How much does it cost to stay at Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart?

As of Oct 20, 2025, prices found for a 1-night stay for 2 adults at Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart on Oct 27, 2025 start from $225.0, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart Reviews, Deals & Photos 2025

Q: Is Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart pet-friendly?

Yes, this property allows dogs (limit 2 total).

Q: Where is Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart located?

Situated in Smith Island, this vacation home is 0.2 mi (0.3 km) from Terrapin Sand Point and 2.4 mi (3.8 km) from Smith Island.

10/10 Excellent

David

Sep 1, 2025

Liked: Cleanliness, amenities, property conditions & facilities, communication

The perfect place to wind down, reconnect with people, culture and a way of life we’ve strayed away from. The house was amazing! The town, the good people and the atmosphere just as much.

Stayed 2 nights in Aug 2025

10/10 Excellent

Samantha J.

Jun 16, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect relaxing weekend

Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life

Stayed 2 nights in Jun 2025

10/10 Excellent

Amy C.

Jun 28, 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

So relaxing!

Smith island is lovely! This house was perfectly located and furnished and the owner super helpful.

Stayed 2 nights in Jun 2024

10/10 Excellent

Karen W.

Jul 13, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

This was a last min trip so it was a lot of info to gather in less a day but we did it and we made the ferry on time and we got here on a very hot and humid day. The ferry ride was fun and the dog didn’t seem to mind it. We should have mapped out where the house was better because when we arrived we were walking with our suitcases and dog and it was hot! We did finally arrive and the house was just as described. The water was right behind the house and the island was so peaceful. We relaxed and took the dog for a walk and got some food at the local restaurant - crab cakes were so good! We enjoyed our time on Smith Island - don’t forget to try the Smith Island Cake, the bakery is two doors away! Thanks for letting us share your little piece of heaven here in the middle of the Chesapeake!

Stayed 2 nights in Jul 2025

10/10 Excellent

Tom K.

Sep 14, 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful house in a unique location.

This beautiful house is perfect for two or three travellers who want to be in the heart of a sleepy waterfront town with lots of heritage. The house is nicely updated and has all the necessary creature comforts and is a very short walk from the town's waterfront.

Stayed 1 night in Sep 2024

8/10 Good

Jean T.

Jun 9, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful little house overall. The small bed was not great. It did not appear clean. The only sheet, the fitted one was in knots under a messy comforter. Since it was a mattress on the floor, jammed into a corner, it was not great for this 71 year old. The shower was not clean. We did not take photos.

Stayed 1 night in Jun 2025

10/10 Excellent

John D.

Jul 1, 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Kayaking on Smith Island

Smith Island is remote, isolated, and a 45 minute ferry trip from Crisfield on lower Maryland's Eastern Shore.The house was recently renovated. It is very well furnished and equipt. Chris has a detailed handbook about what to expect on the island with names and phone numbers for residents who can provide services and give tours including the listing for the ferry boats. He is an engaged, conscientious and outstanding host who quickly and thoroughly responded to our questions. As a waterman community, resturants close very early, so some advance planning is essential. There are fortunately multiple local families that will cook dinners for reasonble prices and deliver food directly to the house.My daughter and I spent two days kayaking various water trails around the island, paddling 7 - 8 miles each day. As this was my second kayaking trip to the island, we knew what to expect and was aided by our hosts excellant handbook. The cultural center in Ewel sells detailed water trail maps published by the State of Maryland. These can also be found online. There is an abundance of wilflife on the island, such as Maryland terrapins, blue crabs, varius types of ducks, geese, great blue herons, great white egrets, commorants and brown pelicans. The waters around the island are shallow, except for the dredged channels. Much of the trails are inaccesible to boats with motors so the experience is very peaceful. Insect repellant is essential.Finally the sunsets are spectacular!

Stayed 3 nights in Jun 2025

10/10 Excellent

Melissa M.

Feb 22, 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Smith Island Getaway

This was just what we needed. The peace and serenity of Smith Island left us feeling renewed. Ran/cycled the distance of the island daily taking in the beautiful scenery, wildlife, and chatting with the residents. We walked to the bakery and bought two Smith Island cakes which were phenomenal! Cooked in the well appointed kitchen and snuggled on the couch every evening. Chickens and ducks greeted us in the mornings and waterfowl throughout the day kept us looking through binoculars. At night we slept like babies in the comfortable, fluffy, loft bed. We actually extended our stay by a day because we weren't ready to say goodbye just yet. We must return to Mr. Winter's haven again soon! Thank you for such a pleasant and memorable experience! D&M

Stayed 4 nights in Feb 2024

10/10 Excellent

Ben H.

Jun 30, 2023

Liked: Cleanliness, check-in, communication, location, listing accuracy

Charm and Adventure

An adventure surely begins with a boat. Easily managed, transportation by one of several boats, but I'd recommend Captain Jason the Red boat gets you on and off the island. Bring some tip cash for luggage handlers both on and off the island as well as a pen and envelop for the lumber yard overnight parking. The home is fitting for a couple or small family. More than two kids might be tough, but the downstairs does offer a bed on the couch. Clean and comfortable and well-accommodated. The screened in porch is perfect for outside sitting and drinking well into the night. The bathroom is very spacious with a hot tub like tub. It was enjoyed especially by my 6 year old; I never saw him so clean. But will sadly be taken out. Washer and dryer help you come home smelling clean and fresh. The place is in easy walking distance to everything but Tylerton. You can't walk to Tylerton; you can swim. And be sure to take advantage of the kayaking and bike. Enjoy your stay but do bring books to read or take advantage of the internet. The internet worked fine with all devices going. And finally, be sure to stop and the Exxon and talk to the local clerk. It is fun to hear all the local's stories; They are more than willing to share some spilled tea. Finally, bring binoculars. The birds are fabulous here.

Stayed 3 nights in Jun 2023

10/10 Excellent

Kevin J.

Sep 2, 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent experience with house, host and location

Everything about the house was as expected from the description. We enjoyed having two kayaks available. As soon as we booked the stay, our host provided a very helpful set of directions about the house and Smith Island. The details of getting to the Island are not totally obvious from anything on the web and the host’s directions provided clear descriptions of how it works and the contact info for the boat captain to set everything up. It’s all more casually organized than a lot of modern travel experiences but all worked out just fine, and the local islanders were very friendly and helpful. We did have a couple of questions before and during our visit and the host, Chris, responded quickly and clearly. We mostly cooked our own meals (dining options on the island are very limited - see the hosts instructions for details). The house kitchen is modern and well equipped. At the advice of our host, we stocked up on groceries in Crisfield and brought everything with us. The house has modern laundry facilities which we used. Smith Island, though not far from DC etc, is a world away and spending 5 nights was a great way to experience it. Not everyone will want to spend time in a place like this, but if kayaking through a salt marsh looking at birds appeals to you, you’ll love it.

Stayed 5 nights in Aug 2024

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

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