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Seaside

3 Bedrooms
2 Baths
8 Guests
Cape Charles
Pet Friendly
Gas Grill
Internet

Welcome to "Seaside", your next relaxation haven! This charming 3-bedroom, 2-bathroom duplex offers the perfect blend of comfort and convenience, nestled in the delightful town of Cape Charles. Whether you're in town to soak up the sun at the beach or simply unwind, this property is designed to suit every aspect of your leisurely needs.

Step inside to discover a cozy atmosphere with well-appointed spaces that promise a homely feel from the moment you walk in. The primary bedroom, a restful retreat, along with two additional amply-sized bedrooms, ensures everyone has their personal space. Entertaining? The open-concept living area present the ideal setting for creating memories with loved ones.

Forget about the hassle of street parking; this house comes with its very own off-street parking spots. And for those who can't bear to leave their furry friends behind, you'll be pleased to know this home is pet friendly!

Just a short stroll away lies Central Park, where you can enjoy everything from a peaceful morning jog to a lively afternoon picnic. Need to pick up some essentials or a quick snack? There are many conveniences downtown, or the grocery store is just a little over 2 miles away—talk about convenient shopping!

Whether you're looking for a calming weekend getaway or seeking a serene place to call home for a while, this house checks all the boxes for a laid-back yet vibrant living experience. Book your stay, pack your bags, and prepare to relax—your beachside vacation awaits!

Located right next door to this beautiful duplex is "Bayside". Larger group? Bring along your friends and family and rent both units! 

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation. 

- This property is pet friendly with a pet fee of $150 per pet (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.

 

zLT - 5457 Warren Street

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Town & Country
Pet Friendly
Screened Porch
Internet

Discover your perfect island getaway at this delightful four-bedroom, two-bathroom house nestled in the peaceful Richardson's Landing community on Chincoteague's quiet north end. This comfortable home offers everything you need for a relaxing vacation, whether you're planning a family retreat or a fun-filled adventure with friends.

Step outside to your own private screened porch, where morning coffee tastes better and evening conversations last longer. The spacious yard provides plenty of room for outdoor games, barbecues, or simply soaking up the island sunshine. Inside, you'll find clean, comfortable living spaces that make it easy to unwind after busy days exploring the area.

The location puts you perfectly positioned to enjoy both tranquility and excitement. When you're ready for some splashing fun, Maui Jack's Waterpark is just a short drive away. Nature and beach lovers will appreciate the nearby Chincoteague National Wildlife Refuge, home to the famous wild ponies and incredible birdwatching opportunities. For your convenience, Island Foods Great Value grocery store ensures you'll have everything needed for home-cooked meals.

This newly available vacation rental combines the best of island living with modern comfort. You'll love the peaceful setting that still keeps you close to all the attractions that make Chincoteague special. From wildlife watching to beachcombing, your island adventure starts here in this welcoming home that's ready to become your home away from home.

- 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.

Beachin' at the Cove

3 Bedrooms
2 Baths
6 Guests
Captain's Cove
Pool

Come and enjoy a private place to call home during your much needed vacation! Beachin' at the Cove has everything you need to enjoy a quick or extended getaway.  The location of this inviting home is superb! Overlooking one of the Shore's best golf courses, Beachin' at the Cove provides a desired location for your perfect beach escape. In this cozy, single family home, you will be greeted by a covered porch where you can sit and sip your morning coffee or tea. You will then enter an inviting, open living area adjacent to the kitchen with access to the large and open back deck. This home offers first floor sleeping quarters as well as a full bathroom and hardwood flooring throughout. Upstairs you will find 2 more bedrooms and another full bath. The beautiful community of Captain's Cove offers many amenities, with something suited for the entire family. Beachin' at the Cove is located just a short distance from waterfront dining on the Chincoteague Bay, 3 pools, a 9 hole golf course, tennis, basketball, fitness, and much more! Conveniently located, you're approximately 20 minutes from Chincoteague Island, 30 minutes from Snow Hill and less than an hour to Ocean City MD.

- 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.

- 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. No Sunday check-ins or check-outs are permitted. 

Crabby Pines

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Town & Country
Pet Friendly
Gas Grill
Internet

Discover comfortable vacation living in this charming one-level ranch home. "Crabby Pines" offers a cozy retreat with three bedrooms and two bathrooms, providing ample room for relaxation and privacy. The house is ideally situated in a serene residential neighborhood and features modern amenities that ensure a seamless, convenient lifestyle.

Enjoy the convenience of being just minutes away from the public boat ramp at Fur Landing. Outdoor enthusiasts will appreciate the close proximity to nature trails and a dog park, perfect for morning jogs or leisurely evening walks with your furry friends. Oh, did we mention this home is pet friendly? Additionally, the property is located near the 'Beach Road,' a vibrant area bustling with mini-golf, dining options, ice cream shops, and boutiques - offering endless entertainment options.

