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Beds/Baths

3 Bedrooms
2 Baths & 1 Half
Max. 8 Guests
Waterfront

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4635 Main Street Chincoteague Island, VA, 23336

Location Area

North Main

Why Choose Chincoteague Resort Vacations?

  • Family owned & operated for over 20 years!
  • Two LOCAL office locations to serve you!
  • Friendly & knowledgable year-round staff!
  • Guest-friendly, flexible cancellation policy!
  • 24/7 After-hours support and emergency service!
  • Thorough cleaning and inspection prior to each arrival!

Save with us - Freebies with each stay!

  • Free Contactless Check-In
  • Free Keyless Entry
  • Free WIFI
  • Free Payment Plans
  • Free Starter Guest Amenity Bag
  • Free Guest Hospitality App with Local Recommendations & Info

Description

You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfront screened gazebo that leads to a dock great for crabbing/fishing. Inside is a large open floor plan with a brand new kitchen, living room with wood burning fireplace and dining area. Walk through the French doors off the living room to a large screened porch and sky deck overlooking the Chincoteague Bay. There is a first floor King bedroom with en-suite bath and two twin bedrooms on the second level. Windshadow is a premier PET FRIENDLY vacation rental.

- Linens and towels are included with your reservation.
- No smoking is permitted on the premises.
- This property is pet friendly with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival.
- Any reservations made for a future year (known as "Advanced Reservations") are subject to rate and availability changes. These reservations will be confirmed in January of the arrival year.

Amenities

Amenities

  • Air Conditioning
  • Cable/satellite TV
  • Dryer
  • Fireplace
  • Heating
  • Internet
  • Washer
  • Hair Dryer
  • Fishing
  • Fitness Center
  • Waterfront
  • Enhanced Cleaning Practices
  • Self Check In / Check Out
  • Decked area
  • Pets allowed
  • Smoking Not Allowed
  • DVD player
  • Coffee Maker
  • Dishwasher
  • Microwave
  • Toaster
  • Boat Dock
  • Charcoal Grill
  • Outdoor Shower
  • Screened Porch

Room Details

Bedroom 1
1 King
Bedroom 2
2 Twin Single
Bedroom 3
2 Twin Single

Availability

Key
#Night Available#Night Unavailable#Arrive Only#Depart Only
June 2025
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Reviews

Average

:
4.8125
(32 Reviews)

"Windshadow April 4 to 7"

5
We have stayed at Windshadow previously in the summertime, but due to missing out one summer, we were not able to book it again for a summer stay. It was great to finally return in the off season. Like our previous visits, we enjoyed this time as well. The addition of your supplying sheets and towels makes for a much easier packing time. Windshadow has such great views. We were able to sit at the windows and eat our breakfast and lunch, while enjoying the different birds flying in and out. The Oyster catcher is my favorite. Also, allowing dogs is a Big Plus for us. The two dogs we have now had never been to Windrush. They enjoyed the screened in porch. We hope to return to Windshadow again. We have been going to Chincoteague for 40 plus years and love going there. The 5hour+ drive is not as easy as it once was, but hopefully we can continue. We are booked for the summer, early June at another rental. Thanks for making our journey to Chincoteague a good one.
- on2025-04-07

"Great house"

5
Stayed in this house for many years. Everything is provided, house is always spotless. Cleaning company is to be commended. Rental agency gets a gold star for providing us with the perfect vacation. It was so wonderful we already booked for next year
- on2024-09-14

"Excellent"

5
Everything was great! The place was ready when we arrived and the services provided made for another wonderful experience in Chincoteague. Thank you!
- on2024-07-20

"Lovely as always"

5
Exactly what we expected after returning for our first time in 15 yrs!
- on2024-07-08

"Very Good"

4
Wonderful House with great location and view of bay. Nice to have a fireplace and wood available. Dog park very close by. Kitchen well stocked for cooking meals. Only downside was that living room furniture ,plastic-wicker not that comfortable more suited to porch furniture. Had a great time
- on2024-01-05

"Windshadow"

5
First time back to the island in 11 years and so worth it! Would have been happy to just to sit in the house and watch the view all day.
- on2023-11-26

"Awesome location and Views"

5
I highly recommend this wonderful house! The location and views are spectacular!
- on2023-11-12
Thank you, Jacqueline! Isn't Windshadow spectacular?! Can't wait for your next stay :)

"Amazing"

5
We’ve stayed in this house for many years, unfortunate circumstances kept us away for some years. But we are once again staying for the week.. love this house, it has everything you could want and need. That includes a walk in put in spot for kayaks. House is well appointed. Property management is the best. See you again next year.
- on2023-09-17
We're so glad to have you back, Mary Lou! Here's to many more Chincoteague Island vacations...

