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.

4.96 out of 5 average rating, 121 reviews

Huge Patio & Outdoor Fireplace ~ Family Friendly!

You'll experience the magic of Cape Charles Historic District in a home where modern convenience meets classic charm! Sunshine Rays is your premier family vacation rental, consistently rated 5 stars by guests who praise its cleanliness, thoughtful stocking, and incredible amenities. Perfect for up to eight guests, you are situated on a quiet, friendly street. You'll enjoy a peaceful walk to the Cape Charles beach and close to Central Park and the bustling shops and restaurants of Mason Avenue.

The red brick duplex features a welcoming front porch with white rocking chairs on both sides. Two main entrances are visible, framed by classic black shutters, while the well-maintained yard is accented with small plants. The evening sky casts a gentle light over the structure.

4.93 out of 5 average rating, 160 reviews

Stylishly Renovated | Golf Cart Avail. | Bakery!

Nectarine 15 is 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)

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.

4.99 out of 5 average rating, 103 reviews

A charming cottage features a covered front porch adorned with rocking chairs and hanging plants. The exterior is painted in soft green with contrasting dark shutters and a metal roof, surrounded by landscaped greenery, creating a welcoming appearance.

Home in Mathews

Couples Cottage with Hot Tub

Wake up surrounded by greenery, sip coffee on a quiet porch, and unwind in the hot tub after a day exploring coastal Virginia. Sugartoad Cottage is a calm, plant-filled retreat designed for couples who want comfort, privacy, and walkable access to the best of small-town Chesapeake Bay life. Though located on Mathews Main Street, the cottage feels surprisingly secluded, with gardens, multiple decks, and thoughtfully designed outdoor spaces that make it easy to slow down.

A spacious two-story house features a light exterior with a welcoming front porch. The porch is adorned with rocking chairs and an American flag. The pathway includes brick accents and is framed by well-maintained grass, adding to the overall charm of the property.

4.89 out of 5 average rating, 131 reviews

HGTV-Featured Coastal Getaway–2 Blocks to Beach!

Welcome to Liberty on the Bay *featured on HGTVs Beachfront Bargain Hunt* Our 4 bedroom/2 bathroom historic stunner includes original hardwood floors, a fully updated kitchen, and two outdoor showers. The beautiful front porch is perfect for people-watching or simply escape to the private backyard to relax under the magnolia tree. This spacious house is a quick 5-minute stroll to either the historic town or the beach—perfect for dining, shopping, and exploring.

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, 281 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

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 26 reviews

A circular arrangement of dark wooden chairs is positioned on a stone pathway, surrounded by manicured grass and blooming flowers. The serene waterfront is visible in the background, framed by lush trees, creating a tranquil outdoor space.

Home in Heathsville

Waterfront Escape Pool Dock Kayaks Chesapeake Bay

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, 125 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

A single-story house is presented with a welcoming exterior, featuring a covered porch and large front windows. The well-maintained yard includes neatly trimmed bushes and a paved walkway leading to the entrance. A bright blue sky with scattered clouds complements the serene setting.

4.93 out of 5 average rating, 85 reviews

Bay Creek (Pool!) Meets Historic Cape Charles!

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

Superhost

The exterior of a vibrant orange house is shown, featuring multiple balconies and a spacious patio area with outdoor seating. A hot tub is visible on the patio, surrounded by landscaping. Nearby, additional homes can be seen, highlighting the neighborhood's character and layout.

4.81 out of 5 average rating, 27 reviews

Private Beach~1st Floor King Suite~Fire Pit~Patio!

4.92 out of 5 average rating, 125 reviews

Home in Hampton

4BD home w/ game room & pool near Langley & PTC!

Weekly house rentals

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

5 out of 5 average rating, 14 reviews

Bayluna - Cape Charles

The exterior of a two-story blue house features a white porch with decorative railings. Red shutters frame the windows, and a flag is displayed at the entrance. The surrounding yard is landscaped, with a small garden area visible beside the path.

4.91 out of 5 average rating, 75 reviews

Pet friendly comfy family home

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 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, 17 reviews

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

5 out of 5 average rating, 93 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

5 out of 5 average rating, 11 reviews

This modern A-frame retreat features a spacious exterior design with large windows, allowing natural light to illuminate the interior. The multi-tiered deck provides access to the calming surroundings, complemented by a screened porch, ideal for enjoying the outdoors. Towering pines frame the serene setting.

Home in White Stone

Modern Bayfront Escape with Sweeping Water Views

4.95 out of 5 average rating, 42 reviews

A charming cottage is depicted, framed by lush green grass and mature trees. The front features a covered porch with multiple large windows, allowing for ample natural light. A serene atmosphere is created by the surrounding open space, inviting relaxation and connection to nature.

Home in Port Haywood

Relax & Heal Cottage Near Ocean & Forest Retreat

Private house rentals

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

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 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

4.94 out of 5 average rating, 49 reviews

A beachfront cottage is situated on sandy terrain, framed by beach grass. The structure features a spacious porch overlooking the water, and the coastline extends toward a secluded jetty in the distance. Clear skies enhance the serene coastal atmosphere.

Home in Port Haywood

Anne's Beachfront Shangri-La

5 out of 5 average rating, 46 reviews

Fully Renovated in 2023

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.

4.97 out of 5 average rating, 37 reviews

Large Charming Renovated Cape Victorian for 12

The exterior of the vacation home displays a charming white facade with wooden shutters and a welcoming porch. Greenery frames the entrance, and a pathway leads to the front door, providing easy access. The bright blue sky overhead adds a refreshing atmosphere.

5 out of 5 average rating, 19 reviews

Amenities in this walk to Beach, New 3bed/3.5bath