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
$220/night
AirDNA Score: 93
$134/night
Renovated Annapolis Row House a Minute''s Walk to USNA
2 beds
2.5 baths
6 guests
Average Price:
$331
60% Cheaper
than normal
AirDNA Score: 86
$165/night
Annapolis Guesthouse - Completely Separate Space
2 beds
1 bath
5 guests
Average Price:
$193
15% Cheaper
than normal
AirDNA Score: 86
$159/night
Charming Row House in Historic District
2 beds
1 bath
6 guests
Average Price:
$285
44% Cheaper
than normal
AirDNA Score: 86
$85/night
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bed
1 bath
4 guests
Average Price:
$136
37% Cheaper
than normal
AirDNA Score: 85
$495/night
Chesapeake Bay View Paradise 3BR/2BA Duplex
3 beds
2 baths
8 guests
Average Price:
$502
1% Cheaper
than normal
AirDNA Score: 85
$89/night
Annapolis Studio Apartment for longer stays - Pool
1 bed
1 bath
1 guest
Average Price:
$82
9% More
than normal
AirDNA Score: 83
$150/night
Walk to Water, State House, USNA
1 bed
1 bath
3 guests
Average Price:
$159
6% Cheaper
than normal
AirDNA Score: 81
$200/night
Private Art-Filled Guesthouse near Naval Academy
studio
1 bath
2 guests
Average Price:
$234
15% Cheaper
than normal
AirDNA Score: 81
$120/night
AirDNA Score: 79
$299/night
Eastport Bungalow - Walk to Downtown & USNA
3 beds
2.5 baths
6 guests
Average Price:
$308
3% 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: 79
$248/night
Beautiful and Tranquil Carriage House
2 beds
1.5 baths
8 guests
Average Price:
$362
31% Cheaper
than normal
AirDNA Score: 78
$99/night
Modern Apartment over the Heart of Main Street!
2 beds
1 bath
6 guests
Average Price:
$172
42% Cheaper
than normal
AirDNA Score: 77
$244/night
Spacious Getaway Family Home
4 beds
3.5 baths
8 guests
Average Price:
$384
36% Cheaper
than normal
AirDNA Score: 76
$950/night
Gorgeous home in historic Annapolis w/parking
4 beds
4.5 baths
12 guests
Average Price:
$1003
5% Cheaper
than normal
AirDNA Score: 73
$449/night
Hideaway in the Middle of Everything near AYC
3 beds
2 baths
10 guests
Average Price:
$508
12% Cheaper
than normal
AirDNA Score: 72
$240/night
AirDNA Score: 71
$475/night
Sophisticated & Spacious Historic Home w/ Parking!
3 beds
2.5 baths
7 guests
Average Price:
$623
24% Cheaper
than normal
AirDNA Score: 71
$145/night
Gybeset Eastport Inn
3 beds
1 bath
5 guests
Average Price:
$238
39% Cheaper
than normal
AirDNA Score: 71
$332/night
Hideaway in the Middle of Everything AYC 2+BR apt
2 beds
1 bath
6 guests
Average Price:
$364
9% Cheaper
than normal
AirDNA Score: 71
$650/night
*Walk to Annapolis Water Taxi, Relax on Decks
3 beds
3 baths
6 guests
Average Price:
$507
28% More
than normal
AirDNA Score: 71
$200/night
Large 1st flr Annapolis/Eastport 3 room Flat
1 bed
1 bath
2 guests
Average Price:
$303
34% Cheaper
than normal
AirDNA Score: 71
$495/night
You''ll Never Want to Leave
5 beds
2.5 baths
13 guests
Average Price:
$612
19% Cheaper
than normal
AirDNA Score: 71
$299/night
Charming Renovated Historic Home Downtown wparking
3 beds
2 baths
6 guests
Average Price:
$347
14% Cheaper
than normal
AirDNA Score: 71
$699/night
Relax on the peninsula in Eastport Annapolis!