"Excellent"

5
Great house! Very clean and well stocked. A bird watchers paradise with a constant turnover of many species on the oyster bar just off the shoreline. Even had a Bald Eagle stop by for a visit. The dock was great for kayaking and the screened in porch was an excellent place to sit and enjoy the evening breezes and watch the sunsets. Have rented many places on Chincoteague - this was the best. Bob Ww will be back.
- on2023-07-31
Isn't 'Windshadow' spectacular?! We're so glad you enjoyed your stay and look forward to hosting your family again!

"Excellent"

5
My fifth year at Windshadow. I love this place and will continue to book my regular two weeks in June.
- on2023-06-17

"Staying at Windshadow"

3
Services from rental manager
3
Cleanliness
1
Location
5
Property condition
2
We have stayed at Wiindshadow a number of times, and this is the first time that it really was not clean. The vacuum cleaner does not work. Beyond unvacuumed/unswept floors, there was substantial dust and dog hair. The house needs a deep cleaning that includes the fans. We also felt that the paper products provided were of the poorest and cheapest quality, esp for an expansive rental. We continue to love the house but feel that it has not been kept up and, compared to other rentals, offers the cheapest products possible. The drain outside one of the sliding doors perpetually drips and will lead to rotting of the wood deck.
- from WASHINGTON, DC United States on2022-11-10

"Beautiful week at Windshadow in Chincoteague!"

5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We had a wonderful week in Chincoteague. Windshadow is a terrific home. It’s design and location are terrific. We have stayed there previously and are always glad to return. The views of the water, with many birds, is fabulous. We also appreciate that it is a pet friendly home and we take our dogs. Both of our daughters and their husbands were also with us. It doesn’t always happen, but the weather was unbelievably great. The ocean breeze on the beach was the best ever. We certainly hope to return to Windshadow next year.
- from Shippensburg, PA United States on2022-07-05
Hi there! Thanks for staying with us at Windshadow! We can't wait to have you back next year!

"Wind shadow, June 2022"

5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
This was our fourth year at Windshadow and our ninth year working with Chincoteague Resort Vacations. As always, the experience was excellent. The house is clean, well-maintained and it has magnificent views to the west over Chincoteague bay.
- from Mercersburg, PA United States on2022-06-21
Hi Paula! Thanks for always trusting us to make your vacation great! See you next year! :)

"Perfect spot on the Island"

5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
Another wonderful time was had at Windshadow this year, it’s our favorite place to stay!
- from Delta, PA United States on2022-04-22
Hi Shawn! Thanks for staying with us! :)

"My favorite place "

5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We had a relaxing and invigorating stay at Windshadow. Chinc has been our"home away from home"for 30+ years. We celebrated my parents' 50th anniversary here and our pets/children grew up summering here. We love it!
- from Harleysville, PA United States on2022-04-20
Hi there! Thank you for staying with us! :)

"Breathtaking views"

5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
This house has a wall of windows facing the bay allowing for wonderful views of sunsets and birds. It's why we keep coming back to this house. The house is also comfortable, clean and well-provisioned for cooking and even grilling. Love this house!
- from WASHINGTON, DC United States on2021-12-01
We love our return guests! Thank your for continuing to choose Chincoteague Resort Vacations. We look forward to your next stay with us!

"Vacation at Windshadow"

5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
5
After renting houses in Chincoteague since the 1980ies - this was the best organized and outfitted house. Especially the kitchen - it was a pleasure to cook in it. Because of the pandemic only Carry Out from Capt. Zack was enjoyed sometimes.
- from Bethesda, MD United States on2021-11-26
Thank you for your kind review! We are so happy to hear you enjoyed your stay!

"Sad to see it end"

4
Services from rental manager
4
Cleanliness
4
Location
4
Property condition
3
We love the house and the island.
- from York, PA United States on2021-08-10

"Sad to see it end"

4
Services from rental manager
4
Cleanliness
4
Location
4
Property condition
3
We love the house and the island.
- from York, PA United States on2021-08-10

"ALWAYS MY FAVORITE!"

