Vacation rentals with outdoor seating in Cape Charles

Vacation home in Cape Charles

5 out of 5 average rating, 68 reviews

Down By The Bay - Cape Charles -1st Floor Primary

🏖Come visit this updated 1930's bungalow. 5 blks to restaurants, shops & beach end of our street 🏠 First Floor master, w/ large bunky upstairs sleeps up to 8 (+ pack and play & air mattress) 🛶 Take stroll/ride to the beach, hose off in outdoor shower, grill on patio & cozy up to a fire. Or relax in the clawfoot tub! 💻 Staying the week & work remote? Work space ready for you! Wifi/Netflix. Updated kitchen & laundry space in your home away from home! 🐶 Dogs <50lbs (2 max) ☀️ Sunday-Sunday June -Aug

The living room is presented with light-toned furnishings, including two inviting armchairs and an accent chair. A soft area rug adds warmth to the hardwood floor, while large windows are draped with sheer curtains, allowing natural light to fill the space. A minimalist fireplace is centered at the back.

4.98 out of 5 average rating, 83 reviews

Cape Charles cottage, family friendly, in town

Welcome to Cape Charles Cottage in the historic district! We are 6 blocks to the beach and 4 blocks to Mason ave (shops, restaurants). The town is very walkable or golf cartable…you can rent ours! We can host up to 10 guests with 4 bedrooms and a bonus room with a daybed w trundle that pulls to side by side twins. One bedroom has an ensuite bathroom and the others share a hall bath with a tub/shower. Kitchen is fully equipped, fenced yard, outdoor shower,fire pit, grill & shed with beach gear.

4.99 out of 5 average rating, 113 reviews

A screened porch is depicted, featuring comfortable seating arranged around a coffee table. A round, high-top dining table is positioned nearby. Natural light filters through the surrounding trees, enhancing the serene outdoor ambiance.

Home in Irvington

The Rosé Retreat: Pool-Screened Porch-RELAX

Escape to The Rosé Retreat for peace and relaxation. Enjoy a romantic getaway sipping wine on the screened porch, unwind by the refreshing pool, navigate the waterways by kayak, and stroll to great restaurants/shopping. Savor local oysters and explore nearby wineries. Bring the family for a memorable NNK adventure. The Rosé Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosé while you're here. Follow on IG:roseretreatva Irvington Occupancy Tax #500

Superhost

A spacious living area features a large sectional couch, a coffee table, and a massage chair. Natural light floods the space through sliding glass doors, illuminating the wood flooring. The open layout connects to a kitchen and dining area, enhancing the communal feel.

4.67 out of 5 average rating, 3 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

Whether you are looking for some rest and relaxation, a home-base for the beach or water activities, or a place that comfortably allows you to bring your pets, you are sure to find your desired experience at Paws at the Beach. Open concept space with large glass doors and window to bring in natural light. Sunset room with multiple entertainment options, a massage chair in the living room and a Hot Tub. Four bedrooms that comfortably sleep 10. Rental includes access to a four-seater golf cart!

4.98 out of 5 average rating, 152 reviews

A spacious deck is shown overlooking a serene waterfront. Several lounge chairs and tables are arranged for relaxation, surrounded by lush greenery. The reflective water subtly mirrors the trees and sky, creating a peaceful atmosphere for outdoor gatherings.

Home in Cobbs Creek

Blue Heron WaterSide

Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

4.94 out of 5 average rating, 115 reviews

Cottage in Hacksneck

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!

5 out of 5 average rating, 12 reviews

Home in Reedville

Main & Guest House on a Private 5-acre Waterfront

Coastal Winns is a secluded retreat located 3hrs south of DC in Reedville, known as "The Fisherman's Town". This 5 acre property includes 2 beautifully decorated homes with views of the Chesapeake Bay & a private beach. Perfect for fishing, quiet getaways, retreats & family gatherings. Includes BBQ grills/griddle, kayaks, crab cages, 3 decks, fire pit (firewood provided), corn hole, hammock, games, picnic area, swing & obstacle play set. Boat landing 3 min drive/0.4 miles away from property.

A charming two-story home is shown with a bright coral front door. The porch features a seating area with a chair, surrounded by small shrubs and plants. The light-colored siding contrasts with the overcast sky, highlighting the home’s inviting presence.

4.99 out of 5 average rating, 101 reviews

Palm Beach by the Bay

This bright and cheery 3-bedroom, 2.5-bath home in the historic section of Cape Charles sleeps up to 8. Great mix of historic charm with all the comforts of a modern home. Located six blocks from the beach, with a direct walk to the gazebo and beach entrance, and one block from the iconic Cape Charles charm of Mason Avenue. This beautiful, completely renovated house includes a well-appointed kitchen, two living spaces (one with daybeds), main bedroom with en suite, and backyard paradise.

The exterior view of a charming two-story house is presented, showcasing a light-colored facade with green shutters. A covered front porch features seating and is surrounded by well-maintained landscaping, while a stone driveway leads to the entrance.

4.92 out of 5 average rating, 25 reviews

Seaville. Cozy 3bed/3bath home. Stunning backyard

The whole group will be comfortable in this spacious and unique space. Fully stocked large spacious kitchen/dining that will make family gatherings a breeze. Big living area with plenty of seating, large screen TV and dozens of games. 3 bedrooms and 3 full baths. Large front porch and a backyard described as an “oasis” by past guests. Outdoor “she shed” fun room with 65” TV, split HVAC system. Storage side has bikes, cornhole, beach chairs and much more beach stuff.

4.95 out of 5 average rating, 106 reviews

Sunshine Rays: Historic district backyard bliss!

Situated on a peaceful block of Cape Charles' charming historic district, Sunshine Rays was designed as a retreat for families visiting the Eastern Shore. With space for up to eight guests, an incredible backyard, and thoughtful amenities throughout, it's the perfect base for your Cape Charles getaway. We are just six blocks from the beach and even closer to our Central Park and the town's main street with all of its restaurants, bakeries, and shops.

Tiny home in Cape Charles

A fenced patio area features a wooden dining table with benches, set for outdoor meals. A large striped umbrella provides shade. The house in the background shows sliding glass doors leading into the interior, complemented by a nearby potted plant.

4.88 out of 5 average rating, 121 reviews

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!