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Homestead

3 Bedrooms
2 Baths
5 Guests
North Main
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Set back across the street from Chincoteague Bay, Homestead sits on 30 acres of basically pristine land. A cozy cottage, originally built in 1890, had been updated but the owners kept the original charm of yesterday but with the comfort of today. Now that charm and comfort has been expanded. A new addition offers a great room with a modern kitchen, dining area and room to stretch out and relax. The design includes oversized windows, sliding doors and a sky light. The house now has 2 screen porches and a balcony that lets you feel as though you are living in in a nature preserve! Homestead sleeps 5 but best suited for 4 adults. There are now 2 full sized bathrooms. Amenities include bikes, beach chairs and umbrellas: games, crayons and colored paper and good parking. And as part of the property, you'll vacation alongside the oldest home on the island, The Captain Timothy Hill House, listed on the National Register of Historic Places. With a tidal pond in front and unspoiled woods in back, Homestead is private, quiet and with lots of room outside. A perfect retreat! So relax on one of the porches, feel the breeze from the bay, watch the animals and birds that come by or take an outside shower under the stars. The Homestead that so many have come to love is still the same just more to love!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- No pets 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 208

3 Bedrooms
2 Baths
8 Guests
Sunset Bay
Waterfront
Pet Friendly
Boat Dock
Pool
Internet

A beautiful seaside villa, professionally decorated, features luxury amenities including a walk-out from the living room area to a private deck and then marina area. The master bedroom suite is a dream come true - beautiful tiled shower, jetted tub and more. The gourmet kitchen will please your senses. As one of the largest at over 1,800 sq ft, this 3 bedroom villa will sleep 8, features wireless internet, TV and iPod dock in every bedroom, and comes with a private boat slip for your use at no extra charge. Sunset Bay Villas also features a pool and fitness room for your enjoyment, as well as a large marina area. There's plenty of parking, and you can stroll to our historic downtown area for shopping, fine dining, movies and more. Come and enjoy! Pet friendly!

- 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.

Junxtion

4 Bedrooms
3 Baths
10 Guests
Cape Charles
Charcoal Grill
Internet
Outdoor Shower

Introducing a captivating vacation home within the charming environs of Cape Charles, VA. This expansive four-bedroom, three-bathroom residence offers a unique blend of classic charm and modern elegance, recently transformed from a duplex into a single, large family home. Situated on a generous corner lot, this property provides ample street parking suitable for boat trailers and features delightful outdoor amenities including a shower, deck, fire pit, grill, and a spacious front porch.

The interior is a testament to meticulous craftsmanship and design. The open-plan first floor anchors the home with a grand gourmet kitchen, fully outfitted with all essential appliances and perfect for culinary enthusiasts. Adjacent to the kitchen, the dining area comfortably seats ten, complemented by a cozy coffee corner and a musical nook equipped with a guitar and microphone—inviting impromptu jam sessions.

Venture further to discover double French doors that reveal an ultra-cool TV room adorned with a personal vinyl collection. A convenient laundry and bathroom complete this level. The second floor boasts two queen-sized bedrooms and a thoughtfully appointed study. Enjoy the comfort of a large California king bedroom, designed with luxurious seating to provide a haven of relaxation.

The home’s crown jewel is the third-floor primary bedroom suite, which includes one king bed, two twin beds, and a sofa bed. A full bath features a large shower and a double slipper Victorian bath, enhancing the spa-like atmosphere. Blackout blinds in all bedrooms ensure a restful night's sleep.

This home is located within walking distance of the pristine Cape Charles Beachfront and a short stroll from the historical delights of the Cape Charles Historic District. Commuting is made easy with proximity to the Chesapeake Bay Bridge-Tunnel. Offering more than just a place to stay, this property encapsulates a meticulously curated lifestyle, infusing a London chic with the serene backdrop of historic Cape Charles. Experience the culmination of a decade’s worth of dedication and a heartfelt invitation to make lasting memories in what can truly be called a dream 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.

Island Thyme

3 Bedrooms
2 Baths
8 Guests
In Town
Gas Grill
Hot Tub
Internet
Outdoor Shower

There's plenty of room for everyone here at Island Thyme! This spacious home features a living room and den, large eat-in kitchen and dining area, and a huge wrap-around deck -- perfect for enjoying the quiet, peaceful setting. The many extras include a hot tub (on back deck), and Foosball table. And, it is conveniently located at the back of the Chincoteague Carnival grounds, so you can walk to the carnival (July only) on those warm summer nights! So come and stay a while; you're on Island Thyme now!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- Pets are not 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.

