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Bayside Bliss

4 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Hot Tub
Internet
Outdoor Shower

Welcome to your serene retreat at Bayside Bliss! This stunning waterfront rental offers a perfect blend of tranquility and convenience, ideal for those who appreciate nature and outdoor activities.

Spanning four generously sized bedrooms and three full bathrooms, this home is a perfect fit for families or groups seeking both comfort and space. Enjoy preparing meals in a fully-equipped kitchen and dine al fresco on the enclosed porch while taking in the breathtaking water views. This space  provides a peaceful spot for morning coffees and cozy evenings alike. You will find one bedroom with a queen size murphy bed, and full bath on the first floor, with all other bedrooms located on the second floor. 

Outdoor enthusiasts will fall in love with the outdoor dock. Whether you’re a fan of boating, fishing, or simply enjoying a sunset over the water, these amenities ensure every day feels like a vacation. The gas grill makes outdoor entertaining a breeze, surrounded by ample deck space that welcomes gatherings under the stars.

The property's location enhances its charm. Nestled just minutes away from essentials, it is conveniently located close to everything you will need to make your vacation enjoyable.

This home not only promises a comfortable and stylish living arrangement but also proximity to local amenities and natural beauty. Embrace a lifestyle marked by peace and relaxation at this Chincoteague charmer. Ready to make it your temporary haven? Contact us today to book your reservation at Bayside Bliss!

- The home does have a hot tub in the enclosed porch but will not be available for this 2024 season.

- 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.

Sunset Bay Villa 312

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
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 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.

Heron's Hideaway

3 Bedrooms
2 Baths
12 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Discover your perfect family retreat at this charming three-bedroom, two-bathroom house nestled in peaceful Oyster Bay II on Chincoteague Island. 'Heron's Hideaway' welcomes up to 12 guests, making it ideal for multi-generational gatherings, friend reunions, or anyone seeking a memorable coastal escape.

The heart of this home lies in its thoughtfully designed layout, offering both communal spaces for togetherness and quiet nooks for those precious moments of solitude. Fall in love with the screened-in porch—your new favorite spot for morning coffee, afternoon board games, or listening to gentle summer rain. When you're ready for fresh air and broader views, head upstairs to the deck where peaceful vistas and cooling breezes create the perfect setting for birdwatching or evening stargazing.

The well-appointed kitchen makes meal preparation a pleasure with its dual-oven electric stove, elegant granite countertops, and full-size appliances. Families will appreciate thoughtful touches like the provided high chair, pack-n-play, and collection of board games suitable for all ages.

Located in a tranquil residential neighborhood, this trusted vacation favorite sits at the end of a quiet cul-de-sac, surrounded by lush trees and natural landscaping that creates a beautifully secluded atmosphere. You'll feel worlds away from everyday stress while remaining just a short drive from Assateague Wildlife Refuge, pristine beaches, local restaurants, and charming shops. Remote workers will appreciate the private business nook complete with desk and monitor, allowing you to balance productivity with relaxation. Since 2018, this beloved hideaway has hosted everything from girls' weekends and holiday celebrations, to hunting expeditions and peaceful solo retreats.

Whether you're seeking adventure at nearby Maui Jack's Waterpark, exploring Waterfront Park, or simply enjoying the serenity of island life, this exceptional rental offers the perfect base for your Chincoteague "home away from home" experience.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. Pet Restriction: NO CATS.  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.

Shady Side

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet

Shady Side is located in Piney Island, which is among the closest communities to the beach. There is community water access, suitable for a kayak or canoe. The house features two queen bedrooms and a full bath downstairs. Upstairs you'll find two additional bedrooms, one has two twins and the other has a queen bed. There is also a full bath on the second floor. The loft features a futon with a full mattress. The large back porch is equipped with a gas grill and picnic table for your cookouts and crab feasts! 

- 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.

Horseshoe Hideaway

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Gas Grill
Screened Porch
Internet

Located in a secluded neighborhood, in the middle of town, 'Horseshoe Hideaway' is comfortably situated back off of a back road, fully enclosed by a fence, and ensconced by a generous yard and mature wooded area. With all the convenience of traveling around the island with ease, this home allows guests to drive or bike to Maddox Blvd, the beach or to the Main Street shops within minutes. Enjoy the outdoors on the fully screened in porches located on both the front and the back of the home, or take advantage of the generous back deck (accessed by a ramp or stairs) and supplied with a large gas grill, picnic table and Adirondack chairs. Inside the home features 3 bedrooms and 2 full bathrooms, a separate dining room, living room and eat in kitchen. There are several seating areas where guests can spread out or congregate as a group. The home is appointed with everything you need to enjoy a vacation at the Beach. This cute-as-a-button rancher home is waiting for your family vacation! Clean, comfortable and modest best describe the single-level home; there's an open kitchen, living and dining area that opens up to a front AND back screened porch. Enjoy all of the outdoor space from one of the 2 screened porches, or the spacious back deck and back yard! Located on a side street just off of Ridge Road, 'Horseshoe Hideaway' is conveniently located just minutes from downtown Chincoteague, as well as the "Beach Road." Come and check it out for yourself!

- 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.

Half Shell

3 Bedrooms
1 Baths & 1 Half
8 Guests
Chincoteague Island
Town & Country
Internet

Check out this clean, modest island duplex home tucked on a quiet side street, just minutes from the action on Maddox Boulevard—close enough for convenience, far enough for peace and quiet (and fewer surprise seagull critiques).

