You are here

Displaying 73 - 84 of 182 results matching your search criteria
Map View
List View

Shore Reflections

4 Bedrooms
2 Baths & 1 Half
12 Guests
Cape Charles
Town & Country
Internet

Now available and awaiting your next vacation adventure, this lovingly restored 4-bedroom Victorian home blends traditional charm with modern convenience. Nestled in a picturesque setting with beautiful landscaping and mature trees, you're just a 10-minute drive from the vibrant Cape Charles community. Explore and enjoy downtown Cape Charles, which features a pristine beach, delicious food offerings, eclectic shopping, ice cream treats, coffee shops and so much more!

Spanning 3,000 sq ft, this exquisite property features a layout with high ceilings and wood flooring throughout, enhancing the airy and expansive feel of each room. The main living spaces boast large windows that flood the home with natural light, creating a warm, welcoming atmosphere. Four generously sized bedrooms offer ample personal space for relaxation and rejuvenation. The home also includes 2.5 bathrooms, each maintaining the character of the house with tasteful touches.

Guests will enjoy a beautifully landscaped yard, ideal for leisurely days spent outdoors or entertaining guests in a serene environment. The kitchen, equipped with essential appliances, provides a comfortable space for culinary exploration and seamlessly caters to both casual dining and larger gatherings.

This property is perfect for those who appreciate the beauty of historic homes but expect the functionality needed for a contemporary lifestyle. Make your "home away from home" in a place where tradition meets comfort in the heart of Eastville, VA. Experience the unique charm of this Victorian beauty and the inviting community that surrounds it.

- 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.

Pearl on the Canal

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Internet

Crafted entirely from the studs up, this four-bedroom, two-bathroom vacation home introduces a refined caliber of island living to one of Chincoteague's most sought-after private enclaves. Discerning craftsmanship announces itself the moment you step inside, where considered design and enduring finishes promise a comfort destined to outlast countless seasons by the sea.

At the heart of the home, the kitchen performs as a true showpiece, appointed with high-end appliances poised for everything from leisurely sunrise breakfasts to ambitious seafood feasts worthy of a celebration. When the cooking concludes, the living room beckons, where an eighty-inch television commands attention for cinematic evenings, spirited game-day gatherings, or the simple luxury of surrendering to the sofa after a sun-drenched afternoon. The primary suite elevates the experience further still, anchored by a jacuzzi tub seemingly engineered to dissolve the day's adventures into tranquil bliss.

Venture outdoors and the home unfurls with effortless grace. Expansive decks, dressed in handsome outdoor furnishings, extend a standing invitation to linger over morning coffee, drift through unhurried afternoons with a novel, and savor evenings as the island sky melts into a painter's palette of color.

The surroundings prove equally generous. The Island Nature Trail rests just up the road, ideal for contemplative strolls amid coastal beauty, while Maui Jack's Waterpark delivers exuberant amusement for the entire entourage. When the ocean calls, the storied Assateague Beach and its celebrated wild ponies await a short drive away, and golf devotees may indulge in a round at nearby Captain's Cove.

Nestled within a gracious, impeccably maintained community brimming with the singular charm Chincoteague is treasured for, this home stands ready to become your coastal sanctuary. 

- 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.

Channel Lookout

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

This property has a location that is rich with 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 at the waterfront Memorial Park. 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 has two twin beds and you'll find another full bathroom upstairs as well. Come and see for yourself! (Waterfront areas, dock, pier and playground area pictured are public property/Memorial Park.)

- 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.

Crabby Pines

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

Discover comfortable vacation living in this charming one-level ranch home. "Crabby Pines" offers a cozy retreat with three bedrooms and two bathrooms, providing ample room for relaxation and privacy. The house is ideally situated in a serene residential neighborhood and features modern amenities that ensure a seamless, convenient lifestyle.

Enjoy the convenience of being just minutes away from the public boat ramp at Fur Landing. Outdoor enthusiasts will appreciate the close proximity to nature trails and a dog park, perfect for morning jogs or leisurely evening walks with your furry friends. Oh, did we mention this home is pet friendly? Additionally, the property is located near the 'Beach Road,' a vibrant area bustling with mini-golf, dining options, ice cream shops, and boutiques - offering endless entertainment options.

This welcoming home is designed with practicality in mind, ensuring that each space is utilized efficiently while still exuding a sense of warmth and comfort. The property's easy access to local amenities, combined with its peaceful surroundings, makes it an ideal choice for anyone looking for a balance between nature and community activities.

Whether you're settling down with family or looking for a tranquil spot to return to after a day of adventures on the island, this home is sure to meet your needs. Embrace a laid-back lifestyle in Chincoteague with this delightful vacation home opportunity.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. Pet Restriction: Small dogs only under 35 lbs. NO CATS. 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.

