Entire home

Spectacular Sunsets- Waterfront Home on Smith Island

Photo gallery for Spectacular Sunsets- Waterfront Home on Smith Island

Beach
Pool
Exterior
4 bedrooms, WiFi, bed sheets
Dining
Reviews
10

Exceptional

Entire home

4 bedrooms2 bathrooms2000 sq ft

Popular amenities

  • Breakfast available
    Breakfast availableBreakfast available
  • Air conditioning
    Air conditioningAir conditioning
  • Kitchen
    KitchenKitchen
  • Outdoor Space
    Outdoor SpaceOutdoor Space
  • Washer
    WasherWasher
  • Dryer
    DryerDryer

Explore the area

Map
Tylerton, Smith Island, MD
  • Popular LocationTerrapin Sand Point7 min walk
  • Popular LocationSmith Island1 min drive

About this property

Entire place

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

Spectacular Sunsets- Waterfront Home on Smith Island

Gorgeously appointed and newly renovated large historic four bedroom, two story home, on the water in Tylerton, Smith Island, Marlyand in the heart of the beautiful Cheseapeake Bay. Comfortably sleeps 9, with 2 queen size beds and 5 single beds (additional beds available upon request)- perfect for large groups of friends or families.

Huge eat in kitchen, PLUS a dining room- total seating for 12. Spectacular water views from dining room, kitchen and three bedrooms. Lovely sunlit living room, two full bathrooms and a full mudroom with a washer and dryer.

Big backyard on the water (with white picket fence for the little ones) for picnicing, barbequing and lounging.

All bedroom and bathroom linens provided, as well as kitchen supplies (pots, pans, dishes, etc.) if you'd like to cook while on the island.

Alternatively, if you would like the B and B experience, we can arrange for your meals to be expertly prepared and delivered by island ladies- to your custom order!

Where is Tylerton, Smith Island? Just a short ferry ride from Crisfield, Maryland- travel back in time with your family and friends to this quaint and blissfully quiet traditional waterman's village. Enjoy kayaking, boating, hiking, fishing, crabbing, harvesting oysters, biking or simply taking long walks along the water. For hunters and fisherman, there is some of the best duck hunting and fishing on the East Coast!

Visit the local Drum Point Market for the world's absolute best crab cakes, or take a stroll along the crab shanty dock and visit local toy and craftmakers. Visit the famous crab picking coop, and play baseball, soccer and lacrosse and fly kites on the baseball field. Explore the incredible Pelican Rookery (right out of National Geographic!) and take a trip to a crab shanty to learn how hard shell crabs become soft shells! Spend time leasurely talking to locals all about the island's history and their life on the island. Become an honorary Junior Fire Fighter at the local fire station, or just spend luxurious hours sitting on the dock, watching the tide ebb and flow, and eventually, the spectacular setting sun. Then watch in awe as the dark night sky comes alive with thousands of brilliantly beaming stars just for you!

Property manager

Gretchen

Languages

English, French, Spanish

Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Car not required

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Breakfast available for a fee

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Bathtub or shower
  • Towels provided

Living spaces

  • Living room
  • Separate dining area

Entertainment

  • Books
  • DVD player
  • Games
  • TV with cable/satellite channels
  • Video library

Outdoor areas

  • Dock
  • Garden

Laundry

  • Washer/dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Housekeeping (on request)
  • Meal delivery service
  • Phone

Location highlights

  • In a rural location
  • In a village
  • Near the bay
  • Near the marina
  • On the waterfront

Things to do

  • Kayak on site
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Hiking/biking trails nearby
  • Hunting nearby
  • Jet skiing nearby
  • Rafting nearby
  • Sailing nearby
  • Snorkeling nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector not reported (host has not indicated whether there is a smoke detector on the property)

General

  • 1 unit
  • Garden
  • Housekeeping (on request)
  • Unit size: 2,000 square feet

Similar properties

Policies

Special check-in instructions

The front desk hours vary at this property
Guests must contact the property for check-in information
To make arrangements for check-in please contact the property ahead of time using the information on the booking confirmation
You will receive an email from the host with check-in and check-out instructions
Check-out time is flexible; to make arrangements, please contact the property ahead of time using the information on the booking confirmation

Pets

Pets not allowed

Children and extra beds

Children are welcome

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
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
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

A car is not required for transportation to and from this property

About the neighborhood

Tylerton

Located in Smith Island, this vacation home is in a rural area and on the waterfront. J. Millard Tawes Museum and Tangier History Museum are cultural highlights, and some of the area's activities can be experienced at Somers Cove Marina and Smith Point Marina. Discover the area's water adventures with jet skiing and snorkeling nearby, or enjoy the great outdoors with hiking/biking trails and ecotours.

What's nearby

  • Terrapin Sand Point - 7 min walk
  • Smith Island - 1 min drive

Restaurants

  • Bayside Inn Restaurant
  • Smith Island Baking Company
  • Smith Island Beans

Frequently asked questions

Is Spectacular Sunsets- Waterfront Home on Smith Island pet-friendly?

