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
$99/night

Renovated Annapolis Row House a Minute''s Walk to USNA

2 beds
2.5 baths
6 guests
Average Price:  
$318
69% Cheaper
than normal
AirDNA Score: 93
$225/night

Old Orchard Cottage

2 beds
1 bath
4 guests
Average Price:  
$220
2% More
than normal
AirDNA Score: 91
$159/night

Private 2B Apt--less than 1 mi to Downtown

2 beds
1 bath
6 guests
Average Price:  
$184
14% Cheaper
than normal
AirDNA Score: 89
$180/night

Downtown Gem in Historic Annapolis

1 bed
1 bath
3 guests
Average Price:  
$201
10% Cheaper
than normal
AirDNA Score: 86
$99/night

Charming Row House in Historic District

2 beds
1 bath
6 guests
Average Price:  
$278
64% Cheaper
than normal
AirDNA Score: 86
$175/night

Adorable Annapolis Apt. Downtown and Navy Stadium.

1 bed
1 bath
4 guests
Average Price:  
$184
5% Cheaper
than normal
AirDNA Score: 86
$120/night

Wall to Wall Cool- Filled with Original Art and Sculpture

1 bed
1 bath
4 guests
Average Price:  
$141
15% Cheaper
than normal
AirDNA Score: 85
$210/night

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

3 beds
2 baths
8 guests
Average Price:  
$499
58% Cheaper
than normal
AirDNA Score: 85
$75/night

Annapolis Studio Apartment for longer stays - Pool

1 bed
1 bath
1 guest
Average Price:  
$82
9% Cheaper
than normal
AirDNA Score: 83
$399/night

Crab Cakes and Football Historic District

2 beds
1 bath
4 guests
Average Price:  
$422
5% Cheaper
than normal
AirDNA Score: 82
$504/night

Beautiful Home in Quiet Private Setting near Annapolis

4 beds
3 baths
8 guests
Average Price:  
$570
12% Cheaper
than normal
AirDNA Score: 81
$200/night

Private Art-Filled Guesthouse near Naval Academy

studio
1 bath
2 guests
Average Price:  
$244
18% Cheaper
than normal
AirDNA Score: 81
$120/night

The Cape Cottage

studio
1 bath
2 guests
Average Price:  
$126
5% Cheaper
than normal
AirDNA Score: 80
$935/night

Modern Waterfront: Quiet but close to Everything.

5 beds
4 baths
12 guests
Average Price:  
$1160
19% 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
$145/night

Cozy Naptown Perch

2 beds
1 bath
4 guests
Average Price:  
$152
5% Cheaper
than normal
AirDNA Score: 79
$165/night

Chesapeake Birdhouse Studio

1 bed
1 bath
2 guests
Average Price:  
$185
11% Cheaper
than normal
AirDNA Score: 79
$199/night

Charming Cottage - easy walk downtown with parking

2 beds
2 baths
6 guests
Average Price:  
$305
35% Cheaper
than normal
AirDNA Score: 79
$199/night

Eastport Bungalow - Walk to Downtown & USNA

3 beds
2.5 baths
6 guests
Average Price:  
$309
36% Cheaper
than normal
AirDNA Score: 79
$399/night

Charming Annapolis Water View Home

4 beds
4 baths
11 guests
Average Price:  
$558
28% Cheaper
than normal
AirDNA Score: 79
$125/night

Brand New Reno in Historic Dist w 2 Parking spots

2 beds
1 bath
4 guests
Average Price:  
$209
40% Cheaper
than normal
AirDNA Score: 78
$89/night

Modern Apartment over the Heart of Main Street!

2 beds
1 bath
6 guests
Average Price:  
$166
46% Cheaper
than normal
AirDNA Score: 77
$229/night

Spacious Getaway Family Home

4 beds
3.5 baths
8 guests
Average Price:  
$369
38% Cheaper
than normal
AirDNA Score: 73
$449/night

Hideaway in the Middle of Everything near AYC

3 beds
2 baths
10 guests
Average Price:  
$519
13% Cheaper
than normal
AirDNA Score: 73
$275/night

Eastport Private Guest House, Perfect location!

2 beds
1 bath
4 guests
Average Price:  
$354
22% Cheaper
than normal
AirDNA Score: 73
$180/night

Soak up the Soothing Vibe at a Grayscale Annapolis Loft

studio
1 bath
2 guests
Average Price:  
$188
4% Cheaper
than normal
AirDNA Score: 73
$275/night

Perfect Eastport location

2 beds
1 bath
4 guests
Average Price:  
$266
3% More
than normal
AirDNA Score: 72
$240/night

New Hotel Chic

2 beds
1 bath
4 guests
Average Price:  
$240
0% Cheaper
than normal
AirDNA Score: 71
$109/night

Private Annapolis Inlaw Apartment

1 bed
1 bath
4 guests
Average Price:  
$123
11% Cheaper
than normal
AirDNA Score: 71
$250/night

Historic Downtown Property

3 beds
2.5 baths
6 guests
Average Price:  
$289
13% Cheaper
than normal
AirDNA Score: 71
$495/night

