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Nov 28 - Nov 30
In two months
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In four months
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Top Cities in Kent County

Somewhere over the rainbow... Terrific view on the plane back to the North.
CottagesCottages

Chestertown

Chestertown

Cottages in Kent County

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!

Saint Michaels
9.6 out of 10, Exceptional, (122)
"The house and location was perfect for a girls weekend with my mom and 2 daughters! The 1/2 bathrooms in each bedroom were nice to have upstairs!"
United States
Kimberly L.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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, (29)
"This was our second time staying at this site. Always very clean, quiet and enjoyable."
United States
Chris S.
$198 nightly
The price is $209
Nov 13 - Nov 14
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit 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)
"A beautiful stay on the Chesapeake."
United States
Craig C.
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
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)
"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
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Elkton
9.8 out of 10, Exceptional, (14)
"It was a lovely home and we very much enjoyed our stay. Clean, comfortable beds and great location. "
United States
Deborah M.
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
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, (222)
"Very nice place, we will be visiting again!"
United States
Karen B.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Outdoor dining
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Nov 12 - Nov 13
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Terrace/patio
The Heron's Nest at Atlantic Marina

The Heron's Nest at Atlantic Marina

Pasadena
9.8 out of 10, Exceptional, (310)
"This place is amazing. We always have such a great time staying here!"
United States
Julie H.
The Heron's Nest at Atlantic Marina
Property grounds
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills

Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills

Wye Mills
9.0 out of 10, Wonderful, (4)
"We had a great stay! Ryan was a great host, and the cottage was perfect for our needs. We would certainly stay here again."
United States
Jennifer B.
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
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
9.6 out of 10, Exceptional, (4)
"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
Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman
9.8 out of 10, Exceptional, (236)
"Enjoyed our stay. Very close to city center for restaurants, shopping, etc. "
United States
Corcoran 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, (58)
"Wonderful house in a welcoming, friendly community. "
United States
Benjamin A.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
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

Saint Michaels
9.8 out of 10, Exceptional, (191)
"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "
United States
Jen R.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Exterior
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

St Michaels
9.6 out of 10, Exceptional, (125)
"Beautiful house Great location. We really enjoyed our first visit to St. Michaels!"
United States
JIM S.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

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

Port Deposit
9.8 out of 10, Exceptional, (10)
"Amy has a beautiful home, filled with character and special touches. We absolutely loved our stay and have zero complaints. The location was wonderful and we were extremely comfortable."
United States
Geoff F.
$200 nightly
The price is $212
Nov 13 - Nov 14
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
Exterior
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

Hillsmere
10.0 out of 10, Exceptional, (170)
"A lovely property in the perfect location! We will definitely rent again!"
United States
Donna R.
The Yellow Cottage on Harness Creek
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
Stevensville
10.0 out of 10, Exceptional, (6)
"This VRBO was very clean. Since it is a fairly new addition to VRBO, we thought it could use a little more info, like a portfolio with the combination to the bike locks, where to go to eat and visit, etc. Also, the only coffeemaker was a Keurig and we didn’t bring any K-cups. The 4 of us had a nice 50th Anniversary long weekend."
United States
Sharon M.
$792 nightly
The price is $874
Dec 1 - Dec 2
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Exterior
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!

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

Cape Saint Claire
10.0 out of 10, Exceptional, (100)
"Thanks for a great stay. The backyard was perfect for the whole family, and the house is lovely - clean, comfortable, and very well stocked! "
United States
Morgan V.
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!
Property grounds
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Epping Forest
9.8 out of 10, Exceptional, (30)
"We loved staying at the cottage. The atmosphere was incredibly peaceful and relaxing and the setting beautiful. Isaac was very helpful and thoughtful in responding to our questions and requests. "
United States
Alizah D.
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Property grounds
Waterfront River Cottage for 2, dog-friendly

Waterfront River Cottage for 2, dog-friendly

Severna Park
9.4 out of 10, Exceptional, (9)
"Great little spot in a private location but close to everything. Super clean and comfy!"
United States
Caely M.
Waterfront River Cottage for 2, dog-friendly
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

Lord Baltimore Hotel

Lord Baltimore Hotel

10/10 Excellent
"I did not eat breakfast"
Jazmin 1-night trip
Posted 18 hours ago
Lord Baltimore Hotel

Find out more about Kent County

Kent County Cottages information

Number of reviews
1,717
Accommodation
115 Cottages
Lowest Price
$209
Highest Price
$874

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