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Search Chestertown Cottages

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Cottages in Chestertown

House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
Rosedale
10.0 out of 10, Exceptional, (1)
$399 nightly
The price is $460
Nov 16 - Nov 17
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Exterior
Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug

Betterton
$395 nightly
The price is $419
Nov 17 - Nov 18
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
United States
Sharon M.
$792 nightly
The price is $874
Dec 1 - Dec 2
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Outdoor dining
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
$579 nightly
The price is $660
Nov 17 - Nov 18
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Exterior detail
Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown

Historic District
9.6 out of 10, Exceptional, (15)
"We had a very lovely stay . This is an excellent location . "
United States
Kimberly B.
$702 nightly
The price is $800
Nov 16 - Nov 17
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Very clean hotel. Perfect if you have to do work at Washington College"
Ada 1-night trip
Posted 1 day ago
Comfort Inn & Suites Chestertown

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
15
Accommodation
58 Cottages
Lowest Price
$419
Highest Price
$874

Frequently asked questions

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What is there to do in Chestertown near my cottage?
If you'd like to fill up your itinerary in Chestertown, find your way to Rolphs Wharf Marina. It's a winner with locals and tourists alike.

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