House - Rating 5 (5)

Lookout on Main

$259 - $885 / night + taxes & fees

Bedroom 5 bedrooms
Bathroom 3 baths
Guests 10 guests
Pets Not Allowed Pets Not Allowed
Parking Spaces 5 Parking Spaces

  • Address: 3535 Main St
  • Location: Chincoteague, VA
  • Type: House
  • View: Bayside

Location Location

Description Description
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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Swipe Swipe for Availability

Bedding Bedding
User User
Bedroom 1
Sleeps: 2
2 Twin

User User
Bedroom 2
Sleeps: 2
1 Pyramid Bunk

User User
Bedroom 3
Sleeps: 2
1 Twin Bunks

User User
Bedroom 4
Sleeps: 2
1 King

Attached Bathroom

User User
Bedroom 5
Sleeps: 2
1 Queen


Amenities 77 Amenities
Attractions
  • Assateague National Seashore
  • Churches
  • Museums
  • Playground
  • Water Parks
Beach Equipment
  • Beach Balls/Toys
  • Beach Chairs
  • Canoe
  • Crabbing Equipment
  • Kayak
  • Paddle Board
  • Umbrellas
Entertainment
  • Games
  • Television
Essentials
  • Air Conditioning
  • Dryer
  • Hair Dryer
  • Heating
  • Iron & Ironing Board
  • Laptop Friendly
  • Private Living Room
  • Satelite or Cable
  • Washer
Facility
  • Balcony
  • Free Parking
Home Safety
  • Fire Extinguisher
  • Smoke Detector
Indoor
  • Wireless Internet
Kitchen
  • "Keurig" Single Cup Coffee Maker
  • Blender
  • Crock Pot
  • Dishes & Silverware
  • Dishwasher
  • Drip Coffee Maker
  • Food Processor
  • Full-Sized Refrigerator
  • Kitchen
  • Microwave
  • Oven
  • Pots & Pans
  • Range
  • Steam Pots
  • Tea Kettle
  • Toaster/Toaster Oven
Leisure
  • Beach Combing
  • Boating
  • Crabbing
  • Miniature Golf
  • Scenic Drives
  • Shopping
  • Sight Seeing
  • Walking
  • Wildlife Viewing
Location
  • Bayside
  • Downtown
  • Water View
  • Waterfront
Outdoor
  • BBQ Area
  • Fire Pit
  • Garden or Backyard
  • Kayaking
  • Outdoor Grill
  • Outdoor Shower
  • Screened-In Porch
  • Water Sports Gear
Special
  • Linens Provided
  • Non-Smoking
Sports
  • Bay Fishing
  • Cycling
  • Equestrian Events
  • Golf
  • Pier Fishing
  • Swimming
Themes
  • Away From It All
  • Family
  • Romantic
  • Sports Activities

Reviews Rating 5 (5) Reviews
Rating 5
Awesome all around!
We stayed at "Lookout on Main" at 3535 Main Street, Chincoteague. The home, the service, and the vacation experience were awesome. Everyone was friendly and helpful as our check-in day approached. Everything was neat and clean when we arrived with a very well stocked kitchen we (7 adults and 3 young children) used every day. The enclosed porch with long dining table accommodated us all and we spent evenings there and by the fire pit and had a wonderful time. The equipment shed had multiple kayaks we also used every day right at the dock, and the beach equipment made other rentals unnecessary. Checkout was easy as well. So, we loved it. Thanks, Seaside, for a wonderful time my family will never forget.
Anonymous - Posted: 6/18/2024
Rating 5
Lookout on Main
We stayed at "Lookout on Main" at 3535 Main Street, Chincoteague. The home, the service, and the vacation experience were awesome. Everyone was friendly and helpful as our check-in day approached. Everything was neat and clean when we arrived with a very well stocked kitchen we (7 adults and 3 young children) used every day. The enclosed porch with long dining table accommodated us all and we spent evenings there and by the fire pit and had a wonderful time. The equipment shed had multiple kayaks we also used every day right at the dock, and the beach equipment made other rentals unnecessary. Checkout was easy as well. So, we loved it. Thanks, Seaside, for a wonderful time my family will never forget.
Jay P - Posted: 6/9/2024
Rating 5
Lovely Getaway
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 - Posted: 6/6/2024
Rating 5
Relaxing 3535 Main
The house was wonderful! Very roomy and clean. Fresh seaside decor. Kitchen was well stocked. Bedrooms were comfy (loved the king loft with private deck). We loved the backyard firepit andbeing on the water. Kayaking was so peaceful. There were kayaks, grill and extra beach chairs. Close to the Carnival grounds were I visited the ponies every day. The nearby sandwich shop was great too. The hosts were easy to communicate with. Such a lovely and relaxing stay! Thank you!
Anonymous U - Posted: 10/27/2021
Rating 5
Loved it!
This house was perfect for our two families. There was plenty of space for everyone to spread out with areas where we could all come together as well. The kids loved using the kayaks and paddle boards in the bay and the sunsets can?t be beat.
Brian G from Hershey, PA - Posted: 9/3/2021
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Want to know specifics? Ask anything about this specific property that you would like to know...

Example: "Is the balcony screened in?" or "Is there a toaster oven?"

I booked so long ago that I can’t remember; is the property pet friendly? We have a well trained 8lb yorkie poo that we would love to bring with us if we can.
Anonymous U - Posted: 10/11/2023

Answer:

Lookout on Main is not pet friendly. We do have a very large selection of pet friendly homes if needed. 

Do we have to bring towels???
Anonymous U - Posted: 11/19/2023

Answer:

All of our rentals include bed linens, bath towels, hand towels, wash cloths, and a kitchen towel.

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