ALL JUNE RENTALS- 20% OFF 3 or MORE NIGHTS! **Some exclusions apply**
Properties on Special
Admiral Benbow
A very nice contemporary home located in Oyster Bay I community. Located next to the community boat ramp - you have access to the water and the kids can fish and crab from the dock areas. This house has an outdoor ramp to the ground level. Don't miss out on the great screened porch for a family dinner! The variety of bed sizes allow the perfect set up for families of all ages! Come and stay at this classic Chincoteague home but don't delay; it books quickly! This home is a Sunday to Sunday home.
- 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.
Trembling Bay
This beautifully renovated 3 bedroom, 2 bath Chincoteague cottage is nestled along the salt marshes in a natural setting on Chincoteague Bay. A few of the fine features include a private pier, a new kitchen & appliances, waterside screen porch & deck, and private master bedroom suite with a custom-designed luxurious bath. The numerous windows and over-sized sliding doors allow panoramic water views from nearly any spot in the house. The first floor is completely wheelchair accessible and features your main living areas, large master bedroom suite (K) with bathroom, and second full bathroom with shower/tub. Upstairs features the second and third bedrooms (D/2T). If relaxation is what you're seeking, look no further. This quiet, peaceful location at the water's edge will delight the senses. Come and see for yourself; you won't be disappointed!
- 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: 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.
La Vie
Views! Views! Views! Enjoy the expansive panorama from all three levels of this prime waterfront location on Chincoteague Bay. With 180 degrees of natural beauty graced by blissful sunsets, “La Vie” invites you to live the life at its most relaxed.
As soon as you enter the home, its light and airy floor plan lifts your spirit, calms your mind, and promises to rejuvenate your body. Meticulously maintained, continuously updated, La Vie features a fully equipped granite counter gourmet kitchen with a new large six burner induction stovetop. You’ll likely want to cook, or eat, or relax as it gives you a chance to take in the breathtaking water views. Watch the sun set from anywhere in this large open space second floor central living area.
The home’s entry level features a newly furnished queen bedroom with sliding glass doors opening to the incredible views on your waterfront deck. Plus another large bedroom has two twin beds! If you need another bed yet, pull the curtain shut to a cozy alcove and sleep soundly on the full sized sofa bed. Extra privacy abounds in the 3rd floor suite! Enjoy more of the spectacular water views from your king-size bed, private balcony, or wicker lounge chairs. Immerse yourself in the large jacuzzi-style tub. La Vie offers plenty of space to share this retreat for friends and family!
Stream away on any one of the four new UHD 4k smart TVs with multiple HDMI ports.
The amenities aren’t confined to the house:
La Vie also includes access to a 700-foot-long shared pier for fishing or launching kayaks.
Don’t forget your boat! La Vie includes exclusive use of boat slip #1
A summertime pool located right across the street.
Shaded parking directly under the unit.
The historic fireman’s carnival grounds across the street; open most July weekends.
On Pony Swim week, the world famous Chincoteague Ponies parade right in front of La Vie (July).
The town July Fourth fireworks are launched about 100 yards away.
However long your stay may be, you’ll make lasting memories and take the positive energy, beauty, and majesty of La Vie and its surroundings home with you. La Vie, “the life,” is short of La Vie en Rose, which can mean life is as beautiful as you wish to see it.
- 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
Sunset Dreams
If you're familiar with the island you know that the best sunsets can be found on Main Street, and the sunsets waiting for you at Sunset Dreams (located on south Main Street), are NO EXCEPTION. A luxury waterfront townhome overlooking Chincoteague Bay, offering 3 bedrooms and two and a half baths - with a private pier, it's the perfect place to unwind and get on "island time". On the lower level you'll find the open area kitchen and dining area that features a stunning view of Chincoteague Bay and the salt marsh - that has everything you'll need to enjoy the various fresh catches waiting for you just off of the dock, or at our local seafood markets. A comfortable living area also boasts a beautiful waterfront view, with sliding doors that open up to a lovely little sitting porch - perfect for taking in the sunset with a cocktail without having to go too far. There is also a bedroom downstairs with two twins, a half-bath powder room, and a beautiful large sunroom/sitting area - great for sneaking away for a minute to get some work done or curl up with a good book. On the upper level you'll find the master bedroom with a queen bed, a full bath, and a beautiful waterfront view. Another bedroom with a queen bed is upstairs as well. A full bath can also be found upstairs in the hallway, and both bedrooms have televisions. Full sized washer and dryer for washing all those beach towels and bathing suits. You have full access to the dock across the street, so bring your fishing poles and crabbing gear (or visit Captain Steve's on Maddox Blvd to get what you need!). You're a quick two-minute ride to downtown to restaurants and the grocery, or an easy bike ride to the carnival or the sub shop to grab a quick bite to eat. Come stay with us and enjoy sweet dreams at Sunset Dreams, and bring along your favorite four-legged friend, as this rental is dog- friendly! Need more space? Rent "Saltwater" right next door! Note: The pier is shared with the other 2 adjoining townhomes.
