See all properties
Entire home

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

Vacation home perfectly located for exploring Downtown Chincoteague

Choose dates to view prices

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

A wooden pier leading to a row of multi-story buildings with balconies, docked boats, and a clear blue sky.
A living room with a fireplace, a television, and a large window with blinds.
A motel with a parking lot, a dock, and a view of the water.
A wooden exterior with a number sign, a door, and a window.
A covered porch with a sliding glass door, two wicker chairs, a small table, and a white railing.

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms3 bathroomsSleeps 81284 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning
  • Parking available

Explore the area

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

Room options

About the neighborhood

Chincoteague

Downtown Chincoteague stay.Within a 10-minute walk of this Downtown Chincoteague vacation home, you'll find Chincoteague Channel and Robert N. Reed Downtown Waterfront Park. Chincoteague National Wildlife Refuge and Captain Timothy Hill House are also within 3 miles (5 km).
View more Vacation Homes in ChincoteagueOpens in a new window

What's nearby

  • Chincoteague Channel - 1 min walk - 0.1 miles
  • beach near Downtown Chincoteague - 3 min walk - 0.2 miles
  • Robert N. Reed Downtown Waterfront Park - 14 min walk - 0.8 miles
  • beach near Down the Marsh - 3 min drive - 1.3 miles
  • beach near Snotty Ridge - 3 min drive - 1.3 miles

Getting around

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

Restaurants

  • ‪Island Creamery - ‬3 min drive
  • ‪McDonald's - ‬6 min drive
  • ‪Ropewalk - ‬7 min walk
  • ‪Amarin Coffee - ‬13 min drive
  • ‪Captain Zack's Seafood - ‬3 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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 King 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.

Similar properties

A cozy cabin interior with a wooden ceiling, large windows, a leather couch, a wooden table, and a view of a lake.
Quaint Chincoteague Island Hideaway w/ 2 Porches!
Chincoteague
  • Kitchen
  • Washer
  • Dryer
  • Parking included
Quaint Chincoteague Island Hideaway w/ 2 Porches!

Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Onsite parking options include a garage

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 3 bedrooms

Bathroom

  • 2.5 shared bathrooms
  • Bathtub or shower
  • Hair dryer

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Furnished lanai

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near the bay

Things to do

  • Fish cleaning table
  • Fishing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 1,284 square feet

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in available

Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Pets

  • Pets are welcome
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

No events allowed

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property is also known as

552523

Frequently asked questions

How close is Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets to the airport?

This vacation home is 48.1 mi (59-min drive) away from the Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional) airport, the closest popular airport to the property.

Does Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets to the beach?

This vacation home is 6.9 mi (25-min drive) from Bow Beach.

Does Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets?

No, there is no casino at this vacation home.

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.

Is there free parking at Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets?

Free parking is not available at this vacation home.

Does Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets have a pool?

This vacation home does not have a pool.

Does Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets have a spa?

There are no spa services available at this vacation home.

How close is Charlie's Bayside Retreat | South Main Waterfront w/ Private Boat Slip, Screened Porch & Pets to downtown Chincoteague?

This vacation home is 0.4 mi away from Chincoteague.

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

Reviews

10

Exceptional

Rating 10 - Excellent. 18 out of 19 reviews
Rating 8 - Good. 1 out of 19 reviews
Rating 6 - Okay. 0 out of 19 reviews
Rating 4 - Poor. 0 out of 19 reviews
Rating 2 - Terrible. 0 out of 19 reviews

10/10

Cleanliness

Reviews

Verified review

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 review

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
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.
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.
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.
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.
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.
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.
From a partner site

10/10 Excellent

Raman K.

August 2021 Stay

Well maintained property in an excellent location.
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!
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.
Verified review

10/10 Excellent

Brian W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in May 2026

Explore More Ways to Travel with Travelocity