Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
72 min drive
Rooms & beds
5 bedrooms (sleeps 10)
Bedroom 1
2 Single Beds
Bedroom 2
1 Double Bed and 1 Single Bed
Bedroom 3
2 Single Beds
Bedroom 4
1 King Bed
Bedroom 5
1 Queen Bed
3 bathrooms
Full Bath 1
Towels provided · Bathtub or shower · Toilet
Full Bath 2
Towels provided · Bathtub or shower · Toilet
Full Bath 3
Towels provided · Bathtub or shower · Toilet
Spaces
Deck or patio
Kitchen
Balcony
Outdoor play area
Garden
Dining area
About this property
Waterfront home with spectacular sunsets by Seaside Vacations & Sales
Traveling - it leaves you speechless, then turns you into a storyteller…..
And oh, the stories that newly renovated ‘Lookout on Main’ has in store for you! This one-of-a-kind Dream Home is located on South Main Street, directly facing THE most amazing Chincoteague Sunsets you could imagine. And you want waterfront, you say? It doesn’t get much more waterfront than at this fantastic home! Lookout on Main’s huge backyard is perched right on the banks of the Chincoteague Bay - 95 wonderful feet of shoreline with both a Dock and a Ladder. You can easily launch your kayak, canoe, or paddleboard right from the Dock, or bring your water shoes and do some clamming! Two kayaks and a canoe will be waiting for you to enjoy, as a matter of fact, along with crab pots, 2 boogie boards, and 4 beach chairs. In the evening, gather around the Fire Pit, sink into an Adirondack, and share stories of the day’s adventures - it doesn’t get much better than this…..
You’ll love relaxing in the Living Area with Soaring Ceilings and floor to ceiling windows. The Wall of Windows lets in stunning Bay Views, right from the sofa. This is a lovely place to curl up with a good book, or catch up on some work with Free WiFi. Wander out the sliders to the huge Screened Porch which lines the back of the home. With a huge 10 person Outdoor Table, it’s the perfect place to enjoy some Local Crabs or the Fresh Catch of the Day - which hopefully you caught! Only steps away from the Living Area is the Family Room/Entertainment Room with a 70 inch Flat Screen TV with DVD/Blu-Ray Player and Sound Bar!
Lookout on Main has the perfect open layout for spending time with those who matter most without ever feeling crowded. The Kitchen and Dining Area are just off the Living Area and also offer lovely water views. The Kitchen is well-stocked with all you need to make mealtime a bay breeze - and talk about dining with a View! Not one to cook on Vacation? Wander down to Main Street for many dining options, or grab some J and B's famous subs - just a short stroll away.
Lookout on Main sleeps 10 more than comfortably in 5 Bedrooms. The Master Bedroom sits on the top floor with great views, a comfy King Bed, and even a Private Waterfront Balcony. Just imagine slipping out to stargaze while everyone else slumbers…..
Bedrooms 2 through 5 are located downstairs, along with yet another Family Room, where you will find Flat Screen Cable TV with Streaming capability. Bedroom 2 has a Queen Bed, Bedroom 3 has a Twin Bunkbed, Bedroom 4 has 2 Twins, and finally, Bedroom 5 has a Pyramid Bunk with Twin over Full - plenty of room for the whole gang!
Not that you’ll ever want to leave this phenomenal Vacation Home, but Lookout on Main is ALL about the experience - definitely Outdoor Living at its finest. The large, level waterfront backyard is perfect for yard games, gathering around the fire, all of your waterfront sports, or just chasing lightning bugs. Sip coffee and watch Herons and Egrets fish for their morning meal, and then enjoy a glass of Pinot as the sun sinks into the water.
Lookout on Main is a true Vacation Experience - Book your time in Paradise today!
Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. We do NOT rent to party groups, high school groups, or bachelor-type parties.
