Photo by Assya A

Search Chestertown Cottage Accommodations

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Sept - 21 Sept
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Featured Cottages in Chestertown

Our top choices for Chestertown cottages

The Heron's Nest at Atlantic Marina
Terrace/patio

The Heron's Nest at Atlantic Marina

9.8 out of 10, Exceptional, (304)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Exterior

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (103)
"Secluded"
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Peaceful getaway convenient to local amenities including beach, boating & food
Exterior

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (117)
"Loved the location, the house, the furnishings, and the cool coastal decor! The kitchen was great for cooking breakfast and dinner before races!"
Peaceful getaway convenient to local amenities including beach, boating & food
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Outdoor dining

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is AU$1,027
includes taxes & fees
8 Sept - 9 Sept
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Thanksgiving!
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Thanksgiving!

10.0 out of 10, Exceptional, (93)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Thanksgiving!
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Outdoor pool

Charming cottage with Pool Access and WiFi in lovely Rock Hall

10.0 out of 10, Exceptional, (2)
"Adorable little cottage and amenities. Owners very nice. Perfect little getaway. "
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Eastern Shore beach cottage get-away
Exterior

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (137)
"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"
Eastern Shore beach cottage get-away
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
Exterior

Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

9.8 out of 10, Exceptional, (34)
"We wanted to celebrate my wife’s birthday with some friends, and a bushel of crabs…and what an incredible house to host a special occasion. The kids had the water/mini beach and plenty of yard space to play; there was a space outside to eat the crabs; and the house was incredibly clean and inviting. "
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
Chesapeake Cottage
Exterior

Chesapeake Cottage

10.0 out of 10, Exceptional, (3)
"Outstanding accommodations in an extraordinary neighborhood!! Many near by options for dining and outdoor activities!! Highly recommended!! "
Chesapeake Cottage
Rock Creek Cottage, Waterfront, Serene Views
Terrace/patio

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (7)
"My husband and I enjoyed our stay. The property was actually quite beautiful. The view was lovely as the home sits on a creek. The home provided everything we needed. Shopping and restaurants were very close. If you need to be in the Baltimore/Annapolis area as we had, this property is perfect."
Rock Creek Cottage, Waterfront, Serene Views
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Exterior

Rare find! Chic cottage, salt water heated pool May 15-Oct15.

10.0 out of 10, Exceptional, (53)
"We stayed at the cottage for a week in late July and could not have been happier! Beautiful house, lots of room to spread out, well appointed kitchen and comfortable beds and furniture. The back yard was paradise with several different sitting areas, plenty of toys for the pool and room to play. The entire family loved the pool as we swam at least once a day the entire week. Location was perfect for day trips to DC, less than an hour each way. Local restaurants were excellent and downtown...
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Cozy, unique, historic registered cottage on the Corsica River!
Exterior

Cozy, unique, historic registered cottage on the Corsica River!

10.0 out of 10, Exceptional, (5)
"Lovely property, cool history beautiful decor"
Cozy, unique, historic registered cottage on the Corsica River!
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Exterior

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (52)
"This exceptional property was our best homestay experience yet across several states and countries. The unit has so many customized features that make it stand out, from the fire pit (fire already built) and sauna (water bucket already filled) to the kitchen and bedrooms, where no detail has been missed. The owners were extremely proactive and responsive throughout our stay, and we look forward to booking again soon. "
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Outdoor dining

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Secluded Cozy Cottage in Historic Downtown
Exterior detail

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (13)
"We had a very lovely stay . This is an excellent location . "
The price is AU$1,236
includes taxes & fees
7 Sept - 8 Sept
Secluded Cozy Cottage in Historic Downtown
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
House (3 Bedrooms) | Interior

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is AU$723
includes taxes & fees
8 Sept - 9 Sept
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Eastern shore beachfront cottage with stunning sunset views!
Interior

Eastern shore beachfront cottage with stunning sunset views!

10.0 out of 10, Exceptional, (2)
"Check in was a breeze. Place was clean. Simply beautiful. Most relaxing place ever. "
Eastern shore beachfront cottage with stunning sunset views!
Waterfront Annapolis Home: Fire Pit & Fishing Pier
House (3 Bedrooms) | Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
13 Mi to Downtown Baltimore: Quiet Home w/ Porch
House (2 Bedrooms) | Interior

13 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
13 Mi to Downtown Baltimore: Quiet Home w/ Porch
Grasonville Home w/ Private Pool on the Water
Interior

Grasonville Home w/ Private Pool on the Water

3.0 star property
Grasonville Home w/ Private Pool on the Water
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Find out more about Chestertown

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
Accommodation
58 Cottages
Lowest Price
AU$723
Highest Price
AU$1,236

Frequently asked questions

What is there to do in Chestertown near my cottage?
The ideal travel accessory is a well-planned itinerary. Historical Society of Kent County Maryland is an excellent place to start your exploration of Chestertown.