Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
Experiences
Experiences
Services
Services
Start your search
Location
Homes in Annapolis
Check in / Check out
Any week
Guests
Add guests
Log in or sign up
Help Centre
Become a host
It’s easy to start hosting and earn extra income.
Refer a host
Find a co-host
Log in or sign up
filters
Filters
Price
Price filter
Type of place
Type of place filter
Show map
Search results; Over 1,000 homes in Annapolis
Over 1,000 homes in Annapolis
Photo 1 of 19
Top guest favourite
Guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
Studio
,
·
2 beds
,
·
1 private bathroom
18–23 Oct
18–23 Oct
$1,324 SGD
$1,147 SGD
Show price breakdown
for 5 nights
,
·
4.96 out of 5 average rating, 179 reviews
4.96 (179)
Photo 1 of 26
Home in Annapolis
The 1845 Outpost
3 bedrooms
3 bedrooms
,
·
3 king beds
3 king beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
$3,574 SGD
$3,175 SGD
Show price breakdown
for 5 nights
Free cancellation
New place to stay
New
Photo 1 of 6
Guest favourite
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,175 SGD
$1,034 SGD
Show price breakdown
for 5 nights
Free cancellation
4.95 out of 5 average rating, 138 reviews
4.95 (138)
Photo 1 of 6
Top guest favourite
Guest favourite
Room in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed
1 bed
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$2,095 SGD
$1,839 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 175 reviews
5.0 (175)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Annapolis
4BR Walk to USNA & Dock · Parking
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
4 bathrooms
4 bathrooms
1–6 Oct
1–6 Oct
$6,724 SGD
$5,469 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Photo 1 of 29
Home in Annapolis
The Melrose Retreat
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
3.5 bathrooms
3.5 bathrooms
1–6 Oct
1–6 Oct
$4,439 SGD
$2,460 SGD
Show price breakdown
for 5 nights
New place to stay
New
Photo 1 of 29
Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms
4 bedrooms
,
·
4 beds
4 beds
,
·
4 bathrooms
4 bathrooms
1–6 Oct
1–6 Oct
$6,520 SGD
Show price breakdown
for 5 nights
$6,520 SGD for 5 nights
Free cancellation
New place to stay
New
Photo 1 of 14
Hotel room in Annapolis
Governor Calvert King | Historic Inns
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
1–6 Nov
1–6 Nov
$1,308 SGD
Show price breakdown
for 5 nights
$1,308 SGD for 5 nights
Free cancellation
4.57 out of 5 average rating, 44 reviews
4.57 (44)
Photo 1 of 6
Guest favourite
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
1 queen bed
,
·
1.5 bathrooms
1.5 bathrooms
8–13 Nov
8–13 Nov
$431 SGD
Show price breakdown
for 5 nights
$431 SGD for 5 nights
Free cancellation
4.94 out of 5 average rating, 191 reviews
4.94 (191)
Photo 1 of 15
Top guest favourite
Guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
3 bedrooms
,
·
2 bathrooms
2 bathrooms
25–30 Oct
25–30 Oct
$2,193 SGD
$1,867 SGD
Show price breakdown
for 5 nights
Free cancellation
4.94 out of 5 average rating, 35 reviews
4.94 (35)
Photo 1 of 21
Top guest favourite
Guest favourite
Home in Annapolis
Walk to Navy Stadium & Shops. No cleaning fee!
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
1–6 Oct
1–6 Oct
$3,572 SGD
$2,999 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 37 reviews
5.0 (37)
Photo 1 of 22
Guest favourite
Guest favourite
Guest suite in Arnold
Pet-Friendly King Suite + Kitchen | Near Annapolis
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,459 SGD
$1,303 SGD
Show price breakdown
for 5 nights
Free cancellation
4.95 out of 5 average rating, 216 reviews
4.95 (216)
Photo 1 of 29
Guest favourite
Guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$2,969 SGD
$2,605 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
1–6 Oct
1–6 Oct
$3,036 SGD
$2,707 SGD
Show price breakdown
for 5 nights
4.98 out of 5 average rating, 55 reviews
4.98 (55)
Photo 1 of 6
Guest favourite
Guest favourite
Room in Annapolis
Laura’s Room
1 double bed
1 double bed
,
·
1 bathroom
1 bathroom
1–6 Oct
1–6 Oct
$1,162 SGD
$1,035 SGD
Show price breakdown
for 5 nights
4.88 out of 5 average rating, 95 reviews
4.88 (95)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
1–6 Oct
1–6 Oct
$2,922 SGD
$2,642 SGD
Show price breakdown
for 5 nights
Free cancellation
4.93 out of 5 average rating, 206 reviews
4.93 (206)
Photo 1 of 24
Guest favourite
Guest favourite
Home in Annapolis
Quiet Home Close to Downtown Annapolis and Parks
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
11–16 Oct
11–16 Oct
$2,462 SGD
Show price breakdown
for 5 nights
$2,462 SGD for 5 nights
Free cancellation
4.91 out of 5 average rating, 65 reviews
4.91 (65)
Photo 1 of 29
Guest favourite
Guest favourite
Home in Annapolis
Family Oasis|Spa Shower|Near USNA stadium & DTA
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
1–6 Oct
1–6 Oct
$4,100 SGD
$3,234 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 21 reviews
5.0 (21)
Photo 1 of 29
Top guest favourite
Guest favourite
Home in Annapolis
Annapolis waterfront, private pier with kayaks
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
3 bathrooms
3 bathrooms
1–6 Oct
1–6 Oct
$5,665 SGD
Show price breakdown
for 5 nights
$5,665 SGD for 5 nights
5.0 out of 5 average rating, 46 reviews
5.0 (46)
1
2
3
4
…
15