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Spectacular Sunsets- Waterfront Home On Smith Island

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Spectacular Sunets!
Front of house
Back of house on waterfront
Living Room
Dining room- seats 6 guests

Reviews

9.4 out of 10
Exceptional
4 bedrooms2 bathroomsSleeps 16185.8 sq m

Popular amenities

  • Breakfast available
  • Dryer
  • Washer
  • Air conditioning
  • Kitchen
  • Outdoor space

Explore the area

Map
Tylerton, Smith Island, MD
  • Somers Cove Marina
  • Horse Hammock
  • Smith Island
    ‪1 min drive‬

Rooms & beds

4 bedrooms (sleeps 16)

Bedroom 2

2 Single Beds and 1 Child Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Single Beds

Master Bedroom- Bedroom 1

1 Single Bed and 1 Queen Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Spaces

Kitchen
Separate dining area
Garden

About this property

Spectacular Sunsets- Waterfront Home On Smith Island

Gorgeously appointed and newly renovated large historic four bedroom, two story home, on the waterfront in Tylerton, Smith Island, Marlyand in the heart of the beautiful Cheseapeake Bay. Smith Island was just voted by National Geographic Travel Magazine as one of the TOP 20 BEST PLACES in the WORLD to visit in 2016!

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.

Expansive 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 Bed and Breakfast 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, beachcombing, 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

Add dates for prices

Amenities

Kitchen
Washer
Dryer
Air conditioning
Outdoor space
Water view

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House Rules

Flexible check-in available (contact host in advance of arrival)
Flexible check-out available (contact host to arrange)
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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
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

We should mention

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

About the area

Tylerton

Located in Smith Island, this holiday home is in a rural area and on the waterfront. Tylerton County Dock and Sea Mark Marine 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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Tylerton, Smith Island, MD

What's nearby

  • Tylerton County Dock - 2 min walk - 0.2 km
  • Terrapin Sand Point - 7 min walk - 0.6 km
  • Smith Island - 1 min drive - 0.0 km

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 holiday home is within a 10-minute walk of Tylerton County Dock and Terrapin Sand Point. Smith Island is 0.1 mi (0.1 km) away.

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 16 out of 19 reviews
Rating 8 - Good. 1 out of 19 reviews
Rating 6 - Okay. 1 out of 19 reviews
Rating 4 - Poor. 1 out of 19 reviews
Rating 2 - Terrible. 0 out of 19 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

9.2/10

Listing accuracy

Reviews

10/10 Excellent

Merritt L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Spot
Great House!
Stayed 4 nights in Jan 2025

10/10 Excellent

Ellen T.

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

6/10 Okay

Don S.

Liked: Cleanliness, check-in, communication, location
Disliked: Listing accuracy
Smith island
Stayed 9 nights in Aug 2024

10/10 Excellent

Anne M.

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

10/10 Excellent

Mike K.

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

10/10 Excellent

Eric F.

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

10/10 Excellent

Holly T.

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

10/10 Excellent

Corinne M.

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

10/10 Excellent

Patsy P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Good location
Enjoyed our stay
Stayed 3 nights in May 2021

10/10 Excellent

Roxana Z.

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

10/10 Excellent

Gloria M.

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

10/10 Excellent

Jeremy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Definitely an island vacation
We had a great time on Smith Island. I will forewarn, bring what you need to begin with. Going back and forth to crisfield for supplies isn’t exactly fun. The property has a well equipped kitchen and everything you need to enjoy the stay. Also, catching 25 inch rockfish off the dock is always fun.

10/10 Excellent

Geraldine G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Quiet , nice place for vacation.
Loved to come back here for weekend vacation. People are so nice and and the place is quiet and serene. They have fresh crabs and the store sells delicious Smith Island cake.
Stayed 1 night in Aug 2019

10/10 Excellent

Don F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place!
Super in all respects, especially the friendliness of the residents, and the help provided by Gretchen, before our arrival.

10/10 Excellent

Sonja A.

Great experience!
We had a wonderful time during our stay in Tylerton! Gretchen’s house was lovely and provided everything we needed. We enjoyed crabbing, swimming and kayaking, and just generally “unplugging” from the typical busyness of everyday life! We attended church on Sunday and enjoyed a freshly baked Smith Island cake, made by our “neighbor” Mary Ada herself!! Smith Island is truly a step back in time and was sooooo refreshing! We will return! Just some helpful info...the store is not open on Sunday and there are no restaurants on Tylerton, so plan ahead! Also, bring as much of your own food as possible, as the stores prices are significantly marked up! With that being said, they had everything we needed, and their food was very good!
Stayed 4 nights in Aug 2018

10/10 Excellent

Joseph C.

Great place
Wonderful people on smith island. I wish I would have brought a boat. The House was nice, roomy, and very clean. Thank you all for having us.
Stayed 2 nights in Jun 2018

4/10 Poor

Harold and Betty B.

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
This review was submitted before 2018 and has not been verified.

8/10 Good

tammy h.

Pauline's House
MY GROUP AND I REALLY LOVED THIS HOUSE. THE ISLAND TAKE YOU BACK IN TIME SOMEWHAT. EVEN THROUGH IT RAINED WE MADE THE BEST OF IT. I WILL GO BACK SOMEDAY! TAMMY HAMMOND
Stayed 3 nights in Jul 2017
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Paula P.

Paradise in Smith Island!
Pauline's house is a lovely home with an absolutely beautiful waterfront view! The sunsets truly are spectacular, like the listing says! Was clean & well furnished. Included a good assortment of kitchen utensils & basic pantry items. Will very comfortably sleep 9 adults & 1 small child. There's plenty of seating for meals with a group this size with a kitchen table + dining room table. Listing says will sleep up to 16, but in my opinion that would be a bit crowded, but I realize everyone's comfort level varies. Pauline's house is close to the Red Drum Market, which we were pleasantly surprised by how well it was stocked. Bottom line - we would love to come back to Smith Island and rent this same house again!
Stayed 3 nights in May 2017

About the host

Hosted by Gretchen

Host profile image
Our family has two small boys, and we first found "Pauline's House" when we were looking for a vacation home off the grid where we could be immersed in nature, culture and history- we found the perfect home and location of Smith Island!

Why they chose this property

"Pauline's House", affectionately named in honor of the home's first owner, is on the waterfront with a big backyard, including a vegetable garden, picnic table and spectacular sunsets! Newly renovated to it's historic charm, the house is furnished with antiques, and all the amenities and comforts of home.

What makes this property unique

Pauline's House is a beautiful waterfront home where you can curl up with a good book while gazing out the windows upon the sparkling Bay, or from which you can get ready for your next eco-adventure! Set out crab pots or go fishing off the dock in the morning while listening to the lullaby of cormorants and gulls. Go progging (what the locals call beachcombing) along the marshy inlets to find thousand year old arrowheads. Watch the shimmering ripple
of the tide as your paddle glides along the water. Feast on the day’s catch while gazing at the warm sun as it melts into the horizon across the Bay. Share laughter and good times with family and friends, and exchange knowing smiles about the secret you share- that you are in the most magical place on earth- Smith Island.

Languages:

English, French, Spanish
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