Spectacular Sunsets- Waterfront Home On Smith Island

Photo gallery for Spectacular Sunsets- Waterfront Home On Smith Island

A white church with a bell tower and a flagpole.
A bedroom with two beds, a small table with a lamp, and a window.
A living room with a blue sofa, a green armchair, and a patterned armchair. There are two wooden doors and a map on the wall.
A dining area with a round table, chairs, and a checkered tablecloth. There is a window with a view of the kitchen.
A laundry room with a front-loading washer and dryer, wooden flooring, a wooden door, and lace curtains on the windows.

Reviews

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

Highlights

  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Air conditioning
  • Breakfast for a fee
  • Refrigerator
  • Internet
  • Washer
  • Garden

Explore the area

View in a map
Tylerton, Smith Island, MD
  • Place, Tylerton County Dock
    ‪2 min walk‬

Rooms & beds

4 bedrooms (sleeps 16)

Bedroom 2

2 Twin Beds and 1 Child Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Twin Beds

Master Bedroom- Bedroom 1

1 Twin Bed and 1 Queen Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Spaces

Kitchen
Separate dining area
Garden

Add dates for prices

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Living area
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About the neighborhood

Tylerton

Located in Smith Island, this vacation home is in a rural area and on the waterfront. Tylerton County Dock and Crisfield City Dock are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Smith Island and Horse Hammock. Discover the area's water adventures with kayaking and snorkeling nearby, or enjoy the great outdoors with cycling and hiking.
View more Vacation Homes in TylertonOpens in a new window
Map
Tylerton, Smith Island, MD

What's nearby

  • Tylerton County Dock - 2 min walk - 0.2 km

Restaurants

  • ‪Drum Point Market - ‬1 min walk
  • Bayside Inn Restaurant
  • The Roost
  • Smith Island Cake Store at the Bayside Inn Restaurant & Carryout

Frequently asked questions

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

No, pets are not allowed at this property.

How much does it cost to stay at Spectacular Sunsets- Waterfront Home On Smith Island?

As of Oct 31, 2026, prices found for a 1-night stay for 2 adults at Spectacular Sunsets- Waterfront Home On Smith Island on Dec 30, 2026 start from $222, 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.

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

Situated on the waterfront, this vacation home is steps from Tylerton County Dock and 0.1 mi (0.1 km) from Smith Island.

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 29 out of 33 reviews
Rating 8 - Good. 2 out of 33 reviews
Rating 6 - Okay. 1 out of 33 reviews
Rating 4 - Poor. 1 out of 33 reviews
Rating 2 - Terrible. 0 out of 33 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.4/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay in Tylerton! We loved it and will be back again. The kayaking is awesome and everyone we met were so friendly and helpful!
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was our second time here. We love the house, we love the location, we love the islanders and also the host! She’s very easy to communicate. This is truly a place to come and relax and enjoy family time. We have plans to come back again!
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house description is accurate. Place was clean and cozy. Quick and easy communication with the host. Would recommend. Can’t wait to go back.
Stayed 2 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Best place to stay in tylerton for larger groups! :-) owner is always incredibly helpful. And you get great access to the world famous drum Point market! :-)
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Another great stay!
Stayed 1 night in Oct 2025
Response from VrboOwner on Oct 22, 2025
Thank you Todd! We are delighted to host you!
Verified review

10/10 Excellent

Liked: Cleanliness, communication, location, listing accuracy
Friendly Island, close access to dock and store!!
Stayed 4 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect and oh, so easy location right near the dock! Made it so easy to visit family who lives at Smith Island but not be a burden to her. Thoroughly enjoyed our stay!
Stayed 2 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Spot

Great House!
Stayed 4 nights in Jan 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great House!

