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Assateague Overlook

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

This property has a location that is rich with views and 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. 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 (upstairs) has two twin beds and you'll find another full bathroom on the second level as well. Need more space? Rent Channel Lookout next door! (Waterfront area, dock, pier and playground equipment pictured are community property at Memorial Park.)

- 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.

The Haven

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

We're pleased to bring you "The Haven" located on the edge of the Assateague Channel! Enjoy spectacular views of the Channel and Lighthouse right from your own private living space! Downstairs features a kitchen, dining area, living room and half bathroom. The second level features 2 bedrooms - one is a master suite with King bed and private bathroom, and the other features a Queen bed. There is also a 2nd full bathroom on this level. The third level features a bedroom (Queen and 2 Twin beds) and a full bathroom. There are multiple decks and there's also 21' of dock space where you can fish, crab, kayak or tie up a small boat. Take a look and book today; this one won't last long!

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.

Our Happy Place

3 Bedrooms
2 Baths
7 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Discover your own piece of paradise at this incredible beach getaway! 'Our Happy Place' is the perfect retreat for up to 7 guests seeking comfortable, tastefully decorated accommodations. This cozy vacation home is clean, simple, and fully furnished, including amenities that will make you feel right at home. Even your furry, 4-legged family members can join in on the fun, small to medium dogs are welcome.

Situated in the desirable Oyster Bay I waterfront community, 'Our Happy Place' is located at the end of a wide-mouth canal, offering unobstructed water views and a private dock platform. You'll love the convenience of being situated next to the community boat ramp, making it easy to launch your watercraft for a day of adventure.

Relax and unwind on the expansive wrap-around screened porch overlooking the water, featuring plenty of comfortable seating and a dining area. Savor your morning coffee or sip a cool drink after a day at the beach.

'Our Happy Place' is a single-level home with 3 cozy bedrooms that can accommodate up to 7 guests. The bedrooms include 1 queen, 2 twins, and 1 bunk bed (twin over double). There are 2 full bathrooms, one of which is a tub shower combo.

- 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. 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.

Pony Dreams

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Town & Country
Gas Grill
Screened Porch
Internet

Welcome to your perfect Chincoteague Island retreat! This brand-new three bedroom, two bathroom house offers the ideal blend of comfort and coastal charm for your vacation getaway. The open floor plan creates a seamless flow between living spaces, making it perfect for gathering with family and friends after days spent exploring this beautiful, picturesque island.

The heart of this home is its fully stocked kitchen, equipped with everything you need to prepare memorable meals using fresh local seafood. Step outside to discover your own screened "crab shack" gazebo – a delightful covered space where you can enjoy meals while staying protected from the elements. Fire up the gas grill for outdoor cooking adventures, whether you're preparing the day's catch or hosting a casual barbecue. 

Location is everything, and this property delivers. Situated close to Maddox Boulevard, you'll have easy access to the island's main thoroughfare leading to pristine beaches. The nearby Bay to Beach Trail access point offers scenic walking and biking opportunities just minutes from your door. Families will appreciate the proximity to Maui Jack's Waterpark for splash-filled fun, while nature lovers can venture to the renowned Assateague Beach to spot wild ponies and enjoy miles of unspoiled coastline.

This thoughtfully designed home provides modern amenities in a relaxed vacation setting. There's plenty of parking, including a space for your boat/trailer (up to 21'). Whether you're planning beach picnics with provisions from your well-appointed kitchen, or simply unwinding after adventures in the comfortable living spaces, every detail has been considered for your enjoyment. Experience the magic of Chincoteague Island living in this exceptional rental home.

- No smoking is permitted on the premises. 

- No pets are permitted on the premises. 

- Linens and towels are included with your reservation.

- 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.

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.

The Pines on Finney Creek

3 Bedrooms
3 Baths
12 Guests
Waterfront
Boat Dock
Gas Grill
Internet
Outdoor Shower

Wake up to birdsong, spend the afternoon paddling around, and wrap up the evening watching the sky light up over Finney Creek. Sounds pretty good, right? This freshly renovated three-bedroom, three-bathroom home makes that whole relaxing routine your new normal.