No, pets are not allowed at this property.

Where is Spectacular Sunsets- Waterfront Home on Smith Island located?

Situated on the waterfront, this vacation home is 0.1 mi (0.1 km) from Smith Island and 0.4 mi (0.6 km) from Terrapin Sand Point. Chesapeake Health Care and Pocomoke River State Park are also within 32 mi (52 km).

Reviews

10

Exceptional

Rating 10 - Excellent. 36 out of 37 reviews" "
Rating 8 - Good. 1 out of 37 reviews" "
Rating 6 - Okay. 0 out of 37 reviews" "
Rating 4 - Poor. 0 out of 37 reviews" "
Rating 2 - Terrible. 0 out of 37 reviews" "

10/10

Cleanliness

Reviews

10/10 Excellent

Maeghan K.

Liked: Cleanliness
Quiet and sublime
It was exactly what we were looking for.
Stayed 3 nights in Apr 2023

10/10 Excellent

Merritt L.

Liked: Cleanliness
Another Great Year!
Great Stay!
Stayed 4 nights in Jan 2024

10/10 Excellent

helen g.

Liked: Cleanliness
Lovely
A fantastic introduction to island life on the eastern shore. Fabulous house, comfy, really well equipped and stocked. Friendly neighbors. Maybe a mosquito or 2, but the sunrises and sunsets and stars made up for them. I hope to return.
Stayed 3 nights in Sep 2023

10/10 Excellent

Gregory P.

Liked: Cleanliness
Perfect place for a group !
Have stayed multiple times with our Sea Kayaking club and we love the place and its owners. It's perfect for a group ! :) thanx again !
Stayed 2 nights in Jul 2023

10/10 Excellent

Felicia S.

Liked: Cleanliness
What a beautiful day in the neighborhood
When I heard the Church bells I remembered my Grandmother
Stayed 4 nights in Jun 2023

10/10 Excellent

Verified traveler

Liked: Cleanliness
Another Great Year
Love this little cottage and Tylerton, great spot!
Stayed 4 nights in Jan 2023

10/10 Excellent

Rebecca B., Waldorf

Liked: Cleanliness
Sunsets and Seafood
If you want to get away from the hustle and bustle, this is the place. Each day we had a seafood sandwich for lunch at the market and seafood for dinner prepared by Kristen. The sunsets were spectacular. We drank wine, strolled, had a paint party with Dennis, boated over to the pelican rookery with Eddie Corbin, and worked on a picture puzzle.
Stayed 3 nights in Oct 2022

10/10 Excellent

Allison R.

Liked: Cleanliness
Truly unique and peaceful experience.
The house itself was charming and beautifully equipped with all that you would need. Tylerton is a unique experience in and of itself. Small and picturesque and very peaceful. If you’re looking for a quiet getaway, this is a perfect spot. You’ll get to know the people, who are very warm and friendly. There aren’t the typical activities you’d find in other beach towns, but there’s plenty of kayaking and fishing opportunities. Highlights are the views, sunsets and people. Captain Larry on the ferry over to the island must be mentioned too. He goes beyond being friendly and helpful but truly was a lifesaver in a difficult moment. I’ll be planning future trips.
Stayed 3 nights in Sep 2022

10/10 Excellent

Ellen C.

Liked: Cleanliness
Quiet and relaxing
We had a lovely weekend in Tylerton, it was super quiet, people were very friendly.
Stayed 2 nights in Jul 2022

10/10 Excellent

Anugraha (Anu) P., Derwood, Maryland, USA

Liked: Cleanliness
Great location on the island and comfortable house
We had an excellent stay over a long weekend. Felt like we were taking a step back in time to a much simpler life — the unique Smith Island experience is very memorable. Really friendly neighbors, excellent crab cake sandwich at Drum Point market, beautiful walks and spectacular sunsets from the backyard. Definitely recommend renting a boat with Eddie to visit the other towns on the island — we unfortunately could not go to the rookery and beaches because it was too windy. The house is exactly as advertised. We hope we get to come back.
Stayed 3 nights in Jun 2022

10/10 Excellent

Bonnie S.

Liked: Cleanliness
A perfect visit
We had bow much fun at this sweet home. Perfect size for three ladies, clean, and perfectly located in town. Kristin was awesome and cooked us delicious meals each night. What a great place to relax and reflect.
Stayed 2 nights in May 2022

10/10 Excellent

Jan B., Freeville

Liked: Cleanliness
Fabulous Getaway
This lovely, comfortable home is a stone's throw from the bay. Sunsets were wonderful. Accommodations were comfortable and "homey." Community members were welcoming and easy to engage in conversation. Though only there for five nights, it felt like I had entered another world, far from the stresses of everyday life. I highly recommend a stay at this property on this island where a way of life is rapidly fading. Be sure to check out the Drum Point Market, church, and boat tour of the communities that are part of "Smith Island."
Stayed 5 nights in Apr 2022

10/10 Excellent

Verified traveler

Liked: Cleanliness
Great Stay...
Perfect, as advertised...
Stayed 4 nights in Jan 2022

10/10 Excellent

Charles J.

