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Serenity at Oyster Bay

3 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Water View
Gas Grill
Screened Porch
Internet
Outdoor Shower

Aptly named, "Serenity at Oyster Bay" is just what you'll find at this delightful vacation home. Located in the highly-demanded community of Oyster Bay I, you'll enjoy the peaceful, quiet area nestled amongst the tall pines and marsh grasses. The main living area features a fantastic open floor plan; perfect for gathering the family and entertaining. The back of the house features a bright sunroom that looks out over a natural preserve - cozy up with a cup of coffee and a nice book! This home also features 3 bedrooms, 2 full bathrooms (completely remodeled) and has undergone a lot of fresh new upgrades! There's a little sitting deck out back, a screened porch, covered picnic/game area (with cornhole boards), fish cleaning station, and so much more! And, as if that's not enough, there are water views and you're very close to the Oyster Bay Community water access! Don't delay - Serenity at Oyster Bay is sure to book quickly!

- 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.

Marsh Point

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

Located just off of Ridge Road on the southern portion of the island, you'll find Marsh Point. A two bedroom, two and a half bath townhome unit with (shared) dock access. A lovely screened in porch dining area for cooking up the crabs you'll catch right off the dock and enjoying with family and friends, you're sure to be comfortable here! On the ground floor you'll find the comfortable living area with plush new furniture, a fully-equipped galley-style kitchen (electric range, refrigerator, dishwasher, microwave), a dining area with table, a utility closet with a washer and dryer, and a half bath/powder room in the hallway. Upstairs you'll find the bedrooms - a master suite with queen bed and a full bath. The other bedroom upstairs boasts a balcony with a beautiful view of the salt marsh below. For sleeping arrangements you'll find a bunk (a full on the bottom and a twin on top - always fun fighting over who gets that one!). Another twin is also located in the second bedroom as well. A full bath is located in the hallway upstairs. If you look to the grassy grove across the street you'll be looking at the location of the former Beebe Ranch, home of Misty of Chincoteague. You can almost see the little pinto paint filly frolicking through the paddock. Sit on the bench at the end of the dock with a cocktail or a cup of coffee at sunset and feel the cool island breezes coming off of the inlet and Curtis Merritt Harbor, just a little further down the road. Ride into town to get a bite to eat, or grab a few ingredients at one of our local seafood markets (a wonderful fishmonger and lobster lady lives just across the street) to make something easy at home. No matter what you decide, make a point to enjoy yourself at Marsh Point.

- 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.

Maryland

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

Newly available on the vacation home market, this two-bedroom, one-and-a-half-bath condominium offers a refined living experience in the heart of downtown Cape Charles. Seamlessly blending quality craftsmanship with simplistic, yet thoughtful, design - this home delivers an ideal mix of comfort and coastal charm.

Step inside to find a sun-splashed living room enhanced by skylights, an ambient fireplace, and a wall-mounted TV—perfect for relaxed evenings or rainy-day movies. The open layout flows effortlessly into the primary suite with king bed and the custom-tiled primary bathroom, revealing attention to detail at every turn. Upstairs, a second bedroom includes an adjoining powder room, offering privacy and convenience for discerning guests.

Where this home truly shines is outdoors. Ascend to the rooftop terrace, where panoramic views of the marina and Chesapeake Bay stretch before you. Entertain under the pergola-covered wet bar—ideal for sunset toasts or brunches with a coastal breeze. The terrace transforms the condo into an entertainer’s dream or a quiet retreat to recharge under the sky.

Situated mere steps from Cape Charles beachfront, you’ll be soaking in the salt air faster than you can say “flip-flop.” With boutique shops, the Cape Charles Distillery, local restaurants, and ice cream parlors within strolling distance, this bayside sanctuary keeps daily conveniences charmingly close. Even grocery runs are a breeze, with a Food Lion just minutes away.

Whether you’re hosting friends for rooftop cocktails or simply kicking back by the fireplace with a book, this home invites you to relax, recharge, and delight in the Cape Charles lifestyle.

PLEASE NOTE: 'Maryland' 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.

Endless Summer

4 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Water Access
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Come enjoy your stay at one of the most sought out locations on the Island. Easy, convenient access to the beach. With the large open floor plan, high ceilings, and easy one level living, you have everything you need at Endless Summer. Bring along your furry friends to make your vacation complete! This home has plenty of room for the whole family to gather. Enjoy the nice screened in porch or the large open front porch with your morning coffee and listen to the serene sounds of nature. The Piney Island Community offers convenient access to a kayak launch located on Pine Drive, just minutes from the 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. BREED RESTRICTIONS DO APPLY

- 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.

