You are here

Displaying 1 - 12 of 51 results matching your search criteria
Map View
List View

Moontide

4 Bedrooms
1 Baths & 1 Half
8 Guests
Cape Charles
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Experience coastal living at its finest in this meticulously preserved 1913 four-square home, perfectly positioned between Cape Charles'most coveted attractions. Just a leisurely one-and-a-half block stroll takes you either to the pristine beaches of the Chesapeake Bay or to the vibrant town park, where summer concerts, tennis matches, and recreational activities create a symphony of community life.

This distinguished residence, graced by Crepe myrtles that line its tranquil street, offers an elegant blend of historic charm and modern comfort. Four well-appointed bedrooms and one-and-a-half bathrooms provide ample space for both family living and gracious entertaining. The home's refined character shines through in its gleaming wood floors, while the upgraded kitchen boasts contemporary appliances for the discerning chef.

Outdoor living reaches new heights with both covered front and back porches, perfect for morning coffee or evening relaxation. The piece de résistance is an elevated screened gazebo nestled in the fenced backyard, accompanied by custom decking that creates an ideal setting for al fresco dining. Practical amenities include an outdoor shower for post-beach rinses and a dedicated fish cleaning station with sink – a nod to the coastal lifestyle.

Convenience meets charm with flexible parking options, including space for two vehicles via the rear alley access, complemented by ample street parking. Situated in the historic district, this home offers privileged access to Cape Charles' boutique shopping, dining, and cultural attractions, making it an ideal residence for those seeking a sophisticated coastal retreat.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- One adult dog is permitted with an additional pet fee of $200. Must be small to medium size (under 50 lbs.) and housebroken. 

- 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.

Mermaid Hideaway

1 Bedroom
1 Bath
4 Guests
Cape Charles
Internet

Escape to the Eastern Shore and discover a delightful coastal retreat that perfectly blends charm, comfort, and convenience. This one-bedroom, one-bathroom rental offers a refreshing getaway experience just minutes from the beloved Cape Charles Beachfront, making it an ideal home base for those seeking sun, sand, and seaside living.

Step inside and prepare to smile. The interior showcases a vibrant mermaid-inspired, tropical décor scheme that brings instant warmth and personality to every corner. Bold colors and playful accents create an atmosphere that feels less like a standard rental and more like a curated coastal escape. It is the kind of space that puts you in vacation mode the moment you walk through the door.

While the home comfortably serves as a cozy retreat for couples or solo travelers, it also accommodates up to four guests thanks to a convenient pull-out sofa bed in the living area. This thoughtful feature makes it equally suitable for small families or friends exploring Virginia's stunning Eastern Shore together.

Situated on the peaceful outskirts of Cape Charles, the location strikes a wonderful balance between tranquil seclusion and easy access to everyday essentials. A well-stocked grocery store is just a short drive away, and the iconic Chesapeake Bay Bridge-Tunnel provides a scenic gateway to the greater Hampton Roads region. Whether you are drawn to waterfront dining, charming boutique shopping, or lazy afternoons on the beach, everything the area has to offer remains comfortably within reach.

This affordable gem delivers an experience that far exceeds expectations. Book your coastal getaway today!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- Pets are permitted on the premises for an additional fee of $150 per pet, two pets 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.

Windsor House

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Gas Grill
Internet

Time to hit the road and get ready for a beachy retreat at "Windsor House"! The moment you step inside, you'll be dazzled by the vibrant colors that'll make you feel like you're in paradise! The spacious living room and kitchen are perfect for whipping up a delicious meal or hosting a fun-filled bash! The primary bedroom is fit for royalty with its king-sized bed, snuggly and inviting. And there's more! The two additional bedrooms have a queen and two double beds to cater to all your guests. And when you want to take things outside, you'll find a grill to cook up a storm and outdoor seating to enjoy the island breeze. Get ready to soak up the sun in style! Located off of Clark street, you are within close proximity of many restaurants, local shops, and a short drive to the beach!

- 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
Chincoteague Island
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.

Princess Anne

1 Bedroom
1 Bath
2 Guests
Cape Charles
Internet

Welcome to the Princess Anne condominium in the heart of charming Cape Charles. Ideally positioned just blocks from the beachfront, this beautifully curated home offers a comfortable balance of modern upgrades and downtown accessibility.