2 beds
1.5 baths
6 guests
Average Price:
$873
20% Cheaper
than normal
AirDNA Score: 71
$325/night
2003 Craftsman; Heart of Eastport!
3 beds
2.5 baths
6 guests
Average Price:
$542
40% Cheaper
than normal
AirDNA Score: 71
$395/night
Annapolis - Crow''s Nest Cottage: Chesapeake Bay
5 beds
3 baths
16 guests
Average Price:
$582
32% Cheaper
than normal
AirDNA Score: 70
$155/night
Charming lower-level apartment in Annapolis
1 bed
1 bath
2 guests
Average Price:
$160
3% Cheaper
than normal
AirDNA Score: 70
$170/night
Eastport-Annapolis Private Bsmt. Apt 1 mile -DTA
1 bed
1 bath
4 guests
Average Price:
$170
0% Cheaper
than normal
AirDNA Score: 69
$390/night
Romantic Carriage House near USNA, free parking
2 beds
1 bath
5 guests
Average Price:
$378
3% More
than normal
AirDNA Score: 69
$370/night
Eastport Haven House
4 beds
4 baths
9 guests
Average Price:
$522
29% Cheaper
than normal
AirDNA Score: 67
$900/night
Newly renovated minutes to downtown
5 beds
3.5 baths
8 guests
Average Price:
$1015
11% Cheaper
than normal
AirDNA Score: 66
$750/night
Full home just blocks from downtown Annapolis
4 beds
2.5 baths
8 guests
Average Price:
$876
14% Cheaper
than normal
AirDNA Score: 65
$400/night
Bungalow Bliss- Cozy, Convenient, City Oasis. Prkg
3 beds
2 baths
6 guests
Average Price:
$337
19% More
than normal
AirDNA Score: 65
$148/night
Clean & comfy guest suite in Eastport
studio
1 bath
2 guests
Average Price:
$178
17% Cheaper
than normal
AirDNA Score: 65
$695/night
Location! Historic home steps from City Dock
4 beds
3 baths
8 guests
Average Price:
$700
1% Cheaper
than normal
AirDNA Score: 65
$139/night
"L''auberge du Cape Saint Claire"
2 beds
1 bath
4 guests
Average Price:
$188
26% Cheaper
than normal
AirDNA Score: 64
$153/night
Independent Access Garage Apartment, Near Downtown
1 bed
1 bath
2 guests
Average Price:
$172
11% Cheaper
than normal
AirDNA Score: 64
$500/night
Waterfront Vacation Home
3 beds
3.5 baths
9 guests
Average Price:
$548
9% Cheaper
than normal
AirDNA Score: 64
$159/night
AirDNA Score: 64
$295/night
Heart of Eastport 4 bedroom Modern Craftsman!
4 beds
3.5 baths
8 guests
Average Price:
$699
58% Cheaper
than normal
AirDNA Score: 64
$325/night
4 bdrm w garage Contemporary in Heart of Eastport!
4 beds
3.5 baths
8 guests
Average Price:
$593
45% Cheaper
than normal
AirDNA Score: 63
$225/night
The Cottage on Spa Creek
2 beds
1.5 baths
6 guests
Average Price:
$293
23% Cheaper
than normal
AirDNA Score: 61
$375/night
Lovely Waterfront Apartment Close to Downtown Annapolis
1 bed
1 bath
4 guests
Average Price:
$417
10% Cheaper
than normal
AirDNA Score: 60
$550/night
Beautiful Large Glass Contemporary Wooded Privacy.