Every effort is made to ensure that all information and photographs in Seaside Vacations' advertising are accurate and complete. Rate information for properties is subject to change and the quote provided online is only valid at the time of booking. Seaside Vacations cannot be held responsible for possible typographical errors; omissions; price changes; changes in taxes; changes to Terms and Conditions; or changes made by vacation home owners in furnishings, equipment, or bed arrangements. Vacation homes are privately owned and changes may be made to homes or their contents. Seaside Vacations reserves the right to correct any errors.
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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 not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Chincoteague
Located on the waterfront, this holiday home is in Down the Marsh, a neighbourhood in Chincoteague. Chincoteague National Wildlife Refuge and Chesapeake Forest - Dunn Swamp Complex reflect the area's natural beauty and area attractions include Maui Jack's Waterpark and Wallops Flight Facility. Power boating, fishing and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
beach near Downtown Chincoteague - 8 min walk - 0.7 km
beach near Snotty Ridge - 14 min walk - 1.2 km
beach near Down the Marsh - 14 min walk - 1.2 km
Robert N. Reed Downtown Waterfront Park - 3 min drive - 2.1 km
Getting around
Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) - 66 min drive
Restaurants
McDonald's - 7 min drive
Steamers - 4 min drive
Island Creamery - 4 min drive
Teaguers - 5 min drive
Ropewalk - 16 min walk
Frequently asked questions
Is Waterfront home with spectacular sunsets by Seaside Vacations & Sales pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Waterfront home with spectacular sunsets by Seaside Vacations & Sales?
As of 10 May, 2026, prices found for a 1-night stay for 2 adults at Waterfront home with spectacular sunsets by Seaside Vacations & Sales on 9 Jun, 2026 start from S$650, 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 Waterfront home with spectacular sunsets by Seaside Vacations & Sales?
On-site parking is available at the property.
What time is check-in at Waterfront home with spectacular sunsets by Seaside Vacations & Sales?
Check-in begins at 4:00 PM.
What time is check-out at Waterfront home with spectacular sunsets by Seaside Vacations & Sales?
Checkout is at 10:00 AM.
Where is Waterfront home with spectacular sunsets by Seaside Vacations & Sales located?
Located in Down the Marsh, this holiday home is within 1 mile (2 km) of Chincoteague Channel and Robert N. Reed Downtown Waterfront Park. Captain Timothy Hill House and Maui Jack's Waterpark are also within 3 miles (5 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Allen, Thank you for the 5 star review! We are happy you enjoyed your visit. We love being a part of great family vacations. Please come again. Best, Lynn with Seaside Vacations
The house and location are just wonderful! It was so nice to have lots of bedrooms and several separate living spaces, perfect for our large family group. Logistics and communication all worked very smoothly. Next time we'll come back in warmer weather so we can enjoy the fire pit and kayaks!
Tyler C.
Stayed 4 nights in Dec 2025
Response from VrboOwner on 5 Jan, 2026
Thanks so much for the great review, Tyler! We're so glad to hear your family enjoyed its time at Lookout on Main, and would love to have you back anytime!
Best, Tim
We loved this house and are looking forward to going back! Everything is as listed, the house is spacious and the views are amazing!!
Michelle B.
Stayed 3 nights in Apr 2023
Response from VrboOwner on 30 Apr, 2023
Thanks so much for choosing to stay with us, Michelle! We're so glad you enjoyed your stay at Lookout on Main. Those sunsets are AMAZING! We hope to have you back soon!
This house was everything the listing said. It was much larger than we expected and very clean. The view was unbeatable. We would definitely stay here again.
Jackie K.
Stayed 2 nights in Oct 2022
Response from VrboOwner on 7 Nov, 2022
Thanks so much for choosing to stay with us, Jackie! We're so glad to hear your family enjoyed Lookout on Main! Those views are the exact reason this home is so popular. You really can't beat those sunsets! We hope to have you all back soon!
Nice roomy home with plenty of amenities. Great location to everything. Easy and professional experience with Seaview!
Victor H.