- 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: 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.
Dockside
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.
Diving Duck
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. 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.
- 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.
Channel Watch
Located down a gravel road that runs parallel to Assateague Channel, you'll find Channel Watch nestled in between the pine trees. The perfect getaway on Chincoteague Island for you and your family! On the ground level you'll find a bedroom with King bed and sitting/television area, an open-floor plan for the living area with plenty of comfortable seating, a fully-equipped gourmet kitchen, and a dining area with table for enjoying family meals together. There is also a large screened in porch area with seating if you want to take in the views and enjoy that meal outside - and honestly, why wouldn't you? A full bath is also located in the hallway downstairs too. Upstairs you'll find two more bedrooms. The master featuring a roomy king bed and private balcony overlooking the water, and the other bedroom with two beds - one Queen sized and one Full size. A full bath is also located upstairs, as well as a utility closet with a full size washer and dryer. Enjoy the island sunshine and cool breezes coming off the water off of the private dock in the back. Bring your fishing poles and crabbing gear, and haul in a bounty to prepare back at the house. Or ride the bike to one of the many favorite restaurants located just up the street on Beach Road - The Village or AJ's for something a little more upscale, or maybe tacos from Pico or a pizza from Famous for something a little easier. You're sure to find something to please everyone! If you happen to be an early bird, you're in for a real treat when it comes to sunrises at Channel Watch. Brew yourself a cup of coffee and take it out on the pier with you, take a seat, and wait for the show. It's just for you. Bring your family and come experience island life for yourself at Channel Watch.
- 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
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.
Shore Thing On Oyster Bay
Enjoy some of the island's best water views overlooking Oyster Bay from nearly every room of this custom beach home! Located on a bulk-headed waterfront lot in Richardson's Landing, you can fish and crab from the backyard! A wonderful feature of this spacious home is that you'll find your bedrooms on the first level and your main living area on the second level. The great room opens to the kitchen and features wood floors throughout. And the views are spectacular! Lots of windows!! Some of the bedrooms have waterside balconies. This home has four televisions- all with cable hooked up! You'll find all the bells and whistles here! So take a look at all the pictures and then give us a call or book online. Make memories to last a lifetime!
- 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.
Creek House
Creek House, Privately located in an imaginative setting; nature and history are perfectly coupled with luxurious accommodations.
Rounding the corner of the private country lane, you'll sense something special unfolding before you. What can best be described as an imaginative setting, nature and beauty are perfectly coupled with luxury - a modern 5 bedroom home that's part of a family compound is before you. It sits at the edge of Holdens Creek, where the Pocomoke Sound meets the Chesapeake Bay. You’ve reached Creek House! Newly renovated and nothing short of spectacular, the WOW factor kicks in as soon as you enter. Large living spaces with breathtakingly scenic and panoramic water views captivate you. There are Waterside balconies on every level and world class amenities at every turn. Professional interior finishes bring true elegance to the home’s aesthetic of simple, sexy... and just plain cool. The natural flow from space to space is perfect for a couple to enjoy a romantic getaway or for a large group gathering. With room for 14 guests, the generous bedrooms offer waterside balconies and marble bathrooms. The kitchen/ dining area can host any size party.
In the garage level of the home, enjoy a game of ping pong on the regulation size table or play a game of cards with the family! Also enjoy the shared use of 2 single kayaks, 1 canoe, and 1 paddleboard.
'Creek House' has partnered with our friends at Sun Outdoors Resort (located less than 2 miles from the house) so that all guests may enjoy the fun resort amenities FREE OF CHARGE. This extra bonus includes a private beach w/ water rentals, pool, playground, "snak shak", comfort stations & more!
Where is Creek House located? Only a 20 minute drive to Chincoteague Island, Creek House is situated on one of the most beautiful slices of Virginia's Eastern Shore. Day trips to the beach are easy and convenient. Other beach towns like Ocean City, MD and Cape Charles, VA are less than an hour away.
Creek House has a boat launch, two docks, five porches and a 20’ radius fire pit with outdoor lighting and wi-fi (Bluetooth) speakers system. Simply staying on the property to enjoy a vacation with down time is an option with endless possibilities. The entire compound is available for events and can accommodate up to 18 people (each of the three dwellings are rented separately). Pets will be considered upon request.
In addition to The Creek House, the compound is also home to two luxurious cottages: Porter’s Barn and Hosta Cottage. Please note that this listing is for Creek House only; the other two cottages - Hosta Cottage and Porter's Barn - must be booked separately. A direct inquiry should be sent for special event pricing or if you wish to rent the entire compound.
GPS is inconsistent on Holden’s Creek Road. Please follow Holden’s Creek Road approximately 1/2 mile and take the first right Drive down the private gravel driveway (labeled: Porterville RD) past the horse pasture. Take a left at the Y and follow the driveway to the property.
- Linens and towels are included with your reservation.
- No smoking is permitted on the premises.
- This property is pet friendly on a case by case basis, with a pet fee per pet. Pet fee is $200 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.









