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!

4.97 out of 5 average rating, 153 reviews

A two-story blue home is surrounded by trees, featuring a spacious deck with railings accessible from the upper level. A gravel patio area with chairs and a fire pit is visible on the ground level, complemented by neatly maintained greenery.

Home in Gloucester Point

Charming coastal home w/ outdoor area and river views

Tucked away at the end of a quiet road, our home welcomes you. This spacious, thoughtfully designed 1 BR/1.5 BA home on 4 acres is ideal for those looking to relax and get away from it all while still being just minutes away from some of the areas best dining and attractions. Whether you want to watch the sun rise over the York River, spend the day exploring the Williamsburg historic triangle (Busch Gardens), or just take it easy around the house and enjoy the outdoor area, the choice is yours.

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, 118 reviews

Outdoor Fireplace- Family Friendly & Huge Patio!

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.

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

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?

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, 328 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.

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, 158 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, 107 reviews

A vibrant sunset paints the sky in shades of orange and pink, casting reflections on the water. Silhouettes of a dock and surrounding trees create a serene waterfront scene, highlighting the natural beauty of the location.

Home in North

The Llama House

Located half-way between Mathews and Gloucester on the beautiful North River with views of the Mobjack Bay, New Point Comfort Lighthouse and Gloucester Point. The ideal spot for anyone needing to reconnect with someone, nature, or themselves. Enjoy fishing, crabbing, kayaking, playing corn hole, birdwatching, napping in a hammock, sipping wine, grilling out, amazing sunsets, listening to old records, playing the ukulele, and other simple pleasures of days gone by.

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, 276 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!

Popular amenities for house rentals in Cape Charles

Kitchen

Wifi

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

4.85 out of 5 average rating, 20 reviews

Home in Hampton

Chesapeake Bay Retreat Waterfront Indoor Pool

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, 33 reviews

Hot Tub - Massage Chair - Golf Cart - Beach Gear

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

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

4.96 out of 5 average rating, 156 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

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 beach cottage features a spacious front porch supported by white columns, offering a welcoming entry. Bright landscaping with fresh plants enhances the exterior, while a gentle ramp leads to the entrance. Windows are framed neatly, inviting natural light into the interior.

4.98 out of 5 average rating, 88 reviews

The Little Gem

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 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

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.

4.97 out of 5 average rating, 39 reviews

The Catch of the Cape- Family friendly, big yard

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, 91 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

Superhost

A historic two-story duplex features a light-colored exterior with four large windows on the upper floor. Two entrances are visible on the lower level, flanked by two American flags. A small garden area lines the front, with a tidy walkway leading to the steps.

4.88 out of 5 average rating, 16 reviews

Sea Glass Hideaway | B

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 cottage features a light-colored exterior with a welcoming porch adorned with white railings. The entrance includes a bright pink door, providing a cheerful contrast to the façade. Lush green lawns and a tree-lined street enhance the charming neighborhood setting.

5 out of 5 average rating, 32 reviews

Slowtide Cottage

5 out of 5 average rating, 46 reviews

Fully Renovated in 2023

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!

4.99 out of 5 average rating, 80 reviews

The exterior of a two-story cottage is visible, featuring vibrant blue siding and a spacious wrap-around deck. The area is surrounded by sandy terrain and greenery, with parking available underneath the house. Tall trees and a clear sky complete the peaceful setting.

Home in Gwynn

Mathews Gwynn's Island Chesapeake Bay- Sand Beach!

A spacious outdoor deck features a dining table with chairs under a large umbrella, providing shade. An American flag is displayed, and a white shed is visible in the backyard, surrounded by a fenced green area. The sky is clear with a few clouds.

4.77 out of 5 average rating, 61 reviews

JC's Retreat; boat parking on site

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.