House holiday rentals in Cape Charles

The exterior of the home is shown, featuring a welcoming porch with ornate detailing and a pair of rocking chairs. Lush greenery, including bushes and flowers, enhances the inviting atmosphere. The blue siding and white trim reflect the home's historic charm.

4.98 out of 5 average rating, 106 reviews

Bayside Bonanza | Off-street Parking | EV Charger

"Bayside Bonanza" is special. Ideally located with the main street of Cape Charles around the corner in either direction, and a 5 minute walk to the bay or Central Park. There's nothing like sitting on the front porch swing, sipping morning coffee or an evening cocktail. The home is bright and cozy, with efforts made to keep as much of the original 1890's charm as possible. We're family owned and managed, and it's our priority to help you have the most relaxing and enjoyable vacation possible!

A green, two-story house with a prominent red door and white trim is visible. A spacious front porch features white railings, while a golf cart is parked nearby. A side door ramp enhances accessibility, and well-kept landscaping adds to the home’s welcoming appearance.

4.97 out of 5 average rating, 143 reviews

Family Reunion on the Bay

Unpretentious, clean & family-friendly. Bright open-plan for easy living. Generous seating throughout. Loads of games, toys. Ideal for extended families. Side-door ramp, 1st-floor ADA bedroom, step-in shower w/seat & grab bar nearby. Backyard fire pit, picnic tables, grill, corn hole. Free firewood, propane, stand-up paddleboard, beach chairs. 3 IMPORTANT NOTES: 1. bedrm #5 reduced to 4 beds in 2026 2. Absolutely NO PETS ALLOWED! ($750 fine) 3. Only 7-day Sat.-to-Sat. rentals June thru Aug. 30.

The kitchen features exposed brick walls and modern finishes. A wooden dining table with four chairs is positioned in front of a window, allowing natural light to illuminate the space. Stainless steel appliances are present, along with a large sink and ample counter space.

4.94 out of 5 average rating, 145 reviews

Bakery Next Door | Renovated | Golf Cart Avail.

Nectarine 13 is a centrally located. Next door, you’ll find the Coastal Bakery. A great place for breakfast or Treat. Relax on the charming front porch and soak in the calm, historic vibe of Cape Charles. A Quick walk to historic Downtown, Take a swim in the bay or cast a line off the dock. Central Park is also nearby, offering a great spot for a family picnic while the kids enjoy the playground. Golf carts are available to rent(Cart Rentals are only available during the House rental period)

Home in Gloucester Courthouse

A spacious outdoor dining area features a long table set with colorful placemats and floral centerpieces. The view overlooks the water and a tree, with a pier visible in the distance under a clear blue sky.

4.97 out of 5 average rating, 330 reviews

"Bee-Z Haven" Waterfront Cottage on the Ware River

Curious about what makes Gloucester so wonderful? Live like a local at this Upscale Waterfront Retreat and find out for yourself why renters say "Enjoy the Breath Taking Views". Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our area is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

4.97 out of 5 average rating, 130 reviews

Four black Adirondack chairs are positioned in a grassy area facing a tranquil body of water. Lush green reeds frame the water's edge, with a blue sky and scattered clouds above. A small dock is visible in the distance, adding to the serene setting.

Home in Belle Haven

Bay Breeze Home on private waterfront

On Virginia's beautiful Eastern Shore, the Bay Breeze Home on Occohannock Creek is the ultimate getaway for two or a large family desiring outside adventures. This 1970's spacious home has plenty of room. Experience the water with our three kayaks or family canoe and watch the abundant wildlife. Right outside your door, you may see Ospreys, Great Blue Herons, Eagles, wild ducks, porpoises, deer, geese, otters, & more. Be our guest and forget your worries in this spacious and serene spot.

