You are here

Displaying 97 - 108 of 187 results matching your search criteria
Map View
List View

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. An additional fee of $150 per pet will apply. Maximum pets allowed: 2. 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.

Poole's Cove

3 Bedrooms
3 Baths
6 Guests
Chincoteague Island
Waterfront
Gas Grill
Screened Porch
Internet
Outdoor Shower

Nestled just off Main Street with the water as your backdrop, Poole's Cove is a lovingly curated escape that feels inspired and inviting. Every detail of this thoughtfully decorated home invites you to slow down, breathe deeply, and truly settle in.

The layout is designed for both togetherness and solitude. The primary bedroom suite anchors the main house, while a breezeway connects you to a separate wing with two additional bedrooms and bathrooms — perfect for families or couples who want space to gather and space to retreat.

Step into a large screened-in deck and up to the rooftop deck, where water views, golden sunsets, open skies, and unforgettable stargazing await. When you're ready to unwind indoors, the upstairs office and library is a wonderful place to lose yourself in a good book.

And the best part? Poole's Cove has just undergone a complete top-to-bottom renovation. Brand new kitchen, floors, bedrooms, bathrooms, and furnishings throughout — plus significant exterior updates. The Poole's Cove you've always loved is now better than ever.

This isn't just a place to stay. It's an experience.

---

Please note: Due to this home's unique floor plan and open deck railings, it may not be suitable for young children. This is a non-smoking, pet-free property. Linens and towels are available.

- 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.

Donovan's Reef

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Internet

Charming Chincoteague coastal cottage doesn't even begin to describe this place, but it's a start. Cheery, bright, and colorful - with some form of island history gracing every nook and cranny. Find the perfect mix of old and new in this unique home. Close enough to the main drag on Maddox Boulevard and Main Street - but out of the hurly-burly here on Ocean Boulevard. Wake up a few minutes before everyone else and head across the street to get fresh donuts from Mister Whippy or chocolate croissants from Amarin to surprise everyone with. You'll be the hero for the day, until someone else brings home oysters that night. Oh, and bring your furry friends along, because this one's PET FRIENDLY! This property features lots of nooks for sleeping spaces - a loft upstairs, featuring skylights that let the bright island sunshine flood in. Up here you'll find a cozy king size bed in one room, and two twins in another, with a full bath that features a gorgeous tiled stand up shower. Downstairs you'll find two more bedrooms - one with two twins, and the other with a king. Three different comfortable living areas, one of which is an outdoor sunroom - and that room has doors that connects to the downstairs king - in addition to the main living area. Small backyard area for letting the puppies play or eating lunch outside at the picnic table. The retro mid-century kitchen has everything you'll need to prepare that island seafood dinner with what you catch down at the town dock, and a lovely dining area to enjoy it as a family. Donovan's Reef is located in the heart of downtown Chincoteague, allowing you an easy walk to all the shopping the island has to offer. Stop by Chincotiki on your way home and grab an orange crush or two!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. 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.

Bayside Bliss at Cape Charles

3 Bedrooms
2 Baths & 1 Half
10 Guests
Cape Charles
Gas Grill
Internet
Outdoor Shower

Welcome to your idyllic retreat in the charming coastal community of Cape Charles. This brand new three-bedroom, two-and-a-half-bathroom residence offers the perfect blend of comfort and sophistication for your Eastern Shore getaway.

Step inside to discover thoughtfully designed living spaces, including a spacious living room and a versatile loft area upstairs (with Queen Sleep Sofa) —perfect for a quiet reading nook, or entertainment zone. The convenience of a first-floor primary bedroom suite means accessibility and privacy for the discerning tenant.

The backyard presents a picturesque setting with a scenic pond, offering tranquil views and a peaceful atmosphere for morning coffee or evening relaxation. Imagine watching herons glide across the water as the sun sets—nature's own entertainment system!

The stunning Cape Charles Beachfront is nearby, providing endless opportunities for seaside adventures. After a day of exploration, return home or indulge in a delicious meal at the local restaurants. This exceptional rental property offers more than just a place to stay—it's a gateway to the coastal getaway you've been dreaming about.

- 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.

 

The Pines on Finney Creek

3 Bedrooms
3 Baths
12 Guests
Waterfront
Boat Dock
Gas Grill
Internet
Outdoor Shower

Wake up to birdsong, spend the afternoon paddling around, and wrap up the evening watching the sky light up over Finney Creek. Sounds pretty good, right? This freshly renovated three-bedroom, three-bathroom home makes that whole relaxing routine your new normal.

Sitting on private acreage in a quiet, tree-lined pocket of the Town of Onancock, this rental is made for folks who take their downtime seriously. You've got your own pier and boat dock reaching right into the creek, so kayaking, fishing, or just dipping your toes in the water is always an option. The sprawling decks and big outdoor area leave plenty of room to grill, hang out with friends, or plant yourself in a lounge chair and stay put for a while.

When the weather isn't cooperating, head into the roomy sunroom. There's a pool table and other activities ready for a little friendly competition. Inside, the upscale kitchen actually makes cooking fun, and the newly remodeled bathrooms have that clean, just-finished feel you'll notice the second you walk in.

Honestly though, the setting steals the show. Wildlife roams around like it owns the place, the pace stays nice and slow, and the quiet here is the kind you didn't realize you'd been missing. Even so, charming downtown Onancock is only a few minutes off. East Point Marina and the Onancock Wharf are close by for some easy waterfront wandering, Food Lion handles the grocery runs, and Chincoteague Island makes for a fun day trip whenever you feel like venturing out.

So if you're ready to swap the everyday noise for the gentle sound of the creek, this place is waiting. Give us a call and schedule your stay today. You'll be glad you did.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This home is pet friendly with an additional 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.

