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Four-Plus Bedroom Rental Homes

Wildcat Cove - Waterfront

Vacationer's Dream Home. Enjoy the panoramic views of Chincoteague Bay and across to Assateague from the widow's walk. Each bedroom has private waterview balcony and bath. Private pier for crabbing or docking small boat.

4 Bedrooms, 5 Baths

Max Occupancy: 10

Weekly Rates: $2600 - $4500


Topaz - Canalfront

Great Family Getaway. Decks, boat dock and a quiet location in the Oyster Bay Community.

4 Bedrooms, 2 Baths

Max Occupancy: 8

Weekly Rates: $1230 - $1850


The Treehouse - Waterview - Piney Island

Enjoy great views from this one-of-a-kind "Tree House". Close to Assateague, perfect for biking and beach access. 2 Kayaks and Smokeless Firepit.

4 Bedrooms, 2 1/2 Baths

Max Occupancy: 12

Weekly Rates: $1645 - $2850


The Blue Heron - Piney Island

New for 2024! Call Now to Book For Next Season!

Excellent location - in the woods and close to the beach.

4 Bedrooms, 2 1/2 Baths

Max Occupancy: 10

Weekly Rates: $1450 - $2350


Sunsinger - Waterfront

Custom home with panoramic views of the island's natural splendour. West facing on the Chincoteague Bay. Shared pier/boat dock, Handicap accessible.

4 Bedrooms, 4 Baths

Max Occupancy: 10

Weekly Rates: $1875 - $3500


Sialang - Waterfront

Situated on the Chincoteague Bay. This fabulous home has views from every room. Private pier for kayaking or crabbing. Off-Season Hot-tub.

4 Bedrooms, 3 Baths

Max Occupancy: 10

Weekly Rates: $2025 - $3750


Shell Seeker - Waterfront

Exceptional bayfront home with outstanding views and sunsets. Semi-Private Pier & Dock. Thoughtfully and tastefully appointed.

4 Bedrooms, 3 Baths

Max Occupancy: 10

Weekly Rates: $1700 - $3350


Scooby Dunes - Bay & Marsh Views

Custom, 3 level floor plan provides views of Oyster Bay or Miflin's Marsh from any room. Enjoy walks, biking, crabbing in quiet, private community.

4 Bedrooms, 3 1/2 Baths

Max Occupancy: 9

Weekly Rates: $1525 - $2595


Sailor's Rest - In-Town

Beautifully renovated Chincoteague home. In-town location - close walk to restaurants and stores. Excellent choice for larger families. 10% Discount for Military families.

4 Bedrooms, 2 1/2 Baths

Max Occupancy: 10-12

Weekly Rates: $1295 - $2350


Sailer Moon - Waterview

Completely renovated Victorian home with great views of Chincoteague Channel and sunsets from balcony. Sunsets.

3 Bedrooms,Private Sleep Loft, 2 1/2 Baths

Max Occupancy: 8

Weekly Rates: $975 - $1535


Prospect Point - Waterfront

New for 2023!

Enjoy unparalleled views - Chincoteague Bay & protected nature conservation. Private pier for crabbing & shallow boat docking.

4 Bedrooms, 4 Baths

Max Occupancy: 10

Weekly Rates: $2500 - $4750


Osprey Nest - Waterfront

Comfortably appointed home on the edge of the Chincoteague bay. All amenities including large screened porch and shared pier for crabbing or fishing.

4 Bedrooms, 4 1/2 Baths

Max Occupancy: 10

Weekly Rates: $1800 - $3245


Lost Pearl

Spacious home on a quiet street. Great for a family vacation.

4 Bedrooms, 2 Baths

Max Occupancy: 8

Weekly Rates: $965 - $1425


Laughing Gull

Quiet location in Oyster Bay. Large screened porch. Very close to community boat launch.

4 Bedrooms, 2 Baths

Max Occupancy: 8

Weekly Rates: $1065 - $1775


Ladybug House

Spacious - Perfect for family vacations! Delightful, comfortable home located in a quiet area.

4 Bedrooms, 3 Baths

Max Occupancy: 8+

Weekly Rates: $1195 - $2225


Kingslanding - Canalfront

Great canal front home in the quiet, private community of Oyster Bay. Boat dock & screened porch.

4 Bedrooms, 1 Bath

Max Occupancy: 8

Weekly Rates: $1050 - $1795


Island Girl - Canalfront

Great canal front home in the quiet, private community of Richardson's Landing. Boat dock & kayaks.

3 Bedrooms + Loft Bedroom, 2 Baths

Max Occupancy: 10

Weekly Rates: $1790 - $3190


Heron's Roost - Waterfront

Situated on Oyster Bay, this inviting home has boat dock and stunning views.

4 Bedrooms, 2 Baths

Max Occupancy: 8

Weekly Rates: $1495 - $2575


Grace Street Refuge - Waterview

Bright and airy open floor plan. Quiet location with sunset views. Firepit, Bikes, Electric Car Charger.

4 Bedrooms, 2 1/2 Baths

Max Occupancy: 10

Weekly Rates: $1295 - $2500


Dockside Dreams - Canalfront

Beautiful updated home in the Oyster Bay Community. Boat Dock on deep water. Superb views from every deck & screened porch. Community boat launch nearby.

4 Bedrooms, 3 Baths

Max Occupancy: 10

Weekly Rates: $1745 - $2995


Cedar Gables - Waterfront

The Ultimate Vacation Rental Home. Stunning views over Little Oyster Bay. Private Pool and Hot Tub in Screened Atrium. Private Pier and Boat Dock. Waterfront Decks and Balconies.

5 Bedrooms, 6 Baths

Max Occupancy: 12

Weekly Rates: $2200 - $6450


Casa dell 'Isola - Canalfront

Easy access to Oyster Bay from this cheerful home. Equipped for a fun vacation with Kayaks, Paddleboards, Game Room and more...Boat Dock.

5 Bedrooms, 3 Baths

Max Occupancy: 12

Weekly Rates: $2100 - $3750


Brittany - Waterfront

Delight the entire family with this superbly appointed and spacious home. Watch the sun rise; canoe, fish or crab. Private Pier and Boat Dock.

4 Bedrooms, 3 1/2 Baths

Max Occupancy: 12

Weekly Rates: $2500 - $3750


Bay View - Waterfront

New Luxury Vacation Rental Home. Enjoy Unobstructed Views of Chincoteague Bay. Deep Water Dock, Hot Tub, Firepit and 2 Kayaks.

4 Bedrooms, 3 Baths

Max Occupancy: 9

Weekly Rates: $2600 - $4500


Bay Watch - Waterfront

Splendid reatreat on the edge of beautiful Oyster Bay. Thoughtfully designed private and gathering areas all with stunning views. Private Boat Dock.

4 Bedrooms, 4 1/2 Baths

Max Occupancy: 8

Weekly Rates: $1875 - $3500


Aramabad

Delightful, country home in peaceful location on Piney Island. Close to entrance of Assateague, perfect for biking and beach access.

4 Bedrooms, 2 Baths

Max Occupancy: 8

Weekly Rates: $875 - $1895


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