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Serendipity

3 Bedrooms
1 Baths & 1 Half
6 Guests
South Main
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, you are within walking distance to most of our shops and restaurants. Serendipity has a very nice screened porch for those memorable Chincoteague Summer evenings. This home also offers a first floor bedroom (Queen) and half bath.

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Diving Duck

5 Bedrooms
2 Baths & 1 Half
10 Guests
Captain's Cove
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Hot Tub
Internet
Outdoor Shower

If you're looking for the complete vacation package, look no further! This 5 bedroom home features a spacious open floor plan with wall-to-wall sliding doors and windows, allowing natural light to permeate throughout the home. Downstairs you'll find the living room and great room with access to the waterside deck, a large dining area, kitchen with all the counter space you'd ever need, a half bathroom, and the master bedroom with private bath (with custom tile shower and soaking tub). Upstairs features a landing area with sofa and foosball table, 4 more bedrooms and another full bathroom. Aptly named, 'Diving Duck' is the perfect spot for watching the ducks and wildlife pitch in the bay just out the back door. There's even a floating dock perfect for launching canoes and kayaks! And as if all of that is not enough, the Captains Cove community features swimming pools (2 outdoor, 1 indoor), a fitness center, marina club restaurant and 9-hole golf course. (Fee applies for usage of community amenities.) This rental home is approximately 20 minutes to Chincoteague/Assateague Island (the beach) and 30 minutes to Ocean City, MD (beach & boardwalk attractions). What more could you ask for? Book your stay at 'Diving Duck' today! Additional game room with wet bar and pool table, and a private hot tub. All of this in addition to interior updates and renovations!

- No smoking is permitted on the premises. 

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- This property is pet friendly with a pet fee 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.

- Community amenities require passes for an additional fee. Although the rental home can accommodate up to 10 guests, only 8 guests are permitted to use the community amenities (pool, etc.) at a time.

- 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. 

 

The Virginian

4 Bedrooms
2 Baths & 1 Half
13 Guests
North Main
Waterfront
Gas Grill
Internet
Outdoor Shower

Welcome to The Virginian, a stunning waterfront residence. This spacious property, boasting 2,296 square feet of living space, offers a serene and picturesque setting that's sure to captivate.

Step inside to discover four generously sized bedrooms, all  located on the second level, providing a private and tranquil retreat for relaxation. The home features 2.5 bathrooms, with a half bath located downstairs.

The heart of this home is its open and inviting living areas, where beautiful views of the waterfront can be enjoyed. These views set the perfect backdrop for both everyday living and entertaining.

Outside, the property continues to impress with its thoughtful amenities designed to enhance your living experience. An outdoor shower provides a refreshing option on warm days, while a propane grill awaits for those delightful gatherings with friends and family. The residence is also accompanied by four parking spaces, accommodating vehicles comfortably.

Recent improvements throughout the home ensure a contemporary and comfortable lifestyle, allowing you to move in and enjoy from day one.

Situated in a peaceful location, this house not only offers stunning views but also provides an ideal setting for those seeking a blend of tranquility and convenience. Whether it's waking up to the gentle sounds of water or hosting memorable get-togethers in a beautiful setting, The Virginian presents an exceptional renting opportunity..

This home features tons of new upgrades for the 2024 season! The Virginian features new paint, bedding, updated furnishings, artwork, new mattresses, curtains and 3 new smart tv's!  Downstairs you'll find a large living/dining room combo and a nice modern kitchen. Off the kitchen is a private den area with a new twin sleeper- a perfect spot to catch up on your reading! There's a half bath on the first floor. All bedrooms are on the second level. There's a owner suite, with a king bed as well as another full bath on the second level. You will also find another bedroom, featuring a new king bed, as well as the 3rd bedroom featuring a queen sized bed. The 4 bedroom is the bonus room- this room is complete with a new full bed and 4 twin beds. The Virginian features central heat and air, laundry facilities, garage, propane grill, outdoor shower, and more! Located on a bulkheaded lot on a canal that comes up from Oyster Bay, you can throw your crab pot in right outside the back door.

