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Conch Shell

3 Bedrooms
1 Bath
6 Guests
Chincoteague Island
Waterfront
Internet
Outdoor Shower

The house is located on Pine Drive in Piney Island - the closest neighborhood to the beach - convenient for shopping and dining on Maddox Blvd. This wonderful waterfront beach bungalow features a wrap around deck with views of Assateague and the light house. You can bring your boat, jet skis or kayaks and keep them tied up out front. There is a spacious living room for entertaining and a nicely remodeled kitchen! Your rental also includes water access (a short walk from the home) to a tidal creek that comes up from Oyster Bay - it's a great place for the kids to crab or to launch a kayak or canoe. 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- 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.

Wildcat Retreat

4 Bedrooms
4 Baths & 1 Half
10 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Only for the discerning traveler, 'Wildcat Retreat' is the newest in luxury vacation accommodations on Chincoteague Island. The reverse floor plan is over 2,800 square feet and offers views of the bay and marshlands where wildlife abounds from nearly every room. The first floor features 4 bedrooms, all en-suite with full bathrooms and a large recreational room with second kitchen and waterside deck. The second floor features the main living areas - living room, dining room, kitchen, powder room - as well as another waterside deck and screened porch. If you enjoy fishing and crabbing, or just sitting at the water's edge, you'll LOVE the 500' private pier that extends into the Chincoteague Bay! Vacationing with a large group? Check out the sister house 'Wildcat Haven' right next door!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.

- Pet friendly with fee.

- 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 Great Escape

5 Bedrooms
3 Baths
11 Guests
Cape Charles
Gas Grill
Screened Porch
Internet
Outdoor Shower

Discover the charm of Cape Charles in this beautifully restored 5-bedroom, 3-bathroom house, available for your next vacation adventure. Nestled in the heart of downtown, "The Great Escape" places you just minutes away from a vibrant selection of shopping, dining, and entertainment options, including local ice cream shops and mini-golf. Whether you're enjoying the bustling town scene or relaxing at home, this property offers both convenience and comfort.

Step onto the inviting open front porch where you can sip your morning coffee while soaking in the town views. Alternatively, the screened porch provides a tranquil retreat to unwind in the evenings without the pesky insects. Inside, you’ll find a clean and comfortable interior with ample living space that caters to both large and small families alike.

"The Great Escape" is ideal for those seeking a blend of small-town charm and modern amenities, all within walking distance of Cape Charles' delightful attractions. Whether you're settling down with your family or looking for a scenic change of pace, this vacation home promises a lifestyle of ease and excitement. Don’t miss out on making this house your new home away from home — book your getaway today!

- 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.

 

High Tide

3 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet
Outdoor Shower

We're pleased to be able to offer 'High Tide' as one of our most popular vacation rental selections! The true epitome of a beach house, you'll enjoy the bright, cheery decor and spacious feel of this fabulous home. The downstairs features an open living room (with fireplace and flat-screen TV), dining area and kitchen, as well as over-sized windows and access to the two (yes, TWO!) screened porches. One porch features a wonderful dining set; perfect for dining al fresco. The second spacious porch features a large hammock and nice sectional lounging sofa. As if that's not enough outdoor space, there are also multi-level, open air decks on the front and back of the home! There's also a bedroom (king) and full bathroom downstairs. The upstairs features two additional bedrooms (one with a queen & two twin beds, and the other with a queen & one twin bed), and a full bathroom. Both upstairs bedrooms are enhanced by sliding doors and private balconies. You'll enjoy snippet water views of the Assateague Channel! Don't delay, 'High Tide' books quickly. Please note: As part of the Piney Island Community, this rental includes water access at a shared community location just a short distance from the home.

- 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.

Castlebar

5 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Luxury waterfront home in Salt Marsh Landing - an upscale residential community on the northern tip of Chincoteague Island. Spectacular sunsets! A long, private pier over the salt marsh leads you to a bay front dock area with shade. It's perfect for crabbing, fishing or canoe and kayak launching. Tastefully appointed and architecturally pleasing, Castlebar features a main level great room flanked by wall of beautiful custom windows and high cathedral ceilings. The views of Chincoteague Bay are priceless. The open kitchen area features ample counter space for meal prep, and the large harvest dining table is perfect for gathering the whole group for a meal. There are hardwood floors, and a two-sided fireplace that is shared with the adjoining cozy den. The first floor also features a full bath and large bedroom that looks out on the bay. The second floor hosts the primary bedroom suite, containing a private bath with separate shower and whirlpool tub. A sliding French door leads out to a balcony providing more views of the bay to enjoy. Two additional bedrooms and full bath complete this floor. Amenities also include a private, full sized outdoor shower, wireless internet service, additional under-counter ice maker & more. Castlebar is available year round!

- 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

Wildflower

3 Bedrooms
3 Baths
6 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio perfect for those summer time seafood feasts. The first level is great room boasting reclaimed barn board walls and wide plank pine floors with a separate den and full bath. There is a second screened porch overlooking that water from the great room. The second level has a large waterfront master suite with a private balcony, two more bedrooms and another full bath. Close to Memorial Park right across the street from a family restaurant! (Spiral staircase in home, may not be suitable for small children.) For larger groups for family reunions, check out nearby Moon Rising or Herbie's Hideaway!

- 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.

Cockleshell Cottage

3 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage! This modern 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite (Queen), all amenities and comfortable furnishings. Upstairs features 2 more bedrooms (Double and Double/pull-out Twin trundle), and a full bathroom. Cockleshell Cottage is handicap accessible. Relax and enjoy the breeze on the open front porch or back screened porch. Call us today; this home books fast!

- 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. Pet restriction: limited to two small dogs only.

