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Sunrise/Sunset

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Town & Country
Gas Grill
Internet

Looking for an island home that won't drain your savings? This two-bedroom, two-and-a-half-bathroom townhouse delivers comfortable Chincoteague Island vacationing with a price tag that actually leaves room for ice cream cones and beach days.

The heart of this home is its standout four-season room, a bright and breezy spot built for year-round enjoyment. Curl up with a book in the dead of winter or throw the windows open when the salt air calls — either way, you'll find yourself drawn back to this cozy corner again and again. An electric fireplace adds a flicker of warmth to chilly evenings, perfect for unwinding after a day of island wandering.

Both bedrooms sit upstairs, tucked away from the main living areas for a little extra peace and quiet when it's time to rest. Step outside and you'll discover a fenced yard, ideal for letting pets roam, hosting a casual cookout, or simply claiming your favorite lawn chair under the open sky.

Location? You've hit the jackpot. Veteran's Memorial Park is practically next door, complete with a playground, courts, and plenty of green space. The annual Carnival is just around the corner for summertime fun, while Island Foods handles grocery runs in a flash. When adventure calls, Maui Jack's Waterpark and the legendary Assateague Beach — wild ponies included — are a short hop away.

Affordable, comfortable, and perfectly positioned. What are you waiting for?

- 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: 3. 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.

Capeville Cottage

3 Bedrooms
2 Baths & 1 Half
8 Guests
Cape Charles
Town & Country
Pet Friendly
Gas Grill
Screened Porch
Internet
Outdoor Shower

Welcome to Capeville Cottage in the heart of Capeville, VA - just 5 miles North of the Chesapeake Bay Bridge Tunnel. The Capeville Cottage is a charming 1700 sq.ft., 2 story home featuring 3 bedrooms and 2.5 baths. Upon pulling into the private driveway, there is a west facing front porch, great for watching the gorgeous Eastern Shore sunsets and relaxing after an active day.  You are welcomed by a large living area, high ceilings, and spacious kitchen with plenty of seating, laundry and a half bath.  There is a screened porch off of the kitchen with a picnic table that seats eight. Downstairs is a large primary bedroom with a king sized bed, high ceilings, a tv, and full bath and separate stand in shower. Upstairs there are two bedrooms. One has a twin over full bunk with a separate full size bed. The 3rd bedroom has a queen bed, tv and a shared full bath. Outside in the garage, you will find a game room with a ping pong table, darts and a large refrigerator. Capeville Cottage offers a large yard with ample parking, and a boat washing station.  Come enjoy Capeville Cottage and let the tranquil lower Eastern Shore wash your worries away!

- 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: Small dogs only, under 25 lbs each. 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.

This rental home is conveniently located:

1 mile to Stingray's Restaurant

2.5 miles to Kiptopeke State Park and boat ramp

5 miles to downtown Cape Charles and public boat ramp

5 miles South of Wise Point boat ramp

3 blocks to the scenic bike path on Capeville Road

Charlotte's Morning Sun

4 Bedrooms
4 Baths & 1 Half
8 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Set in the boutique residential community of Oyster Bay I, 'Charlotte's Morning Sun' is a stunning 5-star waterfront home that offers unobstructed water views and breathtaking vistas of Oyster Bay. Flowing generously over two levels, Charlotte features 4.5 bathrooms and 4 light-filled bedrooms, one of which has it's own balcony that feels like it's floating on water. The stylish design offers private and peaceful lounge and dining areas that embrace sweeping bay views that stretch uninterrupted to the horizon. A state-of-the-art chef's kitchen, a generously-sized waterside screened porch as well as a large observation area allows effortless indoor outdoor living. On the first level you'll find the living room, observation area, chef's kitchen, dining area, 2 bedrooms and a wonderful waterside screened porch. Upstairs you'll find 2 more bedrooms, one with a private balcony. Outside, enjoy exclusive access to the bay via a private dock/boat-slip, or bathe in the outdoor beach shower surrounded by a grassy coastal garden. Just a short drive to the beach, local restaurants and shops, 'Charlotte's Morning Sun' offers an opportunity to secure a luxury vacation home in an exceptional setting. Note: The Oyster Bay I community where this property is located offers a boat ramp that is exclusive to the homes in this community. Water depth may not be suitable for all boats and dock/ramp usability cannot be guaranteed. You can crab and fish at this community harbor area.