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Belle of the Bay

4 Bedrooms
2 Baths
8 Guests
Oyster Bay
Waterfront
Boat Dock
Screened Porch
Internet
Outdoor Shower

Truly the "Belle of the Bay", this beautiful custom waterfront home is tucked away at the very tip of one of Chincoteague's most popular residential communities - Oyster Bay I. This means you'll enjoy unobstructed 360 degree water and marshland views from nearly every space in the home. The decor and local art collection alone will "wow" you! Watch the sun rise as you sip your morning coffee from the balcony or screened porch. Enjoy the quiet and privacy as you watch the wildlife that surrounds this fabulous property. The main house features 3 bedrooms, 2 full bathrooms, and an additional loft sleeping area (twin trundle bed). The detached garage features another living area/bedroom (2 Twin beds) that is available for guest use (lower level garage is not accessible by guests). Enjoy your own "beach area" at Belle of the Bay! The waterfront lawn area of this lovely home has laid sand for your own beach-like experience! NOTE: Living room fireplace is not functional. 

- No smoking is permitted on the premises. 

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Conch Shell

3 Bedrooms
1 Bath
6 Guests
Piney 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 not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Sunset Bay Villa 312

3 Bedrooms
2 Baths
8 Guests
Sunset Bay
Waterfront
Pool
Internet

Villa 312 is a beautiful 3 bedroom villa featuring a master bedroom suite with luxury bath, gourmet kitchen with center island which is great for entertaining, laundry room with washer/dryer and a waterside balcony overlooking Chincoteague Bay. There are tvs in all the bedrooms, and a computer desk to work from. Villa 312 will sleep 8, and features lots of extras including beach gear and baby gear for your use, as well as a 14' boat slip. Your rental also includes the use of the Sunset Bay pool and fitness area. Located adjacent to our historic downtown area, where you'll find gourmet food shops, boutiques, a public library, galleries and fine dining - all with a short stroll. Come and enjoy a Sunset Bay vacation! | | Note: This villa has access to a 14' boat slip.

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Wildcat Retreat

4 Bedrooms
4 Baths & 1 Half
10 Guests
North Main
Waterfront
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 not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Poole's Cove

3 Bedrooms
3 Baths
6 Guests
North Main
Waterfront
Gas Grill
Screened Porch
Internet
Outdoor Shower

Poole's Cove manages to be tucked away right on Main Street. This home has been decorated with an artists' eye and poet's heart. The set up of this home offers plenty of room for the whole family, but enough distance for quiet moments to yourself. The Master bedroom suite is located in the main part of the house. Just a few steps through a breezeway brings you to the second part of the home with 2 more bedrooms and bathrooms. The outside stairs will bring you up to a rooftop lounging area to catch some relaxing rays. Also upstairs is an office with the perfect reading nook to curl up and catch up on some reading. This house doesn't just offer you a stay it offers you the full experience. Poole's Cove has undergone a COMPLETE renovation! The entire interior - kitchen, floors, bedrooms, bathrooms, furniture, everything - is all BRAND NEW! The Poole's Cove you've come to know, and love is even better than before. **IMPORTANT NOTE: Because of this home's unique floor plan and railing-less decks, it may not be suitable for younger children.**

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Sunset Bay Villa 109

3 Bedrooms
2 Baths
8 Guests
Sunset Bay
Waterfront
Pool
Internet

You can't beat the sunset views at Sunset Bay Villa #109. Located on the ground floor, this home boasts a private waterfront deck just off the living room. A cozy living area with a flat-screen, but in all honesty - it's hard for anything to contend with the view of the marina. Stately appointed, top of the line furnishings throughout the villa. A master bedroom suite with jetted tub, for relaxing after an exhausting day at the beach. Or use the beautiful tiled shower for a quick rinse to knock the salt off. Put on your robe and slip out the private exit to the waterfront deck to catch the sun as it sinks below the horizon. There are two additional bedrooms, both with queen beds. A full bath in the hallway, washer and dryer, and a fully-equipped gourmet kitchen with breakfast bar and dining table for enjoying meals together. The open floor plan allows everyone to enjoy time together in the shared spaces. Plenty of books and DVDs to keep you occupied on rainy days, or enjoy the pool or crabbing on the dock on the sunny ones. Enjoy a cup of coffee or a cocktail on the deck and watch the comings and goings of boats out of the marina. Sunset Bay Villas are located just off of Main Street - giving you the ability to walk or ride your bike downtown for shopping, dining, and nightlife.

