Lookout on Main

Lookout on Main

$201.00 - $708.00 /Night

Address: 3535 Main St Location: Chincoteague Island Type: House
5 Bedrooms 3 Baths Sleeps 10 Pets Not Allowed Parking Spaces: 4
Bedroom 1
1 King
Bedroom 2
1 Queen
Bedroom 3
1 Twin Bunks
Bedroom 4
2 Twin
Bedroom 5
1 Pyramid Bunk
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 now accepting Reservations for Summer 2021, and we’ll share updated pics as the renovation progresses, but you do NOT want to pass up the Lookout on Main experience, so call us today or Book Online!

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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  • Museums
  • Water Parks
  • Playground
  • Churches
  • Assateague National Seashore

Beach Equipment

  • Beach Balls/Toys
  • Beach Chairs


  • Television
  • Satellite or Cable
  • DVD Player


  • Dryer
  • Washer
  • Laptop Friendly
  • Iron & Ironing Board
  • Heating
  • Hair Dryer
  • Air Conditioning
  • Private Living Room


  • Balcony
  • Free Parking

General Indoor Amenities

  • Wireless Internet

Home Safety

  • Smoke Detector
  • Fire Extinguisher


  • Oven
  • Steam Pots
  • "Keurig" Single Cup Coffee Maker
  • Kitchen
  • Pots & Pans
  • Dishwasher
  • Toaster/Toaster Oven
  • Range
  • Drip Coffee Maker
  • Full-Sized Refrigerator
  • Dishes & Silverware
  • Microwave


  • Wildlife Viewing
  • Crabbing
  • Beach Combing
  • Boating
  • Miniature Golf
  • Scenic Drives
  • Shopping
  • Sight Seeing
  • Walking


  • Water View
  • Downtown

Location Type

  • Waterfront


  • Kayaking
  • BBQ Area
  • Water Sports Gear
  • Garden or Backyard

Outdoor Amenities

  • Fire Pit
  • Screened-In Porch
  • Outdoor Shower

Outdoor Grill

  • Charcoal Grill


  • Linens Not Included
  • No Smoking


  • Cycling
  • Equestrian Events
  • Fishing - Bay
  • Golf
  • Pier Fishing
  • Swimming


  • Away From It All
  • Family
  • Romantic
  • Sports Activities
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