We had a great stay- very comfortable house with lots of room. Great location!
Stayed 2 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Check-in, communication, location, listing accuracy
The cottage could not be more convenient to the dock for unloading. Cool home in an incredible setting. We are already planning our return.
Stayed 1 night in Sep 2025
Verified review

8/10 Good

Liked: Check-in, communication, location
Disliked: Cleanliness, listing accuracy
As a former Airbnb host, I may hold vacation rentals to a higher standard than the average guest, but I wanted to share some constructive feedback to help improve future stays.A detailed cleaning checklist would help ensure consistency. Upon arrival, the twin bed sheets had visible dirt and were rewashed before use. The first-floor twin mattress also had a large stain. The vacuum canister and filters appeared overdue for cleaning, and the AC filters had visible mold buildup. We cleaned them before using the AC. We also noticed crumbs on the tables, dusty portable fans, and living room cushions that simply needed to be tucked in.A few suggestions: secure homeowner-only areas and personal belongings, as the home is listed for 16 guests but appeared to sleep about nine, with no cots or air mattresses available. Additional lighting would make the home feel more inviting. A laminated guest guide with Wi-Fi information, house rules, local recommendations, emergency contacts, and boat taxi information would also be a great addition. A keypad entry system would improve both convenience and security.Despite these observations, we truly enjoyed our stay. We had a wonderful time crabbing, kayaking, boating, fishing, and, most importantly, making lasting memories together as a family! The home is beautiful, and with a few improvements, it could provide an even better experience for future guests.
Stayed 3 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paulette’s cottage

Such a sweet cottage!! Comfortable with beautiful sunsets!!
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome House

Our visit to Tylerton was nothing short of Awesome. Gretchen is always such a great host! Thank you so much for our stay!!!
Stayed 2 nights in Apr 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing as always!! 3rd time. Missed Marry but still worth it!! So quiet and peaceful. House is beautiful and owner rocks!! If you’re reading this just scroll up and book it!! You won’t regret it and you’ll come back again!!
Stayed 2 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Gretchen was wonderful as our host at Miss Pauline’s Cottage. There is plenty of room, comfy beds, nice big kitchen with plenty of dishes, pots and pans. Nice bathrooms. Everyone on the island is so welcoming and very generous with information. Make sure you go to Drum Point for crab cakes and other yummies! Captain Terry on the Captain Jason got us to and from easily. Captain Eddie Corbin was our awesome pontoon boat host for two days. Everyone is just great. You should definitely visit this cottage and the island.
Stayed 4 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Slowing down in Tylerton

We all enjoyed staying in this older house in Tylerton close to the dock and water. Only a few steps to the Drum Point Market for food supplies. Tylerton is a good place to get away and meet some good friendly people from Smith Island. There aren't a lot of amenties in the town and area, but the house is well-equipped with wifi, heating and cooling. It's quiet - a good place to read and stroll.
Stayed 3 nights in May 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The kitchen was well-prepared for cooking. I did bring a small frying pan as I was told by a previous visitor that they didn't find a small one. One may be there that I missed.If there were a couple of fold-up lawn chairs available, that would be a wonderful addition. We could take them out to the pier to watch the sunset or sit outside in them. The weather was wonderful. The picnic table seats are very low and awkward to use if you're trying to eat from a plate--which we didn't try to do at the picnic table. We received a prompt reply text when asking for the wifi code.
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Dreamy!

We stayed with 5 adults and one infant and the house has plenty of indoor and outdoor space to spread out and relax. The views can’t beat. Look out any window and you know you’re in beautiful Tylerton and I’ve never been anywhere like it. The house is steps away from the county dock and the market. We strolled around wondering at the singular beauty of the place. We sunned ourselves on the dock in the afternoon, watching turtles and marveled at the distant lightning storms. We enjoyed crab cakes from the market, a dinner cooled by Mary, a cake from Kristen and a pontoon cruise to see the Pelican rookery. Everyone we met on the island was lovely. I’m already plotting my next visit.
Stayed 2 nights in Jul 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family getaway

Our family wanted to get away and experience Smith Island and had a great stay at Pauline’s Cottage. You must get the crabcake from Drum Point market (they’re voted best in Md for a reason!) and a float or two! The market is like two doors down. We visited most days. Things to know: * You have to travel by boat, Tylerton is not connected to the other parts of Smith Island or the main land. The Ferry, Captain Jason runs daily to and from the island. * Once you’re on the island, you can also connect with local resident Eddie to get a ride to the other side of the channel, and a tour of the pelican rookery. * The market isn’t open on Sundays or late most days so you will want to pack a cooler with a few meals for your stay. The kitchen is well stocked to cook for yourself.* Water bugs- pack lots of bug spray, and long sleeves/hoods.* The TV is basically a monitor, but there’s a good collection of family friendly movies to watch and board games to play if you’re stuck inside.We also booked kayaks (adventure smith island at 3 point marine will deliver them to Tylerton) for a day and a sunset cruise.
Stayed 5 nights in Jun 2025
Verified review

4/10 Poor

The home was clean and comfortable.