5
Services from rental manager
4
Cleanliness
5
Location
5
Property condition
5
This is my 4th year staying at Windshadow with my family. I'm in love with this home, its amenities and location. Booked for year number 5 before I departed! Only wish it was for sale so I could scoop it up!
- from Blairstown, NJ United States on2021-07-20

"Wonderful stay at Windshadow "

5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We love Chincoteague and have been going there for about 35 years. We have rented about 10 different homes during those years and believe we like Windshadow the most. The view is spectacular and the facilities are excellent. A big plus is that it is also pet friendly and we take our two dogs. I couldn’t find anything unfavorable about Windshadow to say. A great, great place to stay.
- from Shippensburg, PA United States on2021-07-06

"Wonderful stay at Windshadow "

5
Services from rental manager
5
Cleanliness
5
Location
5
Property condition
5
We love Chincoteague and have been going there for about 35 years. We have rented about 10 different homes during those years and believe we like Windshadow the most. The view is spectacular and the facilities are excellent. A big plus is that it is also pet friendly and we take our two dogs. I couldn’t find anything unfavorable about Windshadow to say. A great, great place to stay.
- from Shippensburg, PA United States on2021-07-06

"Windshadow"

5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
5
Excellent. I have rented this property for several years.
- from Mercersburg, PA Unknown on2021-06-22

"Windshadow"

5
Services from rental manager
5
Cleanliness
4
Location
5
Property condition
5
Excellent. I have rented this property for several years.
- from Mercersburg, PA United States on2021-06-22

"Spectacular views of sunsets and birds"

5
Services from rental manager
4
Cleanliness
5
Location
5
Property condition
5
Loved the house - sitting in front of the windows with my binoculars. The birds and incredible sunsets were spectacular.
- from WASHINGTON, DC United States on2021-05-27

"A Beautiful House!"

5
Services from rental manager
4
Cleanliness
5
Location
5
Property condition
5
My family and I had a great winter mid-week getaway at Windshadow. The house was clean, modern and comfortable. We loved the beautiful views out the large windows, especially the nightly sunsets. We could tell the owners had been updating the house over the years, and it was more like staying at a nicely furnished house belonging to friends or family. We had some trouble logging onto the WiFi network, but discovered the password on the handout from the realty office was incorrect. We'd love to return for more time at Windshadow!
- from Chevy Chase, MD United States on2021-02-06

"A Beautiful House!"

5
Services from rental manager
4
Cleanliness
5
Location
5
Property condition
5
My family and I had a great winter mid-week getaway at Windshadow. The house was clean, modern and comfortable. We loved the beautiful views out the large windows, especially the nightly sunsets. We could tell the owners had been updating the house over the years, and it was more like staying at a nicely furnished house belonging to friends or family. We had some trouble logging onto the WiFi network, but discovered the password on the handout from the realty office was incorrect. We'd love to return for more time at Windshadow!
- from Chevy Chase, MD United States on2021-02-06

"September 2020 Stay"

4
Experience Rating
5
Property Rating
5
Value Rating
4
My family "brothers and sisters"are from all over. We decided to have a reunion. The youngest of us is 68 years old!We had a wonderful time together and the accommodations were perfect! we felt very relaxed had a lot of discussions, caught up, played games and laughed till we cried!Loved everything about this trip! Thank you!!!
- from North Carolina on2020-09-28

"June 2019 Stay"

5
Experience Rating
5
Property Rating
5
Value Rating
5
Wind shadow is a beautiful home, with spectacular views and exceptional amenities. We enjoyed beautiful sunsets and great memories. our family is planning to return next year.
- from Rhodesdale on2019-07-09

"July 2017 Stay"

5
Experience Rating
5
Property Rating
5
Value Rating
5
Windshadow is just wonderful! We are second generation renters and love the home and location just as much as our parents did for many years! Thank you for a fun and fabulous week!
- from Landenberg PA on2019-06-11

"July 2018 Stay"

5
Experience Rating
5
Property Rating
5
Value Rating
5
It was such a beautiful house and a lovely place to stay.
- from Philadelphia on2019-06-11

"Picture perfect location with lovely sunsets."

5
Great location, close to town. Beautiful view of the Chincoteague Bay. Lovely, well-organized home. Pet friendly, took our 2 dogs. We have stayed at several homes in Chincoteague and this one ranks at the top. Dock, screened porch, and gazebo added a nice touch. We plan to return next year.
- on2018-07-10

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