You are here

Displaying 49 - 60 of 95 results matching your search criteria
Map View
List View

Avalon

4 Bedrooms
2 Baths & 1 Half
10 Guests
Chincoteague Island
Waterfront
Screened Porch
Internet
Outdoor Shower

Avalon is a charming 4 bedroom, 2.5 bathroom home situated on a bulkheaded waterfront lot on Oyster Bay! There is a large great room that boasts two family rooms, a dining area and large kitchen. From the gas fireplace, to the 16' cathedral knotted pine ceilings, this home is bright, warm and inviting. Avalon offers two queen bedrooms with screened porch access (one private) and two twin bedrooms. Offering over 600 sq. ft. of screened porch - you could live outdoors! The first level also offers a full size futon and 1/2 bath. Avalon is one of our most popular offerings; it books quickly! 

- 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.

Wildflower

3 Bedrooms
3 Baths
6 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Beautiful waterfront home with shared pier plus floating dock on deep water!! Ground level is a large screened patio perfect for those summer time seafood feasts. The first level is great room boasting reclaimed barn board walls and wide plank pine floors with a separate den and full bath. There is a second screened porch overlooking that water from the great room. The second level has a large waterfront master suite with a private balcony, two more bedrooms and another full bath. Close to Memorial Park right across the street from a family restaurant! (Spiral staircase in home, may not be suitable for small children.) For larger groups for family reunions, check out nearby Moon Rising or Herbie's Hideaway!

- 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.

June's Retreat

4 Bedrooms
5 Baths
10 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

June's Retreat is Chincoteague Island's premier luxury vacation rental home, nestled on serene waterfront marshlands just north of town off of Main Street. This custom designed and decorated home leaves no detail unnoticed. From the bright spacious rooms with floor-to-ceiling windows to the expansive wrap-around verandas, you'll feel as though you're one with nature and your surroundings. Downstairs features a chef's quality kitchen, private billiards room, waterside glass atrium, living room, private den, formal dining room, sitting room and a bathroom. Upstairs you'll find 4 bedrooms with bathrooms (en suite), a sitting area and balcony. The panoramic views of Chincoteague Bay are unobstructed and unsurpassed. Come and see for yourself; we promise you won't be disappointed!

- 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.

Serenity at Oyster Bay

3 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Water View
Gas Grill
Screened Porch
Internet
Outdoor Shower

Aptly named, "Serenity at Oyster Bay" is just what you'll find at this delightful vacation home. Located in the highly-demanded community of Oyster Bay I, you'll enjoy the peaceful, quiet area nestled amongst the tall pines and marsh grasses. The main living area features a fantastic open floor plan; perfect for gathering the family and entertaining. The back of the house features a bright sunroom that looks out over a natural preserve - cozy up with a cup of coffee and a nice book! This home also features 3 bedrooms, 2 full bathrooms (completely remodeled) and has undergone a lot of fresh new upgrades! There's a little sitting deck out back, a screened porch, covered picnic/game area (with cornhole boards), fish cleaning station, and so much more! And, as if that's not enough, there are water views and you're very close to the Oyster Bay Community water access! Don't delay - Serenity at Oyster Bay is sure to book quickly!

- 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.

Shreiner's Tradition

2 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Pet Friendly
Screened Porch
Internet
Outdoor Shower

As one of our newest vacation rental offerings, we're pleased to be have this downtown charmer! Shreiner's Tradition is a renovated 2+ bedroom home located just outside the downtown area. Enjoy walking to restaurants, shopping, ice cream and the movie theater! This home features an eat-in kitchen, 2 living room/sitting areas, 2 bedrooms upstairs (each has a double bed) and a walk-through room with bunk beds. Not to mention the great front porch - you'll enjoy mornings and afternoons sipping coffee or relaxing after the beach!

- 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 pet pet. All pets must be disclosed prior to arrival. Pet restriction: 2 dog limit and 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.

