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Gone Coastal

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Pet Friendly
Screened Porch
Internet

Enjoy the cool breezes coming off the Chincoteague Channel while relaxing on the porch at Gone Coastal! Nestled in a grove of pines and tucked just off East Side Drive, this charming unit has everything your family desires for a wonderful stay on Chincoteague Island. Bright and cheery nautical decor will help to put you on "island time". Featuring two bedrooms, two and a half baths, a spacious living and dining area, and a fully-equipped kitchen. The two bedrooms are on the upper level. The master features a full bed with flat screen television, full bath, and balcony with sliding door and comfortable outdoor furnishings. An additional bedroom featuring a full size bed and double bunk, and a full bath is located in the hallway upstairs as well. On the ground floor you'll find a spacious living area with large flat screen tv, plush seating, and plenty of reading material. The eat-in kitchen features everything you'll need to prepare and enjoy meals "at home" - electric range, roomy refrigerator, dishwasher, coffee bar, and dining table. A full-sized washer and dryer are located in a utility closet just off the kitchen, and a barbecue grill is located on the back porch for your convenience. Located centrally on the island - you're a quick bike ride or easy walking distance to the commerce on Maddox Boulevard or downtown Main Street, or to Memorial Park located just down Eastside Drive. Pop into one the oyster farms and grab a sack to bring back and enjoy with a glass of wine as the sun sets on another day Gone Coastal. Please Note: No boats or trailers are allowed at the complex.

- 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.

Sunshine Daydream

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Beautiful 3 bedroom home located in one of Chincoteague Island's private WATERFRONT communities! Formerly known as "Snoozin' Goose", Sunshine Daydream offers multiple outdoor porches, an open floor plan with large, bright rooms and modern amenities -- all in a quiet, peaceful location. Enjoy wonderful water views while sitting directly on a canal leading out to Oyster Bay. Tastefully decorated, and you can bring your dog along also!

- 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.

Salty Sea Lyons Landing

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Town & Country
Pet Friendly
Gas Grill
Screened Porch
Pool
Internet

Escape to the ocean and enjoy this contemporary golf course home! Sit and relax while enjoying the golf course views from the screened porch; boasting easy access to pools, golf course, restaurant, and much more. Come relax in the cozy living room with new furnishings, electric fireplace and smart tv. The well-equipped kitchen boasts stainless steel appliances and kitchen equipment that guests can use to cook tasty snacks.

The home includes four smart TVs, (one in each bedroom) central heat and a/c, and plenty of board games to keep you occupied during your stay.  Bedrooms are equipped with nice mattresses to ensure a good night's rest, along with cozy blankets and thoughtful décor.   The owner's suite features a king sized bed, electric fireplace, on suite bath with a double vanity, large soaking tub as well as a walk in shower. You will find two more bedrooms just down the hall, one with a queen sized bed and another with a double bed. There is also another full bathroom with a tub/shower combo.

The front porch is perfect for sipping your morning coffee, or enjoying an evening beverage of choice. The screened in porch has comfy seating for 6 and a firepit for your enjoyment just off of the steps. Come spend a weekend or an entire week at Salty Sea Lyons, you won't be disappointed!

This home is conveniently located to all the community amenities such as pools (2 outdoor & 1 indoor), fitness center, marina w/ fishing pier, restaurant, tiki bar, and more! (with a fee) If day-tripping is more your style, you'll love the fact that this home is located only 20 minutes from Chincoteague Island and the beach, or 30 minutes to Ocean City, MD and the boardwalk amusements.

- 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. Pet fee is $150 per pet. All pets must be disclosed prior to arrival. Pet restriction: 2 pet max.

- 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.

- Community amenities require passes for an additional fee.

- Additional community requirements: Each occupant must disclose their name. Vehicles must be registered; make and model of each vehicle is required. Incomplete or incorrect information will result in revocation of the use of community amenities and facilities. No Sunday check-ins or check-outs are permitted.

