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In two months
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In three months
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In four months
Mar 27 - Mar 29

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

Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland

Cottage in Wittman

9.8 out of 10, Exceptional, (236)
"Perfect setting! Close to St. Michaels and Tilghman Very comfortable cottage, would recommend! "
United States
michele m.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Cottage in St Michaels

9.6 out of 10, Exceptional, (147)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Exterior
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Cottage in Stevensville

10.0 out of 10, Exceptional, (57)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Exterior
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

Cottage in Port Deposit

10.0 out of 10, Exceptional, (31)
"Wow such a wonderful place, clean, warm, and full of everything you need."
United States
Oswaldo S.
$200 nightly
The price is $211
Dec 7 - Dec 8
Total with taxes and fees
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Outdoor dining
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Cottage in Pasadena

9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
$583 nightly
The price is $665
Dec 8 - Dec 9
Total with taxes and fees
Chesapeake Cottages- 2 Quaint Waterfront Retreats
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Cottage in Saint Michaels

9.6 out of 10, Exceptional, (124)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Exterior
A cottage on the shore of the Delaware River

Cottage in Salem

9.8 out of 10, Exceptional, (68)
"For a long weekend it was good. The home itself was updated and very clean. "
United States
Cameron D.
A cottage on the shore of the Delaware River
Exterior
Charming Waterfront Cottage Retreat near St. Michaels

Cottage in Bozman

10.0 out of 10, Exceptional, (10)
"My husband and I were delighted to stay in this beautiful home located on the most picturesque property for our 30th wedding anniversary. From the design of the house to the small details within it, making it feel like a home away from home, everything was perfect. We will stay here again should we revisit this area! "
United States
Jennifer F.
Charming Waterfront Cottage Retreat near St. Michaels
Outdoor dining
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

Cottage in 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
House (3 Bedrooms) | Interior
5 Mi to Downtown Baltimore: Quiet Home w/ Porch

Cottage in Rosedale

3.0 star property
10.0 out of 10, Exceptional, (1)
$431 nightly
The price is $498
Dec 8 - Dec 9
Total with taxes and fees
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Exterior detail
Secluded Cozy Cottage in Historic Downtown

Cottage in Historic District

9.6 out of 10, Exceptional, (16)
"We had a very lovely stay . This is an excellent location . "
United States
Kimberly B.
$627 nightly
The price is $714
Jan 3 - Jan 4, 2026
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

Cottage in Port Deposit

10.0 out of 10, Exceptional, (11)
"Was a great stay would definitely stay again "
United States
jerel p.
$203 nightly
The price is $215
Dec 7 - Dec 8
Total with taxes and fees
Quarry Landing - Center of Town & River View - 3 Bedroom
Exterior
The Yellow Cottage on Harness Creek

Cottage in Hillsmere

10.0 out of 10, Exceptional, (170)
"Love the decor, the comfort and vibe of the place. Wish I had stayed longer! "
United States
Lauren m.
The Yellow Cottage on Harness Creek
Terrace/patio
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Cottage in Stevensville

2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
United States
shannan t.
$802 nightly
The price is $885
Dec 9 - Dec 10
Total with taxes and fees
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Terrace/patio
Chesapeake City Pool Retreat – Waterfront Stay in the Woods

Cottage in Elkton

8.8 out of 10, Excellent, (15)
"Lovely place. We really enjoyed our stay"
United States
Renae R.
Chesapeake City Pool Retreat – Waterfront Stay in the Woods
Exterior
Firefly Cottage at the Cape, Community beach, spring adventures, fun, bookings.

Cottage in Cape Saint Claire

10.0 out of 10, Exceptional, (101)
"Another fabulous stay at the Firefly Cottage "
United States
Debbie Y.
Firefly Cottage at the Cape, Community beach, spring adventures, fun, bookings.
Property grounds
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

Cottage in Epping Forest

9.8 out of 10, Exceptional, (30)
"We so enjoyed our time at the cottage. Isaac was so helpful and responsive when we had questions. The cottage had everything we needed or wanted and we had a lovely, restful long weekend here with our daughter. What a great cottage in a great location, close to things we needed, but nestled in the woods and on the water. We will be back! Highly recommend. "
United States
M G.
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Interior
6 Mi to Dtwn: Family-friendly Home in Annapolis!

Cottage in Annapolis

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Exterior
Cozy, unique, historic registered cottage on the Corsica River!

Cottage in Centreville

10.0 out of 10, Exceptional, (6)
"Lovely property, cool history beautiful decor"
United States
Christine C.
Cozy, unique, historic registered cottage on the Corsica River!
Exterior
Rare find! Chic cottage, salt water heated pool May 15-Oct15.

Cottage in Arnold

10.0 out of 10, Exceptional, (54)
"The cottage was so lovely! We absolutely loved every detail that Katie and Jack put into making our stay welcoming and comfortable. We hope to visit again in the future."
United States
Elizabeth J.
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
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

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

10/10 Excellent
"Nice clean space huge bathroom "
Jasmine 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Baltimore BWI Airport

Find out more about Kent County

Kent County Cottages information

Number of reviews
1,028
Accommodation
121 Cottages
Lowest Price
$211
Highest Price
$885

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