Inside, you’ll find a comfortable 3-bedroom,1.5-bath layout that’s easy to vacation in and even easier to maintain. The primary bedroom offers a restful retreat after beach days and bike rides, while the additional bedrooms flex nicely for guests, a home office, or that hobby you swear you will start this year. Two full bathrooms keep mornings moving, even when everyone suddenly decides they need to leave at the exact same time.

Step out to the screened porch for morning coffee, evening breezes, and bug-free lounging—the kind of simple luxury you’ll wonder how you ever lived without. The vibe here is relaxed and practical, with a welcoming feel that lets you settle in quickly and start enjoying Chincoteague life right away.

When it’s time to explore, hit the nearby Island Nature Trail, cool off at Maui Jack’s Waterpark, grab essentials at Island Foods Great Valu, or make a beach day out of Assateague Beach.

Ready to claim your slice of island calm? Book your vacation today!

- 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.

Island Sunrise

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

Island Sunrise is a gorgeous 3 bedroom, 2.5 bathroom duplex home located in desirable Piney Island. Not only is this house pet friendly, but it offers a deep water boat dock and 3 spacious decks. Aptly named, the sunrises and views of Assateague Island and the Assateague Channel truly are second to none! If you're looking for a nice, relaxing vacation home to enjoy your vacation, look no further. Island Sunrise is it!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $200 per pet will apply. Maximum number of pets allowed: 2. 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.

Touch of Grey

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Internet
Outdoor Shower

Welcome to "Touch of Grey," a delightful waterfront rental that blends comfort, style, and convenience into a perfect living space suitable for a variety of lifestyles. This well-appointed house includes three bedrooms, two bathrooms, and a range of updated amenities that ensure a seamless living experience.

Inside, discover a thoughtful layout featuring smart TVs throughout, high-speed WIFI, and a mix of privacy and social spaces that cater to both relaxation and entertainment. The screened porch offers a serene retreat, perfect for enjoying the outdoor air without the bother of pests, and the open deck invites you to bask in the stunning views that surround you.

Step outside to explore the  outdoor space that this property generously offers. A large deck overlooks the tranquil waters, ideal for peaceful mornings or lively evening gatherings. The highlights of the outdoor area include a personal boat dock, which provides immediate water access for boating enthusiasts. Meanwhile, the fire pit setup paves the way for memorable weekend cookouts with friends and family. This home also provides 6 bikes for guest use! 

Pet-friendly provisions mean that your beloved animals are just as welcome as you are, making it a true home for everyone. Functional features are balanced with aesthetic touches to create an inviting environment throughout.

"Touch of Grey" not only promises a picturesque setting but also ensures practicality with its various updates and amenities. Whether you’re drawn to the waterside way of life or simply seeking a tranquil place to call home, this property addresses all facets of modern living. Experience the blend of natural beauty and contemporary comforts in a place ready to be called home.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum pets allowed: 3. 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.

Salt & Pine

4 Bedrooms
2 Baths
8 Guests
Cape Charles
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Welcome to Salt & Pine, a beautiful 4-bedroom, 2-bath coastal retreat nestled in the heart of Historic Cape Charles. Just two short blocks from the beach, this charming home offers the perfect blend of small-town charm, modern comfort, and seaside relaxation. 

Spend your days strolling to the sandy shores of Cape Charles Beach, exploring local boutiques, enjoying fresh seafood at nearby restaurants, or simply relaxing on the porch and soaking in the laidback coastal atmosphere. With spacious living areas, comfortable accommodations for the family and friends, and all the conveniences of home, Salt & Pine is designed for making unforgettable memories. 

Whether you're planning a family vacation, a weekend getaway with friends, or a longer stay on Virginia's beautiful Eastern Shore, Salt & Pine places you within walking distance of everything that makes Cape Charles special-while providing a peaceful retreat to return to at the en of each day. 

Come experience the perfect combination of salt air, historic charm, and coastal comfort at Salt & Pine. 

- 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.

Serendipity

3 Bedrooms
1 Baths & 1 Half
6 Guests
Chincoteague Island
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 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.

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 included with your reservation.

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 4. 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. 

 

Surf & Turf

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Town & Country
Charcoal Grill
Gas Grill
Internet
Outdoor Shower

Welcome to your new coastal retreat on charming Chincoteague Island! This delightful three-bedroom, two-bathroom home offers the perfect blend of comfort and convenience for those seeking a relaxed seaside lifestyle.

Step inside to discover a thoughtfully updated interior that's clean, bright, and vacation ready! The home features not one, but two living room areas—because sometimes you need some extra space and a separate sanctuary for escaping when someone insists on watching that show you can't stand. Whether you're entertaining guests or simply enjoying a quiet evening, you'll appreciate the flexibility this layout provides.

Located just off South Main Street, you'll enjoy easy access to everything this beloved island community has to offer. Nature and fitness enthusiasts will appreciate the proximity to Veteran's Memorial Park - perfect for morning walks, afternoon picnics or letting the kiddos expel some energy! Adventure seekers can head to Maui Jack's Waterpark for family fun, while the stunning Assateague Beach beckons with its pristine shoreline and legendary wild horses roaming freely along the sand.

This modest, yet inviting, home captures the essence of coastal Virginia living without unnecessary pretense. It's comfortable, practical, and positioned in one of the most enchanting island communities on the Eastern Shore!

- 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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