You''ll Never Want to Leave

5 beds
2.5 baths
13 guests
Average Price:  
$597
17% 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
$125/night

Gybeset Eastport Inn

3 beds
1 bath
5 guests
Average Price:  
$238
47% Cheaper
than normal
AirDNA Score: 71
$175/night

Hunter 36'' Sailboat

1 bed
1 bath
4 guests
Average Price:  
$192
9% Cheaper
than normal
AirDNA Score: 71
$200/night

Large 1st flr Annapolis/Eastport 3 room Flat

1 bed
1 bath
2 guests
Average Price:  
$259
23% Cheaper
than normal
AirDNA Score: 71
$349/night

Hideaway in the Middle of Everything AYC 2+BR apt

2 beds
1 bath
6 guests
Average Price:  
$391
11% Cheaper
than normal
AirDNA Score: 71
$299/night

Across from stadium - walk to downtown Annapolis!

4 beds
3 baths
10 guests
Average Price:  
$555
46% Cheaper
than normal
AirDNA Score: 71
$689/night

Relax on the peninsula in Eastport Annapolis!

2 beds
1.5 baths
6 guests
Average Price:  
$831
17% Cheaper
than normal
AirDNA Score: 71
$225/night

2003 Craftsman; Heart of Eastport!

3 beds
2.5 baths
6 guests
Average Price:  
$548
59% Cheaper
than normal
AirDNA Score: 71
$350/night

Annapolis Prime Stadium Location

3 beds
1.5 baths
6 guests
Average Price:  
$388
10% Cheaper
than normal
AirDNA Score: 70
$475/night

Gracie''s Gallery & Garden-1 mile to DWTN Annapolis

4 beds
2 baths
9 guests
Average Price:  
$572
17% Cheaper
than normal
AirDNA Score: 70
$125/night

Eastport-Annapolis Private Bsmt. Apt 1 mile -DTA

1 bed
1 bath
4 guests
Average Price:  
$178
30% Cheaper
than normal
AirDNA Score: 69
$275/night

Eastport Haven House

4 beds
4 baths
9 guests
Average Price:  
$527
48% Cheaper
than normal
AirDNA Score: 67
$900/night

Newly renovated minutes to downtown

5 beds
3.5 baths
8 guests
Average Price:  
$1075
16% Cheaper
than normal
AirDNA Score: 66
$400/night

Moose’s Happy Place

3 beds
3.5 baths
8 guests
Average Price:  
$578
31% Cheaper
than normal
AirDNA Score: 66
$750/night

Full home just blocks from downtown Annapolis

4 beds
2.5 baths
8 guests
Average Price:  
$945
21% Cheaper
than normal
AirDNA Score: 65
$425/night

Bungalow Bliss- cozy, convenient, city oasis. prkg

3 beds
2 baths
6 guests
Average Price:  
$355
20% More
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
$145/night

Clean & comfy guest suite in Eastport

studio
1 bath
2 guests
Average Price:  
$167
13% Cheaper
than normal
AirDNA Score: 65
$195/night

Lovely family home just minutes from Annapolis

4 beds
2.5 baths
8 guests
Average Price:  
$302
35% Cheaper
than normal
AirDNA Score: 65
$129/night

"L''auberge du Cape Saint Claire"

2 beds
1 bath
4 guests
Average Price:  
$188
31% Cheaper
than normal
AirDNA Score: 65
$510/night

1920s House in Presidents Hill

3 beds
1.5 baths
5 guests
Average Price:  
$544
6% Cheaper
than normal
AirDNA Score: 64
$119/night

Charming Eastport

1 bed
1 bath
2 guests
Average Price:  
$184
35% Cheaper
than normal
AirDNA Score: 64
$175/night

Independent Access Garage Apartment, Near Downtown

1 bed
1 bath
2 guests
Average Price:  
$176
1% Cheaper
than normal
AirDNA Score: 64
$275/night

Heart of Eastport 4 bedroom Modern Craftsman!

4 beds
3.5 baths
8 guests
Average Price:  
$673
59% Cheaper
than normal
AirDNA Score: 64
$175/night

4 bdrm w garage Contemporary in Heart of Eastport!

4 beds
3.5 baths
8 guests
Average Price:  
$599
71% 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
$550/night

Beautiful Large Glass Contemporary Wooded Privacy.

7 beds
3.5 baths
12 guests
Average Price:  
$636
14% Cheaper
than normal
AirDNA Score: 59
$1000/night

Luxury Waterfront Home Annapolis with beach & dock

3 beds
3.5 baths
6 guests
Average Price:  
$1271
21% Cheaper
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: 59
$935/night

Stunning Historic District Home, Steps to Academy

4 beds
5 baths
10 guests
Average Price:  
$1071
13% 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: 58
$749/night

Annapolis Downtown 4BR - 0045 The Bassford House - Gorgeous!

4 beds
3.5 baths
8 guests
Average Price:  
$1097
32% Cheaper
than normal
AirDNA Score: 57
$150/night

One bedroom apartment in Annapolis

1 bed
1 bath
4 guests
Average Price:  
$200
25% Cheaper
than normal
AirDNA Score: 57
$1500/night

Annapolis Elegance! Minutes from downtown & USNA!

