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Sunset Bay Cottage

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Water View
Pet Friendly
Gas Grill
Internet
Outdoor Shower

Experience island living at its finest in this beautifully restored Victorian home on North Main Street. This 3 bedroom, 2 bathroom rental offers the perfect blend of historic charm and modern comfort. The enchanting enclosed front porch provides the ideal setting for your morning coffee while watching the town come to life.

Step inside to discover a thoughtfully renovated interior that maintains the home's original character while incorporating contemporary amenities. The first floor features the living room with a sleep sofa and full bathroom, while the second floor hosts two bedrooms (each with a Queen bed) and another full bathroom. The entire third floor is a loft-style bedroom that houses a Double + 2 Twin beds. 

One of the property's most captivating features is its magnificent water views of Chincoteague Bay. Imagine ending each day with spectacular sunset vistas painting the sky in brilliant hues of orange and pink. The location couldn't be more perfect — situated across from a waterfront park, you'll have easy access to outdoor recreation.

The carefully landscaped backyard creates a private retreat with a dedicated sitting area perfect for afternoon reading or evening conversations. Enjoy s'mores in the evening over the fire pit. The spacious deck extends your living space outdoors, ideal for entertaining or simply soaking in the island atmosphere.

Located in the heart of Chincoteague, you'll be within walking distance to Island Nature Trail and a short drive to local attractions including Maui Jack's Waterpark and the renowned Chincoteague National Wildlife Refuge & Beach.

This isn't just a house—it's an invitation to embrace the relaxed coastal lifestyle that makes Chincoteague so special. Ready to write your own chapter in this charming island home? Come and see for yourself!

Special Note: The stairway to the third level is narrow and steep. There are adult bicycles and beach gear for guest use. 

- 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. Pet Restriction: Small dogs under 35 lbs only. 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.

 

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. 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.

- 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. 

Seahorse Cove

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Pet Friendly
Screened Porch
Pool
Internet

Welcome to Seahorse Cove! This is an adorable 3 bedroom, 2 bathroom home that has been completely renovated. You will not be disappointed - from the personal touches, to the decor and amenities this lovely home has to offer - no detail has been left untouched. As soon as you enter, you will immediately fall in love with the bright, beachy colors, and the overall feeling of complete relaxation. Seahorse Cove offers a fully equipped kitchen with stainless steel appliances, granite countertops, a breakfast bar, and all of your cooking essentials for providing a delicious meal. Enjoy the sounds of nature from the cozy screened porch, while sipping your morning coffee or enjoying an evening beverage. The owner's suite is furnished with a comfy rocker, plush bedding and a private bath with a tiled shower.  You will also find two additional bedrooms on the opposite end of the home, along with another full bathroom. There is plenty of room outside to enjoy, or to let your fur baby play.

This home is conveniently located to all the community amenities such as pools (2 outdoor & 1 indoor), fitness center, marina w/ fishing pier, restaurant, tiki bar, and more! If day-tripping is more your style, you'll love the fact that this home is located only 20 minutes from Chincoteague Island and the beach, or 30 minutes to Ocean City, MD and the boardwalk amusements.

- 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: 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. 

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. An additional fee of $150 per pet will apply. Maximum number of pets allowed: 2. Pet Restriction: Small dogs only, under 35 lbs. 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.

Dockside

3 Bedrooms
3 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Internet

Located on the Assateague Channel, this is your chance to watch the ponies from your own deck. A wonderful panoramic view awaits you; to the left is the Assateague Bridge; to right of the bridge is the Assateague Lighthouse and ponies; and to the far right is Tom's Cove and the ocean inlet. Come and fish from your own dock and tie your boat along side! Inside you will find central heat/air, 3 decks, all appliances, gas grill, satellite TV & DVD player and internet access. Enjoy evenings resting beside the wood fireplace (off-season).

Please note: Parking is limited to 2 spaces (this includes a boat/trailer if you are bringing one). Max. boat size for docking is 20'. If alternate parking accommodations are needed, please ask. 

- 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.

Salty Oyster

5 Bedrooms
6 Baths
14 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Internet

Welcome to the crown jewel of Chincoteague Island vacationing! This completely renovated five-bedroom, six-bathroom home offers a rental experience that transcends the ordinary, delivering the kind of coastal luxury that transforms a vacation into a lasting memory.

Every detail of this stunning home has been thoughtfully reimagined from the ground up. Floor-to-ceiling windows flood the main rooms with natural light and frame what are arguably the best views on the island. Rise each morning to gorgeous sunrises painting the water in shades of gold and amber — a private spectacle that never grows old, though you might find yourself setting your alarm earlier just to catch every moment.

The open great room serves as the heart of the home, seamlessly connecting the living, dining, and kitchen areas into one magnificent gathering space. Top-of-the-line appliances, including a wine fridge and ice maker, outfit the kitchen, making meal preparation a genuine pleasure rather than a chore. Whether you are hosting an elaborate dinner for the entire group or simply enjoying a quiet morning coffee, this space accommodates every occasion with effortless elegance.

Each of the five bedrooms features its own private bathroom, ensuring every guest enjoys personal comfort and privacy throughout their stay. Spacious and expansive decks extend the living areas outdoors, providing ample room for relaxation, alfresco dining, and soaking in the island atmosphere.

