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Welcome to Tranquility! This show stopper of a home is a brand new construction, featuring  2 bedrooms, 2 bonus rooms and 2.5 baths. Sleeps up to 11 with 1 king, 2 queens, 2 queen conversion sofa/sleepers and a twin fold-out sleeper chair. Deep Hole Hideaway rental properties can accommodate up to 23 people by renting all 3 units in this complex! (based upon availability)  Tranquility Great for family reunions or large gatherings! Please reach out to our office or check out "Escape at Deep Hole " and "Serenity at Deep Hole" for multi home bookings. 

Pet friendly, private and quiet. This property allows for entertainment and relaxation for both you and your kids! There is also outdoor seating, cornhole, a firepit, picnic tables and barbecues for additional recreation for your vacation. Book your stay today, this one won't last long! 

- 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: 4. 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.

Discover the ultimate family retreat in this brand new 5-bedroom, 3.5-bathroom home located in the picturesque Captain's Cove Community, boasting over 2,500 square feet of luxurious living space. With breathtaking natural marshland and water views, this residence is perfect for wildlife watching and enjoying serene sunsets from expansive decks designed for outdoor dining and recreation. The upgraded kitchen and all-new furnishings create an inviting atmosphere for making cherished memories with loved ones. Take advantage of community amenities including indoor and outdoor pools, a 9-hole golf course, fitness room, waterfront restaurant, boat ramp, and fishing pier to ensure endless fun-filled days. Don’t miss out on this exceptional opportunity to create lasting family traditions in a relaxing vacation paradise!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property does not allow pets. 

- 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.

- 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 The Ryokan- a quiet refuge that has everything you need for a relaxing vacation. Offering an unobstructed panoramic view of Oyster Bay, this waterfront home is ideal for daytime birdwatching and nighttime stargazing. Bring fishing poles, crab pots, kayaks or paddle boards to use along the bulkhead or put in your boat from the convenient community boat launch. You will only be a short drive or fun bicycle ride away from Assateague Wildlife Refuge, the beach and Main Street of Chincoteague.

There are many features of The Ryokan to ensure a pleasant stay. The split level design offers a full bath and 3 bedrooms upstairs, two of which are waterfront with balconies. Enjoy the beautiful water view from a spacious main floor kitchen and living room. Early birds will love having coffee watching the sunrise from the deck or screened in porch! Downstairs offers a waterside deck as well as a large family room, bedroom with bunk beds and a full bath. Go under the house for a shaded spot to hang your hammock and enjoy an outdoor shower after a day at the beach!

Located in the ever-popular Oyster Bay 1 community, this home is truly an experience for the nature and island lover. We hope you will find The Ryokan a place to return to year after year.

Please note:

- This home does NOT have a washer and dryer on the premises.

- 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.

Peaceful and stunning waterfront home! Located on a quiet side-street, Heron's Cove features a reverse floor plan with all bedrooms on the first floor, and the main living-level on the second floor. This allows you to capture and maximize the fabulous bay views! The second floor also features a great room with cathedral ceilings, fully equipped kitchen, gas fireplace and screened gazebo. In addition, there's multiple open decks and a shared dock (with Egret's Cove) into Little Oyster Bay. There are three bedrooms that each have a king size bed, and one bedroom that has two sets of bunk beds. Each bedroom has a private bath. Luxurious comfort while surrounded by Chincoteague's natural beauty and wildlife! Floor Plan: Downstairs (first level) features 4 bedrooms, all with attached private bathrooms. Two of the downstairs bedrooms and the sitting area have private waterside balconies. Upstairs features an open floor plan with the kitchen, living room and dining area. There is also a full bathroom (shower only) upstairs.

- 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. BREED RESTRICTIONS APPLY. 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.

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. An additional fee of $150 per pet will apply. Maximum number of 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.