My husband and I had rented this property mid-June. If you are a writer, photographer, artist, birder, or traveling with a group to kayak or paddle board this may be the ideal place.There is a lot of solitude for everyone in your group. Bring EVERYTHING you will need. Drum market has a good convenience store type inventory ie milk,eggs,and excellentl crab cakes and you can get ice at the shed on the dock where the boat (Jason II) drops you off. (Only a stones throw from the house.) The kitchen was good size and most pantry type things stocked. Not any room to put groceries as the owner has their things in the cupboards but there is a large kitchen table to put your groceries. Also don’t plan on using the freezer (ample frig space)the owner has their things occupying freezer space. The home is very comfortable including the beds and linens and plenty of towels. I recommend bringing your own pan scrubbing sponge and handiwipes. The scrubbers there were shall we say less than sanitary. There is no outside grill, no screened porch,or any porch, no WiFi ,no TV(owners say it’s spotty but we had none),no cable (some dated children’s DVD’s but not much for the adults) There is only a small computer screen to view these)There are some games but not a complete deck of cards available. There are no beaches, no place to swim, no lawn chairs, (a picnic table but no umbrella) not a good place for eating as the mosquitos and flies will have a banquet as well. We shared a slice of the famous Smith Island cake but not too impressed. The crab co-ops were not in business at the time ( not there fault) Plan on cooking as the only restaurant is in the Drum market and they close around 3-3:30. We did not have the opportunity to visit Ewell (pronounced Youll) as we had a family matter to attend to. Also since one needs to bring absolutely everything, the good news is you can bring your vehicle right up to the boat to load your stuff and then park your vehicle for $3/day. Just check with the visitors office (right side of the maim street) in Crisfield and they’ll direct you where to park. We didn’t bring any bottled water the tap water was very good. And of course the island is dry so you will need to bring your own alcohol. It would be nice if the owners provided some kayaks or paddle boards as a means to have some fun in the water but you must bring your own toys.As the saying goes “ it is what it is.”(A first-aid may be a good idea too)
Stayed 7 nights in Jun 2018
Response from VrboOwner on Apr 2, 2020
Hi Harold and Betty, Thanks so much for your message. We are glad that overall that you enjoyed your stay, and we hope all is well with your family. If you stay with us again, please do feel free to call us any time before, or during, your stay if you have questions about whether we provide items at the house for our guests, or about questions for fun things to do while at Smith Island. There are actually many lawn chairs for guests to use in our garage that's in the backyard, the TV does in fact have several channels via our cable service, there is a first aid kit in the undercabinet of the smaller bathroom, there are several full decks of cards in the living room, and there are a supply of new scrub brushes and sponges under the kitchen sink or in the mudroom closet if needed. There are also several gorgeous and pristine beaches on Smith Island for lounging, beachcombing and swimming, and many folks also enjoy swimming right off the several docks in front of our house. We do have a kayak and three canoes in the shed, but unfortunately our insurance doesn't allow for guests to use them. We've had many guests enjoy renting kayaks/canoes from Crisfield Kayak and Canoe- they are wonderful- they load the boats for you directly onto the ferry, and pick them up from the Crisfield dock when you return. We hope you have a lovely rest of the summer, and come back to visit Smith Island again soon! Best regards, Gretchen and Eric
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Absolutely loved it here! Everything about it was just fantastic. Relaxing scenic views and lots of kayaking. Everyone is super friendly and we were invited to the 4th of July picnic it was just lovely. This is the perfect place to relax and recharge.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

A true getaway

What a wonderful stay. The host was excellent, the island folks were the friendliest we’ve ever met. The house was very nice and had just about everything we needed. We’d love to come back!
Stayed 6 nights in Jul 2022
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good location

Enjoyed our stay
Stayed 3 nights in May 2021
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful!

The house is neat, comfy, quiet environment. I was looking for a peaceful staying and I got it!
Stayed 2 nights in Sep 2020
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Weekend on the Chesapeake Bay!

My family had a relaxing weekend on Tylerton staying at Pauline's House. We rented kayaks in Crisfield and took them over on the ferry with us. The water was beautiful! The crab cakes and old bay fries at the Drum Point Market were delicious!!! Don't forget the Smith Island Cake!!
Stayed 2 nights in Sep 2020
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