Chincoteague Island

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 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.

We're pleased to offer you 'Utter East'! Tucked off of a quiet side street in the middle of the island, this home features everything you'd need for a wonderful, relaxing vacation. If you love outdoor space, you'll love the huge screened porch, expansive decks, and beautifully landscaped fire pit sitting area on the pond. Inside the home, downstairs you'll find the living room, an additional den/family room, eat-in kitchen, dining room, two bedrooms and a full bathroom. Upstairs features two more bedrooms and another full bathroom. Don't delay; this home will book quickly! "Where sky and water meet, Where the waves grow sweet, Doubt not, Reepicheep, To find all you seek, There is the UTTER EAST." - From "The Chronicles of Narnia" by C.S. Lewis

- Linens and towels are included with your reservation.

- No smoking/vaping is permitted on the premises, including porches and outdoor areas.

- 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 A 'Teague of Our Own! This in-town home is an easy walk or bike to downtown or Maddox Blvd. Nicely decorated in 'beachy-chic' decor! The living room has abundant seating, complete with a flat screen TV and electric fireplace for those off-season stays. The kitchen is stocked to a chef's standards - there's nothing you won't find including a gas stove, sharp knifes and an herb garden. You will also find a queen sized sleeper sofa in the living room. The three bedrooms are upstairs, and the full bathroom (tub and shower) is downstairs. The enclosed porch with sliding windows allow for room to spread out in any weather. Large carport to keep a vehicle and all your gear under cover. A huge yard for cookouts, games and showering in the outdoor Tiki-shower. This fabulous vacation home truly has it all and has become one of our most popular rental homes. Don't delay; book today! 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- 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. Pet restriction: limited to one small dog only.

- 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 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.

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. 

- Pet Friendly with a fee, No cats, 2 dogs max. ($150 per pet) 

- 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.