Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Start your search
Location
Annapolis
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
Canada
Canada
Caribbean
Caribbean
Italy
Italy
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
Lake
Vineyards
Beach
Amazing views
Chef's kitchens
Trending
Play
Cabins
Farms
Beachfront
New
Bed & breakfasts
Lakefront
Design
Tiny homes
Grand pianos
Skiing
Golfing
Camping
Mansions
Surfing
National parks
Filters
0
Display total before taxes
Show map
Search results; Over 1,000 places in Annapolis
Over 1,000 places in Annapolis
Guest favorite
Guest favorite
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
1 king bed
1 king bed
May 30 – Jun 4
May 30 – Jun 4
ﺩ.ﺇ383
night
ﺩ.ﺇ383 per night
4.9 out of 5 average rating, 206 reviews
4.9 (206)
Guest favorite
Guest favorite
Home in Annapolis
Historic Downtown in-law suite
1 bed
1 bed
Nov 18 – 23
Nov 18 – 23
ﺩ.ﺇ553
night
ﺩ.ﺇ553 per night
4.96 out of 5 average rating, 109 reviews
4.96 (109)
Guest favorite
Guest favorite
Condo in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
ﺩ.ﺇ599
night
ﺩ.ﺇ599 per night
4.96 out of 5 average rating, 213 reviews
4.96 (213)
Guest favorite
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
1 queen bed
1 queen bed
Apr 21 – 26
Apr 21 – 26
ﺩ.ﺇ633
night
ﺩ.ﺇ633 per night
4.94 out of 5 average rating, 312 reviews
4.94 (312)
Guest favorite
Guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
Apr 21 – 26
Apr 21 – 26
ﺩ.ﺇ1,353
ﺩ.ﺇ1,225
night
ﺩ.ﺇ1,225 per night, originally ﺩ.ﺇ1,353
4.99 out of 5 average rating, 105 reviews
4.99 (105)
Guest favorite
Guest favorite
Guesthouse in Annapolis
RECENTLY RENOVATED Cottage Near Downtown Annapolis
1 king bed
1 king bed
Apr 22 – 27
Apr 22 – 27
ﺩ.ﺇ467
night
ﺩ.ﺇ467 per night
4.97 out of 5 average rating, 197 reviews
4.97 (197)
Guest favorite
Guest favorite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
ﺩ.ﺇ737
night
ﺩ.ﺇ737 per night
4.94 out of 5 average rating, 351 reviews
4.94 (351)
Guest favorite
Guest favorite
Guest suite in Annapolis
West Annapolis Hidden Gem <1 Mile To Navy Stadium
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
ﺩ.ﺇ793
ﺩ.ﺇ461
night
ﺩ.ﺇ461 per night, originally ﺩ.ﺇ793
5.0 out of 5 average rating, 30 reviews
5.0 (30)
Guest favorite
Guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 king beds
2 king beds
Apr 23 – 28
Apr 23 – 28
ﺩ.ﺇ763
night
ﺩ.ﺇ763 per night
4.96 out of 5 average rating, 332 reviews
4.96 (332)
Guest favorite
Guest favorite
Houseboat in Arnold
Boho Luxe Floating Tiny Home with 360 Views
1 queen bed
1 queen bed
Apr 28 – May 3
Apr 28 – May 3
ﺩ.ﺇ874
ﺩ.ﺇ798
night
ﺩ.ﺇ798 per night, originally ﺩ.ﺇ874
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favorite
Guest favorite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
3 beds
3 beds
Apr 20 – 25
Apr 20 – 25
ﺩ.ﺇ940
ﺩ.ﺇ774
night
ﺩ.ﺇ774 per night, originally ﺩ.ﺇ940
4.94 out of 5 average rating, 287 reviews
4.94 (287)
Guest favorite
Guest favorite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
ﺩ.ﺇ1,049
ﺩ.ﺇ958
night
ﺩ.ﺇ958 per night, originally ﺩ.ﺇ1,049
4.96 out of 5 average rating, 102 reviews
4.96 (102)
Guest favorite
Guest favorite
Townhouse in Annapolis
Historic 3 Bedroom Downtown Annapolis Townhome
5 beds
5 beds
Apr 21 – 26
Apr 21 – 26
ﺩ.ﺇ1,580
ﺩ.ﺇ750
night
ﺩ.ﺇ750 per night, originally ﺩ.ﺇ1,580
4.97 out of 5 average rating, 99 reviews
4.97 (99)
Guest favorite
Guest favorite
Home in Annapolis
Elegant & Authentic Annapolis
1 queen bed
1 queen bed
Apr 28 – May 3
Apr 28 – May 3
ﺩ.ﺇ871
night
ﺩ.ﺇ871 per night
5.0 out of 5 average rating, 37 reviews
5.0 (37)
Guest favorite
Guest favorite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 beds
3 beds
Apr 28 – May 3
Apr 28 – May 3
ﺩ.ﺇ1,095
ﺩ.ﺇ868
night
ﺩ.ﺇ868 per night, originally ﺩ.ﺇ1,095
4.96 out of 5 average rating, 50 reviews
4.96 (50)
Guest favorite
Guest favorite
Cottage in Annapolis
Miller Cottage - near Navy Stadium
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
ﺩ.ﺇ822
night
ﺩ.ﺇ822 per night
4.98 out of 5 average rating, 64 reviews
4.98 (64)
Guest favorite
Guest favorite
Townhouse in Annapolis
★ Midcentury Modern Getaway ★ Prime Location ★
3 king beds
3 king beds
Apr 28 – May 3
Apr 28 – May 3
ﺩ.ﺇ1,426
ﺩ.ﺇ849
night
ﺩ.ﺇ849 per night, originally ﺩ.ﺇ1,426
4.97 out of 5 average rating, 160 reviews
4.97 (160)
Guest favorite
Guest favorite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
5 beds
5 beds
May 19 – 24
May 19 – 24
ﺩ.ﺇ4,092
ﺩ.ﺇ1,953
night
ﺩ.ﺇ1,953 per night, originally ﺩ.ﺇ4,092
5.0 out of 5 average rating, 84 reviews
5.0 (84)
1
2
3
4
…
15