Skip to content
We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.
Homes
Homes
NEW
NEW
Experiences
Experiences, new
NEW
NEW
Services
Services, new
Start your search
Location
Homes in Annapolis
Check in / Check out
Any week
Guests
Add guests
Become a host
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
Type of place
Show map
Search results; Over 1,000 homes in Annapolis
Over 1,000 homes in Annapolis
Top guest favourite
Guest favourite
Guest house in Annapolis
Garden View, a spacious 1 bedroom with loft.
2 bedrooms
,
·
3 beds
,
·
1 private bathroom
31 Jul – 5 Aug
31 Jul – 5 Aug
$1,404 SGD
Show price breakdown
for 5 nights
$1,404 SGD for 5 nights
,
·
4.99 out of 5 average rating, 158 reviews
4.99 (158)
Top guest favourite
Guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms
2 bedrooms
,
·
1 queen bed
1 queen bed
,
·
1.5 bathrooms
1.5 bathrooms
19–24 Jul
19–24 Jul
$1,638 SGD
$1,178 SGD
Show price breakdown
for 5 nights
Free cancellation
4.91 out of 5 average rating, 70 reviews
4.91 (70)
Top guest favourite
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
15–20 Aug
15–20 Aug
$2,043 SGD
$1,688 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Top guest favourite
Guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
29 Jul – 3 Aug
29 Jul – 3 Aug
$1,363 SGD
Show price breakdown
for 5 nights
$1,363 SGD for 5 nights
4.92 out of 5 average rating, 1119 reviews
4.92 (1119)
Superhost
Superhost
Home in Annapolis
Eastport 3 bedroom Cottage: Walk to Downtown
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
1–6 Jul
1–6 Jul
$2,894 SGD
Show price breakdown
for 5 nights
$2,894 SGD for 5 nights
Free cancellation
Top guest favourite
Guest favourite
Flat in Annapolis
The Sail Loft
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
25–30 Jul
25–30 Jul
$2,378 SGD
Show price breakdown
for 5 nights
$2,378 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 33 reviews
5.0 (33)
Guest favourite
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms
5 bedrooms
,
·
9 beds
9 beds
,
·
3.5 bathrooms
3.5 bathrooms
5–10 Jul
5–10 Jul
$9,234 SGD
$6,857 SGD
Show price breakdown
for 5 nights
Free cancellation
4.92 out of 5 average rating, 88 reviews
4.92 (88)
Top guest favourite
Guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
21–26 Jul
21–26 Jul
$2,463 SGD
Show price breakdown
for 5 nights
$2,463 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 35 reviews
4.97 (35)
Guest favourite
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,049 SGD
Show price breakdown
for 5 nights
$1,049 SGD for 5 nights
Free cancellation
4.9 out of 5 average rating, 131 reviews
4.9 (131)
Top guest favourite
Guest favourite
Home in Annapolis
West street historic home
5 bedrooms
5 bedrooms
,
·
6 beds
6 beds
,
·
3 bathrooms
3 bathrooms
1–6 Jul
1–6 Jul
$7,033 SGD
Show price breakdown
for 5 nights
$7,033 SGD for 5 nights
Free cancellation
4.98 out of 5 average rating, 65 reviews
4.98 (65)
Top guest favourite
Guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
5–10 Jul
5–10 Jul
$2,733 SGD
$2,082 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 26 reviews
5.0 (26)
Top guest favourite
Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2.5 bathrooms
2.5 bathrooms
12–17 Jul
12–17 Jul
$3,640 SGD
$3,098 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Guest favourite
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$2,159 SGD
$1,912 SGD
Show price breakdown
for 5 nights
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Top guest favourite
Guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
6–11 Jul
6–11 Jul
$2,878 SGD
$2,061 SGD
Show price breakdown
for 5 nights
Free cancellation
4.99 out of 5 average rating, 153 reviews
4.99 (153)
Guest favourite
Guest favourite
Home in Annapolis
Historic 4BR Naptown Home <1 Mile to Stadium
4 bedrooms
4 bedrooms
,
·
8 beds
8 beds
,
·
3.5 bathrooms
3.5 bathrooms
13–18 Sept
13–18 Sept
$3,545 SGD
$3,265 SGD
Show price breakdown
for 5 nights
Free cancellation
4.98 out of 5 average rating, 65 reviews
4.98 (65)
Top guest favourite
Guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
2 bedrooms
2 bedrooms
,
·
2 double beds
2 double beds
,
·
1 bathroom
1 bathroom
24–29 Jul
24–29 Jul
$1,875 SGD
Show price breakdown
for 5 nights
$1,875 SGD for 5 nights
Free cancellation
5.0 out of 5 average rating, 113 reviews
5.0 (113)
Top guest favourite
Guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
3 bedrooms
,
·
2 bathrooms
2 bathrooms
5–10 Jul
5–10 Jul
$2,023 SGD
Show price breakdown
for 5 nights
$2,023 SGD for 5 nights
Free cancellation
4.92 out of 5 average rating, 26 reviews
4.92 (26)
Top 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
5–10 Jul
5–10 Jul
$3,225 SGD
$2,408 SGD
Show price breakdown
for 5 nights
Free cancellation
4.93 out of 5 average rating, 199 reviews
4.93 (199)
Top guest favourite
Guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms
2 bedrooms
,
·
2 king beds
2 king beds
,
·
1 bathroom
1 bathroom
14–19 Aug
14–19 Aug
$1,766 SGD
Show price breakdown
for 5 nights
$1,766 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 461 reviews
4.97 (461)
1
2
3
4
…
15