Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
annapolis md
Check in / Check out
Any week
Guests
Add guests
Stays
Experiences
Online Experiences
Where
Search by region
I’m flexible
I’m flexible
Europe
Europe
Italy
Italy
Caribbean
Caribbean
Mexico
Mexico
South America
South America
Check in
Add dates
Check out
Add dates
Who
Add guests
Search
Airbnb your home
Sign up
Log in
Airbnb your home
Help Center
%{visible} of %{smart_count_str} Airbnb Category showing||||%{visible} of %{smart_count_str} Airbnb Categories showing
Your search
Rooms
Countryside
Amazing pools
Vineyards
Lake
Amazing views
Beach
Chef's kitchens
Play
Trending
Cabins
Farms
Bed & breakfasts
New
Lakefront
Beachfront
Design
Tiny homes
Skiing
Grand pianos
Golfing
Camping
Mansions
Surfing
National parks
Filters
, 1 filter applied
1
Display total before taxes
Show map
Search results; Over 1,000 places in Annapolis
Over 1,000 places in Annapolis
Guest favorite
Guest favorite
451
Reviews
4.96
Rating
6
Years hosting
Room in Annapolis
Stay with Jennifer
Stay with Jennifer
Hosting for 6 years
,
·
Hosting for 6 years
Chesapeake Mornings
Apr 21 – 26
Apr 21 – 26
R1,180 ZAR
night
R1,180 ZAR per night
4.96 out of 5 average rating, 451 reviews
4.96 (451)
Superhost
Superhost
Home in Annapolis
Historic Luxury Steps to USNA + Vibrant Waterfront
6 beds
6 beds
Apr 1 – 6
Apr 1 – 6
R19,388 ZAR
night
R19,388 ZAR per night
New place to stay
New
Guest favorite
Guest favorite
Home in Annapolis
Historic Downtown in-law suite
1 bed
1 bed
Nov 18 – 23
Nov 18 – 23
R2,886 ZAR
night
R2,886 ZAR per night
4.96 out of 5 average rating, 103 reviews
4.96 (103)
Guest favorite
Guest favorite
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
1 king bed
1 king bed
Apr 7 – 12
Apr 7 – 12
R2,001 ZAR
night
R2,001 ZAR per night
4.9 out of 5 average rating, 202 reviews
4.9 (202)
Guest favorite
Guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
Apr 1 – 6
Apr 1 – 6
R6,590 ZAR
night
R6,590 ZAR per night
4.99 out of 5 average rating, 102 reviews
4.99 (102)
Superhost
Superhost
Apartment in Annapolis
Modern Apartment over the Heart of Main Street!
2 queen beds
2 queen beds
Jul 21 – 26
Jul 21 – 26
R2,656 ZAR
night
R2,656 ZAR per night
4.82 out of 5 average rating, 645 reviews
4.82 (645)
Guest favorite
Guest favorite
Guest suite in Arnold
Old Bay Bungalow
2 beds
2 beds
Apr 6 – 11
Apr 6 – 11
R2,245 ZAR
night
R2,245 ZAR per night
4.96 out of 5 average rating, 560 reviews
4.96 (560)
Home in Annapolis
Quaint in the Heart of Annapolis
2 queen beds
2 queen beds
Apr 1 – 6
Apr 1 – 6
R4,067 ZAR
R3,712 ZAR
night
R3,712 ZAR per night, originally R4,067 ZAR
New place to stay
New
Guest favorite
Guest favorite
Condo in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
2 beds
2 beds
Apr 10 – 15
Apr 10 – 15
R3,192 ZAR
night
R3,192 ZAR per night
4.96 out of 5 average rating, 208 reviews
4.96 (208)
Guest favorite
Guest favorite
79
Reviews
4.9
Rating
2
Years hosting
Room in Annapolis
Stay with Michael
Stay with Michael
Front Room - Private room in Annapolis
Apr 1 – 6
Apr 1 – 6
R1,281 ZAR
night
R1,281 ZAR per night
4.9 out of 5 average rating, 79 reviews
4.9 (79)
Guest favorite
Guest favorite
Apartment in Annapolis
Eastport Bungalow
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
R2,612 ZAR
night
R2,612 ZAR per night
4.92 out of 5 average rating, 59 reviews
4.92 (59)
Guest favorite
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
1 queen bed
1 queen bed
Apr 2 – 7
Apr 2 – 7
R3,707 ZAR
night
R3,707 ZAR per night
4.94 out of 5 average rating, 307 reviews
4.94 (307)
Guest favorite
Guest favorite
Condo in Annapolis
1 Bedroom Apt - Walk to Downtown - With Parking
2 beds
2 beds
Apr 1 – 6
Apr 1 – 6
R2,423 ZAR
night
R2,423 ZAR per night
4.94 out of 5 average rating, 49 reviews
4.94 (49)
Guest favorite
Guest favorite
Guest suite in Annapolis
Annapolis Garden Suite
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
R2,689 ZAR
night
R2,689 ZAR per night
4.94 out of 5 average rating, 67 reviews
4.94 (67)
Guest favorite
Guest favorite
Apartment in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
2 beds
2 beds
Apr 1 – 6
Apr 1 – 6
R2,503 ZAR
night
R2,503 ZAR per night
4.92 out of 5 average rating, 439 reviews
4.92 (439)
Guest favorite
Guest favorite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 beds
2 beds
Apr 12 – 17
Apr 12 – 17
R4,137 ZAR
night
R4,137 ZAR per night
4.94 out of 5 average rating, 349 reviews
4.94 (349)
Guest favorite
Guest favorite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
5 beds
5 beds
Apr 7 – 12
Apr 7 – 12
R7,275 ZAR
R6,616 ZAR
night
R6,616 ZAR per night, originally R7,275 ZAR
5.0 out of 5 average rating, 82 reviews
5.0 (82)
Guest favorite
Guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 king beds
2 king beds
Apr 7 – 12
Apr 7 – 12
R3,812 ZAR
night
R3,812 ZAR per night
4.96 out of 5 average rating, 328 reviews
4.96 (328)
1
2
3
4
…
15