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Princess Anne

1 Bedroom
1 Bath
2 Guests
Cape Charles
Internet

Welcome to this freshly renovated, two-bathroom 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. The full kitchen is outfitted with brand-new appliances, ready to handle everything from your morning coffee to your evening seafood feast.

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, the Cape Charles Distillery, ice cream parlors, boutique shops, and local art galleries. And when everyday errands call, a well-stocked supermarket is just a short drive away.

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.

PLEASE NOTE: 'Princess Anne' 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 on the premises. 

- Linens and towels are included with your reservation.

- No pets are permitted. 

- 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.

Misty's Thicket

2 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Water Access
Charcoal Grill
Screened Porch
Internet

Located on South Ridge Road, this lovely town-home features a private pier, central air conditioning, and galley style kitchen complete with a dining area and all necessary appliances. The cozy living room leads you onto one of two screened in porches perfect for unwinding with family and friends. Upstairs, you find a great master bedroom with en-suite, a full bathroom off the hallway, and a second bedroom that features a bunk bed and a queen size bed that looks out onto the second-level screened in porch affording amazing Chincoteague Island views.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- 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 Grove

4 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Water View
Screened Porch
Internet

Come and relax at this fabulous beach home that is tucked away on the quiet northern end of Chincoteague Island! Aptly named, "Shady Grove" is situated in a natural marshland grove in the Richardson's Landing community. Features include 4 bedrooms, 2 bathrooms, numerous updates and remodeling and a bright, open floor plan. Come and see for yourself - you won't be disappointed!

- 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.

Sea La Vie

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

Aptly named, "Sea la Vie" means "Sea Life" or Life at the Beach. This beautifully upgraded three bed, two and a half bath duplex home is nestled in a small, quiet community. Bright, open floor plan allows plenty of sunshine and space to socialize. Relax by the pool after a long day at the beach. Enjoy a bug-free oasis on the screened porch, or grill out on the open deck. First floor bedroom is situated as a private suite with personal full bathroom. Two additional bedrooms upstairs share a second full bathroom. Picnic area out back, community pool just steps out front, you won't run out of things to do! Hosting a group requiring even more space? Rent Sea La Vie's sister, 'Seas The Day', just next door! **NEW FOR 2025: Kid's bunk room features a single Twin bed + a Bunk bed with a Twin over Full size 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.

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.

Castlebar

5 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Luxury waterfront home in Salt Marsh Landing - an upscale residential community on the northern tip of Chincoteague Island. Spectacular sunsets! A long, private pier over the salt marsh leads you to a bay front dock area with shade. It's perfect for crabbing, fishing or canoe and kayak launching. Tastefully appointed and architecturally pleasing, Castlebar features a main level great room flanked by wall of beautiful custom windows and high cathedral ceilings. The views of Chincoteague Bay are priceless. The open kitchen area features ample counter space for meal prep, and the large harvest dining table is perfect for gathering the whole group for a meal. There are hardwood floors, and a two-sided fireplace that is shared with the adjoining cozy den. The first floor also features a full bath and large bedroom that looks out on the bay. The second floor hosts the primary bedroom suite, containing a private bath with separate shower and whirlpool tub. A sliding French door leads out to a balcony providing more views of the bay to enjoy. Two additional bedrooms and full bath complete this floor. Amenities also include a private, full sized outdoor shower, wireless internet service, additional under-counter ice maker & more. Castlebar is available year round!

- 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 Pearl

4 Bedrooms
3 Baths & 1 Half
8 Guests
Cape Charles
Water View
Gas Grill
Screened Porch
Pool
Internet
Outdoor Shower

Welcome to "The Pearl" - and your next chapter of coastal living in the sought-after Bay Creek community on Virginia's Eastern Shore. This brand new four-bedroom, three-and-a-half-bathroom home is a stunning retreat where modern elegance meets small-town charm, and every detail has been thoughtfully curated for refined living.

Step inside to discover a light, bright, and airy interior that immediately puts you at ease. Professionally decorated from top to bottom, the home showcases a sophisticated aesthetic that blends coastal warmth with contemporary flair. The upscale kitchen serves as the heart of the home, outfitted with premium finishes and designed to inspire both casual meals and memorable gatherings. Generous living spaces flow seamlessly throughout, while serene pond views from the home create a tranquil backdrop you will never tire of admiring.

The spacious primary bedroom offers a private sanctuary, complemented by three additional well-appointed bedrooms that provide ample room for family and guests alike. With three and a half beautifully finished bathrooms, morning routines remain effortless no matter how full the house may be.

Beyond the front door, the Bay Creek community elevates everyday life into something truly extraordinary. Guests enjoy access to world-famous golf courses, resort-style pools, a state-of-the-art fitness and life center, scenic walking trails, and an on-site restaurant. Just a short distance away, the beloved Cape Charles Beachfront awaits with its golden sands and breathtaking Chesapeake Bay sunsets. Stroll through the charming town to explore Central Park, local boutiques, and a vibrant dining scene. Convenient grocery shopping at nearby Food Lion ensures daily errands are a breeze, while the iconic Chesapeake Bay Bridge-Tunnel connects you effortlessly to the greater Hampton Roads region.

This is more than a rental — it is a lifestyle. Book your vacation and experience the best of Eastern Shore living for yourself.

