A coastal town with a marina, a bridge, and a highway.

Cottages in Kent County

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Top Cities in Kent County

An aerial view of a town with a river, buildings, and surrounding greenery.
CottagesCottages

Chestertown

Chestertown

Our top choices for Kent County cottages

Exterior

1. The Heron's Nest at Atlantic Marina

The Heron's Nest at Atlantic Marina
Pasadena
9.8 out of 10, Exceptional, (318 reviews)
"Lovely cottage on the water. The sunrise and sunsets were gorgeous. They have a pool, playground and picnic tables to enjoy. "
United States
Robert W.
The Heron's Nest at Atlantic Marina
Exterior

2. Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
Annapolis
9.8 out of 10, Exceptional, (44 reviews)
"Very nice property, everything was as expected and the entire process was easy. Great, quiet spot to enjoy the Bay close to everything fun in Annapolis. I’d go back."
United States
Brian R.
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
Exterior

3. 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, (137 reviews)
"Fantastic location, the host was quick to respond to questions. Would book again."
United States
Jim K.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Exterior

4. Waterfront Cottage on the C&D Canal!

Waterfront Cottage on the C&D Canal!
Chesapeake City
8.6 out of 10, Excellent, (7 reviews)
"Fantastic location "
United States
Anonymous traveler
Waterfront Cottage on the C&D Canal!
Property grounds

5. 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
10.0 out of 10, Exceptional, (21 reviews)
"Very cute and relaxing cottage. We loved it!"
United States
Kristin H.
Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland
Outdoor dining

6. 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, (70 reviews)
"The cottage is immaculate and comfortable and offers a partial view of the water from the back deck and the kitchen. A very short stroll a block down the street leads to a beautiful full view of the water, amazing sunsets, the turkey point lighthouse and soaring eagles. "
United States
cynthia k.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Exterior

7. 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, (208 reviews)
"Really nice cottage in the middle of everything. Loved the screened in porch and large den."
United States
greg b.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

8. 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, (231 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

9. Charming Cottage - Northeast River / Chesapeake Bay

Charming Cottage - Northeast River / Chesapeake Bay
Perryville
10.0 out of 10, Exceptional, (5 reviews)
"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

10. The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek
Hillsmere
10.0 out of 10, Exceptional, (179 reviews)
"We had a great time and really enjoyed the cottage."
United States
Craig M.
The Yellow Cottage on Harness Creek
Exterior

11. Waterfront Annapolis Cottage: Fire Pit & Pier

Waterfront Annapolis Cottage: Fire Pit & Pier
Annapolis
9.4 out of 10, Exceptional, (45 reviews)
"The place worked well for us. It must be a great place in the warmer months."
United States
John R.
Waterfront Annapolis Cottage: Fire Pit & Pier
Property grounds

12. Waterfront Home, Private Dock, A/C, Amazing Views, Boating, Fishing & Kayaking

Waterfront Home, Private Dock, A/C, Amazing Views, Boating, Fishing & Kayaking
North East
10.0 out of 10, Exceptional, (34 reviews)
"This is definitely a home away from home for us. The hosts were great to work with and the house was stocked with all the things we needed. Thus a definite home to revisit"
United States
Debbie M.
Waterfront Home, Private Dock, A/C, Amazing Views, Boating, Fishing & Kayaking
Outdoor dining

13. Be persuaded to experience this vintage cottage by the Sassa

Be persuaded to experience this vintage cottage by the Sassa
Galena
9.4 out of 10, Exceptional, (14 reviews)
"Had a lovely peaceful stay. Great amenities."
United States
Joe S.
Be persuaded to experience this vintage cottage by the Sassa
Exterior

14. Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Bozman
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful, private setting, but not far from the town of St. Michaels. House was very clean and beds were comfy. The kitchen was very well equipped for preparing meals. We really enjoyed relaxing in the screened in porch and on the Adirondack chairs overlooking the water. There was so much wildlife to view: bald eagles, herons, tree frogs, crabs…We had a great time! Thank you!"
United States
Melissa B.
Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Exterior

15. Ruscincy’s Rest "minutes drive to Orioles stadium"

Ruscincy’s Rest "minutes drive to Orioles stadium"
Arcadia
10.0 out of 10, Exceptional, (2 reviews)
"Host went above the above and beyond bench mark. Extremely pleasant stay"
United States
Stephen R.
Ruscincy’s Rest "minutes drive to Orioles stadium"
Exterior

16. 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, (132 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

17. Eastern Shore beach cottage get-away

Eastern Shore beach cottage get-away
Rock Hall
10.0 out of 10, Exceptional, (141 reviews)
"Great time, great property!"
United States
Madeline C.
Eastern Shore beach cottage get-away
Exterior

18. Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (254 reviews)
"The place was very clean and comfortable. Loved the view. Would definitely stay again."
United States
Susan E.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

19. 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
9.8 out of 10, Exceptional, (51 reviews)
"Very unique and cozy property close to everything we needed. "
United States
John H.
The price is AED 645
AED 777 total
includes taxes & fees
17 Aug - 18 Aug
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Exterior

20. Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.

Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.
West Annapolis
10.0 out of 10, Exceptional, (93 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
Your Annapolis Waterfront retreat for a weekend or any-day getaway!<br>Great lodging for Plebe Parent's Weekend - and all your USNA activities.
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

10/10 Excellent
"The Graduate was extremely convenient to stay. Our son just completed Plebe summer and it was close to the Academy. Parking was included and easy to get in and out of. We had the Presidential Suite, with living room and a deck. We were able to let him relax.. The room was very clean, quiet and the staff was very helpful. It is a short walk or take the shuttle to the City Dock. I would stay there again in a second"
David 3-night trip
Posted 6 hours ago
Graduate by Hilton Annapolis

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