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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 with a pet fee per pet. Pet fee is $150 per pet. All pets must be disclosed prior to arrival. Pet restriction: two 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.

Located on Main Street just north of town, "Lazy Days" may be just the perfect spot for your vacation! Cute and comfortable, this cottage is adorned with nothing but island charm. Downstairs features a cozy living room with flat screen TV, an eat-in kitchen with a back door that leads out to the yard, a full bathroom (tub & shower), a bedroom with a Double bed, and a second bedroom with a Twin bed and Bunk bed (2 Twins). Upstairs you'll find another bathroom (shower only) and bedroom with Queen size bed. (Please note: the stairs are steep and the upstairs has "knee walls".) The Chincoteague Bay is just a stone's throw - across the street - from the front steps... enjoy snippet water views! Nature trails, dog park, and downtown Chincoteague are just a minute or two by car. Enjoy a relaxing vacation at this affordable beach house!

- 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.

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.

Beautiful 3 bedroom home located in one of Chincoteague Island's private WATERFRONT communities! Formerly known as "Snoozin' Goose", Sunshine Daydream offers multiple outdoor porches, an open floor plan with large, bright rooms and modern amenities -- all in a quiet, peaceful location. Enjoy wonderful water views while sitting directly on a canal leading out to Oyster Bay. Tastefully decorated, and you can bring your dog along also!

- 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.

Coastal Living Made Simple in This Delightful Loft Retreat! Sometimes the best things in life come in perfectly sized packages, and this charming upper-level loft apartment is no exception. Nestled on the outskirts of the beloved town of Cape Charles, this open-concept, studio-style, one-bathroom rental offers an inviting blend of character, comfort, and convenience that is difficult to resist.

Step inside and immediately notice the bright, airy atmosphere that fills every corner of this thoughtfully designed space. The loft-style layout creates an open and welcoming environment, while the fun and tasteful decor adds a layer of personality that transforms this apartment from a simple rental into a genuine retreat. Natural light pours through the windows, enhancing the cheerful ambiance and making every day feel like a vacation.

The living area features a comfortable sofa bed, allowing the space to accommodate up to three guests with ease. Whether you are settling in for a quiet evening or hosting a friend for the weekend, the layout adapts effortlessly to your needs. The bedroom and bathroom provide a private sanctuary for rest and relaxation after long days spent exploring the Eastern Shore.

Location is where this property truly shines. The Cape Charles Beachfront is just a short drive away, offering sandy shores and spectacular sunsets over the Chesapeake Bay. Daily conveniences are equally accessible, with grocery shopping and local dining options located nearby. For those with a sense of adventure, the iconic Chesapeake Bay Bridge-Tunnel provides a gateway to the greater Hampton Roads region.

This affordable coastal gem books quickly! For more space, check out the sister unit downstairs - "Mermaid Hideaway". Come and discover the laid-back lifestyle that awaits you at this charming vacation spot!

- No smoking is permitted on the premises. 

- Linens and towels are included with your reservation.

- Pets are permitted on the premises for an additional fee of $150 per pet, two pets 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.