This welcoming home is designed with practicality in mind, ensuring that each space is utilized efficiently while still exuding a sense of warmth and comfort. The property's easy access to local amenities, combined with its peaceful surroundings, makes it an ideal choice for anyone looking for a balance between nature and community activities.

Whether you're settling down with family or looking for a tranquil spot to return to after a day of adventures on the island, this home is sure to meet your needs. Embrace a laid-back lifestyle in Chincoteague with this delightful vacation home opportunity.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This home is pet friendly with an additional fee. Maximum of two dogs under 25 lbs. each; 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. No Sunday check-ins or check-outs are permitted.

Blue Crab Bungalow

1 Bedroom
1 Bath
5 Guests
Chincoteague Island
Pet Friendly
Internet
Outdoor Shower

Welcome to this charming bungalow located in the center of Chincoteague Island! This delightful house offers a cozy and comfortable living space, making it the perfect place to call home. With 1 bedroom and 1 bathroom, this property is ideal for individuals or a small family looking for a serene retreat. As you step inside, the throw-back retro kitchen adds character to the home and makes cooking an enjoyable experience. Whip up your favorite meals while reminiscing about the good old days. The kitchen is equipped with all the necessary appliances to satisfy your culinary desires. You'll be greeted by the warmth of the main bedroom featuring a comfortable queen bed. The second sleep area serves as both a sleeping and an office space, with a twin pull-out sofa providing versatile accommodation options. Whether you work remotely or simply need a quiet space to focus, this flexible layout has got you covered! The bungalow is close to town and 'Beach Road' - convenience is at your fingertips. Enjoy easy access to local amenities such as shops, restaurants, and entertainment options. Whether you're in the mood for a leisurely stroll or need to run some errands, everything is just a short distance away. After a long day, relax and unwind in the enclosed front porch. This inviting space is perfect for enjoying your morning coffee or savoring a glass of wine in the evening breeze. Additionally, there's an outside shower, allowing you to rinse off after spending time at the nearby beach. With parking spaces for 2 vehicles, parking won't be a hassle. Don't miss out on the opportunity to make this charming bungalow your next vacation spot! With its convenient location, versatile layout, and retro charm, it's sure to steal your heart. 

- *NEW FOR 2025: Level 2 EV charger!*

- 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. Small dogs only, restricted to two (2) pets. 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.

Dancing Waters at Sea Tag

2 Bedrooms
1 Bath
6 Guests
Chincoteague Island
Waterfront
Boat Dock
Charcoal Grill
Internet

Do you love to be on the water? Maybe that means casting a line from your fishing pole, trying your hand at crabbing, or just gazing at the sereness of the tide rolling in and out. Either way, you can do all of that - and more - here at 'Dancing Waters at Sea Tag'! This 2 bedroom/1 bathroom remodeled condo is clean, comfortable and waiting for you! Conveniently located within walking distance to boat rentals, Memorial Park and a public boat launch. You'll also be able to enjoy some of the best views on the island - look out over the Assateague Channel and marshlands where wildlife abounds and set your sight on the Assateague Lighthouse. It's all right there!

- 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.

Robert's Retreat

5 Bedrooms
3 Baths & 1 Half
10 Guests
Captain's Cove
Water View
Gas Grill
Pool
Internet

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. 

- 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.

Anchors Away

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

Welcome to "Anchors Away," a captivating waterfront home now available for rent, offering an unparalleled living experience. This remarkable property boasts four generously sized bedrooms and three well-appointed bathrooms, providing ample space for comfort and privacy.

Nestled in a vibrant community known for its welcoming atmosphere and scenic beauty, this home is designed to impress with its stunning waterfront views that can be enjoyed from the spacious decks - perfect for entertaining or simply unwinding in nature's embrace.

The first-floor suite offers convenience and accessibility, ensuring that everyone can enjoy this home's charm without compromise. The interior is just as impressive, featuring granite countertops and stainless appliances that add a touch of elegance to the functional and stylish kitchen. 

With parking space for up to four vehicles, you'll find this property not only beautiful but also practical. The pet-friendly policy ensures that your beloved companions can join you in calling "Anchor's Away" home.

This house is more than just a place to vacation; it's an opportunity to make life-long memories for those who value beauty, community, and comfort. Whether you're gazing at the serene waters from your deck or enjoying the modern amenities inside, this home invites you to live your best life.

Don't miss the opportunity to make "Anchor's Away" your new haven. Contact us today to experience firsthand everything this exceptional rental property has to offer.

- 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: 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.

- 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. No Sunday check-ins or check-outs are permitted. 

