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Belle of the Bay

4 Bedrooms
2 Baths
8 Guests
Chincoteague Island
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). NOTE: Living room fireplace is not functional. 

- 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.

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.

Hosta Cottage

1 Bedroom
1 Bath
2 Guests
Mainland
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Internet
Outdoor Shower

There is a fanciful quality to this secluded property where nature’s beauty and luxurious accommodations coexist in quiet harmony.    Located on the banks of Holden’s Creek, a headwater of the Chesapeake Bay and a 20-minute drive to the pristine white sand Atlantic beach on Assateague Island, The Creek Guest Cottages are private, convenient, and offer bespoke modern amenities. Explore life off the beaten path and take a true vacation. Whether you are kayaking or paddle boarding on the creek, sitting by the fire pit, biking down country roads or going to the beach, you will find plenty to do or enjoy doing nothing at all.  The views of the creek are magical at any time of the day or night from inside your cottage or from any vantage point on the 3-acre property. The cottage has been designed and decorated by a professional interior designer.

'Hosta Cottage' has partnered with our friends at Sun Outdoors Resort (located less than 2 miles from the house) so that all guests may enjoy the fun resort amenities FREE OF CHARGE. This extra bonus includes a private beach w/ water rentals, pool, playground, "snak shak", comfort stations & more! 

On-site amenities include:  a gas grill, 20’ radius fire pit, 2 kayaks, a SUP, and 2 bicycles.  There is a boat launch on the property and two docks (one floating). Linens and towels are provided.

The Hosta Cottage: 850 square ft. Full Kitchen and Laundry. French Limestone Floors and tiled bathroom. Sleeps 2 (Queen Bed). Separate Private Outdoor Dining area (not included in square footage above). Outdoor Shower. Smart TV. WIFI.

In addition to Hosta Cottage, the compound is also home to two other luxurious dwellings: Porter’s Barn and Creek House. All combined, The Creek Compound will accommodate 18 with no parking problems. Please note that this listing is for Hosta Cottage only; the other two homes - Creek House and Porter's Barn - must be booked separately. A direct inquiry should be sent for special event pricing or if you wish to rent the entire compound.

- 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 one small dog 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.

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.

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.

Tall Pines

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

Located in lovely Piney Island within a short bike ride to the beach. This single story 2 bedroom, 1.5 bathroom house offers a large screened porch, fully equipped kitchen and spacious living room. Tall Pines has two bedrooms, one with a queen, and other featuring two twins. There is also an air mattress for guest use.  Piney Island offers community water access great for launching kayaks/canoes. To top it all off, Tall Pines is pet friendly with and outdoor dog run in the yard. You won't be disappointed! | | Note: Water access is a shared with the community just a short distance from the rental home.

- 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.

The Crabby Baker

2 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Internet
Outdoor Shower

Welcome to a waterfront townhome retreat that delivers island living with a front-row view of the lighthouse and sunrises that will surely outshine your alarm clock. Set in one of Chincoteague Island’s most desired areas, this pet-friendly 2-bedroom, 2.5-bath home pairs comfort, charm, and a little vacation energy in all the right ways.

Inside, the layout offers easy everyday living and inviting spaces to unwind after a day on the water or at the beach. The living room is anchored by a 75-inch television, perfect for movie nights, game days, or simply pretending you are “just resting your eyes.” Upstairs, the primary bedroom features a private bathroom and a waterside balcony, creating a peaceful retreat for morning coffee, evening breezes, and uninterrupted water views. A second bedroom and additional baths provide flexibility for guests, work-from-home needs, or both. The extra half bath adds convenience for entertaining, while the townhouse design keeps daily vacationing practical and fun. 

Outdoor living is just as appealing, with a fishing and crabbing pier that invites relaxed afternoons and fresh catches, plus a hot and cold outside shower for easy cleanup after beach trips. Imagine casting a line at dusk, then rinsing off before dinner as the water glows around you. You are also conveniently close to Maui Jack’s Waterpark and Assateague Beach, so fun is never far from home.

