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!
Search for a city
AirDNA Score: 93
$186/night
Wright’s Cottage, Pets Welcome!
1 bed
1 bath
2 guests
Average Price:
$158
18% More
than normal
AirDNA Score: 93
$216/night
Old Orchard Cottage
2 beds
1 bath
4 guests
Average Price:
$228
5% 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: 86
$142/night
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bed
1 bath
4 guests
Average Price:
$146
3% 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: 85
$459/night
Chesapeake Bay View 3BR/2BA Duplex*Spa Tub*
3 beds
2 baths
8 guests
Average Price:
$547
16% Cheaper
than normal
AirDNA Score: 83
$205/night
Walk to Water, State House, USNA
1 bed
1 bath
3 guests
Average Price:
$168
22% More
than normal
AirDNA Score: 83
$399/night
Crab Cakes and Football Historic District
2 beds
1.5 baths
4 guests
Average Price:
$434
8% Cheaper
than normal
AirDNA Score: 82
$605/night
Beautiful Home in Quiet Private Setting near Annapolis
4 beds
3 baths
8 guests
Average Price:
$533
14% More
than normal
AirDNA Score: 79
$280/night
Charming house; walk to everywhere in Annapolis
2 beds
1.5 baths
4 guests
Average Price:
$290
3% Cheaper
than normal
AirDNA Score: 79
$145/night
Chesapeake Birdhouse Studio
1 bed
1 bath
2 guests
Average Price:
$179
19% Cheaper
than normal
AirDNA Score: 73
$250/night
Perfect Eastport location NO added cleaning fees
2 beds
1 bath
4 guests
Average Price:
$299
16% Cheaper
than normal
AirDNA Score: 71
$495/night
You'll Never Want to Leave
5 beds
2.5 baths
13 guests
Average Price:
$562
12% Cheaper
than normal
AirDNA Score: 71
$272/night
Entire floor of single-family Annapolis home.
3 beds
2 baths
8 guests
Average Price:
$313
13% Cheaper
than normal
AirDNA Score: 71
$288/night
Eastport Bungalow
3 beds
1 bath
6 guests
Average Price:
$334
14% Cheaper
than normal
AirDNA Score: 71
$682/night
Relax on the peninsula in Eastport Annapolis!
2 beds
1.5 baths
6 guests
Average Price:
$727
6% Cheaper
than normal
AirDNA Score: 71
$650/night
2003 Craftsman; Heart of Eastport!
3 beds
2.5 baths
6 guests
Average Price:
$526
24% More
than normal
AirDNA Score: 71
$294/night
West Annapolis Free Parking! Close to Navy Stadium
3 beds
1.5 baths
6 guests
Average Price:
$413
29% Cheaper
than normal
AirDNA Score: 67
$900/night
Newly renovated minutes to downtown
5 beds
3.5 baths
8 guests
Average Price:
$917
2% 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
$774/night
Lovely & Spacious Severn River Waterfront
4 beds
4 baths
8 guests
Average Price:
$937
17% Cheaper
than normal
AirDNA Score: 65
$542/night
Location! Historic home steps from City Dock
4 beds
3 baths
8 guests
Average Price:
$746
27% Cheaper
than normal
AirDNA Score: 65
$510/night
1920s House in Presidents Hill
3 beds
1.5 baths
5 guests
Average Price:
$541
6% Cheaper
than normal
AirDNA Score: 65
$159/night
"Cape Saint Claire Hostel"
2 beds
2 baths
4 guests
Average Price:
$181
12% Cheaper
than normal
AirDNA Score: 64
$180/night
Independent Access Garage Apartment, Near Downtown
1 bed
1 bath
2 guests
Average Price:
$197
9% Cheaper
than normal
AirDNA Score: 64
$175/night
Cozy Apt. +beach playground-15mins to Annapolis DT
2 beds
1 bath
4 guests
Average Price:
$305
43% Cheaper
than normal
AirDNA Score: 64
$119/night
AirDNA Score: 64
$435/night
Heart of Eastport 4 bedroom Modern Craftsman!
4 beds
3.5 baths
10 guests
Average Price:
$616
29% 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: 59
$1300/night
Luxury Waterfront Annapolis/ Private Beach & Dock
3 beds
3.5 baths
6 guests
Average Price:
$1247
4% More
than normal
AirDNA Score: 59
$500/night
Beautiful Home in the Heart of Downtown, w/Parking
4 beds
3 baths
9 guests
Average Price:
$526
5% Cheaper
than normal
AirDNA Score: 58
$300/night
2. 20ac wtrfrnt estate - Studio apt
studio
1.5 baths
2 guests
Average Price:
$397
24% Cheaper
than normal
AirDNA Score: 57
$1416/night
Beautiful 5 bdrm - minutes from downtown & USNA!