Serenity at Deep Hole Hideaway

2 Bedrooms
1 Bath
6 Guests
Chincoteague Island
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. An additional fee of $150 per pet will apply. Maximum pets allowed: 2. Cats are considered on a case by case basis. 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.

Vast Views

2 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Water View
Pet Friendly
Boat Dock
Pool
Internet

Welcome to your perfect coastal getaway in charming Chincoteague Island! This newly remodeled townhouse offers the ideal blend of comfort and modern amenities, featuring two cozy bedrooms and three full bathrooms as well as an open floor plan perfect for entertaining! Step into a space where everything sparkles with newness, from the stylish fixtures to the thoughtfully placed flat-screen TVs in every room. The innovative touches, such as bathrooms equipped with cutting-edge built-in Bluetooth speakers, make this home perfect for both relaxation and entertainment.

The location couldn't be better for beach lovers and adventure seekers. Step outside to enjoy exclusive community amenities like a swimming pool and a pier with direct water access to Assateague Channel. Try your hand at fishing or crabbing, or tie up your boat - there’s no better way to end your day than with mesmerizing water and lighthouse views right from your vacation home! The community pool provides a refreshing escape on warm summer days, while the nearby Memorial Park offers tennis courts and a playground for your enjoyment.

The East Side location could not be more ideal - when you're not in the mood to cook, local restaurants are just a short stroll away, serving up fresh seafood and coastal favorites. The area's attractions are sure to keep you entertained, with Maui Jack's Waterpark and the pristine Assateague Beach both within easy reach. Nature lovers can explore the famous wild ponies and abundant wildlife that make this island so special.

This townhouse isn't just a rental – it's your piece of paradise that offers the laid-back coastal lifestyle that Chincoteague is famous for. Whether you're seeking a peaceful retreat or an adventurous beach vacation, this home delivers the best of both worlds.

This pet-friendly home also offers the option to rent neighboring units, making it ideal for larger groups or family gatherings! Make this brand new townhouse your sanctuary on Chincoteague Island, embracing a blend of comfort, convenience, and natural beauty all around. Your island lifestyle awaits!

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum pets allowed: 3. 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.

Heron Landing

2 Bedrooms
1 Baths & 1 Half
6 Guests
Chincoteague Island
Charcoal Grill
Internet

Three words : Charming. Coastal. Cottage. Located just off of Ridge Road, in the center of the island, you'll find this adorable abode. 'Heron Landing' is newly remodeled. Downstairs you'll find an open floor plan with a fully equipped kitchen - with range, refrigerator, and dishwasher. A breakfast bar to enjoy a quick bite before you head to the beach. A comfortable and cozy living area with television. A half bath and washer and dryer can also be found downstairs for your convenience as well. A small porch with sliding door is located off of the living room, allowing you to crack open to let in the island breezes flowing over Assateague Channel. Upstairs you'll find the two bedrooms, both with queen beds. Beautiful, rustic, nautical themed decor. A full bath with tub/shower is also located upstairs as well. Enjoy your cup of coffee or cocktail on the cute patio area outside, or just to get a little extra island sunshine. Memorial Park is an easy walk or bike ride down the street, with a great pier for fishing and crabbing, tennis courts, and walking paths.

- 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.

Windshadow

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

You will enjoy spectacular sunsets from this lovely waterfront home overlooking the Chincoteague Bay. There is a waterfront screened gazebo that leads to a dock great for crabbing/fishing. Inside is a large open floor plan with a brand new kitchen, living room with wood burning fireplace and dining area. Walk through the French doors off the living room to a large screened porch and sky deck overlooking the Chincoteague Bay. There is a first floor King bedroom with en-suite bath and two twin bedrooms on the second level. Windshadow is a premier PET FRIENDLY vacation rental.

- Linens and towels are included with your reservation.

- No smoking is permitted on the premises.

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum pets allowed: 4. 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.

Sunrise View

3 Bedrooms
3 Baths
6 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

**Island Living at Its Finest — Where Sunrises Steal the Show**

Welcome to the most breathtaking views Chincoteague Island has to offer. Nestled in the sought-after Oyster Bay I Community, this stunning three-bedroom, three-bathroom WATERFRONT rental home is a haven for those who crave inspiration from the natural world. If you're an artist, writer, creator, or simply someone who finds peace in golden-hour magic, this is where you belong.

Step inside to discover a thoughtfully designed living space that includes a comfortable living room and an additional den — perfect for curling up with a good book or sketching the marshland views that stretch endlessly beyond your windows. View the water from almost anywhere…Feeling playful? Challenge your guests to a round of bumper pool, because every retreat deserves a touch of friendly competition.

The real magic unfolds across multiple levels, where every room has a view!  Climb the spiral staircase to the third-level tower room, where panoramic vistas will leave you utterly speechless. Gorgeous sunsets paint the sky in hues you didn't know existed, and you'll find yourself reaching for a camera — or a canvas — day after day.

Outdoor living shines here with spacious decks ideal for entertaining and a screened porch complete with a ceiling fan, offering bug-free relaxation while the island breeze does the rest. Quietly listen to music and watch the Purple Martins swirl about … just off the porch. It's the kind of space where conversations linger and worries disappear. It's magical.

Boaters delight in the fact that they can tie-up their boat right at the home. Using the community boat ramp makes this easy. Boat, kayak or fish right from the property.

Beyond the home, adventure awaits. Explore the nearby Island Nature Trails for serene walks through coastal landscapes, catch waves at Assateague Beach where wild ponies roam, or bring the family to Maui Jack's Waterpark for splashing fun on warmer days.

This is more than a rental — it's an experience that feeds the soul. Reach out today to secure your ISLAND ESCAPE and experience these legendary sunrises over the bay.

- 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.

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.

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. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. 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.

 

Pages