Admiral Benbow

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet
Outdoor Shower

A very nice contemporary home located in Oyster Bay I community. Located next to the community boat ramp - you have access to the water and the kids can fish and crab from the dock areas. This house has an outdoor ramp to the ground level. Don't miss out on the great screened porch for a family dinner! The variety of bed sizes allow the perfect set up for families of all ages! Come and stay at this classic Chincoteague home but don't delay; it books quickly!

- 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.

Tranquility

4 Bedrooms
2 Baths & 1 Half
11 Guests
Chincoteague Island
Town & Country
Pet Friendly
Charcoal Grill
Internet

Welcome to Tranquility! This show stopper of a home is a brand new construction, featuring  2 bedrooms, 2 bonus rooms and 2.5 baths. Sleeps up to 11 with 1 king, 2 queens, 2 queen conversion sofa/sleepers and a twin fold-out sleeper chair. Deep Hole Hideaway rental properties can accommodate up to 23 people by renting all 3 units in this complex! (based upon availability)  Tranquility Great for family reunions or large gatherings! Please reach out to our office or check out "Escape at Deep Hole " and "Serenity at Deep Hole" for multi home bookings. 

 

Pet friendly, private and quiet. This property allows for entertainment and relaxation for both you and your kids! There is also outdoor seating, cornhole, a firepit, picnic tables and barbecues for additional recreation for your vacation. Book your stay today, this one won't last long! 

- 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 221

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Pool
Internet

Buckle up, folks, because Sunset Bay Villa 221 is here to light up your vacation! This fresh-faced beauty just hit the market and is ready to become your new home away from home. Prepare to be blown away by water views so gorgeous, you'll want to frame them! Every nook and cranny of this place has a view that will leave you breathless.

The open floor plan allows you to cook and entertain at the same time. And let's not forget the deck, the perfect spot to kick back and enjoy your morning cup of coffee or unwind with a glass of wine as the sun sets over the water. The primary bedroom is fit for royalty with a king-size bed to cocoon you in comfort. But wait, there's more! Two additional rooms, one with a king, one with two twin beds, so everyone can sleep tight and dream big. There are tv's in each bedroom as well. Don't miss out on this gem! The Sunset Bay Villa Community has an outdoor pool, indoor workout room, and outdoor dining area!

- 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.

Fisherman's Cottage

1 Bedroom
1 Bath
4 Guests
Chincoteague Island
Town & Country
Pet Friendly
Gas Grill
Internet
Outdoor Shower

Welcome to this fabulous, cozy retreat on Chincoteague Island! The charming one-bedroom, one-bathroom cottage offers the perfect getaway for up to four guests, and you can bring Fido as well!

Nestled in a quiet location, this delightful home puts you within easy reach of the town's attractions, Beach Road (Maddox Blvd.) the Assateague Lighthouse, Memorial Park and even some wonderful eateries. After a day of exploration or relaxation at the beach, unwind on the screened porch, where you can sip your favorite beverage and listen to the soothing island sounds. Fancy a bit more outdoor living? Fire up the gas grill and enjoy a delicious meal on the patio. It's the perfect spot for swapping stories and making memories under the stars.

Inside, you'll find a tastefully remodeled space that's clean, cute, and comfortable. The house comes equipped with all the modern luxuries you need for a stress-free stay. Coffee lovers, rejoice! You have your choice of a drip pot or Keurig machine to kickstart your mornings. The primary bedroom offers a Queen bed and a peaceful sanctuary for rest, while additional sleeping arrangements (Double-size sleep sofa in the living room) ensure everyone has a comfy spot to drift off to dreamland.

Whether you're here to spot the famous Chincoteague ponies, visit the Assateague Island Lighthouse, or simply soak up the laid-back island vibes, this rental has you covered. It's just a hop, skip, and a jump from local hotspots like Memorial Park! So, pack your flip-flops and your sense of adventure – this little slice of island paradise is waiting for you. Just remember, what happens on Chincoteague stays on Chincoteague... unless, of course, you can't resist posting those amazing vacation pics!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This home is pet friendly - DOGS ONLY - with additional pet fee. 

- 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.

