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

Cozy Naptown Perch

2 beds
1 bath
4 guests
Average Price:  
$147
36% More
than normal
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

Annapolis

1 bed
1 bath
4 guests
Average Price:  
$309
19% Cheaper
than normal
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