Vacation Rental Homes

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. 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.

Welcome to 'Counting Corks' (formerly known as 'Smith Beach Pines'), the moment you step foot in this beautiful waterfront cottage you feel at home. The pet friendly cottage is 1,150 sq ft, featuring 3 bedrooms and 2 full baths. The primary bedroom has a king size bed and TV. On the other end of the home the second bedroom features a queen bed and a TV. The third bedroom features a twin over a full bunk bed. The cottage also has a bar room leading into the deck area, with plenty of seating to entertain. The dock leads to the creek and is just waiting for you to go crabbing, fishing, or kayaking or simply enjoy the beautiful sunrise while drinking a cup of coffee. The property is a short distance to the community beach and to the community boat ramp. Also features an outdoor shower and a firepit area with plenty of seating. The cottage is located just a few short miles from the Historic Town of Cape Charles and about 25 minutes from Kiptopeke State Park.

- 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.

Experience elevated coastal living at 'Sandy Penny', a stunning, brand-new vacation home tucked along peaceful Clarkson Lane with beautiful, snipet water views of the Assateague Channel. Thoughtfully designed with comfort and sophistication in mind, this home is the perfect retreat for families, couples, and friends seeking a luxurious Chincoteague Island getaway.

From the moment you step inside, you’ll notice the premium furnishings, designer finishes, and upscale appliances that set 'Sandy Penny' apart. The bright, open-concept living area features expansive windows that allow natural lighting, and space for gathering or entertaining. Whether you're savoring your morning coffee or winding down after a day of exploring, this space makes every moment feel special.

The chef’s kitchen is fully equipped with top-of-the-line appliances, custom cabinetry, and elegant stone countertops, making it a joy to cook and gather. Enjoy meals indoors or take advantage of the outdoor spaces to dine with soft bay breezes and glimpses of passing wildlife.

Sandy Penny offers three beautifully appointed bedrooms, each with its own private en-suite bathroom, providing exceptional comfort and privacy for every guest. Luxurious bedding, spa-inspired bathrooms, and serene décor ensure a restful experience from start to finish.

Located in one of the island’s most desirable areas, you’ll be just minutes from: Assateague National Seashore and the world-famous wild ponies; downtown Chincoteague’s shops, ice cream parlors, and restaurants; kayaking, boating, and fishing along the Assateague Channel; scenic trails and bike paths and more!

Whether you’re seeking serenity, adventure, or a little of both, Sandy Penny delivers a refined coastal escape with all the comforts of a luxury home. Book your stay today and experience Chincoteague Island from a place where every detail is designed for relaxation and unforgettable memories.

Bed Configuration: Downstairs Bedroom - King bed; Upstairs Bedroom 1 - King bed; Upstairs Bedroom 2 - Triple Bunk Bed & Twin-over-Full Bunk with pull-out Twin Trundle; Living Room - Queen Sleeper Sofa; Additional Rollaway Twin 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.

Introducing a charming, newly renovated house, offering a perfect blend of comfort and convenience. This single-family home features an inviting sunroom, a brand-new kitchen, four well-appointed bedrooms, including a serene primary bedroom, and two modern bathrooms, all professionally decorated with a delightful beach theme.

Designed to accommodate up to eight guests, the house boasts spacious rooms that ensure ample space for relaxation and entertainment. The living areas flow beautifully outdoors to a superb deck, ideal for enjoying your morning coffee or sunset dinners, surrounded by a spacious yard.

Nestled in a vibrant neighborhood, the property promises a vacation of ease and accessibility. It’s centrally located near the heart of the town, close to a pristine beach, restaurants, and family-friendly activities, including mini-golf and Maui Jack's Waterpark. Nature enthusiasts will appreciate the proximity to the Assateague Island National Seashore, a spectacular location for wildlife and scenic views, while the nearby Downtown Chincoteague Waterfront Park provides excellent opportunities for leisurely activities.

Experience the joy of living where every day feels like a vacation. This retreat is not just a place to stay, but a home away from home. Come and see for yourself!

- 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. 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 your next coastal retreat at "Twins at Bay"! This charming 3-bedroom, 2.5-bathroom house offers the perfect blend of historical allure and modern convenience. Each bedroom, situated upstairs, promises peaceful private spaces, while the welcoming front porch invites you to enjoy serene evenings or lively mornings with the convenience of the downtown area. 

Imagine stepping out to bask in the aroma of saltwater only a few short minutes away,  and spending your days exploring local attractions. Perfect for seafood enthusiasts, the area boasts some of the best dining spots where you can indulge in fresh catches daily. If you're feeling sporty, challenge your friends or family to a playful round of miniature golf nearby. For those days when you'd rather stay close to home, the property comes complete with a gas grill—ideal for those impromptu barbecues. The beach is just a heartbeat away, offering endless sand, surf, and sun for all who crave the ocean breeze.

Pet lovers rejoice! This home embraces your furry friends, making it a true family haven. The friendly neighborhood further adds to the vibrant community spirit, ensuring every occupant feels instantly part of the local fabric. Twins at Bay is newly renovated and perfect for your next vacation! 

- 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: 4. 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.