Piney Island Paradise

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

Welcome to Piney Island Paradise! This well-furnished townhouse is nestled in a secluded cul-de-sac along East Side Drive and offers some of the best views of Assateague Island and the historic lighthouse located across the channel. The channel on Eastside offers some of the calmest water for kayaking, plentiful crabbing, and great fishing. Enjoy the most beautiful sunrise views from this vacation home along with quiet solitude! This home also offers 2 kayaks for your enjoyment! 

Upon entering this home, you will find a half bath, first floor bedroom with a queen-sized bed, a well-stocked kitchen, living room, and large waterfront deck with plenty of seating to relax, enjoy the wildlife, and watch the ponies grazing on Assateague Island. On the 2nd floor you will find two more bedrooms as well as the laundry area. The main suite features a king-sized bed with a full bathroom and waterfront deck to enjoy the peaceful sounds of nature and beautiful sunrise views. You will also find a 3rd bedroom that easily accommodates 5 more guests. This room features a twin over twin bunk, a twin over full bunk, and a full bathroom with walk in shower. This home also includes a nice assortment of beach chairs and a small attached garage where you can store your bicycles and kayaks. If you are looking for a home with all the amenities and want to enjoy the beauty of Chincoteague & Assateague Island, this is it!

- 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.

Casa del Mar

5 Bedrooms
4 Baths
12 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Hot Tub
Internet
Outdoor Shower

Casa del Mar - "House by the Sea" - is your home away from home... at the beach! Located in the heart of downtown Chincoteague Island, this grand home has been lovingly maintained and is conveniently situated within walking distance to the waterfront park, boutique shops, restaurants, movie theater and coffee shops! Casa del Mar is one of our newest vacation rental offerings, and we know you'll love it! The spacious, open floor plan features a family room and kitchen, as well as a formal living room and plenty of outdoor space. There's a master bedroom en suite, and the bathroom features a tiled shower and jacuzzi tub. Outside you'll find the perfect backyard, complete with a grill, outside shower. Perfect for relaxing in the evenings after a long day at the beach! And you can even bring the 4-legged family members as well! Don't delay; this one will book quickly! Floor Plan: Downstairs features the living room, family room, kitchen w/ dining area, dining room, master bedroom (King bed & Futon) and full bathroom (shower only). Upstairs features 4 bedrooms - one with a King, one with 2 Queens, one with a Queen, and another with a Queen. The King bedroom and 2 of the Queen bedrooms have attached bathrooms (tub & shower). There is a 3rd upstairs bathroom w/ tub & shower off of the hallway.

- 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.

Trembling Bay

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet

This beautifully renovated 3 bedroom, 2 bath Chincoteague cottage is nestled along the salt marshes in a natural setting on Chincoteague Bay. A few of the fine features include a private pier, a new kitchen & appliances, waterside screen porch & deck, and private master bedroom suite with a custom-designed luxurious bath. The numerous windows and over-sized sliding doors allow panoramic water views from nearly any spot in the house. The first floor is completely wheelchair accessible and features your main living areas, large master bedroom suite (K) with bathroom, and second full bathroom with shower/tub. Upstairs features the second and third bedrooms (D/2T). If relaxation is what you're seeking, look no further. This quiet, peaceful location at the water's edge will delight the senses. Come and see for yourself; you won't be disappointed!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pet Friendly with a fee, No cats, 2 dogs max. ($150 per pet) 

- 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.

Pocahontas

1 Bedroom
1 Bath
2 Guests
Cape Charles
Internet

Nestled in the vibrant heart of Cape Charles, this exquisite one-bedroom condominium represents bayside town living at its most refined. Recently transformed through meticulous renovation, the home seamlessly blends simplistic sophistication with coastal charm to create an atmosphere of understated luxury.

The thoughtfully designed interior showcases an open living space with a fireplace and large TV, sumptuous primary bedroom featuring a king-size bed that promises restful nights after sun-soaked days. Step through the doors onto your private balcony, where panoramic views of downtown and the marina create an ever-changing tableau of maritime activity and small-town vibrancy.

