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

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Top Cities in Kent County

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

Chestertown

Chestertown
A coastal landscape with a sandy beach, a rocky barrier, and a calm sea.
CottagesCottages

Rock Hall

Rock Hall

Our top choices for Kent County cottages

A small, single-story house with a green roof and a covered porch.

1. The Heron's Nest at Atlantic Marina

The Heron's Nest at Atlantic Marina
Pasadena
9.8 out of 10, Exceptional, (331 reviews)
"Perfect little cottage for our weekend getaway! We will definitely be back."
United States
Brian R.
The Heron's Nest at Atlantic Marina
A white colonial-style house with a brick chimney, a wooden picket fence, and a brick pathway leading to the entrance.

2. 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, (135 reviews)
"A beautiful, historic home perfectly situated in the heart of St. Michael’s."
United States
Laura C.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
A two-story house with a front porch, a small attached garage, and a picket fence.

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, (142 reviews)
"Great location in St Michaels at a fun historical house."
United States
Adam
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
A two-story house with a front porch and a small garden area.

4. 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, (45 reviews)
"Second year staying here and absolutely love this place! The private beach is fantastic for all our grandchildren to play and swim."
United States
Gregg L.
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly
A light blue house with a large glass front, a covered porch, and a small front yard with a picnic table set up.

5. Charming Cottage - Northeast River / Chesapeake Bay

Charming Cottage - Northeast River / Chesapeake Bay
Perryville
10.0 out of 10, Exceptional, (13 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
A wooden deck with benches overlooking a beach.

6. Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.

Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.
Cape Saint Claire
10.0 out of 10, Exceptional, (125 reviews)
"We stay here three times each year when we visit Annapolis. Great for a small family with a large back yard and many outdoor amenities."
United States
Nancy A.
Firefly Cottage at the Cape, Hot Tub, Community beach, Boat Show, USNA Football.
A two-story house with a brick roof, a front door, and a picket fence.

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, (212 reviews)
"Awesome place"
United States
John B.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
A white wooden house with a gabled roof, a front porch, and a small flag.

8. Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Downtown St. Michaels
9.6 out of 10, Exceptional, (153 reviews)
"Great house in town well furnished "
United States
Donna M.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
A small, single-story house with a front porch and a small garden area.

9. 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, (130 reviews)
"Very comfortable and cozy place. Great location!"
United States
Mary M.
Peaceful getaway convenient to local amenities including beach, boating & food
A wooden deck with a white railing overlooking a body of water, surrounded by trees.

10. Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Elkton
8.8 out of 10, Excellent, (16 reviews)
"Lovely place. We really enjoyed our stay"
United States
Renae R.
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
A wooden deck with a table and chairs, an umbrella, and a view of houses in the background.

11. 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, (72 reviews)
"The cottage was a great place to stay for a family as we were in the area for a wedding. Our kids really enjoyed the beach. Chris responded quickly via text when we were trying to find beach gear nearby."
United States
Nathan J.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
A wooden deck with outdoor seating, overlooking a lake with boats and a dock.

12. Life is better at the RIVER!--Cozy waterfront cottage

Life is better at the RIVER!--Cozy waterfront cottage
Galena
10.0 out of 10, Exceptional, (122 reviews)
"Absolutely perfect place to retreat. The house are genuinely loving, and it shows in every detail about the cottage."
United States
Katie S.
Life is better at the RIVER!--Cozy waterfront cottage
A gazebo with a view of a lake and park.

13. 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, (39 reviews)
"Cute little cottage on the creek of the North East River. Quiet neighborhood with a beautiful park across the street."
United States
Carol M.
Waterfront Home, Private Dock, A/C, Amazing Views, Boating, Fishing & Kayaking
A stone building with a sloped roof, a picnic table, and a lighthouse with black and white stripes.

14. 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, (57 reviews)
"Unique charming place to relax."
United States
Nimia N.
The price is CA $251
CA $301 total
includes taxes & fees
Oct 14 - Oct 15
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
A modern house with a dark roof, large windows, and a front porch with chairs.

15. 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, (74 reviews)
"An amazing house! Wonderful hosts who were very responsive and paid attention to every detail. Would definitely stay again! "
United States
maria T.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
A two-story house with a light blue exterior, a black roof, and a white fence. There is a lamp post and flowering plants in the front yard.

16. Waterfront Cottage on the C&D Canal!

Waterfront Cottage on the C&D Canal!
Chesapeake City
8.8 out of 10, Excellent, (10 reviews)
"Fantastic location "
United States
Anonymous traveller
Waterfront Cottage on the C&D Canal!
A two-story building with a covered outdoor area, a staircase, and trees with autumn leaves.

17. Your Annapolis Waterfront retreat for a weekend or any-day getaway!

Your Annapolis Waterfront retreat for a weekend or any-day getaway!
West Annapolis
10.0 out of 10, Exceptional, (94 reviews)
"Lovely location and Jim was very helpful all the way around!"
United States
Jill R.
The price is CA $409
CA $616 total
includes taxes & fees
Nov 5 - Nov 6
Your Annapolis Waterfront retreat for a weekend or any-day getaway!
A two-story house with a front porch, a chimney, and a small garden area.

18. Waterfront Annapolis Cottage: Fire Pit & Pier

Waterfront Annapolis Cottage: Fire Pit & Pier
Annapolis
9.4 out of 10, Exceptional, (49 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
A wooden dock leading to a small red cabin by a calm water body, surrounded by lush greenery and a white fence.

19. Waterfront River Cottage for 2, dog-friendly

Waterfront River Cottage for 2, dog-friendly
Severna Park
9.2 out of 10, Wonderful, (14 reviews)
"It was a very clean, pet friendly area that was perfect for a weekend getaway."
United States
James H.
Waterfront River Cottage for 2, dog-friendly
A small, single-story house with a front porch, a wooden deck, and a stone pathway leading to the door.

20. Charming 1-bedroom cottage with AC in cozy Harwood

Charming 1-bedroom cottage with AC in cozy Harwood
Harwood
10.0 out of 10, Exceptional, (4 reviews)
"Very quiet area, cute house for two. Lots of open area for our small dogs to play."
United States
Susan S.
Charming 1-bedroom cottage with AC in cozy Harwood
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

Renaissance Baltimore Harborplace Hotel

Renaissance Baltimore Harborplace Hotel

10/10 Excellent
"Only thing I had an issue with is that they didn’t have a full body mirror. The bathroom mirror didn’t help and the only other mirror was in the bedroom but I was only able to myself chest and up smh. I was having a wardrobe issue and I couldn’t see myself properly to fix it. Kind of threw my birthday off"
Natasha 1-night trip
Posted 1 hour ago
Renaissance Baltimore Harborplace Hotel

Find out more about Kent County

Kent County Cottages information

Number of reviews
1,823
Accommodation
115 Cottages
Lowest Price
CA $301
Highest Price
CA $676

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