Liked: Cleanliness
Great Island Thanksgiving
A gale came up while we were there but the house was very cozy.
Stayed 3 nights in Nov 2021

10/10 Excellent

Maria K.

Liked: Cleanliness
Wonderful, Charming and Spacious House
We had a wonderful time in this beautiful home by the water. Even after three days, I still got turned around in this large, charming space with ample rooms, nooks, and stairs. The hostess answered all of my questions quickly and we just couldn't have been more comfortable. It was a perfect girls' getaway for my teens and me. Thank you, Gretchen!
Stayed 3 nights in Oct 2021

10/10 Excellent

kiley f.

Liked: Cleanliness
A special community
A very quiet place with a tight-knit community. Everyone was so friendly. Shout out to @SmithIslandArt for a warm welcome, and in terms of food -- we shouldn't have brought so much to cook with and simply eaten the most delicious crab cakes for every meal.
Stayed 2 nights in Sep 2021

10/10 Excellent

Karen H.

Liked: Cleanliness
We shall return. We loved Tylerton and we loved everything about the charming house.
like a wonderful dream of friends to keep
Stayed 2 nights in Aug 2021

10/10 Excellent

debra b.

Liked: Cleanliness
Smith Island
We went for peace and quiet and that is what we got. People in Tylerton were very helpful. We prepared for the fact that everything in Tylerton closes at 3pm and Ewell at 4pm so no surprises. Lovely views. House well kept and Kristen was especially kind.
Stayed 2 nights in Aug 2021

10/10 Excellent

debra b.

Liked: Cleanliness
Smith Island
Nice place to stay if you want peace and quiet
Stayed 2 nights in Aug 2021

10/10 Excellent

Jessica M.

Liked: Cleanliness
Very laid back
The house was beautiful and the community was very welcoming and kind. We love to kayak and we brought our boats over on the ferry. There are gorgeous and well marked water trails for kayaks. I tagged our trip in several kayaking groups because these were honestly was some of the best water trails that I have been on. The children had a blast.
Stayed 3 nights in Jul 2021

10/10 Excellent

Kasia T.

Liked: Cleanliness
Family getawaaaaaaay
We had a lovely time on Tylerton and this was a safe, clean and affordable place to stay. Property Manager Kristen took excellent care of us and prepared delicious meals. Our best moments were pontoon boat rides with Eddie. When you’re close to your date, ask for the number and let him know when you’re there and interested in a ride. Don’t worry about scheduling an exact time or getting formal confirmation—it all happens very casually. One day, Eddie dropped us off on the other two islands that make up Smith Island and we rented a golf cart. In four hours, we rode there, toured both islands, visited the bakery and museum and ate lunch. We took our other rides through the gut and enjoyed uninhabited places, like Pelican Island. Tylerton has historic value and most of the people have lived there for generations. They welcomed the few tourists on the island with friendly smiles and informative conversation. They love sharing how much the island means to them. You’ll sit alongside them as you take the ferry to and from Cristfield. You’ll quickly figure out who is currently in which house and learn through storytelling who grew up in others. Pack minimally. Bring bug spray. No beach really means no beach—beautiful doc from which you can catch the sunset. My cell phone service wasn’t very reliable and we didn’t stream, though internet was available. Best for people who are comfortable immersing in and appreciating a different way of life. Take a book. Take a few naps. Walk early in the morning and in the evening. Eat the cake.
Stayed 3 nights in Jul 2021

8/10 Good

David G., Levittown, PA

Liked: Cleanliness
Perfect get-a-way!
My wife and I stayed at this lovely remote house on the island for two nights and truly enjoyed our stay. Looking forward to returning in either the Fall or Spring for another retreat weekend! People on the island are extremely friendly and helpful! Great place to get away from it all!

10/10 Excellent

mei x.

Liked: Cleanliness
Great!
Great quiet time with family!
Stayed 6 nights in Jun 2021

10/10 Excellent

Charles H.

Liked: Cleanliness
Second Visit
Different season yet just as stunning. Don't get off the boat unless you're willing to RELAX
Stayed 2 nights in May 2021

10/10 Excellent

Bradley G., Washington, District Of Columbia

Liked: Cleanliness
A Most Relaxing Spot
We had a lovely time staying at Gretchen's. Tylerton is one of the most remote places I've been to, and the peace and quiet of the house and the island exceeded my expectations. The house has everything you could need, and the neighbors are willing to help with anything you might ask them for, whether it be catering dinner or taking you over to Ewell by boat. We definitely would stay at Gretchen's again!
Stayed 3 nights in Apr 2021