than normal
AirDNA Score: 79
$165/night
Chesapeake Birdhouse Studio
1 bed
1 bath
2 guests
Average Price:
$183
10% Cheaper
than normal
AirDNA Score: 76
$950/night
Gorgeous home in historic Annapolis w/parking
4 beds
4.5 baths
12 guests
Average Price:
$1011
6% Cheaper
than normal
AirDNA Score: 73
$300/night
AirDNA Score: 71
$495/night
You''ll Never Want to Leave
5 beds
2.5 baths
13 guests
Average Price:
$620
20% Cheaper
than normal
AirDNA Score: 71
$109/night
Private Annapolis Inlaw Apartment
1 bed
1 bath
4 guests
Average Price:
$128
15% Cheaper
than normal
AirDNA Score: 71
$718/night
Crow''s Nest Cottage: Chesapeake Bay View*HOT TUB*
6 beds
3 baths
16 guests
Average Price:
$642
12% More
than normal
AirDNA Score: 70
$160/night
Eastport-Annapolis Private Bsmt. Apt 1 mile -DTA
1 bed
1 bath
4 guests
Average Price:
$166
4% Cheaper
than normal
AirDNA Score: 69
$425/night
Eastport Haven House
4 beds
4 baths
9 guests
Average Price:
$504
16% Cheaper
than normal
AirDNA Score: 69
$395/night
Carriage House near Navy Stadium, parking, pets
2 beds
1 bath
6 guests
Average Price:
$418
6% Cheaper
than normal
AirDNA Score: 69
$800/night
Burley on the Bay
5 beds
4.5 baths
12 guests
Average Price:
$921
13% Cheaper
than normal
AirDNA Score: 65
$489/night
Getaway On The Bay
3 beds
3 baths
8 guests
Average Price:
$494
1% Cheaper
than normal
AirDNA Score: 65
$865/night
Spacious Commissioning or Induction week home!
4 beds
4.5 baths
10 guests
Average Price:
$930
7% Cheaper
than normal
AirDNA Score: 65
$695/night
Location! Historic home steps from City Dock
4 beds
3 baths
8 guests
Average Price:
$803
13% Cheaper
than normal
AirDNA Score: 65
$115/night
Clean & comfy guest suite in Eastport
studio
1 bath
2 guests
Average Price:
$148
22% Cheaper
than normal
AirDNA Score: 65
$129/night
"L''auberge du Cape Saint Claire"
2 beds
1 bath
4 guests
Average Price:
$176
27% Cheaper
than normal
AirDNA Score: 64
$182/night
Independent Access Garage Apartment, Near Downtown
1 bed
1 bath
2 guests
Average Price:
$188
3% Cheaper
than normal
AirDNA Score: 64
$190/night
Cozy Apt. +beach playground-15mins to Annapolis DT
2 beds
1 bath
4 guests
Average Price:
$301
37% Cheaper
than normal
AirDNA Score: 64
$119/night
AirDNA Score: 64
$500/night
Waterfront Vacation Home
3 beds
3.5 baths
11 guests
Average Price:
$559
11% Cheaper
than normal
AirDNA Score: 60
$576/night
Newly renovated downtown home with enclosed yard, gas grill, and wet bar
4 beds
3.5 baths
8 guests
Average Price:
$962
40% Cheaper
than normal
AirDNA Score: 60
$800/night
Beautiful Large Glass Contemporary Wooded Privacy.
7 beds
3.5 baths
12 guests
Average Price:
$644
24% More
than normal
AirDNA Score: 59
$900/night
Luxury Waterfront Annapolis/ Private Beach & Dock
3 beds
3.5 baths
6 guests
Average Price:
$1336
33% Cheaper
than normal
AirDNA Score: 59
$1200/night
Stunning Historic District Home, Steps to Academy
4 beds
5 baths
10 guests
Average Price:
$1071
12% More
than normal
AirDNA Score: 59
$1057/night
Upscale & updated multi-level home with private courtyard, grill & gas fireplace
5 beds
3.5 baths
10 guests
Average Price:
$1249
15% Cheaper
than normal
AirDNA Score: 58
$300/night
2. 20ac wtrfrnt estate - Studio apt
studio
1.5 baths
2 guests
Average Price:
$400
25% Cheaper
than normal
AirDNA Score: 57
$200/night
One bedroom apartment in Annapolis
1 bed
1 bath
4 guests
Average Price:
$194
3% More
than normal
AirDNA Score: 57
$1500/night
Annapolis Elegance! Minutes from downtown & USNA!