4.99 out of 5 average rating, 105 reviews

A two-story beach house stands amidst lush greenery, featuring a spacious wrap-around porch with multiple seating areas. Large windows allow for ample natural light, while the light-colored exterior complements the serene surroundings. The property is partially surrounded by trees, enhancing privacy.

Home in Machipongo

Private Country Beach Retreat

Welcome to Mason Jar Retreats Beach Home. Our home is a private beachfront property with the best of both country and beach living. Located on 6 acres on a private road with only a few steps to take to your private oasis on the Chesapeake Bay. Enjoy sunsets from the beautiful porches while taking in the natural surroundings. Our home is only three miles from a vineyard and winery and 20 minutes to Cape Charles with lots of shopping and dining in a quaint beach town. *LGBTQ+Friendly Home

The exterior of the cottage features a charming design with a sloped roof and textured blue siding. A welcoming porch is supported by white railings, inviting visitors to relax. Surrounding greenery adds to the serene atmosphere, complemented by clear skies overhead.

4.98 out of 5 average rating, 267 reviews

Bay Breeze on Tazewell (Sun-Sun rental June-Aug.)

Bay Breeze on Tazewell is a recently remodeled Cassatt cottage with historic charm and modern amenities. The home includes a fabulous, sunny kitchen stocked to meet your needs. We provide fresh linens and towels for your stay. In the shed, you will find lots of items for the beach, a wagon, and bikes which we are happy to share. Bay Breeze is just a short walk to the beach, various restaurants, boutiques, and marina. If our home is not available, try our new Airbnb home ...Harbor View!

4.99 out of 5 average rating, 131 reviews

An inviting outdoor fire pit area features turquoise Adirondack chairs arranged around a stone fire ring. The charming blue farmhouse, with a metal roof, is partially shaded by trees, and sprawling green grass surrounds the property, enhancing the space for relaxation.

Home in White Stone

1891 Coastal Charmer: fully renovated farmhouse

Built in 1891, this farmhouse has been totally renovated by a professional designer. The Cottage is filled with coastal colors and accessories so it feels fun and updated but still retains the feeling of walking into a well loved family beach cottage. We are pet friendly as any beach cottage should be and love seeing our guests and their pets enjoying the cottage. Follow the cottage on social media @ BlueOysterCottage for more pictures, design ideas and local places to visit.

Superhost

The exterior of the home features a welcoming yellow door framed by blue and white stripes. Surrounded by green foliage, the porch includes a wooden ramp for accessibility. Large windows provide a glimpse of the interiors, softly illuminated by warm lighting.

4.84 out of 5 average rating, 118 reviews

"Live Life Sunnyside Up" - Minutes From The Beach!

Welcome to "Live Life Sunnyside Up" on the Shore! Take a trip off the busy beaten path and kick your feet up at our little slice of paradise. Kid friendly with plenty of amenties for you and your family. On a quiet street, less than 4 miles from the historic town of cape charles and beach, get ready to take a load off and enjoy the many treasures Cape Charles has to offer! Just 5 short minutes from the Oyster Boat Ramp, fishermen are sure to find their honey hole here!

The duplex features a light blue exterior with a welcoming front porch. Rocking chairs are arranged alongside the entrance, inviting relaxation. The well-maintained lawn is complemented by tidy landscaping and a concrete pathway leading to the front steps.

4.96 out of 5 average rating, 278 reviews

Steps to the Sea at Salt Box

Escape to The Salt Box, a charming 1915 duplex just one block from the beach in the heart of Cape Charles' Historic District. This cozy, private retreat sits on a peaceful, tree-lined street and is a short stroll to the beach, pier, shops, restaurants, and more! Check out our local Guidebooks or text us anytime—we're happy to share our favorite local spots! Looking for even more space? You can also book the other half of our duplex, Salt Box II!

The charming brick house features a welcoming front porch with white railings. Lush greenery and colorful blooms adorn the front yard, framed by neatly manicured shrubbery. Natural light brightens the exterior, highlighting the multi-pane windows and the peaked roof.

