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
30 Jul – 4 Aug
30 Jul – 4 Aug
$1,448 SGD
Show price breakdown
for 5 nights
$1,448 SGD for 5 nights
,
·
4.99 out of 5 average rating, 161 reviews
4.99 (161)
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
19–24 Jul
19–24 Jul
$440 SGD
Show price breakdown
for 5 nights
$440 SGD for 5 nights
Pay $0 today
Free cancellation
4.93 out of 5 average rating, 179 reviews
4.93 (179)
Guest favourite
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom
1 bedroom
,
·
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
10–15 Aug
10–15 Aug
$844 SGD
Show price breakdown
for 5 nights
$844 SGD for 5 nights
4.89 out of 5 average rating, 358 reviews
4.89 (358)
Top guest favourite
Guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$1,966 SGD
Show price breakdown
for 5 nights
$1,966 SGD for 5 nights
Pay $0 today
Free cancellation
4.98 out of 5 average rating, 142 reviews
4.98 (142)
Top guest favourite
Guest favourite
Apartment in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
24–29 Aug
24–29 Aug
$1,506 SGD
Show price breakdown
for 5 nights
$1,506 SGD for 5 nights
Pay $0 today
Free cancellation
4.96 out of 5 average rating, 338 reviews
4.96 (338)
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
16–21 Jul
16–21 Jul
$1,796 SGD
$1,610 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
4.92 out of 5 average rating, 72 reviews
4.92 (72)
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
$3,527 SGD
$2,726 SGD
Show price breakdown
for 5 nights
Pay $0 today
Free cancellation
5.0 out of 5 average rating, 8 reviews
5.0 (8)
Top guest favourite
Guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
29 Nov – 4 Dec
29 Nov – 4 Dec
$808 SGD
Show price breakdown
for 5 nights
$808 SGD for 5 nights
Pay $0 today
Free cancellation
4.97 out of 5 average rating, 454 reviews
4.97 (454)
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
10–15 Aug
10–15 Aug
$1,216 SGD
Show price breakdown
for 5 nights
$1,216 SGD for 5 nights
4.92 out of 5 average rating, 1121 reviews
4.92 (1121)
Top guest favourite
Guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
28 Jul – 2 Aug
28 Jul – 2 Aug
$2,175 SGD
$1,593 SGD
Show price breakdown
for 5 nights
4.97 out of 5 average rating, 72 reviews
4.97 (72)
Top guest favourite
Guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
26–31 Jul
26–31 Jul
$2,395 SGD
Show price breakdown
for 5 nights
$2,395 SGD for 5 nights
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Superhost
Superhost
Flat in Annapolis
Gybeset Eastport Inn
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1 bathroom
1 bathroom
6–11 Jul
6–11 Jul
$1,319 SGD
Show price breakdown
for 5 nights
$1,319 SGD for 5 nights
Pay $0 today
Free cancellation
4.88 out of 5 average rating, 303 reviews
4.88 (303)
Guest favourite
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$1,281 SGD
Show price breakdown
for 5 nights
$1,281 SGD for 5 nights
Pay $0 today
Free cancellation
4.96 out of 5 average rating, 240 reviews
4.96 (240)
Guest favourite
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
1 queen bed
,
·
3 bathrooms
3 bathrooms
26–31 Jul
26–31 Jul
$440 SGD
Show price breakdown
for 5 nights
$440 SGD for 5 nights
Pay $0 today
Free cancellation
4.95 out of 5 average rating, 180 reviews
4.95 (180)
Top guest favourite
Guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
2 beds
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$1,082 SGD
Show price breakdown
for 5 nights
$1,082 SGD for 5 nights
4.96 out of 5 average rating, 155 reviews
4.96 (155)
Guest favourite
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
1 queen bed
,
·
1.5 bathrooms
1.5 bathrooms
24–29 Jul
24–29 Jul
$492 SGD
Show price breakdown
for 5 nights
$492 SGD for 5 nights
Pay $0 today
Free cancellation
4.93 out of 5 average rating, 179 reviews
4.93 (179)
Guest favourite
Guest favourite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
25–30 Jul
25–30 Jul
$1,401 SGD
Show price breakdown
for 5 nights
$1,401 SGD for 5 nights
4.94 out of 5 average rating, 418 reviews
4.94 (418)
Top guest favourite
Guest favourite
Boat in Annapolis
Welcome Aboard!
2 bedrooms
2 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
30 Jul – 4 Aug
30 Jul – 4 Aug
$2,640 SGD
Show price breakdown
for 5 nights
$2,640 SGD for 5 nights
Pay $0 today
Free cancellation
4.96 out of 5 average rating, 111 reviews
4.96 (111)
Superhost
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium- Renovated 2BR Downtown
2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
1.5 bathrooms
1.5 bathrooms
20–25 Jul
20–25 Jul
$1,652 SGD
Show price breakdown
for 5 nights
$1,652 SGD for 5 nights
Pay $0 today
Free cancellation
4.86 out of 5 average rating, 72 reviews
4.86 (72)
1
2
3
4
…
15