5 beds
4.5 baths
12 guests
Average Price:
$1555
4% Cheaper
than normal
AirDNA Score: 57
$190/night
"Jode''s Retreat" Your Home Away From Home
3 beds
1 bath
6 guests
Average Price:
$257
26% Cheaper
than normal
AirDNA Score: 57
$358/night
Murray Hill Home-Walk to Downtown, Close to water
4 beds
2.5 baths
11 guests
Average Price:
$369
3% Cheaper
than normal
AirDNA Score: 55
$649/night
Bay Ridge! Seaglass House by-the-Bay
5 beds
2 baths
10 guests
Average Price:
$684
5% Cheaper
than normal
AirDNA Score: 55
$490/night
Annapolis Nautical Cottage EASTPORT NAVY BOAT SHOW
2 beds
1.5 baths
8 guests
Average Price:
$559
12% Cheaper
than normal
AirDNA Score: 55
$650/night
Downtown Annapolis Home
3 beds
2.5 baths
6 guests
Average Price:
$613
6% More
than normal
AirDNA Score: 55
$900/night
Excellent Location, Super Clean, Super Spacious !
7 beds
4.5 baths
15 guests
Average Price:
$921
2% 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: 53
$169/night
Charming Detached Studio w/ easy walk to Downtown.
1 bed
1 bath
2 guests
Average Price:
$242
30% Cheaper
than normal
AirDNA Score: 53
$649/night
AirDNA Score: 52
$149/night
Tranquil apartment in the woods
1 bed
1 bath
4 guests
Average Price:
$165
10% Cheaper
than normal
AirDNA Score: 52
$235/night
The Apartment ...relax and enjoy Annapolis.
1 bed
1.5 baths
4 guests
Average Price:
$260
10% Cheaper
than normal
AirDNA Score: 51
$575/night
Luxury50ft Catamaran YachtAnnapolis
3 beds
3 baths
9 guests
Average Price:
$579
1% 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
$200/night
AirDNA Score: 51
$1000/night
Perfect home for Annapolis Boat Shows!
4 beds
3 baths
10 guests
Average Price:
$1090
8% Cheaper
than normal
AirDNA Score: 50
$675/night
Annapolis Waterfront Cottage
4 beds
2 baths
8 guests
Average Price:
$675
0% Cheaper
than normal
AirDNA Score: 50
$549/night
0.5 Miles From Navy Stadium/1.5 From Naval Academy
2 beds
1.5 baths
4 guests
Average Price:
$775
29% 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:
$976
10% Cheaper
than normal
AirDNA Score: 50
$265/night
Fabulous Waterfront Annapolis Apartment!
2 beds
1 bath
4 guests
Average Price:
$297
11% Cheaper
than normal
AirDNA Score: 50
$399/night
4 Bed 3 Bath Modern Annapolis Home
4 beds
2.5 baths
12 guests
Average Price:
$432
8% Cheaper
than normal
AirDNA Score: 47
$250/night
Charming Guest House-Annapolis
1 bed
1 bath
2 guests
Average Price:
$287
13% Cheaper
than normal
AirDNA Score: 45
$550/night
Charming Townhouse in Murray Hill
3 beds
3.5 baths
8 guests
Average Price:
$561
2% 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: 43
$175/night
1B Annapolis Apartment
1 bed
1 bath
4 guests
Average Price:
$200
12% Cheaper
than normal
AirDNA Score: 40
$613/night
Gorgeous Renovated Home in the Historic District
2 beds
2.5 baths
5 guests
Average Price:
$613
0% Cheaper
than normal
AirDNA Score: 37
$1484/night
Renovated historic home with courtyard, balcony, grill, great downtown location
4 beds
2.5 baths
8 guests
Average Price:
$1635
9% Cheaper
than normal
AirDNA Score: 36
$195/night
Chesapeake Bird Nest
1 bed
1 bath
4 guests
Average Price:
$212
8% 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: 31
$345/night
Families & Friends gather here to enjoy
5 beds
2.5 baths
10 guests
Average Price:
$375
8% Cheaper
than normal
AirDNA Score: 31
$179/night
Check yourself in! 3-Br House near Annapolis Mall
3 beds
2.5 baths
8 guests
Average Price:
$263
32% Cheaper
than normal
AirDNA Score: 29
$874/night
Waterfront Annapolis home for rent
4 beds
3 baths
10 guests
Average Price:
$994
12% Cheaper
than normal
AirDNA Score: 22
$2350/night
22 Fleet St. - History & Charm Near the Annapolis
3 beds
2.5 baths
6 guests
Average Price:
$1043
125% More
than normal
AirDNA Score: 21
$1250/night
Craftsman Home in Eastport
3 beds
2.5 baths
6 guests
Average Price:
$1550
19% 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
$300/night
A Waterfront Upscale Annapolis Condo
1 bed
1 bath
2 guests
Average Price:
$325
8% Cheaper
than normal