Shady Side

4 Bedrooms
2 Baths
10 Guests
Piney 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.

Beach Bettie's

3 Bedrooms
1 Bath
6 Guests
Cape Charles
Waterfront
Internet
Outdoor Shower

Discover coastal living at its finest in this enchanting three-bedroom cottage nestled along the pristine shores of the Chesapeake Bay. This waterfront retreat offers an unparalleled opportunity to experience the serene beauty of Virginia's Eastern Shore while enjoying the perfect blend of comfort and bayside charm.

The thoughtfully designed interior features three inviting bedrooms and a full bathroom, creating an ideal space for multi-seasonal getaways. Water-facing windows throughout the home frame spectacular views of the bay while allowing natural light to cascade through the living spaces, creating an atmosphere of warmth and tranquility.

Step outside onto your private slice of paradise, where meticulously maintained landscaping creates a picturesque setting for outdoor entertainment and relaxation. Multiple seating areas have been strategically placed to maximize the breathtaking vistas, making it the perfect spot to unwind while watching the sun paint the sky in brilliant hues during the legendary Chesapeake Bay sunsets.

This exceptional property's location offers the best of both worlds – peaceful seclusion with convenient proximity to beloved local attractions. Just minutes away, you'll find the renowned Cape Charles Beach, where soft sands and gentle waves await. The historic downtown district, with its charming boutiques, restaurants, and galleries, is also within easy reach. Nature enthusiasts will appreciate being near the Savage Neck Dunes State Natural Area Preserve, offering pristine hiking trails and unspoiled coastal wilderness.

Whether you're seeking a peaceful year-round residence or a memorable vacation retreat, this bayside haven provides an extraordinary opportunity to embrace the coveted coastal lifestyle. The combination of waterfront splendor, thoughtful design, and prime location creates an unmatched living experience on Virginia's celebrated Eastern Shore.

- 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.

Serenity at Deep Hole Hideaway

2 Bedrooms
1 Bath
6 Guests
In Town
Pet Friendly
Charcoal Grill
Internet

Welcome to your blissful oasis, "Serenity at Deep Hole Hideaway!" This charming haven has been given a complete makeover to cater to all your vacation dreams. The kitchen is stacked with top-notch gadgets to whip up that perfect meal. The living room features a cozy sleeper sofa to squeeze in a few extra guests. The main bedroom boasts a luxurious queen-sized bed, while the guest room offers a snug twin daybed, providing ample space for up to six guests. Step outside and relax on the deck, indulging in a long-awaited book. And, if you're in the mood for some classic campfire fun, gather around the firepit and toast up some scrumptious S'mores and hotdogs!

- 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.

Artist Apartment

2 Bedrooms
1 Bath
6 Guests
Wachapreague
Water View
Gas Grill
Screened Porch
Internet

Discover coastal charm and artistic flair at this newly renovated condo nestled in the picturesque village of Wachapreague, Virginia. Perfect for those who love the outdoors, this "Artist Apartment" sits above the Current Reflections-Fine Arts Gallery, providing a unique living experience that merges creativity with comfort. Guests have their private entrance at the back of the Art Gallery building, ensuring your peace and privacy on the second floor, including the rooftop deck access.

Spanning the second floor, this condo boasts two versatile bedrooms and a well-appointed kitchen ready to handle your culinary adventures. Whether you're a novice cook or a seasoned chef, you'll find everything you need to whip up delicious meals. The living spaces are furnished for comfort and style, ensuring a cozy ambiance that feels like home.

Step outside to the exclusive low roof deck, where dining, sunning, and relaxing take a whole new meaning. Complete with partial cover, an outdoor TV, and a fridge, this space is tailor-made for enjoying those beautiful coastal sunsets.

When you're ready to explore, the location could not be better. The condo is just footsteps away from delicious dining options like the Island House Restaurant, famous for its "Frozen Orange Crushes" and fried flounder. Nature lovers will appreciate the proximity to eco-tours, kayak rentals, and water taxis to nearby barrier islands – perfect for bird watching and shelling excursions.

Immerse yourself in the serene and artistic lifestyle of Wachapreague in this one-of-a-kind rental. Whether you're here to fish, kayak, or simply unwind among the creations of local artists, this condo offers the perfect retreat for every endeavor.

- No smoking is permitted on the premises. 