Step into an open living area that features a cozy fireplace and large television, perfect for unwinding after a day by the shore. A full kitchen lets you whip up a quick morning coffee or cook a meal, all in the comfort of your own space..

Take advantage of the rooftop terrace which offers relaxation while overlooking downtown and the Bay after a long day at the beach. Complete with a wet bar area under a pergola, this is sure to become one of your favorite hangout spots. 

The primary bedroom offers a private retreat with its own balcony — an ideal spot for enjoying gentle breezes. An adjacent custom-tiled bathroom adds convenience and a touch of refinement.

Outdoor enthusiasts and leisurely strollers alike will appreciate the condo's proximity to the Cape Charles Beachfront, mere minutes away on foot. The neighborhood's inviting walkability extends to nearby restaurants, ice cream parlors, boutique shops, and local art galleries. Just a short drive away, you'll find grocery, convenience, dollar, and liquor stores stocked with everything you need for your vacation.

If convenience, style, and coastal charm are on your checklist, this condo just might check every box. With a location that makes spontaneous ice cream excursions and sunset beach walks a regular thing — it isn't just a rental, it's a lifestyle.

- 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

Blue Sea Star

3 Bedrooms
2 Baths & 1 Half
12 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Screened Porch
Internet

Welcome to Blue Sea Star! You'll fall in love with this fabulous 3 bedroom home from the moment you walk in the door. Bright open spaces, lots of windows, wood floors, first floor master bedroom/bathroom, and too much more to name! Located on a quiet cul-de-sac in the popular Oyster Bay II Community just off of North Main Street. Conveniently located just a few minutes from the downtown waterfront park, shopping, restaurants, movie theater and more! Blue Sea Star features a screened back porch, open side and front porches - perfect for relaxing with a cup of coffee in the morning, or cool drinks after a day at the beach, and a great backyard. As a pet friendly rental, you can even bring your four-legged family member!

- 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.

Coastal Cottage

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Internet
Outdoor Shower

Nestled on a quiet cul-de-sac in the popular Oyster Bay II community is where you'll find our newest vacation home addition - ' Coastal Cottage'! Completely remodeled and adorned with simple, beachy-chic decor, you'll enjoy a most comfortable stay at this lovely home. The open floor plan features a main living room area, sitting area, dining room and large kitchen space with breakfast bar/center island. All of the bedrooms and both full bathrooms are on one level making it convenient for single-level living. The master bedroom with en suite bath has a queen bed, the second bedroom has a queen bed, and the third (large) bedroom has 2 queen beds side-by-side. Come for a stay at 'Coastal Cottage' - it may just become your next favorite beach home!

- 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.

Modest Junxtion

3 Bedrooms
2 Baths
6 Guests
Cape Charles
Charcoal Grill
Internet

Nestled in the heart of historic Cape Charles, this meticulously renovated family residence stands as a testament to thoughtful design and artistic vision. Originally conceived as a duplex, this home has been masterfully transformed into a spacious single-family haven, where European sophistication meets coastal charm.

The first floor unfolds with an open-concept design, anchored by a gourmet kitchen that would delight any culinary enthusiast. Equipped with premium appliances and an impressive array of cooking accessories, including three distinct coffee-making options, the space beckons both casual cooks and seasoned chefs. The dining area comfortably seats eight, while a cozy coffee nook and music corner, complete with guitars and microphones, add playful touches to the living space. Through elegant French doors, discover an entertainment room featuring a carefully curated vinyl collection for music aficionados.

Ascending to the second floor, two identical queen bedrooms offer serene retreats, while the California king guest room provides a luxurious escape with its distinguished wingback chair and footstool arrangement. A dedicated study space ensures connectivity with fiber optic internet, perfect for remote work or planning your next coastal adventure. The crown jewel of the upper level is the remarkably spacious family bathroom, spanning 250 square feet of pure indulgence.

The outdoor space embraces coastal living with a welcoming front porch, expansive deck, and thoughtful amenities including a fire pit, and grill area. The corner lot location provides ample street parking, accommodating boats and extra vehicles with ease.

This home's proximity to Cape Charles' treasured attractions enhances its appeal, with the historic district and beautiful beachfront just moments away. A decade of careful curation by its overseas owners has infused this residence with a distinctive London-inspired aesthetic, creating an unexpected and delightful fusion of sophisticated urban style and relaxed coastal living.

