South Main

Come stay in this classic Eastern Shore Style home. Located just a few blocks from our famous downtown Main Street area, you are within walking distance to most of our shops and restaurants. Serendipity has a very nice screened porch for those memorable Chincoteague Summer evenings. This home also offers a first floor bedroom (Queen) and half bath.

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Welcome to ‘Saltwater', formerly known as 'Logan's Sunset.' A lovely 2 story waterfront townhouse on Chincoteague Bay with gorgeous views from both floors. Experience beautiful sunsets and NASA rocket launches from the front balcony. The screened back porch offers a great source of private outdoor entertainment as it boasts a comfortable six-person dining area. All three bedrooms have their own flat screen tv with cable. The main bedroom includes a desk perfect for working from home, virtual learning and streaming. Saltwater includes high-speed internet and free Wi-Fi. The main bedroom has it's own ensuite full bath with jetted tub/shower. The additional bedroom has a private full tub/shower. The 3rd bedroom has a bunk with two full size beds with an additional twin bed.  Guests can also enjoy the coastal outdoor shower. The private expansive 600 foot shared deep water dock provides hours of endless Saltwater fun! 

Need more space? Rent "Sunset Dreams" right next door! 

Saltwater has a fully stocked kitchen including an outdoor charcoal grill.

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee 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.

Just off Beebe Road, named after the family in Misty of Chincoteague, you'll find a cute little cottage called Pony Pen. Located on the southern end of the island - you're a quick bike ride to Memorial Park or Curtis Merritt Harbor to do a little fishing or crabbing, to enjoy carnival, or check out downtown. The home features a sunroom/open living area when you walk in, along with an open dining/kitchen area - with everything you'll need (refrigerator, electric range, dishwasher, coffee maker) to make meals at the house if you'd like. The master bedroom is bright and sunny and boats a queen bed and full bath, and has a television. There is also another bedroom with a queen and a television as well. A full bath is located in the hallway in between the two bedrooms. Upstairs you'll find a converted loft area that has three twins and a sleeper sofa. On the back of the home, off the kitchen, you'll find a screened in porch with a picnic table for enjoying a meal al-fresco. It overlooks the lush green backyard that's fenced in - perfect for letting the little ones play hide and seek while you play cards or read a book on the back porch, enjoying the island sunshine and breezes. Don't dilly-dally, this property books up fast. Round up your family and friends and corral them all at Pony Pen on Chincoteague Island!

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- 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.

Views! Views! Views! Enjoy the expansive panorama from all three levels of this prime location on Chincoteague Bay. With 180 degrees of natural beauty graced by blissful sunsets, La Vie invites you to live the life at its most relaxed. As soon as you enter the home, its light and airy floor plan lifts your spirit, calms your mind, and promises to rejuvenate your body. Newly painted and decorated, La Vie features a fully equipped modern kitchen with granite breakfast bar, large six burner induction stovetop; four new UHD 4k smart TVs with multiple HDMI ports (bring your streaming devices), and a master suite with king-size bed, large jacuzzi-style tub, private balcony, and picture windows overlooking the bay. Plus, theres plenty of space to share this retreat with friends and family: The home?s entry level features a newly furnished queen bedroom with sliding glass doors opening onto a waterfront deck, another large bedroom containing two twin beds, and a shared full bathroom with an extra long six-foot tub. The central living space is on the second level, where you?ll find the open-plan living room, kitchen and dining room connected to a large outdoor deck with glass table and deck chairs, as well as a laundry room and powder room. Yet the amenities arent confined to the house. La Vie also includes access to a 700-foot-long shared pier for fishing or launching kayaks, a pool located right across the street, and shaded parking directly under the unit. Dont forget your boat! La Vie features access to boat slip #1. However long your stay may be, youll make lasting memories and take the positive energy, beauty, and majesty of La Vie and its surroundings home with you. La Vie, the life, is short of La Vie en Rose, which can mean life is as beautiful as you wish to see it.

- Linens and towels are not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee per pet. All pets must be disclosed prior to arrival. Pet restriction: No cats.

- 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 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 Queen 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 not included with your reservation. Please inquire about our new attractive linen packages!

- No smoking is permitted on the premises. 

- This property is pet friendly with a pet fee 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.