Cottages in Kent County

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sep - 6 Sep

Top Cities in Kent County

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA
CottagesCottages

Chestertown

Chestertown

Our top choices for Kent County cottages

Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (243 reviews)
"A cozy cottage, definitely met our needs. Beautiful view!"
United States
Cynthia Louise C.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Property grounds

Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland

Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland
Charlestown
9.8 out of 10, Exceptional, (6 reviews)
"Clean and has everything you need. Awesome location!"
United States
Scott L.
Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland
Exterior

The Heron's Nest at Atlantic Marina

The Heron's Nest at Atlantic Marina
Pasadena
9.8 out of 10, Exceptional, (313 reviews)
"Great location and charming place. "
United States
Anita B.
The Heron's Nest at Atlantic Marina
Exterior

Secluded Waterfront Cottage on 200 acre farm near Queenstown

Secluded Waterfront Cottage on 200 acre farm near Queenstown
Centreville
10.0 out of 10, Exceptional, (105 reviews)
"Great stay!"
United States
Scott L.
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Exterior

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
10.0 out of 10, Exceptional, (42 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is AED 645
AED 765 total
includes taxes & fees
13 May - 14 May
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Exterior

Charming Cottage - Northeast River / Chesapeake Bay

Charming Cottage - Northeast River / Chesapeake Bay
Perryville
10.0 out of 10, Exceptional, (1 review)
"Beautiful sunrises. Quiet spot on the water. Enjoyed the area and being close to Havre de Grace and Aberdeen. "
United States
Rachel M.
Charming Cottage - Northeast River / Chesapeake Bay
Exterior

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Downtown St. Michaels
9.6 out of 10, Exceptional, (131 reviews)
"Our dog was so comfortable and welcome at this rental!"
United States
Kathie F.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Exterior

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Downtown St. Michaels
9.8 out of 10, Exceptional, (202 reviews)
"Perfect house close to St Michael’s attractions"
United States
Carolyn E.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Property grounds

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Downtown St. Michaels
9.6 out of 10, Exceptional, (127 reviews)
"We had a great time. The house was so charming and the location was perfect. Can't wait to go back!"
United States
Anonymous traveler
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Exterior

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
West River
9.8 out of 10, Exceptional, (45 reviews)
"This was such a beautiful property right on the water! It was everything I wanted for a quiet weekend away. The host was quick to respond and full of great recommendations. I am definitely planning on staying here again and will recommend it to anyone else 10/10"
United States
Meghan G.
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Exterior

Beachfront Home Minutes to Downtown Annapolis Dogs OK

Beachfront Home Minutes to Downtown Annapolis Dogs OK
Annapolis
9.8 out of 10, Exceptional, (40 reviews)
"Excellent location for a relaxing weekend with our dogs and midshipman! "
United States
Celine D.
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Exterior

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

Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall
9.8 out of 10, Exceptional, (119 reviews)
"Great place, calming vibe, located in the middle of everything you may need. "
United States
Kim
Peaceful getaway convenient to local amenities including beach, boating & food
Outdoor dining

Be persuaded to experience this vintage cottage by the Sassa

Be persuaded to experience this vintage cottage by the Sassa
Galena
9.2 out of 10, Wonderful, (11 reviews)
"We had a nice stay! The house had everything we needed and was comfortable for our trip. Overall the place was in good shape and worked well for us."
United States
Kristen P.
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Edgewater
10.0 out of 10, Exceptional, (225 reviews)
"Awesome location and very nice, we had a great stay! "
United States
Megan B.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Property grounds

Charming Waterfront Cottage with Private Boat Dock

Charming Waterfront Cottage with Private Boat Dock
North East
10.0 out of 10, Exceptional, (23 reviews)
"Was an adorable little cottage with amazing views amazing property grounds everything you needed was there highly recommend it"
United States
Iisa K.
Charming Waterfront Cottage with Private Boat Dock
Property grounds

Quarry Landing - Center of Town & River View - 3 Bedroom

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (12 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is AED 631
AED 954 total
includes taxes & fees
13 May - 14 May
Quarry Landing - Center of Town & River View - 3 Bedroom
Property grounds

Firefly Cottage at the Cape, Community beach, spring adventures, hot tub, USNA

Firefly Cottage at the Cape, Community beach, spring adventures, hot tub, USNA
Cape Saint Claire
10.0 out of 10, Exceptional, (104 reviews)
"We love our stay at the Firefly Cottage, our home away from home. "
United States
Debbie Y.
Firefly Cottage at the Cape, Community beach, spring adventures, hot tub, USNA
Smart TV

Lovely 2-bedroom waterfront cottage in charming Wittman

Lovely 2-bedroom waterfront cottage in charming Wittman
Wittman
10.0 out of 10, Exceptional, (1 review)
"I recently stayed at this lovely VRBO, and it exceeded my expectations in every way. From the moment I walked in, the home felt incredibly cozy and welcoming. Everything was spotless—truly one of the cleanest vacation rentals I’ve stayed in—which immediately set the tone for a relaxing visit.The space itself is bright and airy, with plenty of natural light that makes the home feel open and refreshing throughout the day. It’s thoughtfully furnished and had everything I needed for a comfortable...
United States
Mario V.
Lovely 2-bedroom waterfront cottage in charming Wittman
Sun loungers

Eastern Shore beach cottage get-away

Eastern Shore beach cottage get-away
Rock Hall
10.0 out of 10, Exceptional, (139 reviews)
"Host seemed welcoming."
United States
Deborah G.
Eastern Shore beach cottage get-away
Exterior

The Cottage at Merryland Farm

The Cottage at Merryland Farm
Hydes
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful stay. The host was very accommodating and the house was so cozy."
United States
Marta B.
The Cottage at Merryland Farm
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 Kent County Hotel Reviews

SpringHill Suites by Marriott Baltimore Downtown Convention Center Area

SpringHill Suites by Marriott Baltimore Downtown Convention Center Area

10/10 Excellent
"Great location! Will be staying again when I return."
Dayonna 2-night trip
Posted 1 hour ago
SpringHill Suites by Marriott Baltimore Downtown Convention Center Area