Lookout on Main - Your Waterfront Wonderland!

Top rated by guests
Welcome to Lookout on Main on Chincoteague Island!
Open Layout with Soaring Ceilings and New Flooring.
Well-Stocked Kitchen has all you need.
Take in Views even from the Kitchen.
Truly a very special place.....
review stars
10.0Outstanding
(14 Ratings)
"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 s..."
Kathy B.
Don't miss out! Price and availability may change
10.0 / 10.0
Outstanding(14 Ratings)

House in Chincoteague Island, VA

10 guests · 5 bedrooms · 3 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

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.

Amenities at Lookout on Main - Your Waterfront Wonderland!

Free WiFi/internet
Air conditioning
Non-smoking
TV
Coffee/tea maker
Refridgerator
Kitchen
Balcony/Terrace
WiFi/Internet
Microwave
Dishwasher
Washing machine
Dryer
Patio
Kitchenware
No pets allowed
Garden
Oven
Stove
Laundry services
Bath or shower
Ironing facilities
Towels
Desk
Hairdryer

Map of Chincoteague Island, VA


Ratings and reviews

10.0 / 10.0
Outstanding(14 Ratings)
10.0 / 10.0Outstanding·Apr 2025
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!
10.0 / 10.0Outstanding·May 2024
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. 😊
10.0 / 10.0Outstanding·Oct 2023
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.
10.0 / 10.0Outstanding·Aug 2023
Very nice location, easily accessible to everything the island has to offer. Large, clean and open spaces! Loved our stay and will be back next year!

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Lookout on Main - Your Waterfront Wonderland!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Lookout on Main - Your Waterfront Wonderland! pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Lookout on Main - Your Waterfront Wonderland!?

We found 25 amenities for this rental. This includes free wifi/internet, air conditioning, non-smoking, tv, and coffee/tea maker.


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