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
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
Home in Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms
,
·
2 beds
,
·
1 private bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,716 SGD
$1,508 SGD
Show price breakdown
for 5 nights
,
·
5.0 out of 5 average rating, 119 reviews
5.0 (119)
Top guest favourite
Guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds
2 beds
,
·
1 bathroom
1 bathroom
4–9 Oct
4–9 Oct
$2,027 SGD
Show price breakdown
for 5 nights
$2,027 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 98 reviews
4.97 (98)
Superhost
Superhost
Home in Annapolis
Anchorbrook Downtown 3BR Garage • Walk to Dock
3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$2,515 SGD
$2,038 SGD
Show price breakdown
for 5 nights
New place to stay
New
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
20–25 Sept
20–25 Sept
$433 SGD
Show price breakdown
for 5 nights
$433 SGD for 5 nights
Free cancellation
4.93 out of 5 average rating, 193 reviews
4.93 (193)
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
4–9 Oct
4–9 Oct
$955 SGD
$828 SGD
Show price breakdown
for 5 nights
4.89 out of 5 average rating, 370 reviews
4.89 (370)
Guest favourite
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed
1 queen bed
,
·
3 bathrooms
3 bathrooms
20–25 Sept
20–25 Sept
$433 SGD
Show price breakdown
for 5 nights
$433 SGD for 5 nights
Free cancellation
4.95 out of 5 average rating, 190 reviews
4.95 (190)
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
20–25 Sept
20–25 Sept
$6,655 SGD
$4,448 SGD
Show price breakdown
for 5 nights
4.91 out of 5 average rating, 92 reviews
4.91 (92)
Top guest favourite
Guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
2 beds
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$1,262 SGD
$1,094 SGD
Show price breakdown
for 5 nights
4.96 out of 5 average rating, 172 reviews
4.96 (172)
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
3–8 Oct
3–8 Oct
$1,969 SGD
$1,726 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 470 reviews
4.97 (470)
Top guest favourite
Guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1.5 bathrooms
1.5 bathrooms
25–30 Oct
25–30 Oct
$1,945 SGD
$1,654 SGD
Show price breakdown
for 5 nights
4.98 out of 5 average rating, 104 reviews
4.98 (104)
Guest favourite
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
2 bedrooms
,
·
1.5 bathrooms
1.5 bathrooms
20–25 Sept
20–25 Sept
$2,504 SGD
$1,778 SGD
Show price breakdown
for 5 nights
Free cancellation
4.97 out of 5 average rating, 66 reviews
4.97 (66)
Guest favourite
Guest favourite
Guest suite in Arnold
Captains Quarters Oasis Near Annapolis, Sleeps 4
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
13–18 Sept
13–18 Sept
$1,364 SGD
$1,015 SGD
Show price breakdown
for 5 nights
Free cancellation
4.95 out of 5 average rating, 214 reviews
4.95 (214)
Top guest favourite
Guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed
1 queen bed
,
·
1 bathroom
1 bathroom
27 Sept – 2 Oct
27 Sept – 2 Oct
$752 SGD
$656 SGD
Show price breakdown
for 5 nights
Free cancellation
5.0 out of 5 average rating, 33 reviews
5.0 (33)
Top 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
13–18 Sept
13–18 Sept
$1,333 SGD
Show price breakdown
for 5 nights
$1,333 SGD for 5 nights
4.94 out of 5 average rating, 424 reviews
4.94 (424)
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
6–11 Sept
6–11 Sept
$5,967 SGD
Show price breakdown
for 5 nights
$5,967 SGD for 5 nights
5.0 out of 5 average rating, 45 reviews
5.0 (45)
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
13–18 Sept
13–18 Sept
$1,497 SGD
$1,332 SGD
Show price breakdown
for 5 nights
Free cancellation
4.87 out of 5 average rating, 77 reviews
4.87 (77)
Top guest favourite
Guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 1
1 king bed
1 king bed
,
·
1 bathroom
1 bathroom
7–12 Sept
7–12 Sept
$682 SGD
Show price breakdown
for 5 nights
$682 SGD for 5 nights
4.94 out of 5 average rating, 359 reviews
4.94 (359)
Top guest favourite
Guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
25–30 Oct
25–30 Oct
$1,499 SGD
$1,003 SGD
Show price breakdown
for 5 nights
Free cancellation
4.91 out of 5 average rating, 120 reviews
4.91 (120)
Top guest favourite
Guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom
1 bedroom
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
3–8 Dec
3–8 Dec
$778 SGD
Show price breakdown
for 5 nights
$778 SGD for 5 nights
Free cancellation
4.97 out of 5 average rating, 460 reviews
4.97 (460)
1
2
3
4
…
15