Nestled within the popular Oyster Bay I neighborhood, this home places you in an enviable position to explore everything the island has to offer. Nearby attractions include the scenic Island Nature Trail for peaceful walks, the beloved Island Creamery for indulgent treats, and Maui Jack's Waterpark for family-friendly thrills. The pristine shores of Assateague Beach, home to the island's famous wild ponies, await just a short drive away.

This exceptional vacation home represents Chincoteague Island living at its absolute finest. Book your stay and see what it's all about - there's no doubt you'll want to return time and time again!

- 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.

Blue Marlin

3 Bedrooms
2 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Internet

Blue Marlin is a brand new home that is now available exclusively - you will NOT want to miss your opportunity. Visitors from all around fall in love with the charm and beauty of our small town. Blue Marlin is nestled just a few short minutes from the heart of our downtown and offers everything you will need to enjoy a true Island vacation. Spectacular views are abound from just about every room of this gorgeous home. From the time you enter, become enamored with the fresh, beach-like feel of this well thought out Island Home. Blue Marlin offers first floor living, complete with a half bath off of the well-equipped kitchen, a king sized bedroom with beautiful bay views, TV, and en-suite bathroom. Upstairs you will find a spacious sitting entertainment area featuring a sleeper sofa and large TV, as well as two bedrooms. Each bedroom is tastefully decorated and comfortably furnished for a wonderful vacation stay. There are two twin beds, as well as a queen sized bed (with 40 in. TV) upstairs, along with a full bathroom. You may take notice to the many handcrafted furnishings in the home that the owners have taken great pride in creating. Blue Marlin offers front porch sitting, breathtaking sunset views, an outdoor grill, long dock with ladder, (yes, bring your boat!) - there's even extra parking for your boat trailer (behind the yellow house). Everything you need for a perfect vacation is here.. Oh, did we mention this home is pet friendly too?! 

- 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 number of pets allowed: 2. Cats will be 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.

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.

Channel Lookout

2 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Water View
Charcoal Grill
Internet

This property has a location that is rich with amenities. Situated right next to Memorial Park, you can sit on the deck and enjoy the water views as the kids run and play, or fish and crab at the waterfront Memorial Park. The first floor is an open room consisting of the kitchen, dining area and living room (with queen sleeper sofa). You'll also find a full bath on this level. The second floor offers a queen bedroom with a private deck that has unlimited views of the Assateague Channel! The second bedroom has two twin beds and you'll find another full bathroom upstairs as well. Come and see for yourself! (Waterfront areas, dock, pier and playground area pictured are public property/Memorial Park.)

- 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.

Serendipity

3 Bedrooms
1 Baths & 1 Half
6 Guests
Chincoteague Island
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

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 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.

Langtree

3 Bedrooms
3 Baths
10 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Screened Porch
Internet
Outdoor Shower

Your home away from home... enjoy the water views, bring your boat and use your own dock, or just relax and listen to the whispering pines. 3 Bedrooms, 2 full baths (plus another shower/bath downstairs), outside shower, washer and dryer, satellite TV, and PET FRIENDLY! Great views of Oyster Bay from the front and back decks, and there's a large screened porch for outdoor enjoyment. On the lower (first level) of the home you'll find a large open room with a Queen and 2 Twin beds, as well as a large utility room and bathroom with shower. The main living level (second level) of the home features the living room, kitchen & dining area, as well as 3 bedrooms (K/K/Q) and 2 full bathrooms. Note: This property has a 7 night minimum stay during all seasons.

-Parking only for 4-5 Cars

- SPECIAL NOTE: This rental home has a 7 night minimum year 'round. 

- 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. 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.

Beach Haven

3 Bedrooms
2 Baths & 1 Half
9 Guests
Chincoteague Island
Town & Country
Charcoal Grill
Internet

If you enjoy being close to town and activities, 'Beach Haven' is most likely your perfect spot! Located on just one block off of Main Street, this lovely home is conveniently located to downtown Chincoteague Island, the movie theater, restaurants, famous Island Creamery, adventure park and more! The wrap around second-level deck is nicely furnished and inviting - it's the ideal place to relax with a cup of coffee in the morning or a cool drink after a long day at the beach. 

As you enter this fantastic modern home, you're greeted by an open floor plan. The main level features the living room, kitchen with breakfast bar, dining room and half bath/powder room. The lower level is entirely a two-car garage that is accessible by guests; it's a wonderful place to store your bikes or beach gear! Upstairs you'll find 3 bedrooms and 2 full bathrooms, one of them being a master bedroom en-suite. Two bedrooms feature a queen bed each, and the third (kid's) bedroom features a bunk bed (2 Doubles) and a Twin bed. 

Lets talk electronics! This home has been carefully and tastefully furnished for the discerning traveler. The living room and all 3 bedrooms all have large Smart TVs, and the kid's bedroom includes an HDMI cable for easily connecting gaming consoles, etc. You'll also enjoy amenities such as keyless self check-in and check-out.

Come for a week in the summer, or come for a shorter stay in the spring or fall. 'Beach Haven' is available year-round and the island is gorgeous the whole year through!

- 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.

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