An aerial view of a town with a river, buildings, and surrounding greenery.

Search Chestertown Cottages

Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Chestertown cottages

House (3 Bedrooms) | Interior

1. Idyllic Pasadena Retreat With Garden + Hot Tub!

Idyllic Pasadena Retreat With Garden + Hot Tub!
3.0 star property
Green Haven
$426 nightly
The price is $485
Oct 8 - Oct 9
Total with taxes and fees
Idyllic Pasadena Retreat With Garden + Hot Tub!
Outdoor dining

2. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
$552 nightly
The price is $629
Sep 21 - Sep 22
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Exterior

3. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (93 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
$433 nightly
The price is $487
Oct 5 - Oct 6
Total with taxes and fees
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
Marina

4. Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (22 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
$760 nightly
The price is $866
Sep 20 - Sep 21
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
House (3 Bedrooms) | Interior

5. Lakefront Home Firepit BWI Marleycreek River

Lakefront Home Firepit BWI Marleycreek River
3.0 star property
Marley
$270 nightly
The price is $308
Sep 21 - Sep 22
Total with taxes and fees
Lakefront Home Firepit BWI Marleycreek River
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
"Quiet and clean."
Darryl 1-night trip
Posted 4 hours ago
Comfort Inn & Suites Chestertown

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
Accommodation
63 Cottages
Lowest Price
$308
Highest Price
$485

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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