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Compare 74 Cottages in Kent Island with updated reviews, rates, and availability.

Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
10.0 out of 10, Exceptional, (76)
"The cottage was a great place to stay with charming outdoor spaces nestled in a lovely neighborhood with easy access to Sandy Point and other local attractions. The hosts were gracious and ensured our needs were met throughout our stay."
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (149)
"Highly recommend. Beautiful spot and a wonderful cottage. Rhonda does an amazing job of making you feel at home. My son is at the Academy and with all the pressures they have on them, to see him be able to sit out by the water so peacefully and just relax was so enjoyable. We'll be back for sure."
The Yellow Cottage on Harness Creek
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home. Very nice and quiet neighborhood on the water. "
The price is ¥72,185
¥146,238 total
includes taxes & fees
Oct 4 - Oct 5
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (212)
"As always our stay was amazing from kayaking, bird watching, sunsets. The cove is a special place."
Relaxing Waterfront Cottage Near St Michaels, Maryland
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (107)
"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!
The Heron's Nest at Atlantic Marina
10.0 out of 10, Exceptional, (279)
"Would definitely stay again, host was very kind and house was perfect."
The Heron's Nest at Atlantic Marina
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (165)
"Great little cottage and plenty of space for our family of 3 to have an end-of-Summer getaway to one of our favorite towns. Prompt and easy communication with the owner, Tom, both before and during our stay. We loved the back porch and were blessed with some cooler temps and were able to enjoy sitting out there. FYI - Den has a door (third bedroom with pull out sofa). We have rented on Carpenter Street before, and the location cannot be beat as far as walkability to everything in town and along...
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (18)
"Wonderful property in a beautiful setting. We had a lovely weekend with family. Would highly recommend the property!"
Eastern Shore Waterside Cottage Near St. Michaels
Waterfront River Cottage for 2, dog-friendly
8.8 out of 10, Excellent, (5)
"It’s a wonderful place. Ideal for sleeping one or two. I hosted 10 of my family for a crab roll feed down by the water. It was delightful and I was glad to get back in the kitchen after seven days on I-90 and fast food."
Waterfront River Cottage for 2, dog-friendly
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (130)
"It's a great property, exactly as described. I love Rock Hall, and this location is perfect for enjoying the beach and boats, looking forward to returning again! "
Eastern Shore beach cottage get-away
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (6)
"Our stay was amazing! Words cannot say enough! The view is magical. We enjoyed coffee on the porch to watch the sunrise and the crab/oyster boats going in and out. Maria, is a wonderful and very thoughtful host. At her recommendation, we went to the free wine tasting at the General Store at the end of the street. We met several local residents who could not be more kind and fun to talk with. We can't wait to come back and stay again."
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (199)
"Couples getaway weekend to Annapolis. This was the perfect place to have our Basecamp. Absolutely beautiful location, quiet, and peaceful and easy to get everywhere!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (130)
"Had a wonderful time. This home was just perfect for us. Great location and charming. Would definitely stay here again"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.8 out of 10, Exceptional, (32)
"Beautiful setting, the house was clean, and the host communicative when needed."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Cottage at Goose Neck Point
10.0 out of 10, Exceptional, (28)
"What a little slice of heaven. Checkin was easy peasy. Owner left a welcome basket w goodies and wine. That was a very nice gesture. The property and area is beautiful. I wish I could call it my home away from home:). The home was perfect, clean and everything the pictures showed. Just a perfect getaway to escape the craziness of life. Didn’t want to leave. "
Cottage at Goose Neck Point
Peaceful getaway convenient to local amenities including beach, boating & food
9.8 out of 10, Exceptional, (108)
"Bay Haven was in a great lication and property mananger was very responsive to al my questions. "
Peaceful getaway convenient to local amenities including beach, boating & food
House w/Water Views of Rock Creek 2BA 2BA Cottage
10.0 out of 10, Exceptional, (16)
"What a fantastic, peaceful, and cozy place to stay! My friend and I were seeking a clean and comfy place to crash during an intensive 4-day martial arts seminar. This was perfect, from the comfy sectional to the spacious open floor plan, great TV channel options, and clean kitchen and bathrooms. Additionally, there was space for us and our stuff in closets, kitchen cabinets, and the bathrooms. After long days of training, we celebrated having no stairs to navigate! It was summer and super...
House w/Water Views of Rock Creek 2BA 2BA Cottage
Pet-friendly Annapolis Home: Walk to Beach!
3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (71)
"Our stay at this Vrbo in Annapolis was nothing short of spectacular! The property is beautifully maintained, offering the perfect blend of comfort and style. The attention to detail was evident, from the cozy living spaces to the well-appointed kitchen that had everything we needed for our stay. The location is unbeatable—close enough to all the attractions, restaurants, and shops make Annapolis the charming city that it is (1.2 miles walk to the Naval Academy), while distanced enough to be a...
Amazing views, short walks to great dining!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (114)
"Waters edge is just a few steps away to sit and watch boats come in and out. So cute and the most amazing artifacts decorating the place made it even more captivating. Short walk to coffee, food and shopping local. The owner was responsive and kind as well as super easy to work with. Will definitely return."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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Other property types in Kent Island

Waterfront Cottage on the Eastern Shore
9.6 out of 10, Exceptional, (7)
"We rented the house for the weekend and to host a surprise birthday party. We had the party right at the beach and the host/concierge were able to help us with everything we needed. They really went out of their way for us, and it made a huge difference in the party’s success! Plus, you can’t beat the view and the Chesapeake Bay sunsets !!"
The price is ¥50,486
¥118,472 total
includes taxes & fees
Oct 1 - Oct 2
Waterfront Cottage on the Eastern Shore
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (24)
"We loved everything about the Kent Island House! Would book again in a hot minute"
Pool and Bay Views on wrap around deck in Kent Island
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (26)
"We had a great weekend on Kent Island. We loved the area. It was so family friendly. We had lots of young children in our group, and this house worked great for us. The inside was nice with modern, but minimal decor, which was perfect for toddlers. The fenced in backyard was also just what we needed to let them run around."
The price is ¥10,633
¥37,185 total
includes taxes & fees
Sep 29 - Sep 30
Relax on Kent Island in 3 Bedroom Home w/Waterview
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.