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Search Cottages in Chestertown

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Check prices for these dates

Next weekend
9 Jum. I - 11 Jum. I
In two weeks
16 Jum. I - 18 Jum. I
In one month
30 Jum. I - 1 Jum. II
In two months
27 Jum. II - 29 Jum. II

Compare 54 Cottages in Chestertown with updated reviews, rates, and availability.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (47)
"We really enjoyed the water views & walking by the water. It was a very enjoyable and relaxing stay."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
On the beach, sun loungers, beach towels

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

9.8 out of 10, Exceptional, (29)
"Really like this place "
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Property grounds

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

10.0 out of 10, Exceptional, (25)
"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels

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

9.8 out of 10, Exceptional, (110)
"Bay Haven was in a great lication and property mananger was very responsive to al my questions. "
Peaceful getaway convenient to local amenities including beach, boating & food
Amazing views, short walks and quick access to USNA events/Commissioning Week and stadium.
View from property

Amazing views, short walks and quick access to USNA events/Commissioning Week and stadium.

10.0 out of 10, Exceptional, (80)
"Great spot, loved the place and the area. James was super helpful and seemed to want to do everything possible to make sure we had a great stay."
Amazing views, short walks and quick access to USNA events/Commissioning Week and stadium.
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun loungers, beach towels

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (97)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Terrace/patio

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (26)
"Great location and very clean property. Cyndi was responsive and a great host. Would definitely stay again."
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
The Heron's Nest at Atlantic Marina
Exterior

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (288)
"Great location, wonderful interactions with owners, beautiful scenery, and easy check-in"
The Heron's Nest at Atlantic Marina
Eastern Shore beach cottage get-away
Sun loungers

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (133)
"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
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
Exterior

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

10.0 out of 10, Exceptional, (86)
"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Property grounds

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

10.0 out of 10, Exceptional, (8)
"Easy and flexible check in, clean and comfortable in a great location. Darling home. "
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Waterfront River Cottage for 2, dog-friendly
On the beach

Waterfront River Cottage for 2, dog-friendly

9.2 out of 10, Wonderful, (7)
"It's a beautiful location and we enjoyed our visit."
Waterfront River Cottage for 2, dog-friendly
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

Be persuaded to experience this vintage cottage by the Sassa

9.4 out of 10, Exceptional, (8)
"Had a lovely peaceful stay. Great amenities."
Be persuaded to experience this vintage cottage by the Sassa
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
View from property

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

10.0 out of 10, Exceptional, (40)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Secluded Cozy Cottage in Historic Downtown
Terrace/patio

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (9)
"Perfect little cottage for 4 adults and an infant. Loved its location! "
The price is SAR 1,500
SAR 2,523 total
includes taxes & fees
5 May - 6 May
Secluded Cozy Cottage in Historic Downtown
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"10 family members from age 88 to 10 years old. It’s our 2nd visit and we’ve not been to any place more welcoming and peaceful. The location is just heaven and the docks and water views are just unbelievably gorgeous. It’s going to be an annual trip for our family."
The price is SAR 1,500
SAR 2,689 total
includes taxes & fees
5 May - 6 May
Chesapeake Cottages- 2 Quaint Waterfront Retreats
House w/Water Views of Rock Creek 2BA 2BA Cottage
Terrace/patio

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

10.0 out of 10, Exceptional, (26)
"Very quiet street, our stay was relaxing and just what we needed! "
House w/Water Views of Rock Creek 2BA 2BA Cottage
Cozy Cottage
Terrace/patio

Cozy Cottage

10.0 out of 10, Exceptional, (1)
"Lovely home with everything you need."
Cozy Cottage
Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach
Living area

Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach

The price is SAR 2,250
SAR 3,908 total
includes taxes & fees
1 Jun - 2 Jun
Charming Bay Ridge Cottage with Chesapeake Bay Views – Just Steps to the Beach
Rock Creek Cottage, Waterfront, Serene Views
Fridge, microwave, oven, stovetop

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (2)
"Absolutely amazing place for my husband and I to relax with our midshipmen. Very clean, beautifully decorated and the view on the dock each morning was stunning! Close to restaurants (loved 3 B’s Bakery) and host was awesome! "
Rock Creek Cottage, Waterfront, Serene 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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Other property types in Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Exterior

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (214)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.6 out of 10, Exceptional, (24)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
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.