SPECIAL NOTES:

This rental home is NO SMOKING and NO PETS.

Linens and towels are included with your reservation.

Usage of the Bay Creek Resort amenities and golf cart requires an additional fee of $75 per day*.

BAY CREEK RESORT AMENITIES:

Waterfront area perfect for kayaks, canoe, fishing or crabbing.

27 hole World-class golf course (requires additional golf fee).

Golf lessons and clinics available for all skill levels.

Member lounge with billiards and entertainment.

Cardio and weight training studio.

Two outdoor pools w/ decks and furniture.

350 acre Nature Preserve w/ trails and wildlife viewing.

Clubhouse with private restaurant and dining experiences.

Structured activities and programs such as bird watching, paddleboarding, beach yoga, kid's camps & more. 

*Fee is subject to change without prior notice or authorization. Bay Creek Amenity offerings can be seasonal and may change without prior notice or authorization.

- 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 Marlin

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

Blue Marlin is a brand new home that is now available exclusively - you will NOT want to miss your opportunity. Visitors from all around fall in love with the charm and beauty of our small town. Blue Marlin is nestled just a few short minutes from the heart of our downtown and offers everything you will need to enjoy a true Island vacation. Spectacular views are abound from just about every room of this gorgeous home. From the time you enter, become enamored with the fresh, beach-like feel of this well thought out Island Home. Blue Marlin offers first floor living, complete with a half bath off of the well-equipped kitchen, a king sized bedroom with beautiful bay views, TV, and en-suite bathroom. Upstairs you will find a spacious sitting entertainment area featuring a sleeper sofa and large TV, as well as two bedrooms. Each bedroom is tastefully decorated and comfortably furnished for a wonderful vacation stay. There are two twin beds, as well as a queen sized bed (with 40 in. TV) upstairs, along with a full bathroom. You may take notice to the many handcrafted furnishings in the home that the owners have taken great pride in creating. Blue Marlin offers front porch sitting, breathtaking sunset views, an outdoor grill, long dock with ladder, (yes, bring your boat!) - there's even extra parking for your boat trailer (behind the yellow house). Everything you need for a perfect vacation is here.. Oh, did we mention this home is pet friendly too?! 

- 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.

Daisey Cottage

2 Bedrooms
1 Bath
7 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Internet

Come visit Chincoteague Island and stay in this adorable coastal cottage with your family. Lovingly remodeled and updated, this charmer located on Ridge Road is sure to book up fast! Close enough to hustle and bustle of carnival and downtown, but far enough away to enjoy some peace and quiet - you'll find all the comforts of home at Daisey Cottage. Upon entering you'll be greeted by a comfortable living area with television. Skylights to let in a ton of natural light, letting you bask in island sunshine. A cute kitchen featuring everything (electric range, fridge, dishwasher, coffee maker) you'll need to make a family meal, if you're heart so desires. A bright and cheery open dining area is connected to the kitchen - allowing you to chat while preparing meals or snacks. A full bathroom. A utility closet with washer and dryer. Two bedrooms - the master with a queen and television. And the second bedroom boasts a bunk that has a full on the bottom and a twin on the top - how fun is that?! Bring your bikes and ride down to Memorial Park for a little fishing or crabbing. Outside you'll find a cute patio area with sitting area, as well as a small fenced in area that is perfect for your four legged friends to enjoy while you're outside as well. Daisey Cottage is pet-friendly, all members of the family are welcome - book today!

- 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.

Egret's Walk

2 Bedrooms
1 Bath
5 Guests
Chincoteague Island
Town & Country
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Discover the charm of coastal living in this delightful 2-bedroom, 1-bath cottage nestled in a serene area north of Chincoteague town center. This home offers a unique blend of comfort and tranquil views of the surrounding marshland and creek. Watch the abundant wildlife from the comfort of your living room, adding a touch of nature’s television to your daily routine.

Inside, the home is accented with personal decor touches that provide a warm, inviting atmosphere. Though compact, the layout ensures efficient use of space, creating cozy yet comfortable living areas. Step outside and you're just a short drive from Assateague Beach, where wild ponies roam freely – a sight that never fails to amaze. For your everyday needs, Island Foods Great Value is conveniently located nearby, and for a sweet treat, the Island Creamery can be reached within a few minutes' drive, offering the best ice cream on the shore.

This home is perfect for those looking for a peaceful retreat with the convenience of community features within reach. Make this cottage your own secluded getaway and enjoy the laid-back lifestyle that Chincoteague is famous for. Experience the joy of waking up to soothing water views and the melodious sounds of local wildlife every morning!

- 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 212

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Waterfront
Pet Friendly
Pool
Internet

Cozy and luxurious, three bed, two bath waterfront villa with private balcony. Beautiful kitchen space overlooks the bright, open dining/living area. Step out onto the waterside balcony and enjoy the water, wildlife, and sunset views. Bedrooms are spaced nicely - one full, one with two twins, and one king suite. King suite includes two mirrored closets, large bathroom with stand-up shower, and an additional entryway to the private balcony overlooking the Chincoteague Bay. Enjoy access to the community pool and fitness center within the villa complex. Conveniently located to our historic downtown area, you can walk to dinner, movies, shopping, galleries and more. This unit does not include a private boat slip, however, use of the common area marina is included.

- 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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