4.94 out of 5 average rating, 105 reviews

Celebrating 100 years!

Welcome to The MT Nest! Relax in our charming 100 year old Sears house in the heart of historic Cape Charles. Enjoy mornings on the porch in the shade of majestic trees. Walk to the beach in the afternoon. Then stroll a few blocks to restaurants and shops in the evening. Central park across the street offers summer concerts, a playground, and a splash fountain. Enjoy the quiet and slow your life down for a few days of bliss!

A charming duplex exterior features a light yellow facade with blue shutters and a welcoming covered porch. White steps lead to two front doors, flanked by lush greenery, including flowering hydrangeas. The evening sky adds a soft hue in the background.

4.94 out of 5 average rating, 105 reviews

The Shore House on Madison - Pet Friendly Unit!

The Shore House on Madison was fully renovated in 2019 and located in the Cape Charles Historic District within walking distance to the beach, park, the shops and restaurants. Our pet friendly unit can host up to 7 guests with 3 bedrooms, 2 full baths and 1 outdoor shower. Bedroom #1 includes 1 Queen bed, TV and work desk. Bedroom #2: 1 Queen bed. Bedroom #3: Bunk Bed (1 double / 1 twin). Fenced in backyard with patio.

Popular amenities for Cape Charles house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 205 reviews

A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.

Home in Gloucester Point

York River Vacation Home

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.

4.94 out of 5 average rating, 35 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

Superhost

A two-story house features a light-colored exterior with a peaked roof. A spacious driveway leads to a garage door, framed by manicured grass and trees. A balcony extends from the top floor, providing outdoor space above the ground level.

Home in Norfolk

4.93 out of 5 average rating, 123 reviews

Gorgeous Vacation House

4.98 out of 5 average rating, 164 reviews

A spacious deck extends towards the waterfront, surrounded by lush trees. Lounge chairs and seating areas are positioned for relaxing views of the calm water. A sunroom is visible to the right, offering additional indoor space. The overall setting invites outdoor leisure and tranquility.

Home in Cobbs Creek

Blue Heron WaterSide

4.97 out of 5 average rating, 226 reviews

A modern kitchen area is visible, featuring stainless steel appliances and a granite countertop with bar seating. Two stylish light fixtures hang above, while the space is illuminated by natural light from large windows covered with light curtains. A seating arrangement includes sleek black bar stools.

Home in Virginia Beach

Sunrise, North End Beach

4.99 out of 5 average rating, 125 reviews

The entrance to The Rosé Retreat features a welcoming porch with multiple chairs arranged for relaxation. Arching glass doors provide a view into the inviting interior, framed by decorative wreaths that add a touch of seasonal charm. Lush green foliage surrounds the exterior.

Home in Irvington

The Rosé Retreat: Fireplace-Screened Porch-RELAX

An aerial view captures a vibrant Victorian-style home featuring teal and yellow siding. A striped awning provides shade over the front porch, where two chairs sit beside potted plants. Neatly trimmed hedges line the walkways, and a neighboring home adds to the charming streetscape.

5 out of 5 average rating, 35 reviews

East of the Sun Victorian - Private Pool

4.96 out of 5 average rating, 158 reviews

A private hot tub is situated on a wooden deck surrounded by trees, offering a serene retreat. Sunlight filters through the branches, creating dappled shadows on the tub's surface. A wooden wall adds a rustic touch, featuring a decorative crab motif.

Home in Irvington

Magical wooded cottage pool +priv hottub walk2town

Weekly house rentals

A charming blue house is presented with a welcoming front porch and white railings. Lush flower beds featuring vibrant pink roses and other greenery surround the entryway, while a neatly landscaped walkway leads to the front steps, inviting guests to explore the home.

