Kayak Friendly Home on the Chesapeake Bay with Bikes, Paddle Board & Golf Cart
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All properties in Smith Island
Kayak Friendly Home on the Chesapeake Bay with Bikes, Paddle Board & Golf Cart
Smith Island, Maryland 21824, United States
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Amenities
Fitness Room
Table Tennis Room
Wi-Fi in Public Areas
Kayaking
Water Sport Equipment
Beach Towel
Barbecue
Garden
All amenities
Property Description
Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. A short 3 minute walk from the ferry dock for the boat Island Belle II by Harborside restaurant to the house. Comfortable family room with new furniture and seating for 5. Enclosed patio with new screens is ideal in the summer. Large kitchen fully stocked to cook your meals. Large bathroom recently renovated (Summer ‘23) with new shower, vanity and washer/dryer. Easy access to the water. Kayak, SUP, and bikes are available. Island is only accessible by boat. Keypad entrance is on the side patio door.Enjoy the tranquility of this unique place. Truly a special place never to be forgotten. Golf cart is included and may be covered and parked on the property. You may use but please rinse off entire cart including underside and on bricks to side of house and cover (if it was covered) and strap down the cover. Ferry boat leaves Crisfield,MD daily at 12:30pm. Park one block away at Tawes lumber yard for $3/night or about 10 minutes walk from ferry at Somers Cove Marina which is gated, lit and secured for$5-$10/night. Ferry (Island Belle II or Capt Jason) leaves the island at 7:30am Mon-Sat and 11:00am on Sunday (weather dependent). It is about a 40 minute ride and around $25 cash per person plus luggage(check with captain on price but around $5/luggage.About pets:Pets allowed: dogs (limit 2 total).$50 for each pet per stay.About checkOut:Check out before 8:00 AM.About children:Children allowed: ages 0-17.About customRules:Place dirty linens on floor in bathroom. Take trash outside to bins. Unplug both a/c units in summer, turn 2 downstairs thermostats to 57 in winter.If using bikes or kayaks please rinse after use. Return bikes to shed and kayaks to the stand with covers.,Rinse golf cart including underneath with hose in back of house. Park on bricks to side of house and cover and secure with straps. Key on kitchen wall.About checkIn:Check in after 1:00 PM.About smoking:Smoking allowed: in designated areas.Use ashtray and empty ashes. Ok to smoke outside..About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
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10.0/10
Cleanliness10.0
Amenities10.0
Location10.0
Service10.0
All 13 reviews
Surroundings
Landmarks: Smith Island Cultural Center
(220m)
Landmarks: Smith Island Cruises
(230m)
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Overview
Rooms
Guest Reviews
Services & Amenities
Policies
Host
13
1 Bedroom Private Vacation Home
1 queen bed
Free Wi-Fi
Smoking Permitted
Air conditioning
Refrigerator
TV
Wi-Fi in room
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Guest Reviews
10.0/10
Outstanding
13 reviews
Verified Reviews- Cleanliness10.0
- Amenities10.0
- Location10.0
- Service10.0
Average for similar properties in Smith Island
Book now and leave a review after your stay to earn up to 120 Trip Coins (approx. NZD 2.13). Trip Coins can be used to save instantly on room rates.
Karen T.
July 28, 2025
Very comfortable house that had everything we needed. Having the golf cart included in the rental was super convenient. The only downside was the sulphur smell of the water but otherwise the property was well cared for and a great location. First time to the island but we had a great time. Pelican island was amazing
Trevor H.
July 28, 2025
Great stay, Christopher was accommodating. Great place for 2-3 people. Golf cart was a great add on. Friendly neighbors. Very short walk from boat ( use green boat) Otis
Samantha J.
June 16, 2025
Perfect relaxing weekend
Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life
Jean T.
June 9, 2025
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.
Tom K.
September 15, 2024
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.
Kevin J.
September 3, 2024
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.
Amy C.
June 28, 2024
So relaxing!
Smith island is lovely! This house was perfectly located and furnished and the owner super helpful.