Day Dream Believer

4 Bedrooms
4 Baths
10 Guests
Cape Charles
Waterfront
Gas Grill
Screened Porch
Pool
Internet
Outdoor Shower

Welcome to 'Day Dream Believer' on Virginia's coastline in Cape Charles, VA. This remarkable house is now available for rent, offering a fantastic opportunity to experience luxurious coastal living. With 4 bedrooms, 4 bathrooms, and ample parking for 4 vehicles, this new construction home caters to luxury, comfort and convenience!  This beautiful home is located in the coveted resort community of Bay Creek and is awaiting your ideal vacation experience.

As you step inside, you'll be greeted by the exquisite craftsmanship and attention to detail that defines this property. The stunning quartz countertops add a touch of elegance to the spacious kitchen, which will aspire the chef within you. Boasting a  48” Wolf stove/oven with 4 burners and a 24” griddlehard surface countertops, a breakfast nook and uncompromised views; this room is open to the spacious living area with high ceilings and abundant natural light. Whether you're hosting a feast or enjoying a quiet meal with family, this kitchen is sure to impress. Spread across three levels, the home offers plenty of room for everyone to find their own space. Take in the grandeur of the vaulted ceilings while cozying up next to the inviting gas fireplace on chilly evenings. With two primary bedroom en suites, this property caters to those seeking privacy and luxury. Each bedroom is designed with your comfort in mind, providing a serene retreat after a long day. Enjoy the convenience of having your own private bathroom where you can unwind in style. In fact, on the 3rd floor you are greeted with the spacious owner's suite, complete with a private sitting area that is perfect for reading, watching your favorite show, or enjoying a cup of coffee. 

On the lower level, you have the convenience of a two car garage for loading and unloading - complete with another bedroom, full bathroom, and featuring a tub/shower combo. Restore and relax out back, while taking in the beautiful water views or make your way into town where you will find all the charming town of Cape Charles has to offer. This remarkable vacation spot will leave you with only one regret - that you didn't book a longer stay!

But that's not all – residing in this house means gaining access to the resort amenities at Bay Creek Resort. Dive into a world of relaxation and entertainment as you indulge in community offerings such as golf courses, swimming pools, dining options, nature preserve and more. Discover a lifestyle that blends tranquility with fun-filled activities right at your fingertips.

Located in beautiful Cape Charles, VA, this house positions you just moments away from pristine beaches and charming downtown shops and restaurants. Embrace the coastal lifestyle as you soak up the sun on sandy shores or embark on boating adventures along the Chesapeake Bay. Don't miss out on this incredible rental opportunity at Day Dream Believer! Experience the epitome of beach and resort living with its modern features, community amenities, and prime location. 

BED CONFIGURATION: Primary Bedroom 1: King & Queen Sleeper Sofa (in separate sitting area) // Primary Bedroom 2: Queen bed // Bedroom 3: Queen bed // Bedroom 4: Queen Sleeper Sofa

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 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, paddle-boarding, 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.

Lazy Days

3 Bedrooms
2 Baths
7 Guests
Chincoteague Island
Pet Friendly
Screened Porch
Internet

Located on Main Street just north of town, "Lazy Days" may be just the perfect spot for your vacation! Cute and comfortable, this cottage is adorned with nothing but island charm. Downstairs features a cozy living room with flat screen TV, an eat-in kitchen with a back door that leads out to the yard, a full bathroom (tub & shower), a bedroom with a Double bed, and a second bedroom with a Twin bed and Bunk bed (2 Twins). Upstairs you'll find another bathroom (shower only) and bedroom with Queen size bed. (Please note: the stairs are steep and the upstairs has "knee walls".) The Chincoteague Bay is just a stone's throw - across the street - from the front steps... enjoy snippet water views! Nature trails, dog park, and downtown Chincoteague are just a minute or two by car. Enjoy a relaxing vacation at this affordable beach house!

- 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.

Assateague Overlook

2 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Water View
Charcoal Grill
Internet

This property has a location that is rich with views and amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run and play, or fish and crab. The first floor is an open room consisting of the kitchen, dining area and living room (with queen sleeper sofa). You'll also find a full bath on this level. The second floor offers a queen bedroom with a private deck that has unlimited views of the Assateague Channel. The second bedroom (upstairs) has two twin beds and you'll find another full bathroom on the second level as well. Need more space? Rent Channel Lookout next door! (Waterfront area, dock, pier and playground equipment pictured are community property at Memorial Park.)

- 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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