Culinary enthusiasts will appreciate the full kitchen appointed with premium new appliances, inviting both casual meals and ambitious dinner preparations. The custom-tiled bathroom elevates daily routines to spa-like experiences, reflecting the property's commitment to refined comfort.

Location defines true luxury, and this residence delivers magnificently. Mere blocks from the shimmering shores of the Chesapeake Bay, you'll find yourself effortlessly immersed in the coastal lifestyle. The convenience of having Cape Charles' most coveted attractions just steps from your door cannot be overstated—savor artisanal spirits at the local distillery, browse distinctive boutiques and art galleries, indulge in gourmet ice cream, or select from diverse dining options.

For the discerning individual seeking a harmonious blend of tranquility and accessibility, this sanctuary offers a rare opportunity to embrace the quintessential Cape Charles experience.

PLEASE NOTE: 'Pocahontas' 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.

Wildcat Haven

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

Only for the discerning traveler, 'Wildcat Haven' 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 love to fish and crab, or just sit at the water's edge, you'll LOVE the 500' private pier! Vacationing with a large group? Check out the sister house 'Wildcat Retreat' 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.

Windshadow

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

You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfront screened gazebo that leads to a dock great for crabbing/fishing. Inside is a large open floor plan with a brand new kitchen, living room with wood burning fireplace and dining area. Walk through the French doors off the living room to a large screened porch and sky deck overlooking the Chincoteague Bay. There is a first floor King bedroom with en-suite bath and two twin bedrooms on the second level. Windshadow is a premier PET FRIENDLY vacation rental.

- 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.

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.

Almost Heaven

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Internet

Private pier with boat docking, Waterfront, Pet friendly, Internet, A/C, Fireplace, Charcoal grill. Vintage charm with all modern comforts!

Welcome to your new favorite island getaway! This charming Victorian cottage on Chincoteague's popular South Main Street offers the perfect blend of traditional character and modern comfort. With 3 bedrooms and 2 bathrooms, there's plenty of space for family and friends to unwind after a day of island exploring and adventures.

Step onto the open front porch and prepare to be amazed — breathtaking bayside sunsets await you nearly every evening. Pour yourself something refreshing, kick back in a rocking chair, and watch as the sky transforms into a canvas of orange and pink hues over Chincoteague Bay.

One of this home's standout features is the private pier extending directly into the bay, complete with boat dockage capabilities. Imagine morning fishing sessions, dropping a crab line to try your hand at catching dinner, or evening cruises right from your rental home! No need to haul your boat to a public launch — your nautical adventures begin here.

Traveling with 4-legged family members? No problem here - 'Almost Heaven' welcomes your pet(s)!

Location? Simply perfect. You're just minutes from downtown's delightful shops, restaurants, and even the downtown movie theater. Grocery runs are a breeze with Island Foods just a short drive away. For summer fun, Maui Jack's Waterpark is nearby, and the stunning Assateague Beach is waiting to capture vacation memories, and for your footprints in the sand.

The primary bedroom on the first floor offers a peaceful retreat after long days exploring island trails or collecting seashells. The second floor features two more bedrooms and a full bathroom (shower only). This isn't just a rental — it's your ticket to the relaxed island lifestyle you've been dreaming about. Make it your "home away from home'... at the beach!

- 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. 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.

Blue Pointe Bayside

3 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Waterfront
Gas Grill
Screened Porch
Internet
Outdoor Shower

Spectacular waterfront home on the end of a cul-de-sac! Bright, airy and immaculate! Four decks, including one off of the stunning 2nd floor Private Master Suite. Dramatic cathedral ceiling in the cozy, waterfront living room. A screened porch to host an outdoor dinner. Central heat for those off-season stays, and Central A/C for the summer stays, make this the perfect vacation house all year 'round. A sunny, well equipped, eat in kitchen for the gourmet cook. Down-draft cook top and gas grill; perfect for any meal. Beautiful sunsets on the Chincoteague Bay - Water views from every room! Large, hot water outside shower and an oyster shell path to the water so you can easily walk out to the bay to crab, fish and kayak.

- 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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