If you have been searching for a vacation spot that feels equal parts coastal escape and everyday comfort, this one checks all the boxes. Book today and see why this waterfront townhouse is easy to love.

- 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.

Charlie's Bayside Retreat

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

This is it! Are you looking for your perfect vacation getaway spot? Look no further. 'Charlie's Bayside Retreat' is everything you'll need for your home away from home, at the beach! The first main level features an open floor plan with a living room that opens up to a wonderful screened porch with comfortable outdoor dining furniture. The open living area also features a large Smart TV with cable and an electric fireplace. A modern kitchen that is fully stocked with everything you could possibly need, also has new appliances and a Keurig coffee maker, breakfast bar, open dining area, and powder room complete the first-floor living space. On the second floor, you'll find two bedrooms, one with a Queen bed and Smart TV and the other with 2 Twins & a Full - both with balconies and a shared full bathroom with dual sinks. The entire third floor is a spacious, private primary oasis with a King bed, and a luxurious en suite featuring a deep jetted tub and dual sinks. This bedroom is also equipped with a Smart TV and a balcony with amazing views & Adirondack chairs making it perfect for relaxing or sunbathing. Additional features of this fabulous vacation home include your own private boat slip (#7), pier for fishing and crabbing, fish cleaning station, covered parking area, grill, picnic table, and tons of extras! There's an outdoor shower, and beach gear including beach chairs, beach toys, and an umbrella. Not to mention you're conveniently located on South Main Street - walk to the downtown area (including Ropewalk for food and drinks) or to the annual Fireman's Carnival. The possibilities are endless. Some of the most gorgeous sunsets ever witnessed are from this spot on South Main Street & it is the perfect spot to watch rocket launches from Wallops. It doesn't get much better than this!

- 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.

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.

The Beach Peach

2 Bedrooms
2 Baths
5 Guests
Cape Charles
Pet Friendly
Internet

Welcome to your relaxed beach lifestyle in this delightful 2 bedroom, 2 bathroom home nestled in downtown Cape Charles. This thoughtfully renovated property offers the perfect blend of simplistic charm and modern conveniences.

Step inside and discover a space that feels like a vacation every day. The home features all the comforts you need, including a washer and dryer, dishwasher, and other contemporary amenities that make daily life a breeze. The primary bedroom provides a peaceful retreat after a day of coastal adventures.

Location is everything, and this home delivers! Just a short stroll from the beautiful Cape Charles Beachfront - you can start your mornings with barefoot walks along the shore, or end the evenings with sunset picnics on the sand.

Downtown living means everything is at your fingertips. Satisfy your cravings at nearby restaurants, indulge in a sweet treat at the local ice cream shop, catch a show at the theater, or browse unique finds in boutique stores—all within walking distance!

When you need supplies, Food Lion and the Beach Market are just a quick drive away. And for those weekend adventures across the bay, the Chesapeake Bay Bridge-Tunnel connects you to Norfolk and Virginia Beach.

This rental isn't just a place to stay—it's an invitation to embrace the laid-back coastal lifestyle that Cape Charles is famous for. Whether you're looking to make new vacation memories, or wanting to explore the charming Eastern Shore, this home offers the perfect balance of comfort and convenience!

- 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: limited to one small dog 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.

Turtle Bay

4 Bedrooms
3 Baths
8 Guests
Captain's Cove
Waterfront
Screened Porch
Pool
Internet

Treat yourself to an unforgettable stay at Turtle Bay! This brand new construction will leave you in awe. The coastal décor is everything perfect for a beautiful vacation. Immerse yourself in the plentiful views, sit and sip your morning coffee or evening beverage from the screened porch or cozy up by the fire in the living room. Cooking will be a breeze in the tastefully laid out kitchen featuring stainless steel appliances and granite countertops. Enjoy the large open floor plan and the inviting owners suite with a queen sized bed and  a walk in shower. The other 3 bedrooms also feature queen sized beds, one with a smart tv as well as two full bathrooms.

Turtle Bay is nestled in the beautiful community of 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).

- 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.

- 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. 

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.

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