7 beds
3.5 baths
12 guests
Average Price:
$625
12% Cheaper
than normal
AirDNA Score: 59
$1150/night
Luxury Waterfront Home Annapolis with beach & dock
3 beds
3.5 baths
6 guests
Average Price:
$1393
17% Cheaper
than normal
AirDNA Score: 59
$1092/night
Upscale & updated multi-level home with private courtyard, grill & gas fireplace
5 beds
3.5 baths
10 guests
Average Price:
$1248
12% Cheaper
than normal
AirDNA Score: 59
$950/night
Stunning Historic District Home, Steps to Academy
4 beds
5 baths
10 guests
Average Price:
$1080
12% Cheaper
than normal
AirDNA Score: 59
$339/night
3-story Eastport (Annapolis) Spa Creek townhome
3 beds
3.5 baths
6 guests
Average Price:
$362
6% Cheaper
than normal
AirDNA Score: 58
$1500/night
Annapolis Waterfront - Commissioning Week
4 beds
2 baths
8 guests
Average Price:
$1500
0% 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:
$200
0% Cheaper
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
$315/night
Murray Hill Home-Walk to Downtown, Close to water
4 beds
2.5 baths
11 guests
Average Price:
$361
13% Cheaper
than normal
AirDNA Score: 57
$190/night
"Jode''s Retreat" Your Home Away From Home
3 beds
1 bath
6 guests
Average Price:
$235
19% Cheaper
than normal
AirDNA Score: 57
$303/night
Annapolis - near everything - quiet neighborhood
4 beds
3 baths
10 guests
Average Price:
$298
2% More
than normal
AirDNA Score: 57
$249/night
Red Brick Inn, Apt. #1 - Downtown Annapolis
3 beds
1 bath
8 guests
Average Price:
$332
25% Cheaper
than normal
AirDNA Score: 56
$175/night
GREAT LOCATION ON SPA CREEK
1 bed
1 bath
4 guests
Average Price:
$180
3% Cheaper
than normal
AirDNA Score: 55
$800/night
Eastport Peninsula Charm
4 beds
2.5 baths
8 guests
Average Price:
$672
19% More
than normal
AirDNA Score: 55
$700/night
Excellent Location, Super Clean, Super Spacious !
7 beds
4.5 baths
16 guests
Average Price:
$877
20% Cheaper
than normal
AirDNA Score: 54
$295/night
Contemporary in Heart of Eastport w 2 car garage!
3 beds
2.5 baths
6 guests
Average Price:
$517
43% Cheaper
than normal
AirDNA Score: 53
$175/night
Charming Studio offering an easy walk to Downtown.
1 bed
1 bath
2 guests
Average Price:
$239
27% Cheaper
than normal
AirDNA Score: 53
$400/night
Modern home w/garage; short walk to Navy Stadium!
3 beds
2.5 baths
7 guests
Average Price:
$526
24% Cheaper
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: 52
$425/night
Downtown Annapolis Apartment
2 beds
2 baths
6 guests
Average Price:
$464
8% Cheaper
than normal
AirDNA Score: 51
$750/night
Entire home just blocks from downtown Annapolis
4 beds
2.5 baths
8 guests
Average Price:
$753
0% Cheaper
than normal
AirDNA Score: 51
$750/night
Spacious Murray Hill - 6 BR walk downtown & Navy
6 beds
4.5 baths
12 guests
Average Price:
$848
12% 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:
$950
8% Cheaper
than normal
AirDNA Score: 50
$700/night
0.5 Miles From Navy Stadium/1.5 From Naval Academy
2 beds
1.5 baths
4 guests
Average Price:
$663
6% More
than normal
AirDNA Score: 50
$625/night
Annapolis Waterfront Cottage
4 beds
2 baths
8 guests
Average Price:
$697
10% Cheaper
than normal
AirDNA Score: 50
$605/night
Waterfront Beach House
3 beds
3 baths
8 guests
Average Price:
$749
19% Cheaper
than normal
AirDNA Score: 50
$275/night
Fabulous Waterfront Annapolis Apartment!
