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Featured Cottages in Chestertown

Our top choices for Chestertown cottages

The Heron's Nest at Atlantic Marina

9.8 out of 10, Exceptional, (305)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (104)
"Secluded"
Secluded Waterfront Cottage on 200 acre farm near Queenstown

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

9.8 out of 10, Exceptional, (118)
"Great property to relax and stroll around town"
Peaceful getaway convenient to local amenities including beach, boating & food

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is NZ$1,118
includes taxes & fees
22 Sept - 23 Sept
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Beachfront Home Minutes to Downtown Annapolis Dogs OK

9.8 out of 10, Exceptional, (36)
"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. "
Beachfront Home Minutes to Downtown Annapolis Dogs OK

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

Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills

9.0 out of 10, Wonderful, (2)
"This cottage was a great place to stay. It had everything needed for a comfortable stay. "
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills

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 NZ$1,248
includes taxes & fees
21 Sept - 22 Sept
Secluded Cozy Cottage in Historic Downtown

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

2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
The price is NZ$1,594
includes taxes & fees
21 Sept - 22 Sept
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

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

10.0 out of 10, Exceptional, (94)
"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!

Waterfront River Cottage for 2, dog-friendly

9.2 out of 10, Wonderful, (7)
"Great little spot in a private location but close to everything. Super clean and comfy!"
Waterfront River Cottage for 2, dog-friendly

House w/Water Views of Rock Creek 2BA 2BA Cottage

10.0 out of 10, Exceptional, (30)
"Perfect location, we were in town for birthdays and a wedding shower. Short drive to our favorite spots, Two Rivers, Primos & Seaside for steamed crabs. House has everything you need. Will return on our future visits to the Dena. "
House w/Water Views of Rock Creek 2BA 2BA Cottage

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

10.0 out of 10, Exceptional, (54)
"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!

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

10.0 out of 10, Exceptional, (52)
"My wife and I have stayed at many different places over the years but this may be one of the most well maintained properties I've ever seen. It was a great place for us to unwind with our dog and we would certainly recommend this location for anyone looking to stay in the area"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (56)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Charming cottage with Pool Access and WiFi in lovely Rock Hall

10.0 out of 10, Exceptional, (3)
"Wonderful 2 night stay at this charming cottage in Rock Hall. We would definitely recommend. "
Charming cottage with Pool Access and WiFi in lovely Rock Hall

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (137)
"A perfect stay, as always :) House was impeccably clean, well stocked, and the location can't be beat!"
Eastern Shore beach cottage get-away

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is NZ$795
includes taxes & fees
22 Sept - 23 Sept
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Eastern shore beachfront cottage with stunning sunset views!

10.0 out of 10, Exceptional, (2)
"Our family had a great time at the cottage. It is very well appointed and a great place to connect with family. They kayaks were fun to use and we caught a catfish right from the bank. "
Eastern shore beachfront cottage with stunning sunset views!
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

Find out more about Chestertown

Find out more about Chestertown

Chestertown Cottages information

Number of reviews
945
Accommodation
57 Cottages
Lowest Price
NZ$795
Highest Price
NZ$1,248

Frequently asked questions

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.