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Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets

Photo gallery for Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets

Front Exterior
Deck View
Living Room
Bedroom
Deck

Reviews

10 out of 10
Exceptional
3 bedrooms2+ bathroomsSleeps 8

Popular amenities

  • Garage parking available
  • Pet-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue

Explore the area

View map
Chincoteague Island, VA
  • Place, beach near Downtown Chincoteague
    ‪3 min walk‬
  • Place, Robert N. Reed Downtown Waterfront Park
    ‪14 min walk‬
  • Place, beach near Snotty Ridge
    ‪3 min drive‬
  • Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    ‪70 min drive‬

Rooms & beds

3 bedrooms (sleeps 8)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Single Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Bathtub or shower · Toilet

Half Bathroom 3

Toilet

Spaces

Kitchen
Balcony
Dining area

About this property

Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets

This is it! Are you looking for your perfect vacation getaway spot? Look no further. 'Charlie's Bayside Retreat' is everything you'll need for your home away from home, at the beach! The first main level features an open floor plan with a living room that opens up to a wonderful screened porch with comfortable outdoor dining furniture. The open living area also features a large Smart TV with cable and an electric fireplace. A modern kitchen that is fully stocked with everything you could possibly need, also has new appliances and a Keurig coffee maker, breakfast bar, open dining area, and powder room complete the first-floor living space. On the second floor, you'll find two bedrooms, one with a Queen bed and Smart TV and the other with 2 Twins & a Full - both with balconies and a shared full bathroom with dual sinks. The entire third floor is a spacious, private primary oasis with a Queen bed, and a luxurious en suite featuring a deep jetted tub and dual sinks. This bedroom is also equipped with a Smart TV and a balcony with amazing views & Adirondack chairs making it perfect for relaxing or sunbathing. Additional features of this fabulous vacation home include your own private boat slip (#7), pier for fishing and crabbing, fish cleaning station, covered parking area, grill, picnic table, and tons of extras! There's an outdoor shower, and beach gear including beach chairs, beach toys, and an umbrella. Not to mention you're conveniently located on South Main Street - walk to the downtown area (including Ropewalk for food and drinks) or to the annual Fireman's Carnival. The possibilities are endless. Some of the most gorgeous sunsets ever witnessed are from this spot on South Main Street & it is the perfect spot to watch rocket launches from Wallops. It doesn't get much better than this!

- 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.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

About the area

Chincoteague

Downtown Chincoteague, a neighbourhood in Chincoteague, is home to this holiday home. Captain Timothy Hill House and Assateague Lighthouse are local landmarks, and the area's natural beauty can be seen at Chincoteague National Wildlife Refuge and Chesapeake Forest - Dunn Swamp Complex. Maui Jack's Waterpark and Wallops Flight Facility are also worth visiting. Take the opportunity to explore the area for water adventures such as fishing.
View more Holiday homes in ChincoteagueOpens in a new window
Map
Chincoteague Island, VA

What's nearby

  • beach near Downtown Chincoteague - 3 min walk - 0.3 km
  • Robert N. Reed Downtown Waterfront Park - 14 min walk - 1.2 km
  • beach near Snotty Ridge - 3 min drive - 2.1 km
  • beach near Down the Marsh - 3 min drive - 2.1 km
  • Chincoteague National Wildlife Refuge - 6 min drive - 4.8 km

Getting around

  • Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) - 59 min drive

Restaurants

  • ‪McDonald's - ‬6 min drive
  • ‪Steamers - ‬3 min drive
  • ‪Island Creamery - ‬3 min drive
  • ‪Teaguers - ‬4 min drive
  • ‪Ropewalk - ‬7 min walk

Frequently asked questions

Is Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets?

As of 8 May 2026, prices found for a 1-night stay for 2 adults at Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets on 22 May 2026 start from NZ$859, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets?

On-site parking is available at the property.

What time is check-in at Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets?

Check-in begins at 4:00 PM.

What time is check-out at Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets?

Checkout is at 10:00 AM.

Where is Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets located?

Located in Downtown Chincoteague, this holiday home is within 1 mile (2 km) of Robert N. Reed Downtown Waterfront Park and Chincoteague Channel. Captain Timothy Hill House and Maui Jack's Waterpark are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 15 out of 16 reviews
Rating 8 - Good. 1 out of 16 reviews
Rating 6 - Okay. 0 out of 16 reviews
Rating 4 - Poor. 0 out of 16 reviews
Rating 2 - Terrible. 0 out of 16 reviews

10/10

Cleanliness

8.0/10

Check-in

9.0/10

Communication

9.0/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Heather P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice stay

We had a nice stay. Place the big enough for 4 adults and 4 kids. Kitchen was stocked with appliances. Location was nice. House was clean.
Stayed 4 nights in Aug 2025
Verified

10/10 Excellent

Andrew G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely Apartment

Well appointed kitchen and comfortable beds. Three floors to spread out.
Stayed 14 nights in Oct 2022
Response from VrboOwner on 5 September 2023
We look forward to having you again Andrew!
From a partner site

10/10 Excellent

Susan T.

Weekend getaway

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location and clean townhouse. Had all the comforts we needed.
From a partner site

10/10 Excellent

Jo Anne and Bill S.

