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
$425/night

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

2 beds
2.5 baths
6 guests
Average Price:  
$299
42% More
than normal
AirDNA Score: 93
$197/night

Wright’s Cottage, Pets Welcome!

1 bed
1 bath
2 guests
Average Price:  
$158
25% More
than normal
AirDNA Score: 85
$514/night

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

3 beds
2 baths
8 guests
Average Price:  
$547
6% Cheaper
than normal
AirDNA Score: 83
$399/night

Crab Cakes and Football Historic District

2 beds
1.5 baths
4 guests
Average Price:  
$434
8% Cheaper
than normal
AirDNA Score: 82
$578/night

Beautiful Home in Quiet Private Setting near Annapolis

4 beds
3 baths
8 guests
Average Price:  
$533
8% More
than normal
AirDNA Score: 79
$366/night

Beautiful and Tranquil Carriage House

2 beds
1.5 baths
8 guests
Average Price:  
$394
7% Cheaper
than normal
AirDNA Score: 78
$99/night

Modern Apartment over the Heart of Main Street!

2 beds
1 bath
4 guests
Average Price:  
$172
42% Cheaper
than normal
AirDNA Score: 73
$250/night

Perfect Eastport location NO added cleaning fees

2 beds
1 bath
4 guests
Average Price:  
$299
16% Cheaper
than normal
AirDNA Score: 72
$240/night

New Hotel Chic

2 beds
1 bath
4 guests
Average Price:  
$238
1% More
than normal
AirDNA Score: 71
$105/night

Our Annapolis Penthouse

1 bed
1 bath
3 guests
Average Price:  
$108
3% Cheaper
than normal
AirDNA Score: 71
$281/night

Eastport Bungalow

3 beds
1 bath
6 guests
Average Price:  
$334
16% Cheaper
than normal
AirDNA Score: 71
$116/night

Private Annapolis Inlaw Apartment

1 bed
1 bath
4 guests
Average Price:  
$132
12% Cheaper
than normal
AirDNA Score: 71
$536/night

You'll Never Want to Leave

5 beds
2.5 baths
13 guests
Average Price:  
$562
5% Cheaper
than normal
AirDNA Score: 71
$299/night

Across from stadium - walk to downtown Annapolis!

4 beds
3 baths
10 guests
Average Price:  
$447
33% Cheaper
than normal
AirDNA Score: 71
$475/night

Sophisticated & Spacious Historic Home w/ Parking!

3 beds
2.5 baths
6 guests
Average Price:  
$622
24% Cheaper
than normal
AirDNA Score: 71
$165/night

Gybeset Eastport Inn

3 beds
1 bath
5 guests
Average Price:  
$230
28% Cheaper
than normal
AirDNA Score: 71
$674/night

Relax on the peninsula in Eastport Annapolis!

2 beds
1.5 baths
6 guests
Average Price:  
$727
7% Cheaper
than normal
AirDNA Score: 71
$650/night

2003 Craftsman; Heart of Eastport!

3 beds
2.5 baths
6 guests
Average Price:  
$526
24% More
than normal
AirDNA Score: 71
$295/night

West Annapolis Free Parking! Close to Navy Stadium

3 beds
1.5 baths
6 guests
Average Price:  
$413
29% Cheaper
than normal
AirDNA Score: 70
$135/night

Charming lower-level apartment in Annapolis

1 bed
1 bath
2 guests
Average Price:  
$156
13% Cheaper
than normal
AirDNA Score: 70
$160/night

Eastport-Annapolis Private Bsmt. Apt 1 mile -DTA

1 bed
1 bath
4 guests
Average Price:  
$165
3% Cheaper
than normal
AirDNA Score: 69
$392/night

Eastport Haven House

4 beds
4 baths
9 guests
Average Price:  
$555
29% Cheaper
than normal
AirDNA Score: 67
$900/night

Newly renovated minutes to downtown

5 beds
3.5 baths
8 guests
Average Price:  
$917
2% Cheaper
than normal
AirDNA Score: 65
$865/night

Spacious Commissioning or Induction week home!

4 beds
4.5 baths
10 guests
Average Price:  
$953
9% Cheaper
than normal
AirDNA Score: 65
$595/night

Beautiful Home-Steps to Navy Stadium & Downtown!

