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Shore Thing On Oyster Bay

4 Bedrooms
3 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Enjoy some of the island's best water views overlooking Oyster Bay from nearly every room of this custom beach home! Located on a bulk-headed waterfront lot in Richardson's Landing, you can fish and crab from the backyard! A wonderful feature of this spacious home is that you'll find your bedrooms on the first level and your main living area on the second level. The great room opens to the kitchen and features wood floors throughout. And the views are spectacular! Lots of windows!! Some of the bedrooms have waterside balconies. This home has four televisions- all with cable hooked up! You'll find all the bells and whistles here! So take a look at all the pictures and then give us a call or book online. Make memories to last a lifetime!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- 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.

Capeville Cottage

3 Bedrooms
2 Baths & 1 Half
8 Guests
Cape Charles
Town & Country
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Welcome to Capeville Cottage in the heart of Capeville, VA - just 5 miles North of the Chesapeake Bay Bridge Tunnel. The Capeville Cottage is a charming 1700 sq.ft., 2 story home featuring 3 bedrooms and 2.5 baths. Upon pulling into the private driveway, there is a west facing front porch, great for watching the gorgeous Eastern Shore sunsets and relaxing after an active day.  You are welcomed by a large living area, high ceilings, and spacious kitchen with plenty of seating, laundry and a half bath.  There is a screened porch off of the kitchen with a picnic table that seats eight. Downstairs is a large primary bedroom with a king sized bed, high ceilings, a tv, and full bath and separate stand in shower. Upstairs there are two bedrooms. One has a twin over full bunk with a separate full size bed. The 3rd bedroom has a queen bed, tv and a shared full bath. Outside in the garage, you will find a game room with a ping pong table, darts and a large refrigerator. Capeville Cottage offers a large yard with ample parking, and a boat washing station.  Come enjoy Capeville Cottage and let the tranquil lower Eastern Shore wash your worries away!

- Linens and towels are included with your reservation. 

- No smoking is permitted on the premises. 

- This property is pet friendly with an additional pet fee of $150 per pet. All pets must be disclosed prior to arrival. Limitations: 2 dogs max (cannot exceed 50 lbs.); no cats. 

- 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.

This rental home is conveniently located:

1 mile to Stingray's Restaurant

2.5 miles to Kiptopeke State Park and boat ramp

5 miles to downtown Cape Charles and public boat ramp

5 miles South of Wise Point boat ramp

3 blocks to the scenic bike path on Capeville Road

Dockside

3 Bedrooms
3 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Internet

Located on the Assateague Channel, this is your chance to watch the ponies from your own deck. A wonderful panoramic view awaits you; to the left is the Assateague Bridge; to right of the bridge is the Assateague Lighthouse and ponies; and to the far right is Tom's Cove and the ocean inlet. Come and fish from your own dock and tie your boat along side! Inside you will find central heat/air, 3 decks, all appliances, gas grill, satellite TV & DVD player and internet access. Enjoy evenings resting beside the wood fireplace (off-season).

Please note: Parking is limited to 2 spaces (this includes a boat/trailer if you are bringing one). Max. boat size for docking is 20'. If alternate parking accommodations are needed, please ask. 

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- 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.

Misty's Thicket

2 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Water Access
Charcoal Grill
Screened Porch
Internet

Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style kitchen complete with a dining area and all necessary appliances. The cozy living room leads you onto one of two screened in porches perfect for unwinding with family and friends. Upstairs, you find a great master bedroom with en-suite, a full bathroom off the hallway, and a second bedroom that features a bunk bed and a queen size bed that looks out onto the second-level screened in porch affording amazing Chincoteague Island views.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pets are not permitted on the premises.

- 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.

Moon Rising

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Screened Porch
Internet
Outdoor Shower

Very nice waterfront home overlooking Assateague Island and lighthouse. Satellite TV, all amenities. Nice waterside deck areas. Long pier and dock (deep water) shared with house next door. New waterside screened porch and upper level balcony. Relax and chill out after a long day at the beach. Close to Memorial Park right across the street from a family restaurant! This is the perfect place for your island vacation -- and for larger groups or family reunions, check out nearby Herbie's Hideaway or Wildflower!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- 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.

