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Joint Venture

2 Bedrooms
2 Baths & 1 Half
6 Guests
Chincoteague Island
Water View
Pet Friendly
Internet

Joint Venture is the perfect townhouse for an affordable vacation! Take a short stroll to Maddox Blvd (Beach Road) and enjoy ice cream, mini golf or any of the shops & restaurants. Bike or drive to the beach! Joint Venture offers a water view of Little Oyster Bay (tidal creek) that can be enjoyed any time of year. This property offers Wi-Fi and is pet friendly! Don't miss out!

- 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.

- 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.

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.

Minchew

5 Bedrooms
3 Baths & 1 Half
12 Guests
Cape Charles
Town & Country
Pet Friendly
Screened Porch
Internet

Welcome to this charming new rental Minchew, a delightful 5-bedroom, 3.5-bathroom house that mixes modern amenities with cozy, family-friendly comfort. This home features a bonus space perfect for the family to spread out, and a welcoming fireplace in the living area perfect for chilly evenings. Upon entering you are greeted with a spacious living room, formal dining room, the kitchen has an eating nook and a desk. Home features an open concept living area that leads out to a great screened in porch where you can dine Al Fresco. You will find a suite on the first floor with a walk-in shower and a soaking tub, and the rest of the bedrooms are located upstairs.  The front porch adds to the home's appeal, providing a quaint space to enjoy the neighborhood's friendly atmosphere.

 

Residents will appreciate the very convenient location, offering abundant outdoor activities including trails and picnics with scenic views. Daily errands are a breeze with a local grocery store, Food Lion, less than two miles away, ensuring everything you need is always within reach.

 

This home is not only about comfort but also practicality, and a location near the beach that makes it ideal for those who love the ocean. The property is also pet-friendly, acknowledging the important role pets play in many families..

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- This property is pet friendly with an additional fee of $150.  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 Bay Villa 212

3 Bedrooms
2 Baths
6 Guests
Chincoteague Island
Waterfront
Pet Friendly
Pool
Internet

Cozy and luxurious, three bed, two bath waterfront villa with private balcony. Beautiful kitchen space overlooks the bright, open dining/living area. Step out onto the waterside balcony and enjoy the water, wildlife, and sunset views. Bedrooms are spaced nicely - one full, one with two twins, and one king suite. King suite includes two mirrored closets, large bathroom with stand-up shower, and an additional entryway to the private balcony overlooking the Chincoteague Bay. Enjoy access to the community pool and fitness center within the villa complex. Conveniently located to our historic downtown area, you can walk to dinner, movies, shopping, galleries and more. This unit does not include a private boat slip, however, use of the common area marina is included.

- 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. 

- 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 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.

Stingray

2 Bedrooms
2 Baths
4 Guests
Chincoteague Island
Waterfront
Internet

Luxurious 2nd-level waterfront condo with views you won't believe! Tastefully decorated with work of local artisans, features all amenities, as well as master bedroom suite with king bed & waterside balcony. Many extras like a flat screen TV and a Lazy Boy leather recliner. The open floor plan is great and features a breakfast bar between the kitchen & dining area!

- 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.

Play by the Bay

3 Bedrooms
2 Baths & 1 Half
6 Guests
Cape Charles
Town & Country
Internet
Outdoor Shower

New to the rental market, "Play By The Bay" is a brand-new 3-bedroom, 2.5-bath house designed for easy coastal living in Cape Charles—where your biggest daily decision is beach time or backyard time.

Step inside to fresh finishes and a bright, open layout that keeps everyone connected, from morning pancake duty to game night. The upgraded chef’s kitchen is the star of the show, with plenty of workspace for slicing, sautéing, and showing off your “I totally meant to do that” plating skills. The main living area flows naturally for lounging, streaming, and post-sunshine naps.

The primary en suite offers a calm retreat, while two additional bedrooms provide flexible space for guests, kids, or that quiet workspace that you may need on occasion. With two full baths plus a convenient half bath, morning routines stay conveniently civilized.

Outside, enjoy a large yard set up for fun—bring your competitive spirit for lawn games or simply claim a chair and supervise like a professional. Bicycles are included, because Cape Charles is better at a relaxed pace and parking worries are not invited.

You’re close to historic downtown Cape Charles for shops, dining, and strolling, and the beachfront is an easy ride away when the water starts calling your name. Groceries are nearby too, so ice cream runs can remain an important part of your schedule.

Ready to make this coastal getaway your 'home away from home'? Book today and start your annual vacation tradition!

- 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

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

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. 

- Pet Friendly with a fee, No cats, 2 dogs max. ($150 per pet) 

- 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.

Herbie's Hideaway

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

Luxury water view vacation rental home with dock access. This home boasts a full ensemble of amenities and the most beautiful views of Assateague Island. The oversized chef's kitchen offers ample room for family gatherings and preparing meals, and it compliments the spacious dining area that opens up to the large screened porch. Beautiful custom windows and large sliding doors complete the open and airy floor plan. The geothermal heating/ac system lends to your ultimate vacationing comfort! Close to Memorial Park (playground, basketball, tennis, trails, water access) and directly across the street from a family restaurant! For larger groups or family reunions, check out nearby Moon Rising or Wildflower!

- 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.

Endless Summer

4 Bedrooms
2 Baths
9 Guests
Chincoteague Island
Water Access
Pet Friendly
Charcoal Grill
Screened Porch
Internet
Outdoor Shower

Come enjoy your stay at one of the most sought out locations on the Island. Easy, convenient access to the beach. With the large open floor plan, high ceilings, and easy one level living, you have everything you need at Endless Summer. Bring along your furry friends to make your vacation complete! This home has plenty of room for the whole family to gather. Enjoy the nice screened in porch or the large open front porch with your morning coffee and listen to the serene sounds of nature. The Piney Island Community offers convenient access to a kayak launch located on Pine Drive, just minutes from the 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. Pet fee is $150 per pet. All pets must be disclosed prior to arrival. BREED RESTRICTIONS DO APPLY

- 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.

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