4 beds
3 baths
8 guests
Average Price:  
$635
6% Cheaper
than normal
AirDNA Score: 65
$787/night

Lovely & Spacious Severn River Waterfront

4 beds
4 baths
8 guests
Average Price:  
$937
16% Cheaper
than normal
AirDNA Score: 65
$545/night

Location! Historic home steps from City Dock

4 beds
3 baths
8 guests
Average Price:  
$746
27% Cheaper
than normal
AirDNA Score: 65
$510/night

1920s House in Presidents Hill

3 beds
1.5 baths
5 guests
Average Price:  
$541
6% Cheaper
than normal
AirDNA Score: 64
$175/night

Cozy Apt. +beach playground-15mins to Annapolis DT

2 beds
1 bath
4 guests
Average Price:  
$305
43% Cheaper
than normal
AirDNA Score: 64
$175/night

Independent Access Garage Apartment, Near Downtown

1 bed
1 bath
2 guests
Average Price:  
$197
11% Cheaper
than normal
AirDNA Score: 64
$650/night

4 Bed & 3 Bath Contemporary in Heart of Eastport!

4 beds
3.5 baths
12 guests
Average Price:  
$575
13% More
than normal
AirDNA Score: 60
$600/night

Beautiful Large Glass Contemporary Wooded Privacy.

7 beds
3.5 baths
12 guests
Average Price:  
$744
19% Cheaper
than normal
AirDNA Score: 58
$300/night

2. 20ac wtrfrnt estate - Studio apt

studio
1.5 baths
2 guests
Average Price:  
$397
24% Cheaper
than normal
AirDNA Score: 57
$1427/night

Beautiful 5 bdrm - minutes from downtown & USNA!

5 beds
4.5 baths
12 guests
Average Price:  
$1516
6% Cheaper
than normal
AirDNA Score: 57
$198/night

"Jode's Retreat" Your Home Away From Home

3 beds
1 bath
6 guests
Average Price:  
$257
23% Cheaper
than normal
AirDNA Score: 57
$250/night

Red Brick Inn, Apt. #1 - Downtown Annapolis

3 beds
1 bath
8 guests
Average Price:  
$430
42% Cheaper
than normal
AirDNA Score: 55
$490/night

Annapolis Nautical Cottage EASTPORT NAVY BOAT SHOW

2 beds
1.5 baths
8 guests
Average Price:  
$571
14% Cheaper
than normal
AirDNA Score: 55
$625/night

Eastport Peninsula Charm

4 beds
2.5 baths
8 guests
Average Price:  
$655
5% Cheaper
than normal
AirDNA Score: 55
$746/night

Excellent Location, Super Clean, Super Spacious !

7 beds
4.5 baths
15 guests
Average Price:  
$933
20% Cheaper
than normal
AirDNA Score: 54
$550/night

Contemporary in Heart of Eastport w 2 car garage!

3 beds
2.5 baths
6 guests
Average Price:  
$483
14% More
than normal
AirDNA Score: 53
$169/night

Charming Detached Studio w/ easy walk to Downtown.

1 bed
1 bath
2 guests
Average Price:  
$260
35% Cheaper
than normal
AirDNA Score: 52
$159/night

Tranquil apartment in the woods

1 bed
1 bath
4 guests
Average Price:  
$157
1% More
than normal
AirDNA Score: 52
$425/night

Downtown Annapolis Apartment

2 beds
2 baths
5 guests
Average Price:  
$480
11% 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
$349/night

Welcome Aboard!

2 beds
2 baths
4 guests
Average Price:  
$390
11% Cheaper
than normal
AirDNA Score: 51
$750/night

Charming Annapolis Victorian

6 beds
4.5 baths
12 guests
Average Price:  
$792
5% Cheaper
than normal
AirDNA Score: 51
$207/night

Eastport Cottage

1 bed
1 bath
2 guests
Average Price:  
$239
13% Cheaper
than normal
AirDNA Score: 51
$1000/night

Perfect home for Annapolis Boat Shows!