Stayed 3 nights in Oct 2022
Response from VrboOwner on 14 Nov, 2022
Victor, Thank you for the 5 star review. We are so happy you enjoyed the home and location. That view is perfect! Please visit us again! Best, Lynn with Seaside Vacations
The location is stunning and the house was cozy and perfect
We highly recommend this property. Everything was easy and the house well stocked. It was cosy and cute. The house in right on the water and O won’t even try to describe the beautiful sunsets. Hope to come back and stay again!
Jenny F.
Stayed 2 nights in Oct 2022
Response from VrboOwner on 18 Oct, 2022
We're so glad your family enjoyed its visit to Lookout on Main! Those sunset views are one of the main reasons this home's calendar stays so full! We hope to have you back soon! :)
Had a great 3 nights here with our large family. Very much enjoyed the screened in back porch, the fire pit and canoe and kayaks. Takes about 28 minutes to walk into a couple shops but everywhere is easy to drive to. Loved Amarin coffee shop! The Pearl restaurant and Ropewalk. 😊
Bethany C.
Stayed 3 nights in May 2024
Response from VrboOwner on 6 Jun, 2024
Hi, Bethany! Thank you so much for choosing us during your stay! We are so glad that you had a wonderful time, and hope that you enjoyed calling the Lookout on Main your home during your stay! Come back and see us again soon :-)
Could not have asked for a more prefect vacation. With four kids under the age of 9 years old there were so many amenities at our fingertips… fishing from the backyard, playing ball, and canoeing. The house was beautiful and it was the perfect spot on the water. The communication with the host as superb. Would stay again!
Wayne C.
Stayed 3 nights in Sep 2022
Response from VrboOwner on 3 Oct, 2022
Wayne, Thank you for the 5 star review. We appreciate and agree with everything you said about the home and location. We are happy we met your needs and hope you do return soon! Best, Lynn with Seaside Vacations
Seven of us (3 generation) stayed at Lookout on Main Easter week, 2025. The house was wonderful as described. The weather was cool, but we got to spend part of every day on the beach, with campfires several nights in the back yard. We used the host’s kayaks and beach chairs, which were very convenient. The kitchen was extensively stocked with equipment and spices, which made it easy to cook nice meals. We would love to stay here again!
Kathy B.
Stayed 7 nights in Apr 2025
Response from VrboOwner on 29 Apr, 2025
It sounds like your family had an amazing Easter holiday, Kathy! Thanks so much for allowing Seaside Vacations to be a small part of your family gathering, and we hope to have you all back for many years to come!
Best, Tim
Lookout on Main wrapped us in a warm, welcoming environment to share after the sudden death of our oldest brother. There was plenty of space for gathering both in and out with space for our individual private times as well. It was very healing.
Kent G.
Stayed 7 nights in May 2023
Response from VrboOwner on 3 Jun, 2023
Thank you so much for choosing to stay with us. We're so sorry to hear about your brother's passing, and hope your stay was exactly what your family needed. Please feel free to reach out to us directly if you visit the area again. We'd be happy to give you a repeat guest discount for any week stay!
Could do better, by supplying inexpensive condiments
Nice property, a little older, but still a beautiful house, nice view over the bay, fun time fishing and kayaking from the back yard. Would be nice if they could supply some of the small inexpensive condiments.
Verified traveller
Stayed 3 nights in Sep 2022
Response from VrboOwner on 26 Sept, 2022
Philip, Thank you for the review. We are glad you enjoyed the home and those beautiful views. Unfortunately, we are not able to provide those items. We hope you visit us again! Best, Lynn with Seaside Vacations
We had 6 adults and 4 children, ages infant to 4. It was great to have so many bedrooms to accommodate everyone. We had to be very vigilant with safety as the stairs are open and a little one could fall through them. We blocked them at bottom so that worked for us. The view is beautiful and the house is very well equipped. We would stay here again.
Linda E.
Stayed 4 nights in Sep 2023
Response from VrboOwner on 5 Oct, 2023
Thanks so much for choosing to stay with us, Linda! We're so glad your family enjoyed its visit, and would love to have you back anytime! Those views really are amazing from the back yard!