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 Chestertown MD US
Check in / Check out
Any week
Guests
Add guests
Filters
0
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
Show map
Search results; 399 homes in Chestertown
399 homes in Chestertown
The home you selected
Guest favourite
Guest favourite
Home in Chestertown
NEW Chestertown Retreat
6 guests
·
3 bedrooms
·
4 beds
·
1.5 bathrooms
8–13 Aug
|
More
8–13 Aug
|
More
4.98
(47 reviews)
₹97,148
Show price breakdown
₹97,148 for 5 nights
for 5 nights
Explore more homes
Top guest favourite
Guest favourite
Flat in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
1 king bed
1–6 Aug
1–6 Aug
₹87,703
Show price breakdown
₹87,703 for 5 nights
for 5 nights
5.0 out of 5 average rating, 117 reviews
5.0 (117)
Top guest favourite
Guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
2 beds
2 beds
26–31 Aug
26–31 Aug
₹65,652
Show price breakdown
₹65,652 for 5 nights
for 5 nights
4.98 out of 5 average rating, 167 reviews
4.98 (167)
Guest favourite
Guest favourite
Guest house in Chestertown
Cozy Carriage House
1 queen bed
1 queen bed
1–6 Aug
1–6 Aug
₹66,457
Show price breakdown
₹66,457 for 5 nights
for 5 nights
4.89 out of 5 average rating, 177 reviews
4.89 (177)
Top guest favourite
Guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
2 beds
1–6 Aug
1–6 Aug
₹1,15,997
Show price breakdown
₹1,15,997 for 5 nights
for 5 nights
4.98 out of 5 average rating, 99 reviews
4.98 (99)
Top guest favourite
Guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
2 beds
2 beds
4–9 Aug
4–9 Aug
₹71,390
Show price breakdown
₹71,390 for 5 nights
for 5 nights
4.92 out of 5 average rating, 154 reviews
4.92 (154)
Guest favourite
Guest favourite
Home in Chestertown
Charming Haven on High
3 beds
3 beds
1–6 Aug
1–6 Aug
₹1,07,237
Show price breakdown
₹1,07,237 for 5 nights
for 5 nights
4.97 out of 5 average rating, 32 reviews
4.97 (32)
Top guest favourite
Guest favourite
Flat in Chestertown
Private cozy cottage - center of Chestertown .
1 king bed
1 king bed
10–15 Aug
10–15 Aug
₹87,976
Show price breakdown
₹87,976 for 5 nights
for 5 nights
4.96 out of 5 average rating, 241 reviews
4.96 (241)
Guest favourite
Guest favourite
Home in Chestertown
River Cottage, Chestertown
2 queen beds
2 queen beds
1–6 Aug
1–6 Aug
₹1,22,844
Show price breakdown
₹1,22,844 for 5 nights
for 5 nights
4.94 out of 5 average rating, 32 reviews
4.94 (32)
144
Reviews
4.87
Stars
Rating
8
Years hosting
Room in Chestertown
Stay with Oksana
Stay with Oksana
Hosting for 8 years
,
·
Hosting for 8 years
Private Bedroom and bath in Chestertown, MD
1–6 Aug
1–6 Aug
₹43,298
Show price breakdown
₹43,298 for 5 nights
for 5 nights
4.87 out of 5 average rating, 144 reviews
4.87 (144)
Top guest favourite
Guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 queen beds
3 queen beds
23–28 Aug
23–28 Aug
₹1,05,324
Show price breakdown
₹1,05,324 for 5 nights
for 5 nights
4.97 out of 5 average rating, 135 reviews
4.97 (135)
Guest favourite
Guest favourite
Cottage in Centreville
Captain’s Quarters - Unique home on Corsica River!
2 beds
2 beds
3–8 Aug
3–8 Aug
₹93,140
Show price breakdown
₹93,140 for 5 nights
for 5 nights
4.94 out of 5 average rating, 48 reviews
4.94 (48)
Top guest favourite
Guest favourite
Home in Chestertown
The Portside Manor - Queen Street Chestertown
4 beds
4 beds
3–8 Aug
3–8 Aug
₹1,99,370
Show price breakdown
₹1,99,370 for 5 nights
for 5 nights
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Top guest favourite
Guest favourite
Home in Chestertown
Magnolia House: walk to shops, restaurants, river
4 beds
4 beds
1–6 Aug
1–6 Aug
₹1,43,989
Show price breakdown
₹1,43,989 for 5 nights
for 5 nights
5.0 out of 5 average rating, 44 reviews
5.0 (44)
Guest favourite
Guest favourite
50
Reviews
4.86
Stars
Rating
6
Years hosting
Room in Still Pond
Stay with Nancy
Stay with Nancy
Hosting for 6 years
,
·
Hosting for 6 years
Room 2 Civil War Era House
1–6 Aug
1–6 Aug
₹48,836
Show price breakdown
₹48,836 for 5 nights
for 5 nights
4.86 out of 5 average rating, 50 reviews
4.86 (50)
Top guest favourite
Guest favourite
Home in Chestertown
Entire River Front Home - 4 Bedrooms 4.5 Baths
5 beds
5 beds
2–7 Aug
2–7 Aug
₹2,76,902
Show price breakdown
₹2,76,902 for 5 nights
for 5 nights
4.99 out of 5 average rating, 108 reviews
4.99 (108)
Guest favourite
Guest favourite
Home in Chestertown
River front cottage with private dock & water fun
11 beds
11 beds
9–14 Sept
9–14 Sept
₹2,42,667
Show price breakdown
₹2,42,667 for 5 nights
for 5 nights
4.97 out of 5 average rating, 91 reviews
4.97 (91)
Top guest favourite
Guest favourite
Home in Betterton
Grandma’s Cottage
4 beds
4 beds
4–9 Aug
4–9 Aug
₹1,00,692
Show price breakdown
₹1,00,692 for 5 nights
for 5 nights
5.0 out of 5 average rating, 7 reviews
5.0 (7)
Guest favourite
Guest favourite
Home in Chestertown
Waterfront w/ Hot Tub + Dock | Harbor View Haven
6 beds
6 beds
25–30 Aug
25–30 Aug
₹2,15,984
Show price breakdown
₹2,15,984 for 5 nights
for 5 nights
4.95 out of 5 average rating, 77 reviews
4.95 (77)
1
2
3
4
…
15