Trembling Bay

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet

This beautifully renovated 3 bedroom, 2 bath Chincoteague cottage is nestled along the salt marshes in a natural setting on Chincoteague Bay. A few of the fine features include a private pier, a new kitchen & appliances, waterside screen porch & deck, and private master bedroom suite with a custom-designed luxurious bath. The numerous windows and over-sized sliding doors allow panoramic water views from nearly any spot in the house. The first floor is completely wheelchair accessible and features your main living areas, large master bedroom suite (K) with bathroom, and second full bathroom with shower/tub. Upstairs features the second and third bedrooms (D/2T). If relaxation is what you're seeking, look no further. This quiet, peaceful location at the water's edge will delight the senses. 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. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum pets allowed: 2. Pet Restriction: NO CATS. 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.

Hidden Treasure

4 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Screened Porch
Internet
Outdoor Shower

"X" marks the spot here at Hidden Treasure. Nestled in a cove along the shoreline of the island's most exclusive neighborhood on the northern end, you'll have everything you need for a perfect family vacation. ENDLESS outdoor space in the form of a long private dock with a large sitting area at the end, huge deck off the living area overlooking the water, a screened in dining area off the deck, and a large shared balcony off of two of the bedrooms on the upper level. The spacious home offers 4 bedrooms and 3 bathrooms. On the ground level you'll find the fully-equipped kitchen with breakfast bar and dining area. The kitchen opens up to the cozy living area, with a fireplace and an unbelievable view of Chincoteague Bay. You'll find plenty of seating for your family, just around the corner is another sitting area for overflow - or if you just want to curl up with a good book alone (no judgement!). Also located on the ground level is a full bath and bedroom with two twins - ideal for putting the little ones to bed but still being able to keep an eye on them. Upstairs you'll find the other 3 bedrooms. The master suite - furnished with a king bed, bath with Jacuzzi soaking tub and shower, flat-screen, and yet another knockout view on the balcony. The balcony runs the length of the house and is shared on the other end with a bedroom with a queen. An additional full bath, and another bedroom with two twins is also found upstairs as well. Crab and fish right off the dock, and enjoy cooking and enjoying your bounty together al-fresco at the screened-in porch on the deck. Or pour yourself a nice chilled beverage and walk down to the end of the dock and wait for the sun to slip under the horizon over Chincoteague Bay - bringing the end to another day of treasured memories made at Hidden Treasure.

- *NEW FOR 2025: Level 2 EV charger!*

- 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.

Hill House

4 Bedrooms
2 Baths & 1 Half
9 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Gas Grill
Screened Porch
Internet
Outdoor Shower

Welcome to Hill House! Wonderful traditional island home with fantastic new upgrades! The kitchen has been renovated, along with the bathrooms. Excellent in town location - walk to dinner, movie, shopping & galleries. Enjoy the beautiful Chincoteague sunsets with a beautiful water view! Hill House features 4 bedrooms and 2.5 bathrooms, with a first floor bedroom (double/twin Bunk) & 1/2 bath. Three more bedrooms on the second floor with a master suite (king) that offers a private staircase to the dining room. The third bedroom (queen) and fourth (two twins) are also located on the second floor. Enjoy the modern amenities of this lovingly restored island home, all while being in the middle of downtown Chincoteague's happenings.

- 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: 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.

Sunset Dreams

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

If you're familiar with the island you know that the best sunsets can be found on Main Street, and the sunsets waiting for you at Sunset Dreams (located on south Main Street), are NO EXCEPTION. A luxury waterfront townhome overlooking Chincoteague Bay, offering 3 bedrooms and two and a half baths - with a private pier, it's the perfect place to unwind and get on "island time". On the lower level you'll find the open area kitchen and dining area that features a stunning view of Chincoteague Bay and the salt marsh - that has everything you'll need to enjoy the various fresh catches waiting for you just off of the dock, or at our local seafood markets. A comfortable living area also boasts a beautiful waterfront view, with sliding doors that open up to a lovely little sitting porch - perfect for taking in the sunset with a cocktail without having to go too far. There is also a bedroom downstairs with two twins, a half-bath powder room, and a beautiful large sunroom/sitting area - great for sneaking away for a minute to get some work done or curl up with a good book. On the upper level you'll find the master bedroom with a queen bed, a full bath, and a beautiful waterfront view. Another bedroom with a queen bed is upstairs as well. A full bath can also be found upstairs in the hallway, and both bedrooms have televisions. Full sized washer and dryer for washing all those beach towels and bathing suits. You have full access to the dock across the street, so bring your fishing poles and crabbing gear (or visit Captain Steve's on Maddox Blvd to get what you need!). You're a quick two-minute ride to downtown to restaurants and the grocery, or an easy bike ride to the carnival or the sub shop to grab a quick bite to eat. Come stay with us and enjoy sweet dreams at Sunset Dreams, and bring along your favorite four-legged friend, as this rental is dog- friendly! Need more space? Rent "Saltwater" right next door! Note: The pier is shared with the other 2 adjoining townhomes.

- 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.

Escape at Deep Hole Hideaway

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

Enter a world of tranquility at Deep Hole Hideaway! Need a break from the daily grind? We've got you covered! Our chic and well-equipped living space will make you feel right at home. And when your tummy rumbles, our kitchen is your culinary sanctuary. Two snug bedrooms await you, furnished with a Queen bed, a Twin daybed, plus a sleeper sofa for your whole posse! The elegant and refreshing décor will overwhelm you with happiness as soon as you step through the front door!

- 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. 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.

Ms. Kitty's Bayside Bungalow

2 Bedrooms
1 Bath
6 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Internet

Welcome to Ms Kitty's Bayside Bungalow!  A charmingly remodeled home now available for rent on Eastside Drive. This delightful two-bedroom house offers comfortable living with modern amenities in a serene bayside setting. Each bedroom is furnished with a plush double bed, ensuring a restful night's sleep.

As you step inside, you'll be welcomed by a fresh, contemporary interior that has been newly updated to provide both style and function. The living area is equipped with a Smart Tv and Roku as well as a work desk, perfect for entertainment and relaxation. The kitchen features all the necessary appliances and ample space, making it ideal for cooking and dining.

One of the highlights of this home is its expansive, fenced backyard. It’s an ideal space for pets  and for you to enjoy outdoor activities. The nice deck area offers a perfect spot for barbecues or simply soaking up the calm atmosphere of the neighborhood. Also enjoy a large firepit for smores in the evening hours!

Situated within close proximity to Memorial Park, the location offers convenience with easy access to the boat launch, fishing pier,  playgrounds, basketball and scenic views—perfect for outdoor enthusiasts and families alike.

This rental home captures the essence of convenient and laid-back bayside living. Whether you're looking for a peaceful retreat or a cozy place close to amenities, Ms Kitty's Bayside Bungalow provides an excellent choice for individuals, couples, or small families. 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum pets allowed: 2. Pet Restriction: NO CATS. Breed restrictions apply. (Please inquire). 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.

Bay Haven

3 Bedrooms
2 Baths & 1 Half
6 Guests
Captain's Cove
Waterfront
Boat Dock
Pool
Internet

Ever dreamed of a home where water views greet you from literally every room? This contemporary three-bedroom, two-and-a-half-bathroom house turns that daydream into your everyday reality, blending sleek modern design with the kind of relaxed waterfront rhythm that's tough to beat.

Walk through the door and the open floor plan immediately shows off, letting light and shimmering water views flow freely from one space to the next. Whether you're whipping up dinner, sprawling on the couch, or catching up with family, the sparkle of the water stays in view the entire time. It's the sort of layout that makes hosting feel effortless and lazy days feel downright luxurious.

Three comfortable bedrooms give everyone space to spread out, with the primary bedroom carving out a peaceful spot to recharge. The contemporary finishes lend a crisp, current feel throughout, so the whole place reads clean and bright.

Then there's the neighborhood, and Captain's Cove genuinely delivers. Think swimming pools, a fitness center, a playground for the little ones, golf for the swing enthusiasts, an on-site restaurant, and a marina for boat lovers. It's practically a vacation resort you get to call home away from home.

When wanderlust strikes, adventure sits close by. Maui Jack's Waterpark brings splashy thrills, the legendary Assateague Beach offers wild ponies and endless beach shoreline, and the boardwalk buzz of Ocean City is an easy day trip away.

Ready to live where the water never leaves your sight? Book your vacation today.

- 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.

- 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. 

Herbie's Hideaway

3 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet

Luxury water view vacation rental home with dock access. This home boasts a full ensemble of amenities and the most beautiful views of Assateague Island. The oversized chef's kitchen offers ample room for family gatherings and preparing meals, and it compliments the spacious dining area that opens up to the large screened porch. Beautiful custom windows and large sliding doors complete the open and airy floor plan. The geothermal heating/ac system lends to your ultimate vacationing comfort! Close to Memorial Park (playground, basketball, tennis, trails, water access) and directly across the street from a family restaurant! For larger groups or family reunions, check out nearby Moon Rising or Wildflower!

- 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.

Pages