5 beds
4.5 baths
12 guests
Average Price:
$1516
7% 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
$249/night
Red Brick Inn, Apt. #1 - Downtown Annapolis
3 beds
1 bath
8 guests
Average Price:
$430
42% Cheaper
than normal
AirDNA Score: 56
$183/night
GREAT LOCATION ON SPA CREEK
1 bed
1 bath
4 guests
Average Price:
$207
12% Cheaper
than normal
AirDNA Score: 55
$310/night
Annapolis Maryland Home in Fantastic Location!
4 beds
3 baths
8 guests
Average Price:
$427
27% Cheaper
than normal
AirDNA Score: 55
$627/night
Eastport Peninsula Charm
4 beds
2.5 baths
8 guests
Average Price:
$655
4% Cheaper
than normal
AirDNA Score: 55
$632/night
Excellent Location, Super Clean, Super Spacious !
7 beds
4.5 baths
15 guests
Average Price:
$933
32% Cheaper
than normal
AirDNA Score: 55
$225/night
Country House on the Bay
5 beds
3 baths
10 guests
Average Price:
$225
0% 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
$475/night
Nautical Touches to This Beautiful Eastport Home
2 beds
2.5 baths
6 guests
Average Price:
$503
6% Cheaper
than normal
AirDNA Score: 53
$194/night
Charming Detached Studio w/ easy walk to Downtown.
1 bed
1 bath
2 guests
Average Price:
$260
25% Cheaper
than normal
AirDNA Score: 52
$158/night
Tranquil apartment in the woods
1 bed
1 bath
4 guests
Average Price:
$157
1% More
than normal
AirDNA Score: 52
$425/night
Downtown Annapolis Apartment
2 beds
2 baths
5 guests
Average Price:
$480
11% 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
$700/night
Classic Victorian home in the heart of Eastport
3 beds
2.5 baths
6 guests
Average Price:
$601
16% More
than normal
AirDNA Score: 51
$750/night
Charming Annapolis Victorian
6 beds
4.5 baths
12 guests
Average Price:
$791
5% Cheaper
than normal
AirDNA Score: 51
$222/night
AirDNA Score: 51
$349/night
AirDNA Score: 51
$1000/night
Perfect home for Annapolis Boat Shows!
4 beds
3 baths
10 guests
Average Price:
$1101
9% 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:
$956
8% Cheaper
than normal
AirDNA Score: 50
$265/night
Dazzling day/night water views,1st class amemities
2 beds
1 bath
4 guests
Average Price:
$297
11% Cheaper
than normal
AirDNA Score: 50
$750/night
Annapolis Waterfront Cottage
4 beds
2 baths
8 guests
Average Price:
$708
6% More
than normal
AirDNA Score: 48
$1000/night
Eastport 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:
$421
30% Cheaper
than normal
AirDNA Score: 48
$1128/night
Gorgeous Historic Downtown Annapolis House
5 beds
3.5 baths
12 guests
Average Price:
$1138
1% Cheaper
than normal
AirDNA Score: 47
$587/night
Waterfront Oasis in Eastport-Easy Walk to Downtown
5 beds
3.5 baths
10 guests
Average Price:
$742
21% 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
$551/night
Charming Townhouse in Murray Hill
3 beds
3.5 baths
8 guests
Average Price:
$567
3% Cheaper
than normal
AirDNA Score: 45
$270/night
Historic Home Steps from City Center & Waterfront
2 beds
2 baths
6 guests
Average Price:
$344
22% 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
$1600/night
Garden House next to USNA & Harbor
3 beds
3.5 baths
6 guests
Average Price:
$1430
12% More
than normal
AirDNA Score: 38
$199/night
Red Brick Inn, Apt. #B - Downtown Annapolis
2 beds
1 bath
6 guests
Average Price:
$281
29% 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
$165/night
2B One Bedroom Annapolis Apartment
2 beds
1 bath
4 guests
Average Price:
$181
9% Cheaper
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
$164/night
Chesapeake Bird Nest
1 bed
1 bath
4 guests
Average Price:
$199
18% Cheaper
than normal
AirDNA Score: 36
$163/night
1A Annapolis Apartment
1 bed
1 bath
4 guests
Average Price:
$183
11% Cheaper
than normal
AirDNA Score: 33
$435/night
2 blocks from Stadium and walking distance to Town
4 beds
3 baths
10 guests
Average Price:
$613
29% 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:
$286
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
$353/night
Restful and Charming Home in Eastport
3 beds
1.5 baths
6 guests
Average Price:
$319
11% More
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
$275/night
Upscale Waterfront Condo Annapolis
1 bed
1 bath
2 guests
Average Price:
$292
6% Cheaper
than normal