Entire home
Lookout on Main - Your Waterfront Wonderland!
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Reviews
10 out of 10, Loved by Guests
Top 10% based on
5 bedrooms3 bathroomsSleeps 10
Popular amenities
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
Lookout on Main - Your Waterfront Wonderland!
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.
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.
Our prices include all fees. No hidden fees.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
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- Kitchen
- Washing machine
- Dryer
- Free Wi-Fi
10.0 out of 10, Exceptional, (153 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
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.

Chincoteague Island, VA
What's nearby
- Chincoteague Channel - 1 min walk - 0.0 km
- Robert N. Reed Downtown Waterfront Park - 3 min drive - 1.7 km
- Maui Jack's Waterpark - 6 min drive - 4.2 km
- Chincoteague National Wildlife Refuge - 7 min drive - 4.5 km
- Assateague Lighthouse - 9 min drive - 6.2 km
Getting around
Restaurants
- Island Creamery - 4 min drive
- McDonald's - 7 min drive
- Steamers - 4 min drive
- Famous Pizza & Sub Shoppe - 6 min drive
- Teaguers - 5 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.8/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
4 Jan 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in Dec 2025
10/10 Excellent
ALYCIA K.
27 Aug 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lookout on Main is perfect
ALYCIA K.
Stayed 7 nights in Aug 2023
10/10 Excellent
Allen h.
28 May 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
great time with the family
Allen h.
Stayed 4 nights in May 2022
10/10 Excellent
Michelle B.
29 Apr 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful getaway
Michelle B.
Stayed 3 nights in Apr 2023
10/10 Excellent
Keith T.
15 Sept 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Was a great location and great view
Keith T.
Stayed 3 nights in Sep 2022
10/10 Excellent
Jackie K.
23 Oct 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fall Getaway
Jackie K.
Stayed 2 nights in Oct 2022
10/10 Excellent
Victor H.
29 Oct 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Roomy and Centrally Located
Victor H.
Stayed 3 nights in Oct 2022
10/10 Excellent
Jenny F.
17 Oct 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
The location is stunning and the house was cozy and perfect
Jenny F.
Stayed 2 nights in Oct 2022
10/10 Excellent
Bethany C.
22 May 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely Getaway
Bethany C.
Stayed 3 nights in May 2024
10/10 Excellent
Kathy B.
23 Apr 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Waterfront Wonderland
Kathy B.
Stayed 7 nights in Apr 2025
10/10 Excellent
Wayne C.
2 Oct 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Getaway by the Water
Wayne C.
Stayed 3 nights in Sep 2022
10/10 Excellent
Kent G.
1 Jun 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Celebration of Life
Kent G.
Stayed 7 nights in May 2023
8/10 Good
Verified traveller
21 Sept 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Could do better, by supplying inexpensive condiments
Verified traveller
Stayed 3 nights in Sep 2022
10/10 Excellent
Linda E.
3 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family getaway
Linda E.
Stayed 4 nights in Sep 2023
About the host
Hosted by Seaside Vacations & Sales
Languages:
English
Premier Host
They consistently provide great experiences for their guests
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