A perfect little get away

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This was a perfect little get away/anniversary! The rental was immaculate. It was just my wife, our small dog and me. Probably way too much condo for us, but nonetheless a beautiful place. We are in our 60s, so the trip up the flights of stairs to the master bedroom was challenging, especially when the dog wanted to go out twice a night. Lol. 42 steps down and then 42 steps up. Good exercise, though. We did some crabbing off the dock and caught quite a few big blue crabs. Would definitely recommend this rental.
Response from VrboOwner on 2 August 2023
Thank you for staying with us William! :) WE will see you next year!
From a partner site

10/10 Excellent

A guest from Somerdale, NJ

Tucked away at the Bay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Loved this rental property. The home was right off the bay. It is beautifully decorated to give you that summer vibe. Would definitely recommend and would definitely stay here again.
Response from VrboOwner on 2 August 2023
Thank you for staying with us Cheryl! WE are happy to hear you enjoyed the home! :)
From a partner site

10/10 Excellent

Chris C.

September 2022 Stay

Our family had a great week at Chincoteague experiencing the shore, crabbing,fishing and good seafood, the best was at Ray's Shanty. Famous Pizza never disappoints. Our rental, Charlie's Bayside, was very nicely decorated, comfortable, well stocked and a great location for our planned activities due to the private pier. We have been visiting the island for over 40 years but never had the chance to do it with our adult children and grandchildren until now.
Response from VrboOwner on 2 August 2023
We are thrilled you and your family had a great time! :) We look forward to having y'all again!
From a partner site

10/10 Excellent

Danielle S.

Girls Getaway Galore

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This is the second year in a row that I brought my two daughters, plus their BFFs, plus my BFF. We always have a blast and appreciate the space and adorable decor. The house is ready for my female fur baby- treats, bowls, and cleaning supplies are already available. Will continue to return! Close to downtown- 7 minute walk at most. Loved all the cute shops.
Response from VrboOwner on 2 August 2023
Thank you for staying with us Danielle! We cannot wait to have y'all back! :) See you next year!
From a partner site

10/10 Excellent

Mark S.

What a great rental!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: My family and I had an amazing week at Charlie's Bayside. This is the perfect place to stay. It was a beautiful house that was clean and had everything we need. If you like to fish, you have your own private pier and you are in a great location where you can walk down town. I would definitely recommend this place to anyone looking to visit the island. We have gone to Chincoteague 6 years in a row and rented 6 different places. This was the best and we would definitely go back.
Response from VrboOwner on 2 August 2023
Thank you for staying with us Mark! We hope to have you back again soon! :)
From a partner site

8/10 Good

Margaret P.

November 2021 Stay

It’s a lovely property with pretty decor and a very well equipped kitchen. But even though the building is “waterfront,” this unit really isn’t. We couldn’t see the bay at all from the front deck—a bit of a disappointment.
Response from VrboOwner on 2 August 2023
Hi there! Very sorry to hear you were disappointed! Next time give us a call and we can make sure you are more directly on the water. :) Nonetheless, we hope you had a great time in Chincoteague!
From a partner site

10/10 Excellent

Raman K.

August 2021 Stay

Well maintained property in an excellent location.
Response from VrboOwner on 2 August 2023
Thank you for staying with us! :) See you next year! Best, Lea Anna
From a partner site

10/10 Excellent

Margaret S.

July 2021 Stay

We really enjoyed staying in Charlie’s Retreat. It was in a convenient location and so many nice amenities. It was the nicest property we have stayed in since we have been coming to Chincoteague. We have been coming to Chincoteague since 1993.
From a partner site

10/10 Excellent

Margaret S.

Nicest Property that we have rented in Chincoteague

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The Rental was roomy and extremely clean. Many extras like the Keurig. Tissues and air freshener in the bathrooms.
From a partner site

10/10 Excellent

Kendra D.

Great Stay on Chincoteaque

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Charlie's Bayside Retreat was wonderful. The property was clean and well provisioned. The decor very pleasing. You could definitely feel the care of warmth of the owners.
From a partner site

10/10 Excellent

Eric F.

Great location

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: As usual, our home away from home was great.easy booking, easy check in/check out.
From a partner site

10/10 Excellent

Nate F.

My favorite place to stay in Chincoteague

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: I REALLY love this place! It is super nice, roomy, has a perfect location, and is pet friendly! Being able to bring my boyfriend's dog with us on vacation has been the best thing ever! You can walk to downtown, house is close to everything! House also has everything... parking, coffee makers, condiments, and fully stocked kitchen, and there are all kinds of surprisingly thoughtful touches and supplies in the home that are left there to make your visit even sweeter! I know I will be back.... many more times! Trust me, you will love this place!
Response from VrboOwner on 2 August 2023
Thank you for the positive review! We are thrilled you and your pup enjoyed your vacation!
From a partner site

10/10 Excellent

Brad E.

Best Home Rental Ever!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This home was better than we could've expected. The home was very well thought out with very functional details, such as storage shelving, automatic night lights, USB plugs, etc. There were also several welcome items such as coffee, hand soap, tissues, etc. The home was exactly as it was represented in pictures. The location was perfect, as it allowed privacy for relaxing, but was close enough to town that anything you needed was within walking distance. The sunsets from the dock were phenomenal! Be sure to stop by Amazon for coffee and the best cinnamon twist (roll) that you will ever taste! Black Narrows Brewing had some great craft beer, with a unique twist by featuring local ingredients.

About the host

Hosted by Resort Vacations

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