Blue Heron's Hideaway

3 Bedrooms
2 Baths
12 Guests
Chincoteague Island
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Discover your perfect family retreat at this charming three-bedroom, two-bathroom house nestled in peaceful Oyster Bay II on Chincoteague Island. 'Blue Heron's Hideaway' welcomes up to 12 guests, making it ideal for multi-generational gatherings, friend reunions, or anyone seeking a memorable coastal escape.

The heart of this home lies in its thoughtfully designed layout, offering both communal spaces for togetherness and quiet nooks for those precious moments of solitude. Fall in love with the screened-in porch—your new favorite spot for morning coffee, afternoon board games, or listening to gentle summer rain. When you're ready for fresh air and broader views, head upstairs to the deck where peaceful vistas and cooling breezes create the perfect setting for birdwatching or evening stargazing.

The well-appointed kitchen makes meal preparation a pleasure with its dual-oven electric stove, elegant granite countertops, and full-size appliances. Families will appreciate thoughtful touches like the provided high chair, pack-n-play, and collection of board games suitable for all ages.

Located in a tranquil residential neighborhood, this trusted vacation favorite sits at the end of a quiet cul-de-sac, surrounded by lush trees and natural landscaping that creates a beautifully secluded atmosphere. You'll feel worlds away from everyday stress while remaining just a short drive from Assateague Wildlife Refuge, pristine beaches, local restaurants, and charming shops. Remote workers will appreciate the private business nook complete with desk and monitor, allowing you to balance productivity with relaxation. Since 2018, this beloved hideaway has hosted everything from girls' weekends and holiday celebrations, to hunting expeditions and peaceful solo retreats.

Whether you're seeking adventure at nearby Maui Jack's Waterpark, exploring Waterfront Park, or simply enjoying the serenity of island life, this exceptional rental offers the perfect base for your Chincoteague "home away from home" experience.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- Pets are permitted with an additional fee. Limit of two dogs only. All pets must be disclosed. 

- 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.

Diving Duck

5 Bedrooms
2 Baths & 1 Half
10 Guests
Captain's Cove
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Hot Tub
Internet
Outdoor Shower

If you're looking for the complete vacation package, look no further! This 5 bedroom home features a spacious open floor plan with wall-to-wall sliding doors and windows, allowing natural light to permeate throughout the home. Downstairs you'll find the living room and great room with access to the waterside deck, a large dining area, kitchen with all the counter space you'd ever need, a half bathroom, and the master bedroom with private bath (with custom tile shower and soaking tub). Upstairs features a landing area with sofa and foosball table, 4 more bedrooms and another full bathroom. Aptly named, 'Diving Duck' is the perfect spot for watching the ducks and wildlife pitch in the bay just out the back door. There's even a floating dock perfect for launching canoes and kayaks! And as if all of that is not enough, the Captains Cove community features swimming pools (2 outdoor, 1 indoor), a fitness center, marina club restaurant and 9-hole golf course. (Fee applies for usage of community amenities.) This rental home is approximately 20 minutes to Chincoteague/Assateague Island (the beach) and 30 minutes to Ocean City, MD (beach & boardwalk attractions). What more could you ask for? Book your stay at 'Diving Duck' today! Additional game room with wet bar and pool table, and a private hot tub. All of this in addition to interior updates and renovations!

- 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.

- Community amenities require passes for an additional fee. Although the rental home can accommodate up to 10 guests, only 8 guests are permitted to use the community amenities (pool, etc.) at a time.

- 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. No Sunday check-ins or check-outs are permitted.

 

Eastside Escape

4 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Town & Country
Gas Grill
Screened Porch
Internet

Discover the perfect blend of comfort, convenience, and coastal charm at 'Eastside Escape', a beautifully updated vacation home ideally located in the center of Chincoteague Island. Whether you’re here for wild pony sightings, beach days on Assateague, or simply to unwind in a peaceful seaside town, this home offers the ideal setting for your getaway!

Step inside and you’ll find a bright, welcoming interior designed for relaxation. The cozy living area invites you to kick back after a day of exploring, while the fully equipped kitchen makes it easy to prepare your favorite meals. Thoughtful touches throughout the home provide the comfort of modern amenities with the warmth of traditional island style.

Featuring four spacious bedrooms and two full bathrooms, this home provides plenty of room for families, couples, or small groups—offering privacy and comfort for everyone in your group. The outdoor space is just as inviting: enjoy morning coffee on the porch, gather for an evening barbecue, or unwind under the stars after a day at the beach.

Conveniently located on Church Street, you’re moments from everything that makes Chincoteague special: charming downtown shops, cafés, and restaurants; the waterfront and iconic sunsets; bike paths and nature trails; Assateague National Seashore with its beaches and wild ponies, and so much more!

Whether you’re seeking relaxation, adventure, or a little of both, 'Eastside Escape' offers the perfect home base for your island getaway. Book your stay today and experience the magic of Chincoteague—from a home that feels like your own.

- 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.

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