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Check prices for these dates

In two weeks
5 Sep - 7 Sep
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Cottages in Chestertown

Our top choices for Chestertown cottages

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Exterior

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

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, summer fun!
The Heron's Nest at Atlantic Marina
Exterior

The Heron's Nest at Atlantic Marina

9.8 out of 10, Exceptional, (302)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Fridge, microwave, oven, stovetop

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
Eastern Shore beach cottage get-away
Sun loungers

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (136)
"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
Eastern shore beachfront cottage with stunning sunset views!
Interior

Eastern shore beachfront cottage with stunning sunset views!

10.0 out of 10, Exceptional, (1)
"Check in was a breeze. Place was clean. Simply beautiful. Most relaxing place ever. "
Eastern shore beachfront cottage with stunning sunset views!
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Interior

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

10.0 out of 10, Exceptional, (51)
"Beautiful home with LOTS of attention to detail. The backyard was a beautiful oasis and we LOVED the “swing bed” on the screened-in porch. Mark and Karen add lots of fine touches to make your stay special. Plenty of room for two, cozy for four, and comfortable for four legged friends with the fenced in back yard. Quiet and private with a short 10 minute drive to town. Can’t wait to return!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books

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 SAR 1,876
SAR 3,033 total
includes taxes & fees
24 Aug - 25 Aug
Secluded Cozy Cottage in Historic Downtown
Chesapeake Cottage
1 bedroom, iron/ironing board, WiFi, bed sheets

Chesapeake Cottage

10.0 out of 10, Exceptional, (2)
"Outstanding accommodations in an extraordinary neighborhood!! Many near by options for dining and outdoor activities!! Highly recommended!! "
Chesapeake Cottage
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
On the beach, sun loungers, beach towels

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
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, (116)
"Great location and local restaurants. Perfect side for small group to do paper crafting. Would definitely book this place again. "
Peaceful getaway convenient to local amenities including beach, boating & food
Rock Creek Cottage, Waterfront, Serene Views
Terrace/patio

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (6)
"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
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds

Chesapeake Cottages- 2 Quaint Waterfront Retreats

9.6 out of 10, Exceptional, (22)
"Excellent Property"
The price is SAR 1,351
SAR 2,494 total
includes taxes & fees
25 Aug - 26 Aug
Chesapeake Cottages- 2 Quaint Waterfront Retreats
2 Mi to Sandy Point State Park: Home w/ Deck!
Interior

2 Mi to Sandy Point State Park: Home w/ Deck!

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was clean and nice. The beds choices were comfortable and keyless checkin was convenient. "
2 Mi to Sandy Point State Park: Home w/ Deck!
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, (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
Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games
Interior

Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games

10.0 out of 10, Exceptional, (85)
"Nice small property. Great for get aways and amazing service."
Your Annapolis Waterfront retreat - a short walk to Navy Football Home Games
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
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
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Exterior detail

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

10.0 out of 10, Exceptional, (11)
"We really enjoyed our long weekend at The Oyster Cottage. We needed some rest and relaxation and this cottage was perfect. Very well maintained and stocked! "
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"There were no ghosts!"
judith 1-night trip
Posted 19 hours ago
Historic Inns of Annapolis

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