Kayak Friendly Home on the Chesapeake Bay with Bikes, Paddle Board & Golf Cart
Select date
-
Select date
1 night
1 room, 2 adults, 0 children
All properties in Smith Island
Kayak Friendly Home on the Chesapeake Bay with Bikes, Paddle Board & Golf Cart
Smith Island, Maryland, 21824
Show on map
Complete address will show after booking
We Price Match
Amenities
Gym
Table tennis room
Wi-Fi in public areas
Kayaking
Water sports equipment
Beach towels
BBQ
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 11:00 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 is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Show more
10.0/10
Cleanliness10.0
Amenities10.0
Location10.0
Service10.0
All 10 reviews
Surroundings
Landmarks: Smith Island Cultural Center
(220m)
Landmarks: Smith Island Cruises
(230m)
View on map
Overview
Rooms
Guest Reviews
Services & Amenities
Policies
Host
12
1 Bedroom Private Vacation Home
1 queen bed
Free Wi-Fi
Smoking Permitted
Air conditioning
Refrigerator
TV
Wi-Fi in room
Check Availability
Guest Reviews
10.0/10
Outstanding
10 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. £0.89). Trip Coins can be used to save instantly on room rates.
David
September 1, 2025
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.
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
Services & Amenities
Most popular amenities
Gym
Table tennis room
Wi-Fi in public areas
Gym
More Amenities
Internet
Wi-Fi in public areas
Health & wellness
Kayaking
Table tennis room
Water sports equipment
Gym
Activities
Beach towels
Public areas
BBQ
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.
Cribs and Extra Beds
Please contact the hotel for details about crib and extra bed policies.
Age Requirements
The main guest checking in must be at least 18 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 11:00 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 is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.
Show Full Description
Frequently Asked Questions
How do I book a hotel on Trip.com?
To book a hotel on Trip.com, simply enter your destination, travel dates, and the number of guests on the page. Then, browse through the available hotels and select the one you want to book. Follow the prompts to enter your payment information and complete the booking. How do I book a hotel on Trip.com?
How do I get hotel deals on Trip.com?
There are several ways to find affordable hotels on Trip.com. You can narrow down your search results by filtering hotels according to your preferred price range, or you can sort the results by price to view the cheapest options first.How do I get hotel deals on Trip.com?
Where can I find hotel deals on Trip.com?
Trip.com offers a wide variety of hotel deals and promotions that are available throughout the year. You can easily find these special offers on our deals page. What's more, if you are a member of our loyalty program, you can sign in to your account and discover exclusive discounted rates at hotel list pages.Where can I find hotel deals on Trip.com?
How can I get lower prices for hotels?
Sometimes booking hotels midweek is cheaper, but it also depends on the season.How can I get lower prices for hotels?
How many hotels are listed on Trip.com?
You can find over 5 million hotels in more than 230 countries or regions on Trip.com. Haven't decided which hotel to book? Browse our site to get ideas!How many hotels are listed on Trip.com?
Can I cancel or change my hotel bookings on Trip.com?
It depends on the hotel policy and date of cancellation. Please check the policy section of the related hotel pages. To cancel or change your bookings, sign in to your Trip.com account, go to "My Bookings", and follow the instructions.Can I cancel or change my hotel bookings on Trip.com?
How do I contact Trip.com customer support?
You can contact Trip.com's 24/7 customer support by visiting the Help Center on Trip.com and submitting a request. You can also contact us by phone or service chat, depending on your location.How do I contact Trip.com customer support?
About This Property
| Hotel Star Rating | 4 |
|---|