- 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.

Blue Crab Bungalow

1 Bedroom
1 Bath
5 Guests
Chincoteague Island
Pet Friendly
Internet
Outdoor Shower

Welcome to this charming bungalow located in the center of Chincoteague Island! This delightful house offers a cozy and comfortable living space, making it the perfect place to call home. With 1 bedroom and 1 bathroom, this property is ideal for individuals or a small family looking for a serene retreat. As you step inside, the throw-back retro kitchen adds character to the home and makes cooking an enjoyable experience. Whip up your favorite meals while reminiscing about the good old days. The kitchen is equipped with all the necessary appliances to satisfy your culinary desires. You'll be greeted by the warmth of the main bedroom featuring a comfortable queen bed. The second sleep area serves as both a sleeping and an office space, with a twin pull-out sofa providing versatile accommodation options. Whether you work remotely or simply need a quiet space to focus, this flexible layout has got you covered! The bungalow is close to town and 'Beach Road' - convenience is at your fingertips. Enjoy easy access to local amenities such as shops, restaurants, and entertainment options. Whether you're in the mood for a leisurely stroll or need to run some errands, everything is just a short distance away. After a long day, relax and unwind in the enclosed front porch. This inviting space is perfect for enjoying your morning coffee or savoring a glass of wine in the evening breeze. Additionally, there's an outside shower, allowing you to rinse off after spending time at the nearby beach. With parking spaces for 2 vehicles, parking won't be a hassle. Don't miss out on the opportunity to make this charming bungalow your next vacation spot! With its convenient location, versatile layout, and retro charm, it's sure to steal your heart. 

- *NEW FOR 2025: Level 2 EV charger!*

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly with a pet fee per pet. Small dogs only, restricted to two (2) pets. 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.

Joint Venture

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Water View
Pet Friendly
Internet

Joint Venture is the perfect townhouse for an affordable vacation! Take a short stroll to Maddox Blvd (Beach Road) and enjoy ice cream, mini golf or any of the shops & restaurants. Bike or drive to the beach! Joint Venture offers a water view of Little Oyster Bay (tidal creek) that can be enjoyed any time of year. This property offers Wi-Fi and is pet friendly! Don't miss out!

- 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.

Sunkissed Shores

4 Bedrooms
4 Baths
15 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Sunkissed Shores invites you to experience waterfront living at its finest. This expansive four‑bedroom, four‑and‑a‑half‑bathroom retreat sits directly on Chincoteague Bay, offering sweeping water views and unforgettable sunsets from every room. Each bedroom features its own private balcony and ensuite bath, including two king suites on separate levels for added privacy. A cheerful bunkroom provides flexible sleeping for families and groups, and thoughtful touches like two pack ’n plays and a highchair make traveling with little ones effortless.

The heart of the home is the stunning great room, where soaring ceilings and dramatic walls of windows bring the bay right inside. During cooler months, the seasonal fireplace transforms this space into a warm, inviting haven—perfect for watching winter sunsets or enjoying a quiet evening indoors. A fully equipped  kitchen—with generous counter space, quality cookware, and every gadget you could need—makes meal preparation and entertaining a pleasure. Just off the living area, an enclosed all‑weather gazebo opens to a large waterside deck, creating the perfect setting for crab feasts, morning coffee, or simply relaxing as the sky shifts from gold to pink each evening.

Upstairs, the game loft offers entertainment for all ages with a classic 1980s Space Invaders arcade machine, a commercial‑grade 4‑player arcade table with over 2,500 games, a 77" TV, board games, a chess/checkers table, and a giant wall‑mounted Connect 4. A queen sleeper sofa provides additional space for guests, and each upstairs bedroom sits in its own private wing for a peaceful retreat.

Step outside to your private pier, where you can fish, crab, or launch kayaks directly into the bay. The bulkheaded shoreline offers easy access to the water, and the eastern side of the property provides serene sunrise views over the marsh—giving you the rare opportunity to enjoy both sunrise and sunset from the same home. With unmatched views, thoughtful amenities, and room for everyone to unwind, Sunkissed Shores stands apart as a place where memories are made and every day ends with a sunset worth savoring.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- 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.

Marsh Point

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

Located just off of Ridge Road on the southern portion of the island, you'll find Marsh Point. A two bedroom, two and a half bath townhome unit with (shared) dock access. A lovely screened in porch dining area for cooking up the crabs you'll catch right off the dock and enjoying with family and friends, you're sure to be comfortable here! On the ground floor you'll find the comfortable living area with plush new furniture, a fully-equipped galley-style kitchen (electric range, refrigerator, dishwasher, microwave), a dining area with table, a utility closet with a washer and dryer, and a half bath/powder room in the hallway. Upstairs you'll find the bedrooms - a master suite with queen bed and a full bath. The other bedroom upstairs boasts a balcony with a beautiful view of the salt marsh below. For sleeping arrangements you'll find a bunk (a full on the bottom and a twin on top - always fun fighting over who gets that one!). Another twin is also located in the second bedroom as well. A full bath is located in the hallway upstairs. If you look to the grassy grove across the street you'll be looking at the location of the former Beebe Ranch, home of Misty of Chincoteague. You can almost see the little pinto paint filly frolicking through the paddock. Sit on the bench at the end of the dock with a cocktail or a cup of coffee at sunset and feel the cool island breezes coming off of the inlet and Curtis Merritt Harbor, just a little further down the road. Ride into town to get a bite to eat, or grab a few ingredients at one of our local seafood markets (a wonderful fishmonger and lobster lady lives just across the street) to make something easy at home. No matter what you decide, make a point to enjoy yourself at Marsh Point.

- 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.

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