Get away to relax on Smith Island in the Chesapeake Bay with golf cart included Reviews, Deals & Photos 2025

Q: 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).

Q: 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 Jul 30, 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 Jul 31, 2025 start from $191.25, excluding 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.

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

Situated in Smith Island, this vacation home is 0.2 mi (0.3 km) from Terrapin Sand Point and 2.4 mi (3.8 km) from Smith Island.

Similar properties

10/10 Excellent

Amy C.

Jun 28, 2024

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.

Sep 14, 2024

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.

Feb 22, 2024

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.

Jun 30, 2023

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.

Sep 2, 2024

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

Unlock instant savings with Member Prices

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

Entire home

Popular amenities

Add dates for prices

About this property

Entire place