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Entire home·Private host

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Photo gallery for Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

Interior
Outdoor dining
Welcome to this charming home, featuring a front porch with a welcoming sign and a wreath above the door.
Cozy retreat with a flat-screen TV, office chair, and desk, perfect for remote work or short stays.
Smart TV, fireplace, ping pong, books

Entire home

1 bedroom1 bathroomSleeps 390 sq m

Popular amenities

  • Parking available
  • Pet-friendly
  • Gym
  • Dryer
  • Fireplace
The current price is €302
includes taxes & fees
30 Jul - 31 Jul

About this property

Entire place

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

Get away to relax on Smith Island in the Chesapeake Bay with golf cart included

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. 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

Property manager

Christopher Winters

Add dates for prices

Property amenities

Beach

  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Electric kettle
  • Hob
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • 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
  • Smoke-free property

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 organised 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

Similar properties

Interior

Pet-Friendly Smith Island Cottage w/ Golf Cart!

  • Kitchen
  • Washer
  • Dryer
  • Pet-friendly
10.0 out of 10, Exceptional, 17 reviews
Pet-Friendly Smith Island Cottage w/ Golf Cart!

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 to 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 rubbish
Turn off the lights and lock the doors
If golf cart was used spray down with hose and cover
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

Pets

Pets are 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

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
On-site parties or group events are strictly prohibited
This property uses eco-friendly cleaning products
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
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 any lifts

About the area

Map
Smith Island, MD

What's nearby

  • Terrapin Sand Point - 5 min walk - 0.4 km

Restaurants

  • ‪Bayside Inn Restaurant - ‬5 min walk
  • ‪Smith Island Baking Company - ‬1 min walk
  • ‪Smith Island Beans - ‬7 min walk

Frequently asked questions

Is Get away to relax on Smith Island in the Chesapeake Bay with golf cart included pet-friendly?

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

How much does it cost to stay at Get away to relax on Smith Island in the Chesapeake Bay with golf cart included ?

As of 23 Jul 2025, prices found for a 1-night stay for 2 adults at Get away to relax on Smith Island in the Chesapeake Bay with golf cart included on 30 Jul 2025 start from €302.13, including 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 Get away to relax on Smith Island in the Chesapeake Bay with golf cart included ?

Check-in begins at 1:00 PM.

What time is check-out at Get away to relax on Smith Island in the Chesapeake Bay with golf cart included ?

Checkout is at 11:00 AM.

Where is Get away to relax on Smith Island in the Chesapeake Bay with golf cart included located?

Situated in Smith Island, this holiday 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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Get away to relax on Smith Island in the Chesapeake Bay with golf cart included Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 8 out of 9 reviews
Rating 8 - Good. 1 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

9.4/10

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