Skip to main content
Entire home

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Photo gallery for Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Sunset on the Bay in Ewell harbor 5 minute walk from the house.
View as you enter the bathroom from the kitchen
Seating for 4. perfect for morning coffee or evening drinks. Deck to be stained.
Kitchen island on locking wheels can be moved to fit your needs
View towards the bay at sunrise

Reviews

9.8 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Wildlife at your doorstep
    Guests love spotting wildlife right on the property grounds.
  • Ping pong on-site
    A rare find — challenge friends and family to endless matches.
  • Walkable and wonderful
    Guests love the walkable location for its easy access on foot.
1 bedroom1 bathroomSleeps 3

Popular amenities

  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue grill

Explore the area

View in a map
Smith Island, MD

Rooms & beds

1 bedroom (sleeps 3)

Bedroom 1

1 Queen Bed

Office 1

1 Single Bed

1 bathroom

Bathroom 1

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Porch or lanai
Kitchen
Garden

About this property

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

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 included. 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. 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.
Our prices include all fees. No hidden fees.

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Exterior
Walkable Beach Retreat on Chesapeake Bay!
Tangier
  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
10.0 out of 10, Exceptional, (1 review)
Walkable Beach Retreat on Chesapeake Bay!

House Rules

Check in after 1:00 PM
Minimum age to rent: 21
Check out before 8:00 AM
default

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

Pets allowed: dogs (limit 2 total)
$50 for each pet per stay
default

Smoking

Smoking allowed: in designated areas
Use ashtray and empty ashes. Ok to smoke outside.

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 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.
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

Important information

You need to know

Property # 3345492vb
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
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

About the area

Ewell

Smith Island is home to this holiday 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.
View more Holiday homes in EwellOpens in a new window
Map
Smith Island, MD

Restaurants

  • Drum Point Market
  • ‪Bayside Inn Restaurant - ‬2 min walk
  • ‪Smith Island Beans - ‬7 min walk
  • ‪Smith Island Cake Store at the Bayside Inn Restaurant & Carryout - ‬2 min walk
  • ‪Smith Island Baking Company - ‬1 min walk

Frequently asked questions

Is Summer is here on Smith Island! Come out and enjoy a great season on the Bay pet-friendly?

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

How much does it cost to stay at Summer is here on Smith Island! Come out and enjoy a great season on the Bay?

As of 18 Jul 2026, prices found for a 1-night stay for 2 adults at Summer is here on Smith Island! Come out and enjoy a great season on the Bay on 19 Jul 2026 start from £269, 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.

How much is parking at Summer is here on Smith Island! Come out and enjoy a great season on the Bay?

On-site parking is available at the property.

What time is check-in at Summer is here on Smith Island! Come out and enjoy a great season on the Bay?

Check-in begins at 1:00 PM.

What time is check-out at Summer is here on Smith Island! Come out and enjoy a great season on the Bay?

Checkout is at 8:00 AM.

Where is Summer is here on Smith Island! Come out and enjoy a great season on the Bay located?

Situated in Smith Island, this holiday home is 2.4 mi (3.8 km) from Smith Island.

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 13 out of 15 reviews
Rating 8 - Good. 2 out of 15 reviews
Rating 6 - Okay. 0 out of 15 reviews
Rating 4 - Poor. 0 out of 15 reviews
Rating 2 - Terrible. 0 out of 15 reviews

9.6/10

Cleanliness

10/10

Amenities

10/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Samantha J.

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
Response from VrboOwner on 16 Jun 2025
Son happy to hear you enjoyed your stay. You experienced what Smith Island is all about. Perfect guest! Come back anytime.
Verified

10/10 Excellent

David

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
Verified

10/10 Excellent

Timothy S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent property, excellent host. This is a very well-appointed property located very close to the ferry dock. Golf cart, bikes, and kayaks were in great shape. Chris could not have been a more responsive or helpful host.
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Amanda W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our first visit to Smith Island and the Double H was perfect. It was close to the ferry landing so getting there was very easy. The house was well appointed and felt like home as soon as we arrived. We enjoyed the quiet of the island and we were able to fully disconnect and relax Thank you for a great day.
Stayed 5 nights in Oct 2025
Verified

10/10 Excellent

Debra M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Such a lovely, cozy little house. Right in town. We could walk to restaurants and the bakery. We really enjoyed talking with the islanders and the walk out to Rhodes Point was beautiful.
Stayed 2 nights in Aug 2025
Verified

8/10 Good

Karen T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 2 nights in Jul 2025
Verified

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
Verified

10/10 Excellent

Trevor H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 2 nights in Jul 2025
Verified

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
Verified

8/10 Good

Jean T.

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
Verified

10/10 Excellent

Karen W.

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
Response from VrboOwner on 15 Jul 2025
Karen was a perfect guest. We are glad you experienced all that the island has to offer. We are sorry about not finding the house. It is a 3 minute walk from the dock by Harborside restaurant. Just let the captain know and they are always happy to help you with luggage and tell them the house and they can direct you. We hope to see you back again!
Verified

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
Verified

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
Response from VrboOwner on 7 Sept 2024
Thanks Kevin! It was nice to host you and I’m glad you got to use the kayaks and explore the beauty of Smith Island. You’re welcome to come back anytime!
Verified

10/10 Excellent

John D.

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!
Ferry to Smith Island- waiting to leave
Ewel from main channel
Maryland Terrapin
Great Blue Heron in the marsh
Stayed 3 nights in Jun 2025
Response from VrboOwner on 2 Jul 2025
You hit all the highlights of the island. We enjoyed having you as a guest especially one who appreciates kayaking. John was the absolute perfect guest that communicated well before during and after the stay. I hope to see you return again and it was an honor to host you.
Verified

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

About the host

Hosted by Christopher Winters

Host profile image
I am from the Midwest but fell in love with Smith Island and this home. I love to kayak and get away from the big city. This is the perfect place to relax and take in the beauty of nature and the Bay. I especially love the kayak water trails around the island.

Why they chose this property

It is a 110 year old home that has some modern amenities. I have been and will continue working on the house over the next few years and have made several changes already. It is open for rental year round and has a/c and heat and a screened in patio which is ideal year round. Propane fireplace that works and puts out quite a bit of heat. Only one bedroom upstairs with a second sleeping area (not a true bedroom) to the left of the stairs upstairs. The main and only bedroom is upstairs to the right. Air mattresses are also available. The kitchen is fully functional with plates, glasses, coffee machines, and pots and pans and a crock pot. You have everything there to cook a fine Chesapeake Bay meal. Bike and kayak will be available for use. Front porch has been (Sept 2024) updated and has new comfortable furniture to sit out in the evening and watch people go by on the street.
Please note there are 2 ferry boats that leave Crisfield every day at 12:30pm sharp. They leave the island at 7:30am every day except Sunday at 11:00am. The boats may not run every day depending on the captain's preference and weather. The boats I use are Capt. Jason or the Island Belle. The captain of the Capt. Jason boat can carry your luggage from the dock in Ewell (it's about a 45 min boat ride) in his yellow pickup truck directly to your house. Once you are there you will relax and enjoy the Water's Edge Retreat.

What makes this property unique

Golf cart, bikes and kayaks and inflatable stand up paddle board are available for guest use. Can walk to the water from the property to the left. Everything in the house is available for guests to use except locked owner’s closet under the stairs. The upstairs attic is also locked and not accessible Otherwise everything in the house is available for your enjoyment.

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback