Waterfront Rentals

This is it! Are you looking for your perfect vacation getaway spot? Look no further. 'Charlie's Bayside Retreat' is everything you'll need for your home away from home, at the beach! The first main level features an open floor plan with a living room that opens up to a wonderful screened porch with comfortable outdoor dining furniture. The open living area also features a large Smart TV with cable and an electric fireplace. A modern kitchen that is fully stocked with everything you could possibly need, also has new appliances and a Keurig coffee maker, breakfast bar, open dining area, and powder room complete the first-floor living space. On the second floor, you'll find two bedrooms, one with a Queen bed and Smart TV and the other with 2 Twins & a Full - both with balconies and a shared full bathroom with dual sinks. The entire third floor is a spacious, private primary oasis with a King bed, and a luxurious en suite featuring a deep jetted tub and dual sinks. This bedroom is also equipped with a Smart TV and a balcony with amazing views & Adirondack chairs making it perfect for relaxing or sunbathing. Additional features of this fabulous vacation home include your own private boat slip (#7), pier for fishing and crabbing, fish cleaning station, covered parking area, grill, picnic table, and tons of extras! There's an outdoor shower, and beach gear including beach chairs, beach toys, and an umbrella. Not to mention you're conveniently located on South Main Street - walk to the downtown area (including Ropewalk for food and drinks) or to the annual Fireman's Carnival. The possibilities are endless. Some of the most gorgeous sunsets ever witnessed are from this spot on South Main Street & it is the perfect spot to watch rocket launches from Wallops. It doesn't get much better than this!

- 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.

Welcome to a remarkable piece of Virginia's coastal heritage - a magnificently restored 17th-century estate nestled along the serene Cherrystone Creek. This distinguished property, set on 14 pristine acres, offers an extraordinary blend of historical grandeur and modern comfort, perfectly positioned just moments from the charming town of Cape Charles.

The residence showcases impeccable architectural details throughout its thoughtfully designed layout. The ground floor presents a series of elegant entertaining spaces, including a stately formal living room and dining room, perfectly suited for sophisticated gatherings. The heart of the home features a thoroughly modernized kitchen that seamlessly bridges centuries of history with contemporary convenience. Perhaps the most captivating space is the family room, where expansive picture windows frame mesmerizing views of the marshlands and bay, creating an ever-changing natural canvas. As an added bonus, this room features a foosball table and card table - perfect for those family game nights. 

Ascend to the second floor to discover four meticulously appointed sleeping quarters. The primary bedroom suite presents a luxurious king-size arrangement, while a second bedroom offers a refined queen-size setting. The third bedroom features two sets of bunk beds, perfect for younger guests or the young at heart. A versatile sleeping/sitting room, complete with two twin-size day beds, rounds out the accommodation options, all serviced by three well-appointed bathrooms.

The estate's grounds are nothing short of magnificent, with sweeping water frontage and pristine marshlands creating a private sanctuary. A dedicated game room provides indoor entertainment, while the expansive outdoor spaces offer unlimited potential for grand celebrations or intimate gatherings.

This exceptional property sits within easy reach of local amenities, including the historic Cape Charles district, known for its boutique shopping and dining experiences, and the beloved Cape Charles Beachfront, offering endless opportunities for coastal recreation. Here lies an unparalleled opportunity to experience luxury living steeped in history, where every detail tells a story and every view inspires.

- 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.

This beautiful 2 bedroom ranch home has a quiet, out-of-the-way location situated on little Oyster Bay. The views of the bay are beautiful and expansive with a long pier straight from the back deck. It's perfect for crabbing, kayaking & canoeing! An Unfettered View features all amenities including a private master suite with full bath, central air, all appliances including dishwasher, washer/dryer, wireless internet service and a wonderful family room on the waterside of the home. Tastefully furnished and very accommodating, this is a great vacation spot! An Unfettered View is wheelchair accessible.

- 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.

Porter's Barn, where luxury meets seclusion on the water's edge...

There is a fanciful quality to this secluded property where nature's beauty and luxurious accommodations coexist in quiet harmony. Located on the banks of Holden's Creek, a headwater of the Chesapeake Bay and a 20-minute drive to the pristine white sand Atlantic beach on Assateague Island, Creek House Guest Cottages are private, convenient, and offer bespoke modern amenities. Explore life off the beaten path and take a true vacation. Whether you are kayaking or paddle boarding on the creek, sitting by the fire pit, biking down country roads or going to the beach, you will find plenty to do or enjoy doing nothing at all. The views of the creek are magical at any time of the day or night from inside your cottage or from any vantage point on the 3-acre property. The Cottages have been designed and decorated by a professional interior designer.

'Porter's Barn' has partnered with our friends at Sun Outdoors Resort (located less than 2 miles from the house) so that all guests may enjoy the fun resort amenities FREE OF CHARGE. This extra bonus includes a private beach w/ water rentals, pool, playground, "snak shak", comfort stations & more! 

Shared amenities include: a gas grill, 20 ft. radius fire pit, 2 kayaks, a SUP, and 2 bicycles. There is a boat launch on the property and two docks (one floating). Linens and towels are provided.

Porter's Barn: 900 square ft. Full Kitchen and Laundry Room. Marble Bathroom. Sleeps 2 (Queen Bed). Outdoor Shower. Smart TV. WIFI

In addition to Porter's Barn, the compound is also home to two other luxurious dwellings: Hosta Cottage and Creek House. All combined, The Creek Compound will accommodate 18 with no parking problems. Please note that this listing is for Porter's Barn only; the other two homes - Creek House and Hosta Cottage - must be booked separately. A direct inquiry should be sent for special event pricing or if you wish to rent the entire compound.

- 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. Limitations: one dog only. No pets on the furniture, please.

- 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.

Private pier with boat docking, Waterfront, Pet friendly, Internet, A/C, Fireplace, Charcoal grill. Vintage charm with all modern comforts!

Welcome to your new favorite island getaway! This charming Victorian cottage on Chincoteague's popular South Main Street offers the perfect blend of traditional character and modern comfort. With 3 bedrooms and 2 bathrooms, there's plenty of space for family and friends to unwind after a day of island exploring and adventures.

Step onto the open front porch and prepare to be amazed — breathtaking bayside sunsets await you nearly every evening. Pour yourself something refreshing, kick back in a rocking chair, and watch as the sky transforms into a canvas of orange and pink hues over Chincoteague Bay.

One of this home's standout features is the private pier extending directly into the bay, complete with boat dockage capabilities. Imagine morning fishing sessions, dropping a crab line to try your hand at catching dinner, or evening cruises right from your rental home! No need to haul your boat to a public launch — your nautical adventures begin here.

Traveling with 4-legged family members? No problem here - 'Almost Heaven' welcomes your pet(s)!

Location? Simply perfect. You're just minutes from downtown's delightful shops, restaurants, and even the downtown movie theater. Grocery runs are a breeze with Island Foods just a short drive away. For summer fun, Maui Jack's Waterpark is nearby, and the stunning Assateague Beach is waiting to capture vacation memories, and for your footprints in the sand.

The primary bedroom on the first floor offers a peaceful retreat after long days exploring island trails or collecting seashells. The second floor features two more bedrooms and a full bathroom (shower only). This isn't just a rental — it's your ticket to the relaxed island lifestyle you've been dreaming about. Make it your "home away from home'... at the beach!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly. A pet 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.