Chesapeake Bay Vacation Homes

Walk to dining and entertainment from these charming locations

Reviews

Sarah
June 2026
We had a great stay! This was our second year staying here-great location by the park and easy to walk into town or take a golf cart to the beach. The house has everything you could need for a week’s stay, and the communication is clear and prompt! It feels like home away from home! Thank you for everything!
Rick
May 2026
This was our second stay at Baydreamin. The owner has taken care to provide an excellent home. Extremely clean, well stocked, large yard with outdoor fire pit and chairs, picnic table and yard games. Inside you have 4 comfortable bedrooms and 2 great bathrooms. Our son and grandkids live in the area so family from Michigan, Kentucky and Florida can meet for family time and great food.
Gus
May 2026
The house was perfect and really clean. It had everything you could want. Even though it rained a few days, it didn’t matter because the pool, hot tub, darts and yard entertained us, plus the covered part of the lanai was perfect for relaxing and talking. The owners were very responsive as well.

Our Properties

Heated Pool & Hot Tub ~ Walk Downtown & 2 The Amp!

Heated Pool & Hot Tub ~ Walk Downtown & 2 The Amp!

St. Augustine, FL, United States

Guests 10

Bedrooms 4

Bathrooms 2
Walk to Dining, Beach & Park~Family Friendly Home!

Walk to Dining, Beach & Park~Family Friendly Home!

Cape Charles, VA, United States

Guests 6

Bedrooms 2

Bathrooms 1.5
Walk 2 Beach & Restaurants~Central Park~ King Bed!

Walk 2 Beach & Restaurants~Central Park~ King Bed!

Cape Charles, VA, United States

Guests 6

Bedrooms 2

Bathrooms 1.5
New Build-1st Floor King Suite &Kid Friendly Loft!

New Build-1st Floor King Suite &Kid Friendly Loft!

Cape Charles, VA, United States

Guests 8

Bedrooms 3

Bathrooms 2.5
Convenient Walk 2 Dining~Free Parking+Beach Gear!

Convenient Walk 2 Dining~Free Parking+Beach Gear!

Chincoteague, VA, United States

Guests 6

Bedrooms 2

Bathrooms 2.5
Golf Cart~ Chef Kitchen~ Fire Pit~ Outdoor Shower!

Golf Cart~ Chef Kitchen~ Fire Pit~ Outdoor Shower!

Cape Charles, VA, United States

Guests 8

Bedrooms 4

Bathrooms 2
Ultimate Kid-Friendly Escape! Fenced Yard-Firepit!

Ultimate Kid-Friendly Escape! Fenced Yard-Firepit!

Cape Charles, VA, United States

Guests 8

Bedrooms 4

Bathrooms 2
1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

Mathews, VA, United States

Guests 9

Bedrooms 4

Bathrooms 2
Duplex by Central Park~2 Blocks to Beach~King Bed!

Duplex by Central Park~2 Blocks to Beach~King Bed!

Cape Charles, VA, United States

Guests 12

Bedrooms 4

Bathrooms 3
Waterfront Retreat~Private Dock~Fire Pit~Gameroom!

Waterfront Retreat~Private Dock~Fire Pit~Gameroom!

Onancock, VA, United States

Guests 8

Bedrooms 4

Bathrooms 2.5
Remodeled by the Park-Family Friendly-Fenced Yard!

Remodeled by the Park-Family Friendly-Fenced Yard!

Cape Charles, VA, United States

Guests 4

Bedrooms 2

Bathrooms 2
NEW-Family-Friendly Duplex-Outdoor Shower-Fire Pit

NEW-Family-Friendly Duplex-Outdoor Shower-Fire Pit

Cape Charles, VA, United States

Guests 5

Bedrooms 2

Bathrooms 2
New Hot Tub~1st Floor King Bed~Fire Pit~Bunk Room!

New Hot Tub~1st Floor King Bed~Fire Pit~Bunk Room!

Cape Charles, VA, United States

Guests 11

Bedrooms 4

Bathrooms 3.5