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Our Happy Place

3 Bedrooms
2 Baths
7 Guests
Oyster Bay
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Discover your own piece of paradise at this incredible beach getaway! 'Our Happy Place' is the perfect retreat for up to 7 guests seeking comfortable, tastefully decorated accommodations. This cozy vacation home is clean, simple, and fully furnished, including amenities that will make you feel right at home. Even your furry, 4-legged family members can join in on the fun, as small to medium dogs are welcome.

Situated in the desirable Oyster Bay I waterfront community, 'Our Happy Place' is located at the end of a wide-mouth canal, offering unobstructed water views and a private dock platform. You'll love the convenience of being situated next to the community boat ramp, making it easy to launch your watercraft for a day of adventure.

Relax and unwind on the expansive wrap-around screened porch overlooking the water, featuring plenty of comfortable seating and a dining area. Savor your morning coffee or sip a cool drink after a day at the beach.

'Our Happy Place' is a single-level home with 3 cozy bedrooms that can accommodate up to 7 guests. The bedrooms include 1 queen, 2 twins, and 1 bunk bed (twin over double). There are 2 full bathrooms, one of which is a tub shower combo.

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee 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.

Shreiner's Tradition

2 Bedrooms
2 Baths
6 Guests
In Town
Pet Friendly
Screened Porch
Internet
Outdoor Shower

As one of our newest vacation rental offerings, we're pleased to be have this downtown charmer! Shreiner's Tradition is a renovated 2+ bedroom home located just outside the downtown area. Enjoy walking to restaurants, shopping, ice cream and the movie theater! This home features an eat-in kitchen, 2 living room/sitting areas, 2 bedrooms upstairs (each has a double bed) and a walk-through room with bunk beds. Not to mention the great front porch - you'll enjoy mornings and afternoons sipping coffee or relaxing after the beach!

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. All pets must be disclosed prior to arrival. Pet restriction: 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.

Oasis on Main

3 Bedrooms
1 Baths & 1 Half
8 Guests
In Town
Water View
Pet Friendly
Screened Porch
Internet

Welcome to 'Oasis on Main"! This charming and lovingly restored traditional Chincoteague-style home is ready to welcome you with open arms. Nestled in the heart of downtown on the bustling Main Street, this property offers a unique blend of convenience and tranquility. As you approach this stunning house, you'll be immediately captivated by its striking curb appeal. The beautiful landscaping and gardens surround the property, creating a serene oasis that will make you feel right at home. Imagine enjoying your morning coffee on the front porch (the coffee shop is right next door!), all while soaking in the sights and sounds of the vibrant town. Step inside to discover a tastefully restored interior that seamlessly blends classic charm with modern comforts. With three spacious bedrooms and one and a half bathrooms, there's plenty of room for everyone to have their own space. The open layout creates an inviting atmosphere, perfect for entertaining guests or simply enjoying quality time with your loved ones. The kitchen boasts all the amenities a culinary enthusiast could dream of, from sleek countertops to ample cabinet space. Whether you're preparing a quick snack or hosting a dinner party, this kitchen is sure to inspire your inner chef. One of the standout features of this property is its location. Situated next door to a cozy coffee shop, you'll never have to go far for your caffeine fix or a delightful pastry. Additionally, being conveniently located near 'Beach Road' means that shops, restaurants, mini golf, ice cream and more are just a short jaunt away. Are you a pet lover? Good news - this property is pet friendly! Your furry friends will adore exploring the spacious backyard while you relax in the screened gazebo, savoring every moment of the outdoors. With three parking spaces available, finding a spot for your vehicles will never be an issue. Don't miss out on this opportunity to make Oasis on Main your newest vacation "home away from home". The combination of its historic charm, convenient location, and modern amenities is truly irresistible. Book today - this one won't last long!

- No smoking is permitted on the premises. 

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- This property is pet friendly with a pet fee 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.

 

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