- Linens and towels are provided for your stay. 

- 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.

Osprey

3 Bedrooms
2 Baths
6 Guests
Oyster Bay
Water Access
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

This great contemporary beach home is located at the edge of the community harbor area, a perfect location for you and your guests. As a pet friendly house, you'll enjoy the wide open spaces for your dogs. The home features an open floor plan with a lovely eat-in (and completely renovated!) kitchen and cook area that is flanked by a huge screened porch overlooking the community harbor. You can enjoy all your meals on the porch! In addition, you'll find bright, airy and spacious bedrooms with TVs including a master bedroom suite with King size bed and private bath. There's plenty of parking. You and your guests can crab and fish from the community dock, located just a few steps from your door. Enjoy a great vacation at Osprey!

- 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.

Sunset Bay Villa 116

3 Bedrooms
2 Baths
8 Guests
Sunset Bay
Waterfront
Pool
Internet

A beautiful ground-floor villa with walk out to marina. Luxurious master bedroom with private bath includes both a roomy tiled shower and whirlpool bath. Villa 116 will sleep 8 (beds for 6 plus a queen size air mattress), and includes a full laundry, all appliances, a gourmet kitchen, and more. There's also a pool and fitness room for your enjoyment! Tastefully furnished, you can relax, enjoy and entertain your family and friends in style. | | NOTE: This unit does not have a boat slip, however, use of the marina is included.

- 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.

Southern Breezes Nor' Easter

3 Bedrooms
1 Baths & 1 Half
9 Guests
Cape Charles
Pet Friendly
Internet
Outdoor Shower

Welcome to Southern Breezes Nor'Easter, Unit 104B – your next vacation home that combines comfort, convenience, and the joy of beachside living! This inviting duplex is now available for rent and offers a perfect blend of space and functionality to cater to a variety of living arrangements.

This home features three cozy bedrooms and 1.5 bathrooms, ensuring ample space for up to 9 occupants. Whether you're looking to create memorable moments with family or share a comfortable living space with friends, this property is designed to accommodate your lifestyle.

The ground floor hosts plenty of space and promises delightful meals and gatherings. The kitchen is equipped with essential appliances and ample storage, making meal preparation both enjoyable and efficient. There is even an ice cream maker to enjoy on those warm days! The living area extends onto a covered front porch, offering a serene spot to relax and enjoy the gentle coastal breezes.

Located within one block to the beach, this property positions you perfectly to enjoy sandy shores and spectacular sunsets whenever the mood strikes. Its great location also means you're never far from local amenities, including shops, restaurants, and entertainment options.

Southern Breezes Nor'Easter is more than just a place to live; it's a lifestyle choice for those who value convenience, community, and the allure of coastal living. Discover the joy of making this duplex your new relaxation spot and embrace a life where every day feels like a vacation! 

Located right next door to this beautiful duplex is Southern Breezes Nor'Wester. Larger group? Bring along your friends and family and rent both units! 

 

- 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 (no cats). 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.

Beach Haven

3 Bedrooms
2 Baths & 1 Half
9 Guests
In Town
Town & Country
Charcoal Grill
Internet

If you enjoy being close to town and activities, 'Beach Haven' is most likely your perfect spot! Located on just one block off of Main Street, this lovely home is conveniently located to downtown Chincoteague Island, the movie theater, restaurants, famous Island Creamery, adventure park and more! The wrap around second-level deck is nicely furnished and inviting - it's the ideal place to relax with a cup of coffee in the morning or a cool drink after a long day at the beach. 

As you enter this fantastic modern home, you're greeted by an open floor plan. The main level features the living room, kitchen with breakfast bar, dining room and half bath/powder room. The lower level is entirely a two-car garage that is accessible by guests; it's a wonderful place to store your bikes or beach gear! Upstairs you'll find 3 bedrooms and 2 full bathrooms, one of them being a master bedroom en-suite. Two bedrooms feature a queen bed each, and the third (kid's) bedroom features a bunk bed (2 Doubles) and a Twin bed. 

Lets talk electronics! This home has been carefully and tastefully furnished for the discerning traveler. The living room and all 3 bedrooms all have large Smart TVs, and the kid's bedroom includes an HDMI cable for easily connecting gaming consoles, etc. You'll also enjoy amenities such as keyless self check-in and check-out.

Come for a week in the summer, or come for a shorter stay in the spring or fall. 'Beach Haven' is available year-round and the island is gorgeous the whole year through!

- 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.

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