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Homes in Chestertown MD US
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Search results; 399 places in Chestertown
399 places in Chestertown
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The home you selected
Guest favourite
Guest favourite
Home in Chestertown
Entire River Front Home - 4 Bedrooms 4.5 Baths
10 guests
·
4 bedrooms
·
5 beds
·
4 bathrooms
16–21 Jun
|
More
16–21 Jun
|
More
4.99
(107 reviews)
₹2,74,384
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₹2,74,384 for 5 nights
for 5 nights
Explore more homes
Top guest favourite
Guest favourite
Home in Chestertown
High Tide & Hound
Free cancellation
Free cancellation
5–10 Jul
5–10 Jul
₹90,398
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₹90,398 for 5 nights
for 5 nights
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Top guest favourite
Guest favourite
Flat in Chestertown
Bright, new apartment in the heart of Chestertown
2 beds
2 beds
10–15 Jun
10–15 Jun
₹1,14,741
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₹1,14,741 for 5 nights
for 5 nights
4.98 out of 5 average rating, 92 reviews
4.98 (92)
Top guest favourite
Guest favourite
Guest suite in Chestertown
House On The Hill - Historic Private Second Floor
Free cancellation
Free cancellation
13–18 Jul
13–18 Jul
₹56,673
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₹56,673 for 5 nights
for 5 nights
4.99 out of 5 average rating, 94 reviews
4.99 (94)
Superhost
Superhost
Guest house in Chestertown
Cozy Carriage House
Free cancellation
Free cancellation
30 Jun – 5 Jul
30 Jun – 5 Jul
₹50,885
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₹50,885 for 5 nights
for 5 nights
4.88 out of 5 average rating, 172 reviews
4.88 (172)
Top guest favourite
Guest favourite
Home in Chestertown
Cozy 3-bedroom home w/ Hot tub & firepit
Free cancellation
Free cancellation
26–31 Jul
26–31 Jul
₹1,06,661
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₹1,06,661 for 5 nights
for 5 nights
4.97 out of 5 average rating, 128 reviews
4.97 (128)
Top guest favourite
Guest favourite
Flat in Chestertown
Private cozy cottage - center of Chestertown .
Free cancellation
Free cancellation
27 Jul – 1 Aug
27 Jul – 1 Aug
₹72,860
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₹72,860 for 5 nights
for 5 nights
4.97 out of 5 average rating, 232 reviews
4.97 (232)
Top guest favourite
Guest favourite
Guest suite in Chestertown
Chestertown - Eastern Shore Getaway
Free cancellation
Free cancellation
19–24 Jul
19–24 Jul
₹63,458
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₹63,458 for 5 nights
for 5 nights
4.98 out of 5 average rating, 163 reviews
4.98 (163)
Guest favourite
Guest favourite
Home in Chestertown
Charming Haven on High
Free cancellation
Free cancellation
22–27 Jun
22–27 Jun
₹91,295
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₹91,295 for 5 nights
for 5 nights
4.96 out of 5 average rating, 24 reviews
4.96 (24)
Top guest favourite
Guest favourite
Flat in Chestertown
Waterfront historic district 1BR Apartment
Free cancellation
Free cancellation
20–25 Jun
20–25 Jun
₹86,905
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₹86,905 for 5 nights
for 5 nights
5.0 out of 5 average rating, 109 reviews
5.0 (109)
Top guest favourite
Guest favourite
Guest house in Chestertown
Owl Cottage - Cozy, Private & Walkable to Town
Free cancellation
Free cancellation
25–30 Jun
25–30 Jun
₹1,04,466
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₹1,04,466 for 5 nights
for 5 nights
5.0 out of 5 average rating, 28 reviews
5.0 (28)
Top guest favourite
Guest favourite
Home in Chestertown
2 Beds, 2.5 Baths - Perfect Downtown Location
Free cancellation
Free cancellation
3–8 Aug
3–8 Aug
₹1,02,170
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₹1,02,170 for 5 nights
for 5 nights
4.97 out of 5 average rating, 89 reviews
4.97 (89)
Guest favourite
Guest favourite
Home in Chestertown
Holiday Escape to the Riverside
8 beds
8 beds
11–16 Jun
11–16 Jun
₹1,86,581
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₹1,86,581 for 5 nights
for 5 nights
5.0 out of 5 average rating, 18 reviews
5.0 (18)
Top guest favourite
Guest favourite
Home in Chestertown
Totally Renovated historic house near town center
Free cancellation
Free cancellation
15–20 Jun
15–20 Jun
₹1,79,151
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₹1,79,151 for 5 nights
for 5 nights
5.0 out of 5 average rating, 197 reviews
5.0 (197)
Top guest favourite
Guest favourite
Loft in Chestertown
Loft at Fountain Park - Prime Downtown Location
5 beds
5 beds
14–19 Jun
14–19 Jun
₹1,12,147
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₹1,12,147 for 5 nights
for 5 nights
4.91 out of 5 average rating, 53 reviews
4.91 (53)
Guest favourite
Guest favourite
Home in Chestertown
NEW Chestertown Retreat
4 beds
4 beds
11–16 Jun
11–16 Jun
₹1,24,719
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₹1,24,719 for 5 nights
for 5 nights
4.98 out of 5 average rating, 43 reviews
4.98 (43)
Top guest favourite
Guest favourite
Apartment in Chestertown
Historic Loft w/ Park View & Spa Access
2 queen beds
2 queen beds
13–18 Jun
13–18 Jun
₹1,47,668
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₹1,47,668 for 5 nights
for 5 nights
5.0 out of 5 average rating, 23 reviews
5.0 (23)
Top guest favourite
Guest favourite
Guest suite in Chestertown
Beautiful Waterfront Chestertown Getaway
Free cancellation
Free cancellation
11–16 Aug
11–16 Aug
₹78,024
Show price breakdown
₹78,024 for 5 nights
for 5 nights
4.99 out of 5 average rating, 224 reviews
4.99 (224)
Top guest favourite
Guest favourite
Guest suite in Chestertown
Historic Downtown Garden Oasis with Private Patio
1 queen bed
1 queen bed
15–20 Jun
15–20 Jun
₹87,803
Show price breakdown
₹87,803 for 5 nights
for 5 nights
4.96 out of 5 average rating, 71 reviews
4.96 (71)
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