Sitting on private acreage in a quiet, tree-lined pocket of the Town of Onancock, this rental is made for folks who take their downtime seriously. You've got your own pier and boat dock reaching right into the creek, so kayaking, fishing, or just dipping your toes in the water is always an option. The sprawling decks and big outdoor area leave plenty of room to grill, hang out with friends, or plant yourself in a lounge chair and stay put for a while.

When the weather isn't cooperating, head into the roomy sunroom. There's a pool table and other activities ready for a little friendly competition. Inside, the upscale kitchen actually makes cooking fun, and the newly remodeled bathrooms have that clean, just-finished feel you'll notice the second you walk in.

Honestly though, the setting steals the show. Wildlife roams around like it owns the place, the pace stays nice and slow, and the quiet here is the kind you didn't realize you'd been missing. Even so, charming downtown Onancock is only a few minutes off. East Point Marina and the Onancock Wharf are close by for some easy waterfront wandering, Food Lion handles the grocery runs, and Chincoteague Island makes for a fun day trip whenever you feel like venturing out.

So if you're ready to swap the everyday noise for the gentle sound of the creek, this place is waiting. Give us a call and schedule your stay today. You'll be glad you did.

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This home is pet friendly with an additional fee. 

- 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.

My Island Escape

3 Bedrooms
2 Baths
7 Guests
Chincoteague Island
Water Access
Boat Dock
Charcoal Grill
Internet
Outdoor Shower

Tucked away on a quiet lane off of North Main is where you will find My Island Escape. This brand-new home is absolutely immaculate! Luxury finishings, tastefully appointed furniture and decor make for a flawless backdrop to your next vacation. The living room at My Island Escape features ample comfortable seating and a flat screen television, and flows into the fully equipped, gourmet, eat-in kitchen that features a large island and plenty of space for cooking, dining, and enjoying meals with the family. The master bedroom features a Queen size bed with an en suite highlighted by a large soaking tub, double vanity, and separate glass stand up shower. The two other bedrooms in the home are close by a full bathroom located off the hallway. Another bonus in this home is the spacious laundry room complete with a full-size washer and dryer, iron and an ironing board, and connects to a convenient half bath. Outside, you will find deck space with outdoor furniture, and a picnic table with umbrella for outdoor dining. If you are looking for a clean, relaxing, upscale rental with great attention to detail ? look no further and escape to My Island Escape!

- 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.

Fisherman's Cottage

1 Bedroom
1 Bath
4 Guests
Chincoteague Island
Town & Country
Pet Friendly
Gas Grill
Internet
Outdoor Shower

Welcome to this fabulous, cozy retreat on Chincoteague Island! The charming one-bedroom, one-bathroom cottage offers the perfect getaway for up to four guests, and you can bring Fido as well!

Nestled in a quiet location, this delightful home puts you within easy reach of the town's attractions, Beach Road (Maddox Blvd.) the Assateague Lighthouse, Memorial Park and even some wonderful eateries. After a day of exploration or relaxation at the beach, unwind on the screened porch, where you can sip your favorite beverage and listen to the soothing island sounds. Fancy a bit more outdoor living? Fire up the gas grill and enjoy a delicious meal on the patio. It's the perfect spot for swapping stories and making memories under the stars.

Inside, you'll find a tastefully remodeled space that's clean, cute, and comfortable. The house comes equipped with all the modern luxuries you need for a stress-free stay. Coffee lovers, rejoice! You have your choice of a drip pot or Keurig machine to kickstart your mornings. The primary bedroom offers a Queen bed and a peaceful sanctuary for rest, while additional sleeping arrangements (Double-size sleep sofa in the living room) ensure everyone has a comfy spot to drift off to dreamland.

Whether you're here to spot the famous Chincoteague ponies, visit the Assateague Island Lighthouse, or simply soak up the laid-back island vibes, this rental has you covered. It's just a hop, skip, and a jump from local hotspots like Memorial Park! So, pack your flip-flops and your sense of adventure – this little slice of island paradise is waiting for you. Just remember, what happens on Chincoteague stays on Chincoteague... unless, of course, you can't resist posting those amazing vacation pics!

- 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. 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.