Melissa M.
February 23, 2024
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
Ben H.
June 30, 2023
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.
Services & Amenities
Most popular amenities
Fitness Room
Table Tennis Room
Wi-Fi in Public Areas
Fitness Room
More Amenities
Internet
Wi-Fi in Public Areas
Health & wellness
Kayaking
Table Tennis Room
Water Sport Equipment
Fitness Room
Activities
Beach Towel
Public areas
Barbecue
Garden
Smoking Area
Cleaning services
Clothes Dryer
Facilities for children
Children's Toys
Property Policies
Check-in and Check-out Times
Check-in: after 13:00
Check-out: Before 12:00
Child policies
Children of all ages are welcome at this property.
Additional fees may be charged for children using existing beds. Add the number of children to get a more accurate price.
Cots and Extra Beds
Please contact the hotel for details about cot and extra bed policies.
Age Requirements
The main guest checking in must be at least 21 years old
Property host
Christopher Winters
About this property
Relax in this 1910 era Smith Island home. Has one large upstairs bedroom with second twin bed separate from main bedroom. A short 3 minute walk from the ferry dock for the boat Island Belle II by Harborside restaurant to the house. Comfortable family room with new furniture and seating for 5. Enclosed patio with new screens is ideal in the summer. Large kitchen fully stocked to cook your meals. Large bathroom recently renovated (Summer ‘23) with new shower, vanity and washer/dryer. Easy access to the water. Kayak, SUP, and bikes are available. Island is only accessible by boat. Keypad entrance is on the side patio door.Enjoy the tranquility of this unique place. Truly a special place never to be forgotten. Golf cart is included and may be covered and parked on the property. You may use but please rinse off entire cart including underside and on bricks to side of house and cover (if it was covered) and strap down the cover. Ferry boat leaves Crisfield,MD daily at 12:30pm. Park one block away at Tawes lumber yard for $3/night or about 10 minutes walk from ferry at Somers Cove Marina which is gated, lit and secured for$5-$10/night. Ferry (Island Belle II or Capt Jason) leaves the island at 7:30am Mon-Sat and 11:00am on Sunday (weather dependent). It is about a 40 minute ride and around $25 cash per person plus luggage(check with captain on price but around $5/luggage.About pets:Pets allowed: dogs (limit 2 total).$50 for each pet per stay.About checkOut:Check out before 8:00 AM.About children:Children allowed: ages 0-17.About customRules:Place dirty linens on floor in bathroom. Take trash outside to bins. Unplug both a/c units in summer, turn 2 downstairs thermostats to 57 in winter.If using bikes or kayaks please rinse after use. Return bikes to shed and kayaks to the stand with covers.,Rinse golf cart including underneath with hose in back of house. Park on bricks to side of house and cover and secure with straps. Key on kitchen wall.About checkIn:Check in after 1:00 PM.About smoking:Smoking allowed: in designated areas.Use ashtray and empty ashes. Ok to smoke outside..About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
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Frequently Asked Questions
What are the check-in and check-out times at Kayak Friendly Home on the Chesapeake Bay with Bikes, Paddle Board & Golf Cart?
Check-in at Kayak Friendly Home on the Chesapeake Bay with Bikes, Paddle Board & Golf Cart is from 13:00 and check-out is by 12:00.What are the check-in and check-out times at Kayak Friendly Home on the Chesapeake Bay with Bikes, Paddle Board & Golf Cart?
How much does it cost to stay at Kayak Friendly Home on the Chesapeake Bay with Bikes, Paddle Board & Golf Cart?
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What is the cancellation policy for Kayak Friendly Home on the Chesapeake Bay with Bikes, Paddle Board & Golf Cart?
The cancellation policy for Kayak Friendly Home on the Chesapeake Bay with Bikes, Paddle Board & Golf Cart depends on the room type and booking terms.What is the cancellation policy for Kayak Friendly Home on the Chesapeake Bay with Bikes, Paddle Board & Golf Cart?
About This Property
| Hotel Star Rating | 4 |
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