Southern Exposure

4 Bedrooms
2 Baths
7 Guests
Chincoteague Island
Waterfront
Boat Dock
Screened Porch
Internet
Outdoor Shower

Southern Exposure is nestled along the natural shoreline of the Assateague Channel, offering some of the most beautiful water views on Chincoteague Island. Conveniently located in one of Chincoteague's most popular residential communities, you're only minutes from the beach and attractions - shopping, mini golf, restaurants and more! This ranch-style home features 4 bedrooms, and all your main living areas, on one level. Enjoy relaxing moments on the waterside screened porch or private deck overlooking the marsh and Assateague Channel. And you can crab/fish, kayak or dock your boat from the deep-water pier (with ladder and floating dock). It doesn't get much better than this!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- 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.

Sunrise Shore

3 Bedrooms
3 Baths & 1 Half
14 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Pool
Hot Tub
Internet

Spend your precious vacation time at this truly stunning, one-of-a-kind architectural masterpiece! From the moment you walk in the French entry doors, you'll be "wowed" by the floor to ceiling windows and 3-sided glass fireplace. The chef's quality kitchen is brand new with stainless steel appliances and granite counter tops. There are multiple decks for enjoying some relaxing downtime and taking in the unobstructed views of Oyster Bay. Professionally decorated with clean, modern Bohemian-chic decor and furnishings, you'll find yourself surrounded by simple, upscale comfort. There's a 70" TV in the living room, and all the bedrooms feature their own flat-screen TVs and Amazon Echo devices. Stream all of your favorite shows from Hulu, Netflix or Disney+! "Sunrise Shore" is located in one of Chincoteague Island's most popular waterfront residential communities - Oyster Bay I. Conveniently located to Maddox Blvd. (Beach Road) and downtown Chincoteague, yet far enough to escape the hustle & bustle. | | The main level of this home features the main living areas (kitchen, dining room, living room), a powder room, a pool shower bathroom ,and the master bathroom en suite. The upstairs features 2 more bedrooms, both with private balconies, and a full bathroom. There's also an additional loft sleeping area. | | The outdoor areas offer exceptional entertaining and relaxation space. Cool off in the 10' x 40' saltwater in-ground pool, or gaze at the stars as you spend the evening in the 6-person hot tub. Dine al fresco on one of the many decks, all while enjoying the water views. There's plenty of room in the yard for a game of corn hole or catch.

- Linens and towels are included with your reservation. 

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- 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.

Robert's Retreat

5 Bedrooms
3 Baths & 1 Half
10 Guests
Captain's Cove
Water View
Gas Grill
Pool
Internet

Discover the ultimate family retreat in this brand new 5-bedroom, 3.5-bathroom home located in the picturesque Captain's Cove Community, boasting over 2,500 square feet of luxurious living space. With breathtaking natural marshland and water views, this residence is perfect for wildlife watching and enjoying serene sunsets from expansive decks designed for outdoor dining and recreation. The upgraded kitchen and all-new furnishings create an inviting atmosphere for making cherished memories with loved ones. Take advantage of community amenities including indoor and outdoor pools, a 9-hole golf course, fitness room, waterfront restaurant, boat ramp, and fishing pier to ensure endless fun-filled days. Don’t miss out on this exceptional opportunity to create lasting family traditions in a relaxing vacation paradise!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property does not allow pets. 

- 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.

Sunset Bay Villa 116

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Pool
Internet

A beautiful ground-floor villa with walk out to marina. Luxurious master bedroom with private bath includes both a roomy tiled shower and whirlpool bath. Villa 116 will sleep 8 (beds for 6 plus a queen size air mattress), and includes a full laundry, all appliances, a gourmet kitchen, and more. There's also a pool and fitness room for your enjoyment! Tastefully furnished, you can relax, enjoy and entertain your family and friends in style. | NOTE: This unit does not have a boat slip, however, use of the marina is included.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises. 

- 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.

Sandy Penny

3 Bedrooms
3 Baths & 1 Half
14 Guests
Chincoteague Island
Water View
Screened Porch
Internet

Experience elevated coastal living at 'Sandy Penny', a stunning, brand-new vacation home tucked along peaceful Clarkson Lane with beautiful, snipet water views of the Assateague Channel. Thoughtfully designed with comfort and sophistication in mind, this home is the perfect retreat for families, couples, and friends seeking a luxurious Chincoteague Island getaway.