Windsor House

3 Bedrooms
2 Baths
8 Guests
Chincoteague Island
Gas Grill
Internet

Time to hit the road and get ready for a beachy retreat at "Windsor House"! The moment you step inside, you'll be dazzled by the vibrant colors that'll make you feel like you're in paradise! The spacious living room and kitchen are perfect for whipping up a delicious meal or hosting a fun-filled bash! The primary bedroom is fit for royalty with its king-sized bed, snuggly and inviting. And there's more! The two additional bedrooms have a queen and two double beds to cater to all your guests. And when you want to take things outside, you'll find a grill to cook up a storm and outdoor seating to enjoy the island breeze. Get ready to soak up the sun in style! Located off of Clark street, you are within close proximity of many restaurants, local shops, and a short drive to the beach!

- 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. 

 

Sunkissed Shores

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

Sunkissed Shores invites you to experience waterfront living at its finest. This expansive four‑bedroom, four‑and‑a‑half‑bathroom retreat sits directly on Chincoteague Bay, offering sweeping water views and unforgettable sunsets from every room. Each bedroom features its own private balcony and ensuite bath, including two king suites on separate levels for added privacy. A cheerful bunkroom provides flexible sleeping for families and groups, and thoughtful touches like two pack ’n plays and a highchair make traveling with little ones effortless.

The heart of the home is the stunning great room, where soaring ceilings and dramatic walls of windows bring the bay right inside. During cooler months, the seasonal fireplace transforms this space into a warm, inviting haven—perfect for watching winter sunsets or enjoying a quiet evening indoors. A fully equipped  kitchen—with generous counter space, quality cookware, and every gadget you could need—makes meal preparation and entertaining a pleasure. Just off the living area, an enclosed all‑weather gazebo opens to a large waterside deck, creating the perfect setting for crab feasts, morning coffee, or simply relaxing as the sky shifts from gold to pink each evening.

Upstairs, the game loft offers entertainment for all ages with a classic 1980s Space Invaders arcade machine, a commercial‑grade 4‑player arcade table with over 2,500 games, a 77" TV, board games, a chess/checkers table, and a giant wall‑mounted Connect 4. A queen sleeper sofa provides additional space for guests, and each upstairs bedroom sits in its own private wing for a peaceful retreat.

Step outside to your private pier, where you can fish, crab, or launch kayaks directly into the bay. The bulkheaded shoreline offers easy access to the water, and the eastern side of the property provides serene sunrise views over the marsh—giving you the rare opportunity to enjoy both sunrise and sunset from the same home. With unmatched views, thoughtful amenities, and room for everyone to unwind, Sunkissed Shores stands apart as a place where memories are made and every day ends with a sunset worth savoring.

- 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.

Pony View

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

Enjoy your cup of coffee as the sun peeks over the salt marshes of Assateague Island. You can often see a herd of our famous wild ponies grazing to the right of the lighthouse from your private waterfront deck and second-floor balcony - not to mention the copious amounts of waterfowl and other wildlife in the channel. Pony View boasts three bedrooms - A master with queen bed, full bath, and balcony on second floor, as well as another bedroom with a queen on the second floor - along with another full size bath. On the third floor you will find an amazing view of the marsh with the panoramic window and four twin beds, and a beautiful bathroom with a rustic wooden sliding door. The ground floor is where you'll find the hub of the house - fully equipped kitchen with refrigerator, electric range, dishwasher, and plenty of counter space. A dining table and bar seating area, a half bath, and a cozy living area with floor-to-ceiling knockout views. Or enjoy the waterfront deck just outside the living room. Pony View is pet-friendly so your furry friend can enjoy the water view as well. Dock access along with a boat slip is available for your use. Crab and fish right from the house! A deep water boat ramp is found just at the end of the complex for you to drop in. Central air/heat will keep you comfortable year round. There is also a washer/dryer, and an outside grill for your use while you're with us. Memorial Park is just a short walk up the street for a wonderful waterfront park and playground, tennis and volleyball courts, fishing pier, picnic areas, and walking trail.

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. 

- This property is pet friendly. An additional fee of $150 per pet will apply. Maximum pets allowed: 4. 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.

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