Cottages in Kent County

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Check prices for these dates

In two weeks
10 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

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

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, (198 reviews)
"Great property! The house has everything you'd need and the location couldnt be better. "
United States
Joe C.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Exterior

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Stevensville
10.0 out of 10, Exceptional, (62 reviews)
"great stay ! all needs where met . "
United States
randall j.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Exterior

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, (126 reviews)
"Ideal location to shops and attractions. Host very easy to reach. "
United States
Don N.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (240 reviews)
"A cozy cottage, definitely met our needs. Beautiful view!"
United States
Cynthia Louise C.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Outdoor dining

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Earleville
9.8 out of 10, Exceptional, (60 reviews)
"Great house and great location!"
United States
Andrew W.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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
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

Cottage downtown on a quiet street

Cottage downtown on a quiet street
Downtown St. Michaels
9.8 out of 10, Exceptional, (59 reviews)
"It's a very nice place and the location is great. Its not a professionally managed house which is fine, but we didn't know that going in. Everything is clean, but not professionally clean i.e. the sheets are clean but the mattress pad was not. I would stay there again."
United States
Casey G.
Cottage downtown on a quiet street
Exterior

The Cottage at Merryland Farm

The Cottage at Merryland Farm
Hydes
10.0 out of 10, Exceptional, (5 reviews)
"The location was great. Private and quiet. "
United States
Jeff S.
The Cottage at Merryland Farm
Property grounds

Firefly Cottage at the Cape, Community beach, spring adventures, fun, bookings.

Firefly Cottage at the Cape, Community beach, spring adventures, fun, bookings.
Cape Saint Claire
10.0 out of 10, Exceptional, (103 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, fun, bookings.
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, (40 reviews)
"Amazing property with tons of charm. A fantastic quick getaway but also we plan on coming back for a longer visit. "
United States
Kostas K.
The price is AED 645
AED 761 total
includes taxes & fees
29 Mar - 30 Mar
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Marina

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (17 reviews)
"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"
United States
Linda Q.
The price is AED 1,064
AED 1,984 total
includes taxes & fees
30 Mar - 31 Mar
Secluded Cozy Cottage in Historic Downtown
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
9.4 out of 10, Exceptional, (130 reviews)
"Beautiful little cottage! Location is perfect."
United States
John B.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds

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
Exterior

The Heron's Nest at Atlantic Marina

The Heron's Nest at Atlantic Marina
Pasadena
9.8 out of 10, Exceptional, (312 reviews)
"Great location and charming place. "
United States
Anita B.
The Heron's Nest at Atlantic Marina
Exterior

Your Annapolis Waterfront retreat - ready for a winter getaway!

Your Annapolis Waterfront retreat - ready for a winter getaway!
West Annapolis
10.0 out of 10, Exceptional, (89 reviews)
"Great location and a beautiful place, thanks Jim. "
United States
Michael M.
Your Annapolis Waterfront retreat - ready for a winter getaway!
Exterior

Waterfront cottage in historic Charlestown, Maryland

Waterfront cottage in historic Charlestown, Maryland
Charlestown
9.8 out of 10, Exceptional, (10 reviews)
"Such a charming property and town. We loved everything about it!"
United States
Holly S.
Waterfront cottage in historic Charlestown, Maryland
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, (43 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.
Interior

Pet Friendly Water View Cottage

Pet Friendly Water View Cottage
Pasadena
10.0 out of 10, Exceptional, (34 reviews)
"The host was very welcoming.We had everything we needed."
United States
Rhetta H.
Pet Friendly Water View Cottage
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4/10 Poor
"The hotel and room were very depressing. I would not go back to that hotel. The staff were nice. The parking attendant was very nice man. "
Aida 1-night trip
Posted 1 hour ago
Graduate by Hilton Annapolis