From the moment you step inside, you’ll notice the premium furnishings, designer finishes, and upscale appliances that set 'Sandy Penny' apart. The bright, open-concept living area features expansive windows that allow natural lighting, and space for gathering or entertaining. Whether you're savoring your morning coffee or winding down after a day of exploring, this space makes every moment feel special.

The chef’s kitchen is fully equipped with top-of-the-line appliances, custom cabinetry, and elegant stone countertops, making it a joy to cook and gather. Enjoy meals indoors or take advantage of the outdoor spaces to dine with soft bay breezes and glimpses of passing wildlife.

Sandy Penny offers three beautifully appointed bedrooms, each with its own private en-suite bathroom, providing exceptional comfort and privacy for every guest. Luxurious bedding, spa-inspired bathrooms, and serene décor ensure a restful experience from start to finish.

Located in one of the island’s most desirable areas, you’ll be just minutes from: Assateague National Seashore and the world-famous wild ponies; downtown Chincoteague’s shops, ice cream parlors, and restaurants; kayaking, boating, and fishing along the Assateague Channel; scenic trails and bike paths and more!

Whether you’re seeking serenity, adventure, or a little of both, Sandy Penny delivers a refined coastal escape with all the comforts of a luxury home. Book your stay today and experience Chincoteague Island from a place where every detail is designed for relaxation and unforgettable memories.

Bed Configuration: Downstairs Bedroom - King bed; Upstairs Bedroom 1 - King bed; Upstairs Bedroom 2 - Triple Bunk Bed & Twin-over-Full Bunk with pull-out Twin Trundle; Living Room - Queen Sleeper Sofa; Additional Rollaway Twin Bed

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises.

- 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.

The Haven

3 Bedrooms
3 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Internet

We're pleased to bring you "The Haven" located on the edge of the Assateague Channel! Enjoy spectacular views of the Channel and Lighthouse right from your own private living space! Downstairs features a kitchen, dining area, living room and half bathroom. The second level features 2 bedrooms - one is a master suite with King bed and private bathroom, and the other features a Queen bed. There is also a 2nd full bathroom on this level. The third level features a bedroom (Queen and 2 Twin beds) and a full bathroom. There are multiple decks and there's also 21' of dock space where you can fish, crab, kayak or tie up a small boat. Take a look and book today; this one won't last long!

Please note: Parking is limited to 2 spaces (this includes a boat/trailer if you are bringing one). Max. boat size for docking is 20'. If alternate parking accommodations are needed, please ask. 

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.

- No pets are permitted on the premises.

- 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.

Princess Anne

1 Bedroom
1 Bath
2 Guests
Cape Charles
Internet

Welcome to this freshly renovated, two-bathroom condominium in the heart of charming Cape Charles. Ideally positioned just blocks from the beachfront, this beautifully curated home offers a comfortable balance of modern upgrades and downtown accessibility.

Step into an open living area that features a cozy fireplace and large television, perfect for unwinding after a day by the shore. The full kitchen is outfitted with brand-new appliances, ready to handle everything from your morning coffee to your evening seafood feast.

Take advantage of the rooftop terrace which offers relaxation while overlooking downtown and the Bay after a long day at the beach. Complete with a wet bar area under a pergola, this is sure to become one of your favorite hangout spots. 

The primary bedroom offers a private retreat with its own balcony — an ideal spot for enjoying gentle breezes. An adjacent custom-tiled bathroom adds convenience and a touch of refinement.

Outdoor enthusiasts and leisurely strollers alike will appreciate the condo’s proximity to the Cape Charles Beachfront, mere minutes away on foot. The neighborhood’s inviting walkability extends to nearby restaurants, the Cape Charles Distillery, ice cream parlors, boutique shops, and local art galleries. And when everyday errands call, a well-stocked supermarket is just a short drive away.

If convenience, style, and coastal charm are on your checklist, this condo just might check every box. With a location that makes spontaneous ice cream excursions and sunset beach walks a regular thing — it isn’t just a rental, it’s a lifestyle.

PLEASE NOTE: 'Princess Anne' is one of 5 luxury apartments offered within the 'Cape Dunes' complex. This being the case, some amenities and spaces are shared. This includes the washer & dryer, ice maker and roof top terrace. Parking is on-street and not reserved. 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted. 

- 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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