5 out of 5 average rating, 11 reviews

A Charming Low Key Luxe Retreat

A two-story blue house is framed by white trim and windows, showcasing a welcoming front porch and a white picket fence. A golf cart is conveniently parked in front, with a patio umbrella visible on the side, indicating outdoor leisure space.

4.95 out of 5 average rating, 88 reviews

Historic, Pet Friendly Cottage-Three Little Birds

A modern two-story home features a welcoming front porch with white railings. Large windows allow natural light to fill the exterior, complemented by manicured lawns and blooming shrubs. A circular driveway leads to the entrance, inviting guests into a comfortable and spacious environment.

4.82 out of 5 average rating, 28 reviews

"Awenasa" Luxury Beach Retreat

A two-story house with a bright white exterior features a welcoming front porch, complete with white railings and two ceiling fans. The entryway is highlighted by a centered pink door, flanked by large windows. Lush green grass surrounds the home.

5 out of 5 average rating, 32 reviews

Cape Cousins

5 out of 5 average rating, 14 reviews

Bayluna - Cape Charles

Superhost

The charming two-story house features a welcoming front porch adorned with white railings and hanging plants. Steps lead to a bright blue front door, surrounded by lush greenery and a well-maintained lawn that invites guests to explore the outdoor space.

4.66 out of 5 average rating, 190 reviews

2 blocks to beach, 1 block to shops, front porch!

The front porch features two bright yellow doors welcoming guests, flanked by white railings and steps leading up to the entry. Potted plants and green grass enhance the outdoor space, while a large tree provides shade in this inviting setting.

5 out of 5 average rating, 87 reviews

The BeeHouse

5 out of 5 average rating, 92 reviews

The front of the house is framed by a large tree, with a pathway leading to the entrance. The porch features a bench for seating, and greenery surrounds the property, creating a welcoming outdoor setting.

Home in Onancock

Egret’s Point on the Creek

Private house rentals

The charming blue exterior of the house is complemented by white trim and a welcoming front porch. Rocking chairs are placed on the porch, and landscaped greenery frames the front walkway leading to the entrance. A clear blue sky enhances the inviting façade.

5 out of 5 average rating, 6 reviews

'25 Reno! 1 block to Shops & Park, 6 to beach

A charming two-story house features pastel-colored shutters and a welcoming front porch with white pillars. Lush greenery and blooming flowers surround the property, while the stone pathway leads to the entrance. A well-maintained yard enhances the inviting exterior.

4.94 out of 5 average rating, 34 reviews

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

An aerial view captures the single-story ranch home positioned across from the beach. Sandy shores extend alongside the calm water, while charming residential streets and greenery surround the property, highlighting its prime coastal location.

4.94 out of 5 average rating, 33 reviews

FREE Luxury Golf Cart - across from CC Beach

A two-story house features a light grey exterior with a distinctive gabled roof. The front porch is decorated with patriotic bunting and potted plants, while ceiling fans are overhead. A small American flag is displayed, adding a welcoming touch to the entrance.

5 out of 5 average rating, 6 reviews

The Love Shack

A well-appointed bedroom features a spacious bed dressed in crisp white linens. Soft light filters through two bright windows with light drapes. A decorative mirror reflects the room's calm aesthetic, complemented by a green area rug and a leafy plant on the bedside table.

4.98 out of 5 average rating, 40 reviews

The Catch of the Cape- Family friendly, big yard

5 out of 5 average rating, 46 reviews

Fully Renovated in 2023

The exterior of Pinkberry Cottage showcases a welcoming porch with two pink chairs placed on a spacious front deck. Fresh landscaping and small shrubs frame the home, which features a blend of tan siding and a pink accent above the upper windows.

5 out of 5 average rating, 16 reviews

Pinkberry Cottage- new 5 bdrm, 3 bath, double lot

A classic Victorian-style home features distinct blue siding and white accents, framed by a welcoming porch. A paved walkway leads through a well-maintained garden with vibrant flowers, suggesting a charming entrance to a spacious and inviting interior.