Vacation rentals with a patio in Gloucester Point

Creekside Cottage Retreat with HotTub!

Relax w/ the whole family at this peaceful place to stay. Hang out in the backyard & enjoy the fire pit or jump in the brand new 7 seater, hot tub and relax your worries away! Go for a fun kayak ride, or Jon boat ride w/ trolling motor on the creek! After your work up an appetite, be sure to enjoy cooking dinner on the grill and hanging out w/ the family on the back deck overlooking the creek as you watch the sunset. After dinner, enjoy a movie with the family in the spacious living room.

Moody Cabin: Hot Tub/ Creek Fire Pit Park Setting

Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

Charming guest house on Jackson Creek

Treat yourself to this unique cozy cottage with views of the creek complete w/ kayaks and bikes. All you need for a weekend get away with equipped kitchen, bath w/ shower and outdoor shower. Relax, enjoy the peace and quiet by the Piankitank at the Chesapeake Bay. This listing is for the guest cottage behind Paddler's End, the main home on the property. The cottage is available when the main house is not booked. If you are interested in renting the cottage please inquire about availability.

Pretty Byrd Cottage, a Victorian Bayfront Getaway!

Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

Historic Charm & Modern Comfort : Downtown Escape

Surrounded by an array of restaurants, bakeries and a variety of unique boutiques and experiences, this apartment offers the perfect blend of charm and convenience. Juliette balconies invite fresh air and natural light, creating a Parisian-inspired ambiance. Inside, a fireplace creates a cozy setting. The state-of-the-art kitchen, designed in a striking 1950s vintage style, features Smeg appliances and bold crimson red accents, seamlessly blending retro elegance with modern functionality.

Close to beach, ON Central Park

In peak summer we have full weeks available (Sun-Sun) or partial (Sun-Thurs). This historic Parkside duplex has been recently renovated to include all the best amenities. This home sits ON the Cape Charles Central Park, giving you not only wonderful views of the park, but a perfect place for kids to run and play, families to walk, picnic and enjoy all the concerts and park festivals. It is also only two blocks to the beach and two blocks to the historic downtown – truly the best location!

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

No congestion, crowds, or commercial big beach resorts here. Experience the exact opposite at Courtyard Cottage just steps away from a quiet and peaceful beach surrounded by sand dunes for a special getaway. A park across the street provides playgrounds and pet-friendly walks and is the home to a local farmers market, 9 a.m. to noon. Saturdays, May 4 through Nov. 23. A past guest wrote "This place brings beach home nostalgia. peace, and a time to relax".

Summer Camp Tiny Cottage Walk to the beach & shops

At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for a couples, friends, and small families! • King sized bed with smart tv on the first floor • Two twin beds in a cozy sleeping loft • Small kitchen with propane stove, Nespresso maker & living space with a smart tv • Patio w/ charcoal grill, solo stove, & dining table • Paddle board & floats Please read through our totally honest disclaimer below!

Captain's Cottage

The Captain's Cottage was originally built in 1886 and has recently undergone extensive renovations to create a home of charm, history, and comfort. Located a block away from Cape Charles's Central Park, four blocks from the beach, and two blocks from Mason Avenue, the Captain's Cottage is in a prime location in Cape Charles.