- SPECIAL NOTE: This rental home has a 5 night minimum during the off season. 

- 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.

Island Estate

5 Bedrooms
3 Baths
14 Guests
Chincoteague Island
Waterfront
Pet Friendly
Boat Dock
Gas Grill
Pool
Internet
Outdoor Shower

Fabulous, fabulous, fabulous! If you're looking for a large space to have a family vacation or reunion, this is it. This beautiful waterfront home is located on a tidal creek and boasts over 3,000 sq ft of living space. All amenities - central air, all kitchen appliances & washer/dryer, and so much more! The formal dining room is great for large gatherings. Beautiful back deck area with private pool for your enjoyment. Island Estate is a PET FRIENDLY home. Please Note: Pool is open Memorial Day weekend through end of season/last renter (weather permitting).

- 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.

Return

4 Bedrooms
3 Baths & 1 Half
11 Guests
Chincoteague Island
Waterfront
Boat Dock
Gas Grill
Screened Porch
Internet
Outdoor Shower

Beautiful waterfront contemporary perched on the edge of Assateague Channel. Enjoy breathtaking vistas of Assateague Island, the lighthouse, the wild ponies and the abundant wildlife. This spacious home boasts a complete line of amenities including a 600' pier/dock with deep water access, and waterside decks and screened porch. This home is great for boaters! The bright and airy open floor plan is highlighted with fine custom windows throughout that frame the beautiful, panoramic water views. In addition, there are 2 private master bedroom suites, both with private full baths, on the main living level. The second level features another two bedrooms and full bath plus a private sleeping area, so there is plenty of room for everyone! Wireless internet available.

- 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.

Bay Breeze Retreat

6 Bedrooms
5 Baths & 1 Half
14 Guests
Cape Charles
Town & Country
Gas Grill
Screened Porch
Pool
Hot Tub
Internet
Outdoor Shower

Discover this exceptional new construction home nestled within the prestigious Bay Creek community, where luxury living meets coastal charm. This stunning six-bedroom, five-bathroom residence showcases meticulous attention to detail and uncompromising quality throughout every square foot.

The welcoming front porch overlooks beautifully landscaped grounds, creating an inviting first impression that sets the tone for the extraordinary experience within. Step inside to find spacious rooms designed for both comfort and elegance, with an open great room featuring a cozy fireplace that seamlessly flows into the formal dining area and chef's dream kitchen. Custom large doors provide effortless access to the back porch, perfect for alfresco dining and entertaining under the coastal sky.

Every bathroom represents a spa-like retreat, featuring luxurious soaking tubs and sophisticated tile and glass showers that transform daily routines into rejuvenating experiences. The primary bedroom, and additional bedrooms alike, offer generous proportions and thoughtful design elements that ensure comfort for both family and guests.

The indoor and outdoor spaces transition seamlessly and continue the home's commitment to exceptional living, with a dedicated kids' play area, multiple sitting areas for quiet contemplation, and a relaxing hot tub for ultimate unwinding. As if that's not enough, the spacious garage hosts a fabulous entertainment room with leather reclining chairs, a large TV, pool table and shuffleboard. Above the garage has been designed as a private 'in-law' suite, featuring a kitchenette, bedroom, bathroom and sitting area. Two custom, 6-seater golf carts are available for convenient transportation throughout the community complete the ultimate experience (additional fee of $200 per day required).

Bay Creek community membership provides access to world-class amenities that rival the finest resorts. Residents enjoy the renowned golf course designed by championship standards, scenic nature trails winding through pristine landscapes, refreshing community pools, a comprehensive fitness and life center, and exclusive access to a private beach along the Chesapeake Bay.

The location offers the perfect balance of tranquil coastal living and convenient access to regional attractions, including proximity to the Cape Charles Beachfront and the engineering marvel of the Chesapeake Bay Bridge-Tunnel. 