Sun Rayes

4 Bedrooms
3 Baths
8 Guests
Captain's Cove
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Internet
Outdoor Shower

We welcome "Sun Rayes"! What does this fabulous home have to offer? The question is: what doesn't it offer?! With 4 bedrooms, 3 bathrooms, 3 stories (with an elevator), a game room (ping pong, pool table, dart board, ring toss) and expansive decks - there's room for everyone! Situated on a canal in the popular Captain's Cove community, you have access to a boat ramp and you can dock your boat right outside your door! Also perfect for fishing, crabbing, kayaks, etc. Sun Rayes is packed full of fun - there are so many great spaces for entertaining and relaxing. The Captain's Cove community offers 3 pools (2 outdoor & 1 indoor), tiki bar, Marina Club and restaurant, 9-hole golf course, kids playground, dog park and more! (amenities are available for use with fee)  And you're only 20 minutes from Chincoteague & Assateague Islands (the beach), and 30 minutes from Ocean City, MD (boardwalk & amusements).

- 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: 2 pet max.

- 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.

- 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. 

Dragonfly Point

4 Bedrooms
3 Baths
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

"DRAGONFLY POINT" is a magnificent waterfront property on Oyster Bay & canal. Surrounded by water on three sides of the home, you see the bay and canals from every window! The abundance of decking for entertaining will amaze you with easy access on both floors. Upper family room/loft with unobstructed views. The home has beachy-chic feel with built in bookcases, shiplap, custom fixtures and bathrooms, and more. Two master bedroom suites - upper and lower. Totally fenced in yard that has mature plantings, kayak launch with concrete pad, 120' pier that extends into the bay, comfortable screened porch and much more! Many updates recently including washer & dryer, brand new kitchen & appliances, new bathrooms, etc. SIMPLY BREATH TAKING VIEWS! Come for a stay at Dragonfly Point - it's one you surely will not forget!

- This property has a 7 night minimum stay year 'round. 

- 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.

All Done

3 Bedrooms
3 Baths & 1 Half
8 Guests
Chincoteague Island
Water View
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

All Done is located on the popular East Side Road, just minutes from downtown, Maddox Blvd (Beach Road), Memorial Park and the beach on Assateague Island. There are snippet water views of the Assateague Lighthouse and Channel. It is a brand-new home just built in Spring of 2024, and features an open first floor plan joining the kitchen, dining and living rooms into one, as well as a first floor bedroom with full bath. The second floor has 2 more bedrooms including individual full bathrooms, with a walk-in shower in the primary bedroom. There is a spacious laundry room also conveniently located on the second level. The outside of All Done includes a screened porch on the side of the home, and a spacious front porch with ample rockers to enjoy the sunsets over the tree line. There is also a charcoal grill, a large yard for games and parking for up to 4 cars.

- 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. 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.

Cockleshell Cottage

3 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Nestled on a quiet cul-de-sac in a private community just off North Main Street (Oyster Bay II) is where you'll find the charming Cockleshell Cottage! This modern 3 bedroom, 3 bathroom home boasts a first-floor master bedroom suite (Queen), all amenities and comfortable furnishings. Upstairs features 2 more bedrooms (Double and Double/pull-out Twin trundle), and a full bathroom. Cockleshell Cottage is handicap accessible. Relax and enjoy the breeze on the open front porch or back screened porch. Call us today; this home books fast!

- 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. Pet restriction: limited to two small dogs 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.

Osprey

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Water Access
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

This great contemporary beach home is located at the edge of the community harbor area, a perfect location for you and your guests. As a pet friendly house, you'll enjoy the wide open spaces for your dogs. The home features an open floor plan with a lovely eat-in (and completely renovated!) kitchen and cook area that is flanked by a huge screened porch overlooking the community harbor. You can enjoy all your meals on the porch! In addition, you'll find bright, airy and spacious bedrooms with TVs including a master bedroom suite with King size bed and private bath. There's plenty of parking. You and your guests can crab and fish from the community dock, located just a few steps from your door. Enjoy a great vacation at Osprey!

- 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.

Ryokan

4 Bedrooms
2 Baths
12 Guests
Chincoteague Island
Waterfront
Gas Grill
Internet
Outdoor Shower

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.

Heron's Cove On Salt Meadow

4 Bedrooms
5 Baths
12 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

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 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.

Pages