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Compare 69 Cottages in Kent Island with updated reviews, rates, and availability.

Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
Property grounds
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
10.0 out of 10, Exceptional, (63)
"Firefly cottage is a beautiful little place, super clean and with every possible convenience - well stocked, with lots of special touches. Terrific hosts and a lovely cottage - we thoroughly enjoyed it! Thank you…. Sheilah"
Firefly Cottage at the Cape, community beach, stand alone house, hot tub, pets.
Cottage at Goose Neck Point
Sun loungers, beach towels
Cottage at Goose Neck Point
10.0 out of 10, Exceptional, (23)
"Wonderful hosts, great before and during stay communication, very friendly and welcoming. Cottage was cozy, well appointed and had the best view from the screened porch for morning coffees and evening glasses of wine!"
Cottage at Goose Neck Point
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
Property grounds
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
9.0 out of 10, Wonderful, (2)
"We thoroughly enjoyed our Memorial Day stay at the Bayburst Lodge! Our son and his wife, our daughter and her boyfriend joined us. This home is located right on the water on a quaint road in Rock Hall. The home was spacious and clean and pet friendly. We enjoyed the small private beach right on the water and also caught some small fish right from the beach. We had amazing weather all weekend until Monday, but the rain held off until we left. We enjoyed eating at the Blue Heron and the Harbor...
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (189)
"Beautiful grounds in a peaceful, isolated neighborhood. Absolutely as described in the listing. Hosts were helpful and responsive and absolutely everything we needed to enjoy the weekend was there."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (106)
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Waterfront property with private boat ramp and new dock!
Outdoor dining
Waterfront property with private boat ramp and new dock!
10.0 out of 10, Exceptional, (2)
"Fun stay in an older refurbished home. All of the amenities one could need with a great water front area"
Waterfront property with private boat ramp and new dock!
Waterfront home with beach mins to downtown boat or car Dog-Friendly
Property grounds
Waterfront home with beach mins to downtown boat or car Dog-Friendly
9.8 out of 10, Exceptional, (20)
"The home was beautiful, the setting was stunning, and the check-in and check-out process was a breeze! Our group of 6 cousins had a fantastic time together enjoying the beautiful views and all that Annapolis has to offer. We are already planning a return trip next year!"
Waterfront home with beach mins to downtown boat or car Dog-Friendly
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun loungers, beach towels
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (90)
"We enjoyed meeting the hosts and their llamas and emus. The home had everything we needed for our stay, and the view of the water from the house could not be better. We watch the sunsets wherever we go, and the colors were spectacular. There were plenty of things to do, and the restaurants were a short drive away. Thank you for sharing this property with others."
Secluded Waterfront Cottage on 200 acre farm near Queenstown
The Heron's Nest at Atlantic Marina
Exterior
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (268)
"Everything is perfect over there … The paradise on earth .. Highly recommended "
The Heron's Nest at Atlantic Marina
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (155)
"Very nice home! It was decorated with many antiques and gave you a feeling of another time but with all the modern amenities for a wonderful time."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (127)
"The house looked better than the pictures. It was very cozy and had everything we needed. It’s probably the best location for walking around town. Water pressure in the shower was decent, and the beds were comfortable."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Eastern Shore beach cottage get-away
Sun loungers
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (123)
"The property was clean and perfectly located across from the Chesapeake Bay. We enjoyed our stay and will definitely book it again!"
Eastern Shore beach cottage get-away
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
View from property
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.8 out of 10, Exceptional, (24)
"Appreciated the lovely waterfront location, independence , nice filtered water tap for drinking and coffee. Especially enjoyed meeting owner, delightful visit."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels
Peaceful getaway convenient to local amenities including beach, boating & food
9.8 out of 10, Exceptional, (105)
"Second time staying as this property and will continue to be our go to vrbo when needed. Very comfortable and has everything needed while in Rock Hall. Had some difficulty opening up door with key pad initially, but was able to figure it out. Highly recommend this property."
Peaceful getaway convenient to local amenities including beach, boating & food
Artist, writer & creative minds stay where inspiration is free & serenity lives
Property grounds
Artist, writer & creative minds stay where inspiration is free & serenity lives
Artist, writer & creative minds stay where inspiration is free & serenity lives
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Beach
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Chessie Cottage-Chesapeake Bay Great views from easy single floor living!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (109)
"We had a wonderful trip to St. Michaels. This house is in the perfect location and has everything you need for a great stay!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (198)
"We love staying at Magee Cottage. It has all you need to relax and enjoy such a comfortable home on the water. This is our second stay and we’ll hurry back in a few months for more of the good life!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Property grounds
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, (18)
"Thoroughly enjoyed staying at this cozy cottage It was very clean, had lots of towels, comfortable beds with soft fluffy bedspreads. We also enjoyed sitting outside on the screened in porch when we weren't in the hot tub. The fact that it was in a gated community with lots of gorgeous flowers and trees it felt very private."
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Pet-friendly waterfront River Cottage for 2
On the beach
Pet-friendly waterfront River Cottage for 2
8.6 out of 10, Excellent, (4)
"Beautiful views, private little cottage ideal for couples visiting with pets."
Pet-friendly waterfront River Cottage for 2
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See all available properties in Kent Island
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.

Other property types in Kent Island

Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Relax on Kent Island in 3 Bedroom Home w/Waterview
Exterior
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (23)
"We'd stay there again but with modified expectations based on our experience. The 'water view' is quite distant and obtuse. The water is hundreds of yards away, and separated from the house by several suburban style homes and an unpaved road."
The price is $205
$416 total
includes taxes & fees
Jul 14 - Jul 15
Relax on Kent Island in 3 Bedroom Home w/Waterview
Waterfront Cottage on the Eastern Shore
Fridge, microwave, oven, stovetop
Waterfront Cottage on the Eastern Shore
9.4 out of 10, Exceptional, (3)
"Very much as pictured in ad. Convenient to we did venue we were attending"
The price is $599
$1,134 total
includes taxes & fees
Jun 24 - Jun 25
Waterfront Cottage on the Eastern Shore
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.

Kent Island Cottages information

Number of reviews
1,541
Accommodation
69 Cottages
Lowest Price
Highest Price

Recent reviews of Kent Island hotels
Expedia verified reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

5/5 Excellent
"Very easy "
A verified traveler stayed at Historic Inns of Annapolis
Posted 2 days ago
Historic Inns of Annapolis