2 beds
1 bath
4 guests
Average Price:
$296
7% Cheaper
than normal
AirDNA Score: 50
$650/night
Townhouse at Naval Academy & Dock
3 beds
1.5 baths
9 guests
Average Price:
$770
16% Cheaper
than normal
AirDNA Score: 48
$295/night
The Very Best location- 50 Steps from Main Street
3 beds
2 baths
7 guests
Average Price:
$415
29% Cheaper
than normal
AirDNA Score: 48
$275/night
Kindred Moss Cottage
3 beds
2 baths
8 guests
Average Price:
$319
14% Cheaper
than normal
AirDNA Score: 48
$1000/night
Gorgeous Historic Downtown Annapolis House
5 beds
3.5 baths
12 guests
Average Price:
$1251
20% Cheaper
than normal
AirDNA Score: 47
$363/night
Spa Creek 2BD Condo, Amazing Views!
2 beds
1 bath
6 guests
Average Price:
$401
9% Cheaper
than normal
AirDNA Score: 47
$250/night
Charming Guest House-Annapolis
1 bed
1 bath
2 guests
Average Price:
$264
5% Cheaper
than normal
AirDNA Score: 45
$350/night
Beautiful Downtown Annapolis Home!
3 beds
2 baths
6 guests
Average Price:
$447
22% Cheaper
than normal
AirDNA Score: 45
$600/night
Charming Townhouse in Murray Hill
3 beds
3.5 baths
8 guests
Average Price:
$619
3% Cheaper
than normal
AirDNA Score: 44
$650/night
Garden House next to USNA & Harbor
3 beds
3.5 baths
6 guests
Average Price:
$766
15% Cheaper
than normal
AirDNA Score: 43
$140/night
1B Annapolis Apartment
1 bed
1 bath
4 guests
Average Price:
$176
20% Cheaper
than normal
AirDNA Score: 43
$140/night
2A One Bedroom Annapolis Apartment
1 bed
1 bath
4 guests
Average Price:
$178
21% Cheaper
than normal
AirDNA Score: 41
$300/night
Annapolis City Dock, USNA visits, short term
3 beds
1.5 baths
6 guests
Average Price:
$334
10% Cheaper
than normal
AirDNA Score: 38
$196/night
Townhouse next to Navy Stadium!
2 beds
1 bath
4 guests
Average Price:
$193
2% More
than normal
AirDNA Score: 38
$130/night
Convenient One Bedroom Apartment
1 bed
1 bath
2 guests
Average Price:
$141
8% Cheaper
than normal
AirDNA Score: 38
$195/night
AirDNA Score: 37
$1475/night
Renovated historic home with courtyard, balcony, grill, great downtown location
4 beds
2.5 baths
8 guests
Average Price:
$1518
3% Cheaper
than normal
AirDNA Score: 36
$190/night
Chesapeake Bird Nest
1 bed
1 bath
4 guests
Average Price:
$212
10% 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: 36
$140/night
2B One Bedroom Annapolis Apartment
1 bed
1 bath
4 guests
Average Price:
$176
20% Cheaper
than normal
AirDNA Score: 36
$39/night
Outdoor Campsite by Navy Stadium
studio
1 bath
3 guests
Average Price:
$44
11% Cheaper
than normal
AirDNA Score: 36
$140/night
1A Annapolis Apartment
1 bed
1 bath
4 guests
Average Price:
$179
22% Cheaper
than normal
AirDNA Score: 33
$495/night
2 blocks from Stadium and walking distance to Town
4 beds
3 baths
10 guests
Average Price:
$538
8% Cheaper
than normal
AirDNA Score: 33
$650/night
Private & close to downtown, water
4 beds
3 baths
10 guests
Average Price:
$681
5% 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:
$307
42% Cheaper
than normal
AirDNA Score: 29
$849/night
Waterfront Annapolis home for rent
4 beds
3 baths
10 guests
Average Price:
$889
4% Cheaper
than normal
AirDNA Score: 14
$329/night
Restful and Charming Home in Eastport
3 beds
1.5 baths
6 guests
Average Price:
$321
2% More
than normal
AirDNA Score: 12
$300/night
A Waterfront Upscale Annapolis Condo
1 bed
1 bath
2 guests
Average Price:
$289
4% More
than normal