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Entire home

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

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

Interior
Property grounds
Exterior
Smart TV, fireplace, table tennis, books
Interior
On the tranquil island, Smith Island Home offers a peaceful retreat. Unwind in the comfortable family room with new furniture or enjoy meals prepared in the fully-stocked kitchen. The enclosed patio is perfect for warm summer days, and easy access to water allows you to kayak or paddleboard at leisure.

Reviews

9.8 out of 10
Exceptional

Entire home

1 bedroom1 bathroomSleeps 3972 sq ft

Popular amenities

  • Parking available
  • Gym
  • Pet-friendly
  • Dryer
  • Air conditioning

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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

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.

Property manager

Christopher Winters

Property amenities

Beach

  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Electric kettle
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Chef service
  • Dining table

Bedrooms

  • Bedroom
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Books
  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Firepit
  • Garden
  • Outdoor furniture
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Upper floors accessible by stairs only
  • Well-lit path to entrance
  • Smoking not allowed

Services and conveniences

  • Meal delivery service

Location highlights

  • Near the bay

Things to do

  • Bicycles
  • Gym
  • Kayak
  • Table tennis
  • Water sports equipment

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • At least 80% lighting from LEDs
  • At least 80% of food locally-sourced
  • Bicycles
  • Eco-friendly cleaning products used
  • Garden
  • Local artist showcase
  • Local culture and ecosystem education
  • Locally-owned and organized tours and activities
  • No plastic coffee stirrers
  • No plastic drinking straws
  • No plastic soft drink bottles
  • No plastic water bottles
  • Recycling
  • Reusable cups
  • Reusable tableware
  • Unit size: 972 square feet

Policies

Check-in

Check-in time starts at 1:00 PM
Minimum check-in age: 18

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Check-out instructions

The host requires you complete the following before checking out:
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights and lock the doors
If golf cart was used spray down with hose and cover (if was covered upon arrival)
If Kayaks were used spray them down and cover them and return to stand
Unplug a/c units and during winter if heat is on turn to 57 place any trash in bags both inside and outside in bins.
Failure to complete these may result in a negative review from the host.

Rules

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

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets
Note from host: $50 for each pet per stay

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
This property uses eco-friendly cleaning products
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

This property does not have elevators

About the area

Smith Island is home to this vacation home. J. Millard Tawes Museum and Tangier History Museum are cultural highlights, and some of the area's activities can be experienced at Tylerton County Dock and Crisfield City Dock.
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Map
Smith Island, MD

What's nearby

  • Terrapin Sand Point - 5 min walk - 0.4 km

Restaurants

  • ‪The Roost - ‬6 min walk
  • ‪Bayside Inn Restaurant - ‬5 min walk
  • Drum Point Market
  • ‪Smith Island Beans - ‬7 min walk
  • ‪Ruke's General Store and Seafood Deck - ‬4 min walk

Frequently asked questions

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

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

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

As of Aug 26, 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 Aug 27, 2025 start from CA $311.09, 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.

What time is check-in at Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart?

Check-in begins at 1:00 PM.

What time is check-out at Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart?

Check-out is at 11:00 AM.

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.

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

Reviews

9.8

Exceptional

Rating 10 - Excellent. 9 out of 11 reviews
Rating 8 - Good. 2 out of 11 reviews
Rating 6 - Okay. 0 out of 11 reviews
Rating 4 - Poor. 0 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 reviews

9.6/10

Cleanliness

Reviews

10/10 Excellent

Amy C.

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

Tom K.

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

10/10 Excellent

Melissa M.

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.

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.

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