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

Old Orchard Cottage

2 beds
1 bath
4 guests
Average Price:  
$209
5% More
than normal
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

The Cape Cottage

studio
1 bath
2 guests
Average Price:  
$125
4% Cheaper
than normal
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

New Hotel Chic

2 beds
1 bath
4 guests
Average Price:  
$242
1% Cheaper
than normal
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

Charming Eastport

1 bed
1 bath
2 guests
Average Price:  
$190
16% Cheaper
than normal
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

The Lobster Loft

2 beds
1 bath
6 guests
Average Price:  
$196
1% Cheaper
than normal
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