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

The Cape Cottage

studio
1 bath
2 guests
Average Price:  
$126
2% Cheaper
than normal
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

Old. Don’t usw

1 bed
1 bath
2 guests
Average Price:  
$550
45% Cheaper
than normal
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

Charming Eastport

1 bed
1 bath
2 guests
Average Price:  
$172
31% Cheaper
than normal
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

Annapolis Life

4 beds
2 baths
10 guests
Average Price:  
$596
9% More
than normal
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

Eastport Cottage

1 bed
1 bath
2 guests
Average Price:  
$242
17% Cheaper
than normal
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