From top to bottom, no detail has been overlooked in creating this masterpiece of modern coastal living. The combination of superior construction quality, premium amenities, and an enviable location within one of Coastal Virginia's most sought-after communities makes this rental opportunity truly extraordinary for discerning tenants who appreciate the finest things in life.

Please note:

- Two custom, 6-seater golf carts are available for convenient transportation throughout the community complete the ultimate experience (additional fee of $200 per day required).

- 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.

- Usage of the Bay Creek Resort amenities requires an additional fee of $75 per day*.

BAY CREEK RESORT AMENITIES:

Waterfront area perfect for kayaks, canoe, fishing or crabbing.

27 hole World-class golf course (requires additional golf fee).

Golf lessons and clinics available for all skill levels.

Member lounge with billiards and entertainment.

Cardio and weight training studio.

Two outdoor pools w/ decks and furniture.

350 acre Nature Preserve w/ trails and wildlife viewing.

Clubhouse with private restaurant and dining experiences.

Structured activities and programs such as bird watching, paddle-boarding, beach yoga, kid's camps & more. 

*Fee is subject to change without prior notice or authorization. Bay Creek Amenity offerings can be seasonal and may change without prior notice or authorization.

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.

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.

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. 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. 

 

Bayside Bliss at Cape Charles

3 Bedrooms
2 Baths & 1 Half
10 Guests
Cape Charles
Gas Grill
Internet
Outdoor Shower

Welcome to your idyllic retreat in the charming coastal community of Cape Charles. This brand new three-bedroom, two-and-a-half-bathroom residence offers the perfect blend of comfort and sophistication for your Eastern Shore getaway.

Step inside to discover thoughtfully designed living spaces, including a spacious living room and a versatile loft area upstairs (with Queen Sleep Sofa) —perfect for a quiet reading nook, or entertainment zone. The convenience of a first-floor primary bedroom suite means accessibility and privacy for the discerning tenant.

The backyard presents a picturesque setting with a scenic pond, offering tranquil views and a peaceful atmosphere for morning coffee or evening relaxation. Imagine watching herons glide across the water as the sun sets—nature's own entertainment system!

The stunning Cape Charles Beachfront is nearby, providing endless opportunities for seaside adventures. After a day of exploration, return home or indulge in a delicious meal at the local restaurants. This exceptional rental property offers more than just a place to stay—it's a gateway to the coastal getaway you've been dreaming about.

- 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.

 

Horseshoe Hideaway

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

Located in a secluded neighborhood, in the middle of town, 'Horseshoe Hideaway' is comfortably situated back off of a back road, fully enclosed by a fence, and ensconced by a generous yard and mature wooded area. With all the convenience of traveling around the island with ease, this home allows guests to drive or bike to Maddox Blvd, the beach or to the Main Street shops within minutes. Enjoy the outdoors on the fully screened in porches located on both the front and the back of the home, or take advantage of the generous back deck (accessed by a ramp or stairs) and supplied with a large gas grill, picnic table and Adirondack chairs. Inside the home features 3 bedrooms and 2 full bathrooms, a separate dining room, living room and eat in kitchen. There are several seating areas where guests can spread out or congregate as a group. The home is appointed with everything you need to enjoy a vacation at the Beach. This cute-as-a-button rancher home is waiting for your family vacation! Clean, comfortable and modest best describe the single-level home; there's an open kitchen, living and dining area that opens up to a front AND back screened porch. Enjoy all of the outdoor space from one of the 2 screened porches, or the spacious back deck and back yard! Located on a side street just off of Ridge Road, 'Horseshoe Hideaway' is conveniently located just minutes from downtown Chincoteague, as well as the "Beach Road." Come and check it out for yourself!

- 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.

Shady Side

4 Bedrooms
2 Baths
10 Guests
Chincoteague Island
Water Access
Gas Grill
Screened Porch
Internet

Shady Side is located in Piney Island, which is among the closest communities to the beach. There is community water access, suitable for a kayak or canoe. The house features two queen bedrooms and a full bath downstairs. Upstairs you'll find two additional bedrooms, one has two twins and the other has a queen bed. There is also a full bath on the second floor. The loft features a futon with a full mattress. The large back porch is equipped with a gas grill and picnic table for your cookouts and crab feasts! 

- 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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