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
$581/night
Rock-n-Row Annapolis
3 beds
2.5 baths
6 guests
Average Price:
$459
27% More
than normal
AirDNA Score: 85
$1073/night
Chesapeake Bay View Paradise 3BR/2BA Duplex
3 beds
2 baths
8 guests
Average Price:
$515
108% More
than normal
AirDNA Score: 79
$40/night
Campsite by the USNA Stadium
1 bed
1 bath
3 guests
Average Price:
$55
27% Cheaper
than normal
AirDNA Score: 79
$200/night
AirDNA Score: 73
$577/night
Hideaway in the Middle of Everything near AYC
3 beds
2 baths
10 guests
Average Price:
$499
16% More
than normal
AirDNA Score: 73
$435/night
Eastport Private Guest House, Perfect location!
2 beds
1 bath
4 guests
Average Price:
$354
23% More
than normal
AirDNA Score: 71
$165/night
Hunter 36'' Sailboat
1 bed
1 bath
4 guests
Average Price:
$191
14% Cheaper
than normal
AirDNA Score: 71
$600/night
Entire floor of single-family Annapolis home.
3 beds
2 baths
8 guests
Average Price:
$271
121% More
than normal
AirDNA Score: 71
$86/night
Private Annapolis Inlaw Apartment
1 bed
1 bath
4 guests
Average Price:
$118
27% Cheaper
than normal
AirDNA Score: 71
$1700/night
Sophisticated & Spacious Historic Home w/ Parking!
3 beds
2.5 baths
7 guests
Average Price:
$542
214% More
than normal
AirDNA Score: 71
$699/night
You''ll Never Want to Leave
5 beds
2.5 baths
13 guests
Average Price:
$574
22% More
than normal
AirDNA Score: 71
$369/night
Hideaway in the Middle of Everything AYC 2+BR apt
2 beds
1 bath
6 guests
Average Price:
$325
14% More
than normal
AirDNA Score: 71
$290/night
Large 1st flr Annapolis/Eastport 3 room Flat
1 bed
1 bath
2 guests
Average Price:
$306
5% Cheaper
than normal
AirDNA Score: 71
$699/night
Relax on the peninsula in Eastport Annapolis!
2 beds
1.5 baths
6 guests
Average Price:
$754
7% Cheaper
than normal
AirDNA Score: 67
$250/night
AirDNA Score: 67
$1400/night
Newly renovated minutes to downtown
5 beds
3.5 baths
8 guests
Average Price:
$938
49% More
than normal
AirDNA Score: 66
$1000/night
Full home just blocks from downtown Annapolis
4 beds
2.5 baths
8 guests
Average Price:
$865
16% More
than normal
AirDNA Score: 66
$400/night
Moose’s Happy Place
3 beds
3.5 baths
8 guests
Average Price:
$518
23% Cheaper
than normal
AirDNA Score: 65
$350/night
Cozy, Comfy & Convenient house in Eastport awaits!
2 beds
2.5 baths
4 guests
Average Price:
$385
9% Cheaper
than normal
AirDNA Score: 64
$425/night
4 bdrm w garage Contemporary in Heart of Eastport!
4 beds
3.5 baths
8 guests
Average Price:
$604
30% Cheaper
than normal
AirDNA Score: 63
$395/night
The Cottage on Spa Creek
2 beds
1.5 baths
6 guests
Average Price:
$280
41% More
than normal
AirDNA Score: 59
$1200/night
Luxury Waterfront Home Annapolis with beach & dock
3 beds
3.5 baths
6 guests
Average Price:
$1359
12% Cheaper
than normal
AirDNA Score: 58
$1500/night
Annapolis Waterfront - Commissioning Week
4 beds
2 baths
8 guests
Average Price:
$1133
32% More
than normal
AirDNA Score: 58
$100/night
Private, King Bed, Quiet near Rt. 50
2 beds
1 bath
4 guests
Average Price:
$100
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
$300/night
As mentioned in the Washington Post
2 beds
1.5 baths
6 guests
Average Price:
$213
41% More
than normal
AirDNA Score: 57
$600/night
Annapolis - near everything - quiet neighborhood
4 beds
3 baths
10 guests
Average Price:
$298
101% More
than normal
AirDNA Score: 55
$1600/night
Commissioning Week 2022 Available!
4 beds
2.5 baths
8 guests
Average Price:
$670
139% More
than normal
AirDNA Score: 51
$1500/night
5 BDR across from USNA Stadium (Comm Week Only)
5 beds
5.5 baths
12 guests
Average Price:
$1500
0% Cheaper
than normal
AirDNA Score: 50
$875/night
Grad Week house with room for a crowd.
4 beds
2.5 baths
12 guests
Average Price:
$906
3% Cheaper
than normal
AirDNA Score: 50
$700/night
0.5 Miles From Navy Stadium/1.5 From Naval Academy
2 beds
1.5 baths
6 guests
Average Price:
$676
4% More
than normal
AirDNA Score: 50
$1200/night
Commissioning Week Gem
5 beds
3.5 baths
12 guests
Average Price:
$962
25% More
than normal
AirDNA Score: 50
$650/night
Annapolis Waterfront Cottage
4 beds
2 baths
8 guests
Average Price:
$680
4% Cheaper
than normal
AirDNA Score: 49
$1200/night
SHORT WALK TO STADIUM! Annapolis Home with Pool!
5 beds
4.5 baths
16 guests
Average Price:
$1257
5% Cheaper
than normal
AirDNA Score: 48
$1500/night
Gorgeous Historic Downtown Annapolis House
5 beds
3.5 baths
12 guests
Average Price:
$1191
26% More
than normal
AirDNA Score: 47
$500/night
Spa Creek 2BD Condo, Amazing Views!
2 beds
1 bath
6 guests
Average Price:
$385
30% More
than normal
AirDNA Score: 47
$288/night
Charming Guest House-Annapolis
1 bed
1 bath
2 guests
Average Price:
$254
13% More
than normal
AirDNA Score: 45
$600/night
Charming Townhouse in Murray Hill
3 beds
3.5 baths
8 guests
Average Price:
$620
3% Cheaper
than normal
AirDNA Score: 38
$599/night
Red Brick Inn, Apt. #B - Downtown Annapolis
2 beds
1 bath
6 guests
Average Price:
$271
121% More
than normal
AirDNA Score: 37
$2214/night
0210 Submariners Gate. Downtown with PARKING! Rich in Naval History!
4 beds
2.5 baths
8 guests
Average Price:
$1483
49% More
than normal
AirDNA Score: 36
$175/night
2B One Bedroom Annapolis Apartment
1 bed
1 bath
4 guests
Average Price:
$166
5% More
than normal
AirDNA Score: 36
$190/night
Chesapeake Bird Nest
1 bed
1 bath
4 guests
Average Price:
$202
6% Cheaper
than normal
AirDNA Score: 29
$899/night
Waterfront Annapolis home for rent
4 beds
3 baths
10 guests
Average Price:
$910
1% Cheaper
than normal
AirDNA Score: 21
$500/night
Best Retreat for USNA & Boat Show Events
4 beds
2.5 baths
8 guests
Average Price:
$355
41% More
than normal
AirDNA Score: 13
$275/night
Upscale Waterfront Condo Annapolis
1 bed
1 bath
2 guests
Average Price:
$245
12% More
than normal
AirDNA Score: 12
$300/night
A Waterfront Upscale Annapolis Condo
1 bed
1 bath
2 guests
Average Price:
$244
23% More
than normal