4 beds
3 baths
10 guests
Average Price:  
$1101
9% Cheaper
than normal
AirDNA Score: 51
$800/night

Spacious Murray Hill - 6 BR walk downtown & Navy

6 beds
4.5 baths
12 guests
Average Price:  
$867
8% Cheaper
than normal
AirDNA Score: 50
$875/night

Class of 2025 Grad Week house w/ room for a crowd

4 beds
2.5 baths
10 guests
Average Price:  
$956
8% Cheaper
than normal
AirDNA Score: 50
$750/night

Annapolis Waterfront Cottage

4 beds
2 baths
8 guests
Average Price:  
$708
6% More
than normal
AirDNA Score: 48
$1000/night

Eastport in Annapolis

4 beds
3 baths
8 guests
Average Price:  
$1035
3% Cheaper
than normal
AirDNA Score: 48
$272/night

Waterfront farm retreat for vacation & telework

3 beds
1.5 baths
7 guests
Average Price:  
$326
17% Cheaper
than normal
AirDNA Score: 48
$953/night

Gorgeous Historic Downtown Annapolis House

5 beds
3.5 baths
12 guests
Average Price:  
$1138
16% Cheaper
than normal
AirDNA Score: 47
$575/night

Waterfront Oasis in Eastport-Easy Walk to Downtown

5 beds
3.5 baths
10 guests
Average Price:  
$742
23% Cheaper
than normal
AirDNA Score: 45
$350/night

Beautiful Downtown Annapolis Home!

3 beds
2 baths
6 guests
Average Price:  
$442
21% Cheaper
than normal
AirDNA Score: 45
$515/night

Charming Townhouse in Murray Hill

3 beds
3.5 baths
8 guests
Average Price:  
$567
9% Cheaper
than normal
AirDNA Score: 45
$249/night

Historic District - One block from Main street

2 beds
1.5 baths
4 guests
Average Price:  
$475
48% 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: 44
$1600/night

Garden House next to USNA & Harbor

3 beds
3.5 baths
6 guests
Average Price:  
$1430
12% More
than normal
AirDNA Score: 43
$153/night

1B Annapolis Apartment

1 bed
1 bath
4 guests
Average Price:  
$200
23% Cheaper
than normal
AirDNA Score: 38
$199/night

Red Brick Inn, Apt. #B - Downtown Annapolis

2 beds
1 bath
6 guests
Average Price:  
$281
29% 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: 36
$453/night

Annapolis Condo - minutes from downtown/Academy

3 beds
2 baths
6 guests
Average Price:  
$442
2% More
than normal
AirDNA Score: 36
$138/night

1A Annapolis Apartment

1 bed
1 bath
4 guests
Average Price:  
$183
25% Cheaper
than normal
AirDNA Score: 36
$152/night

2B One Bedroom Annapolis Apartment

2 beds
1 bath
4 guests
Average Price:  
$181
16% 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: 33
$505/night

2 blocks from Stadium and walking distance to Town

4 beds
3 baths
10 guests
Average Price:  
$613
18% Cheaper
than normal
AirDNA Score: 31
$345/night

Families & Friends gather here to enjoy

5 beds
2.5 baths
10 guests
Average Price:  
$373
8% Cheaper
than normal
AirDNA Score: 31
$176/night

Check yourself in! 3-Br House near Annapolis Mall

3 beds
2.5 baths
8 guests
Average Price:  
$286
38% Cheaper
than normal
AirDNA Score: 23
$275/night

Downtown Annapolis Historic Home!

2 beds
1.5 baths
4 guests
Average Price:  
$338
19% Cheaper
than normal
AirDNA Score: 21
$1250/night

Craftsman Home in Eastport

3 beds
2.5 baths
6 guests
Average Price:  
$1450
14% Cheaper
than normal
AirDNA Score: 14
$1000/night

Annapolis/USNA Commissioning Week Rental

5 beds
3.5 baths
12 guests
Average Price:  
$1036
3% Cheaper
than normal
AirDNA Score: 14
$261/night

Restful and Charming Home in Eastport

3 beds
1.5 baths
6 guests
Average Price:  
$319
18% Cheaper
than normal
AirDNA Score: 13
$300/night

Upscale Waterfront Condo Annapolis

1 bed
1 bath
2 guests
Average Price:  
$292
3% More
than normal