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Island Bay Dreams by Seaside Vacations & Sales

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Island Bay Dreams
Entering through the Kitchen, you'll immediately appreciate how well-stocked and ready to go it is!
With Tropical Colors throughout, you'll get that Vacation Vibe right away!
This adorable 4 Bedroom Townhome is great for your large family, or 2 families traveling together, and sleeps 12!
The Eat-in Kitchen has bar-type seating - such great use of the space!

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4 bedrooms2+ bathroomsSleeps 12

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Parking available

Explore the area

View in a map
Chincoteague Island, VA
  • Place, Oyster Bay
    ‪1 min drive‬
  • Place, Robert N. Reed Downtown Waterfront Park
    ‪3 min drive‬
  • Place, Maui Jack's Waterpark
    ‪3 min drive‬
  • Airport, Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)
    ‪70 min drive‬

Rooms & beds

4 bedrooms (sleeps 12)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Twin Beds and 1 Twin Bunk Bed

Bedroom 4

1 Twin Bed and 1 Queen Bed

2 bathrooms, 1 half bathroom

Full Bath 1

Towels provided · Bathtub or shower · Bathtub · Toilet

Full Bath 2

Towels provided · Bathtub or shower · Bathtub · Toilet

Half Bath

Towels provided · Toilet

Spaces

Kitchen

About this property

Island Bay Dreams by Seaside Vacations & Sales

Welcome to Island Bay Dreams in the very heart of Chincoteague Island! This absolutely adorable 4 Bedroom Townhome truly has it all, and is less than 10 minutes away from Assateague National Seashore, where our famous Wild Ponies roam free!

You know when you walk into a home and instantly feel your worries vanish? That’s exactly the vibe we get from Island Bay Dreams! Decorated with tasteful beach decor, soothing coastal colors, and comfy furnishings, it screams “you’re on island time now”! Which after driving a few hours to get away from the realities of everyday life, is just what you need….

Pinewood is a small grouping of only 4 Townhomes tucked on Deep Hole Road - close to everywhere you want to be, yet you’ll still feel a million miles from the real world. As you enter through the Kitchen, you can see they’ve made such great use of the space. The Eat-in Kitchen has beachy white cabinetry, and bar seating that spans the length of it. With all the comforts of home, mealtime will be easy breezy. If you’re not one to cook on Vacation, you’re only a short stroll from some great dining options, including Captain Zack’s - and trying their Bloody Mary with oysters, crab, and shrimp is an absolute must!

You’ll love grilling some cheeseburgers in paradise on the Charcoal Grill out back, and sinking into the Adirondacks and enjoying the Fire Pit. What a great place to end each day, and share stories of the day’s adventures!

Wandering down just a couple of steps to the Living Area, you’ll find a wonderfully warm and comfortable space with wood walls, beachy flooring, and comfy leather-like sofas to sink into after a fun-filled day at the Beach. There’s room for all here with multiple seating areas and even a Pub Table. Enjoy Free WiFi and Smart TV for a fun family movie night, or just hand out and be together - something that can be hard to find time to do in today’s busy world.

Island Bay Dreams sleeps 12 in 4 Bedrooms, and is perfect for one large family, or for 2 smaller families to share, which definitely helps cut costs! Bedroom 1 is on the 1st Floor just off the Living Area, and has a comfy Queen Bed, Smart TV, and Attached Full Bath with Tub/Shower Combo. The Full Size Washer and Dryer is also housed in this Bathroom. Dressed in colors of sand and sea, it’s sure to be a restful retreat, and perfect for those who don’t want to contend with stairs.

Wandering upstairs, you’ll find 3 more Bedrooms and another Full Bath with Tub/Shower Combo. Bedroom 2 also has a Queen Bed, Smart TV, and beachy decor. The kiddos in your group will adore Bedroom 3, which has 2 Twin Beds and a Pyramid Bunkbed, and can sleep up to 5, along with a Smart TV. Finally, huge Bedroom 4 has a Queen Bed, Smart TV, and a Twin Bed - a perfect family suite for parents who may want to keep a child nearby.

All of this, and you’re just a hop, skip, and jump away from one of the most pristine and visited beaches in America! Whether you’re searching for Wild Ponies, fishing, shelling, surfing, or just sunbathing, our beautiful beaches have something for everyone! There are also 3 kayaks you're welcome to use, as well as a variety of boogie boards and beach toys! Island Bay Dreams is proof that you can have it all without breaking the bank!

No Smoking and No Pets - Owners have a dog. Owners have Exterior Security Cameras. Seaside Vacations does not allow group rentals to guests under age 25. Therefore, online bookings for group rentals will not be honored. 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
Washer
Dryer
Free WiFi
Air conditioning
Parking available

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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

No 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
Onsite parties or group events are strictly prohibited
Host has indicated there are no carbon monoxide detectors or gas appliances on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock

About the neighborhood

Chincoteague

Located in Deep Hole, a neighborhood in Chincoteague, this vacation home is near theme parks and near the beach. 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 Oyster Bay. Maui Jack's Waterpark and Wallops Flight Facility are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails and cycling nearby.
Map
Chincoteague Island, VA

What's nearby

  • Oyster Bay - 1 min drive - 1.1 km
  • Robert N. Reed Downtown Waterfront Park - 3 min drive - 2.5 km
  • Maui Jack's Waterpark - 3 min drive - 2.1 km
  • Captain Timothy Hill House - 3 min drive - 2.8 km
  • Chincoteague National Wildlife Refuge - 5 min drive - 3.5 km

Getting around

  • Ocean City, MD (OCE-Ocean City Municipal) - 70 min drive

Restaurants

  • ‪Island Creamery - ‬15 min walk
  • ‪Steamers - ‬15 min walk
  • ‪McDonald's - ‬4 min drive
  • ‪Teaguers - ‬13 min walk
  • ‪Famous Pizza & Sub Shoppe - ‬3 min drive

Frequently asked questions

Is Island Bay Dreams by Seaside Vacations and Sales! pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Island Bay Dreams by Seaside Vacations & Sales?

As of Apr 23, 2026, prices found for a 1-night stay for 2 adults at Island Bay Dreams by Seaside Vacations & Sales on Jun 4, 2026 start from $343, 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?

Onsite parking is available at the property.

What time is check-in at Island Bay Dreams by Seaside Vacations and Sales!?

Check-in begins at 4:00 PM.

What time is check-out at Island Bay Dreams by Seaside Vacations and Sales!?

Check-out is at 10:00 AM.

Where is Island Bay Dreams by Seaside Vacations and Sales! located?

Located in Deep Hole, this vacation home is within 1 mi (2 km) of Oyster Bay, Maui Jack's Waterpark, and Chincoteague Channel. Captain Timothy Hill House and Robert N. Reed Downtown Waterfront Park are also within 2 mi (3 km).

About the host

Hosted by Seaside Vacations & Sales

Host profile image
Seaside Vacations is a LOCAL family owned and operated Vacation Rental Company serving Chincoteague island, VA and the Mainland, and Ocean City, MD. Here to help you plan THE perfect beach break!

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English
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