Search results; 473 homes in Chestertown

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Guest favourite
Home in Chestertown
Goose Haven, new waterfront house on Fairlee Creek
12 guests4 bedrooms10 beds3 bathrooms
19–24 Sept
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19–24 Sept
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₹2,24,941 for 5 nights

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Top guest favourite
Flat in Chestertown
Chestertown Private cottage with NFL Sun Ticket
1 king bed
29 Sept – 4 Oct
₹80,286 for 5 nights
4.96 out of 5 average rating, 247 reviews
Guest favourite
Home in Chestertown
Charming Haven on High
3 beds
21–26 Sept
₹88,443 for 5 nights
4.92 out of 5 average rating, 37 reviews
Top guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
3 queen beds
19–24 Sept
₹1,04,199 for 5 nights
4.97 out of 5 average rating, 141 reviews
Top guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
3 beds
21–26 Sept
₹56,236 for 5 nights
4.99 out of 5 average rating, 105 reviews
Top guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
21–26 Sept
₹95,089 for 5 nights
4.98 out of 5 average rating, 106 reviews
Top guest favourite
Casa particular in Chestertown
Red, White & Waterview Studio Apt with pool
2 beds
21–26 Sept
₹63,904 for 5 nights
4.93 out of 5 average rating, 161 reviews
Top guest favourite
Home in Chestertown
High Tide & Hound
3 beds
19–24 Oct
₹84,353 for 5 nights
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
2 beds
5–10 Nov
₹63,904 for 5 nights
4.98 out of 5 average rating, 175 reviews
Top guest favourite
Home in Chestertown
Historic home near town center with NFL Sun Ticket
5 beds
28 Sept – 3 Oct
₹1,89,472 for 5 nights
5.0 out of 5 average rating, 208 reviews
Top guest favourite
Home in Chestertown
Relaxing Waterfront - Golf Course & Sunset Views
6 beds
21–26 Sept
₹1,46,417 for 5 nights
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
2 beds
12–17 Nov
₹71,675 for 5 nights
4.99 out of 5 average rating, 236 reviews
Top guest favourite
Flat in Chestertown
Waterfront historic district 1BR Apartment
1 king bed
10–15 Nov
₹83,331 for 5 nights
5.0 out of 5 average rating, 122 reviews
Guest favourite
Room in Chestertown
Stay with OksanaHosting for 8 years,
Private Bedroom and bath in Chestertown, MD
21–26 Sept
₹43,966 for 5 nights
4.87 out of 5 average rating, 146 reviews
Top guest favourite
Room in Grasonville
Stay with CaraDoula, clc,
Bay Bridge Retreat - 8 mins from the Bridge
21–26 Sept
₹44,477 for 5 nights
4.98 out of 5 average rating, 124 reviews
Guest favourite
Guest house in Rock Hall
Carriage House
2 beds
21–26 Sept
₹86,398 for 5 nights
4.93 out of 5 average rating, 54 reviews
Top guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
2 beds
21–26 Sept
₹1,01,735 for 5 nights
4.98 out of 5 average rating, 42 reviews
Top guest favourite
Home in Chestertown
NEW Chestertown Retreat
4 beds
30 Sept – 5 Oct
₹1,28,094 for 5 nights
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Rock Hall
Traveler Guest Suite - Cinnamon By The Bay
1 bed
28 Sept – 3 Oct
₹69,016 for 5 nights
4.97 out of 5 average rating, 34 reviews