Special Notes:

PET FRIENDLY (with fee). Pet fee is $150 per pet. All pets must be disclosed prior to arrival.

- Linens and towels are included with your reservation.

- No smoking is 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.

Seahorse Cove

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Pet Friendly
Screened Porch
Pool
Internet

Welcome to Seahorse Cove! This is an adorable 3 bedroom, 2 bathroom home that has been completely renovated. You will not be disappointed - from the personal touches, to the decor and amenities this lovely home has to offer - no detail has been left untouched. As soon as you enter, you will immediately fall in love with the bright, beachy colors, and the overall feeling of complete relaxation. Seahorse Cove offers a fully equipped kitchen with stainless steel appliances, granite countertops, a breakfast bar, and all of your cooking essentials for providing a delicious meal. Enjoy the sounds of nature from the cozy screened porch, while sipping your morning coffee or enjoying an evening beverage. The owner's suite is furnished with a comfy rocker, plush bedding and a private bath with a tiled shower.  You will also find two additional bedrooms on the opposite end of the home, along with another full bathroom. There is plenty of room outside to enjoy, or to let your fur baby play.

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! 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.

- 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: 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. 

Seas the Day

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Screened Porch
Pool
Internet

You will LOVE the quiet duplex community where this home is situated. Bright, open floor plan, with adjoining screened and open-air porches - perfect for sipping coffee in the morning or relaxing with a cool drink after a day at the beach. The first floor bedroom offers a private bathroom and the sweetest window nook - bring your book! Two additional bedrooms upstairs share a full bathroom and all bedrooms are tastefully decorated in their own fun personal themes! Hosting a group that requires more space? Rent Seas The Day's sister, 'Sea La Vie', just next door! **NEW FOR 2025: Kid's bunk room features a single Twin bunk bed + a Twin Trundle bed!**

- 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.

Utter East

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Gas Grill
Screened Porch
Internet
Outdoor Shower

We're pleased to offer you 'Utter East'! Tucked off of a quiet side street in the middle of the island, this home features everything you'd need for a wonderful, relaxing vacation. If you love outdoor space, you'll love the huge screened porch, expansive decks, and beautifully landscaped fire pit sitting area on the pond. Inside the home, downstairs you'll find the living room, an additional den/family room, eat-in kitchen, dining room, two bedrooms and a full bathroom. Upstairs features two more bedrooms and another full bathroom. Don't delay; this home will book quickly! "Where sky and water meet, Where the waves grow sweet, Doubt not, Reepicheep, To find all you seek, There is the UTTER EAST." - From "The Chronicles of Narnia" by C.S. Lewis

- Linens and towels are included with your reservation.

- No smoking/vaping is permitted on the premises, including porches and outdoor areas.

- 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.

Virginia Lee

2 Bedrooms
1 Baths & 1 Half
4 Guests
Cape Charles
Internet

Experience vacation living at its finest in this modern two-bedroom, one-and-a-half-bathroom condominium nestled in the heart of Cape Charles. This thoughtfully designed retreat features an open floor plan complemented by a full kitchen with brand-new appliances for the culinary enthusiast.

The inviting living room showcases eye-catching skylights that flood the space with natural light, while a large television and cozy fireplace create the perfect atmosphere for relaxation. The comfortable primary bedroom offers a king bed and connects to a custom-tiled bathroom, while the upstairs bedroom includes an adjoining powder room for added convenience.

What truly distinguishes this property is its spectacular rooftop terrace, complete with a wet bar sheltered by an elegant pergola — ideal for entertaining guests or enjoying breathtaking sunset views over the Chesapeake Bay.

The condo offers unparalleled convenience, situated just blocks from Cape Charles' pristine beachfront and within easy walking distance to the town's vibrant center. Imagine strolling to local restaurants, browsing unique boutique shops and art galleries, or finishing the day with a hand-crafted cocktail or libation at one of the towns favorite night spots — all without needing to use your car.

Whether seeking a peaceful weekend getaway or an extended coastal retreat, this charming condominium offers the perfect blend of modern comfort and small-town bayside living.

PLEASE NOTE: 'Virginia Lee' 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. 

- 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.

 

Pages