5 beds
4.5 baths
12 guests
Average Price:  
$1557
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:  
$246
23% Cheaper
than normal
AirDNA Score: 57
$100/night

As mentioned in the Washington Post

2 beds
1.5 baths
6 guests
Average Price:  
$253
60% 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:  
$369
15% 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:  
$362
31% Cheaper
than normal
AirDNA Score: 56
$175/night

GREAT LOCATION ON SPA CREEK

1 bed
1 bath
4 guests
Average Price:  
$188
7% Cheaper
than normal
AirDNA Score: 55
$490/night

Annapolis Nautical Cottage EASTPORT NAVY BOAT SHOW

2 beds
1.5 baths
8 guests
Average Price:  
$568
14% Cheaper
than normal
AirDNA Score: 55
$600/night

Excellent Location, Super Clean, Super Spacious !

7 beds
4.5 baths
16 guests
Average Price:  
$887
32% Cheaper
than normal
AirDNA Score: 55
$175/night

Country House on the Bay

5 beds
3 baths
10 guests
Average Price:  
$201
13% Cheaper
than normal
AirDNA Score: 55
$600/night

Waterfront home in Annapolis MD with private pier

3 beds
3 baths
10 guests
Average Price:  
$655
8% Cheaper
than normal
AirDNA Score: 54
$195/night

Contemporary in Heart of Eastport w 2 car garage!

3 beds
2.5 baths
6 guests
Average Price:  
$499
61% Cheaper
than normal
AirDNA Score: 53
$458/night

Nautical Touches to This Beautiful Eastport Home

2 beds
2.5 baths
6 guests
Average Price:  
$523
12% Cheaper
than normal
AirDNA Score: 53
$125/night

Charming Studio offering an easy walk to Downtown.

1 bed
1 bath
2 guests
Average Price:  
$266
53% Cheaper
than normal
AirDNA Score: 53
$950/night

Annapolis USNA Family Rental

5 beds
3.5 baths
8 guests
Average Price:  
$1000
5% Cheaper
than normal
AirDNA Score: 52
$154/night

Tranquil apartment in the woods

1 bed
1 bath
4 guests
Average Price:  
$182
15% 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
$200/night

Eastport Cottage

1 bed
1 bath
2 guests
Average Price:  
$243
18% Cheaper
than normal
AirDNA Score: 51
$90/night

My Annapolis Studio

1 bed
1 bath
2 guests
Average Price:  
$119
24% Cheaper
than normal
AirDNA Score: 50
$550/night

Annapolis Waterfront Cottage

4 beds
2 baths
8 guests
Average Price:  
$692
21% 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:  
$963
9% Cheaper
than normal
AirDNA Score: 50
$560/night

0.5 Miles From Navy Stadium/1.5 From Naval Academy

2 beds
1.5 baths
4 guests
Average Price:  
$775
28% Cheaper
than normal
AirDNA Score: 50
$255/night

Fabulous Waterfront Annapolis Apartment!

2 beds
1 bath
4 guests
Average Price:  
$305
16% Cheaper
than normal
AirDNA Score: 50
$605/night

Waterfront Beach House

3 beds
3 baths
8 guests
Average Price:  
$734
18% Cheaper
than normal
AirDNA Score: 48
$225/night

The Very Best location- 50 Steps from Main Street

3 beds
2 baths
7 guests
Average Price:  
$427
47% Cheaper
than normal
AirDNA Score: 48
$740/night

Gorgeous Historic Downtown Annapolis House

5 beds
3.5 baths
12 guests
Average Price:  
$1303
43% Cheaper
than normal
AirDNA Score: 47
$250/night

Charming Guest House-Annapolis

1 bed
1 bath
2 guests
Average Price:  
$272
8% Cheaper
than normal
AirDNA Score: 47
$425/night

Waterfront Oasis in Eastport-Easy Walk to Downtown

5 beds
3.5 baths
10 guests
Average Price:  
$707
40% Cheaper
than normal
AirDNA Score: 47
$325/night

Annapolis Retreat

4 beds
3.5 baths
8 guests
Average Price:  
$288
13% More
than normal
AirDNA Score: 44
$350/night

All Things ANNAPOLIS...

2 beds
2 baths
4 guests
Average Price:  
$425
18% Cheaper
than normal
AirDNA Score: 44
$800/night

Garden House next to USNA & Harbor

3 beds
3.5 baths
6 guests
Average Price:  
$809
1% Cheaper
than normal
AirDNA Score: 43
$130/night

2A One Bedroom Annapolis Apartment

1 bed
1 bath
4 guests
Average Price:  
$185
30% Cheaper
than normal
AirDNA Score: 38
$199/night

Red Brick Inn, Apt. #B - Downtown Annapolis

2 beds
1 bath
6 guests
Average Price:  
$282
29% Cheaper
than normal
AirDNA Score: 38
$223/night

Townhouse next to Navy Stadium!

2 beds
1 bath
4 guests
Average Price:  
$193
16% 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