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, 124 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!

LocationFamilyQuiet

A front porch features a welcoming blue door and cozy seating area with two chairs and a swing. Pillows adorn the chairs, creating a comfortable spot to relax. The porch is surrounded by white railings and offers a glimpse of the neighborhood.

5.0 out of 5 average rating, 102 reviews

Walk 2 Beach & Restaurants~Central Park~ King Bed!

You will be close to everything in Cape Charles! Experience a fully renovated 1900’s Victorian duplex centrally-located! Next to the park, 2 quick blocks to Main St. & beach! The upstairs bedrooms share a Jack and Jill bathroom. Full kitchen with washer/dryer. 2 outdoor living areas to sip your coffee or wine! Your family will feel cozy and relaxed while you're on vacation! • Front Porch Swing & Backyard Brick Patio w/Grill • Beach Gear, Games, Pickleball • Modern Kitchen, Wood Floors, King Bed

FamilyLocationNearby

4.97 out of 5 average rating, 145 reviews

Huge Patio~Outdoor Fireplace & Shower~Family Home!

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.

FamilyLocationKitchen

4.98 out of 5 average rating, 160 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.

LocationFamilyTV

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.

4.94 out of 5 average rating, 193 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)

FamilyValueWifi

4.99 out of 5 average rating, 134 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

ValueFamilyCondition

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.

4.96 out of 5 average rating, 284 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!

ValueLocationHospitality

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.

4.97 out of 5 average rating, 311 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!

ValueFamilyIndoor spaces

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.

5.0 out of 5 average rating, 105 reviews

The BeeHouse

Breathe in the Beehouse! Newly built, this well equipped modern house features high ceilings with a clean crisp design with bright tropical colors and natural touches that truly transport you! Treat yourself to the tranquil Cape Charles lifestyle where you won’t see a clock because the local church chimes on the hour. Huge outdoor living space embraces you and allows you to take it all in. Have the sweetest vacation at the Beehouse!

FamilyValueQuiet

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, 124 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.

LocationFamilyCondition

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.

4.95 out of 5 average rating, 120 reviews

It’s porch season! Welcome to the MT Nest!

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!

FamilyLocationQuiet

4.95 out of 5 average rating, 39 reviews

CC Beachfront: hot tub, golf cart, movie theater

🏖 Steps from the Sand – Unbeatable Location! This stunning, single-story ranch home is directly across from the Cape Charles beach, sitting on the corner of Bay Ave & Monroe Ave—the most coveted location in town! Enjoy breathtaking sunsets, walk to local dining, golf cart or bike through charming streets, all from your front door. Just purchased a 6 seater golf cart, and decided to make it free for the 1st year!

ValueLocationView

Popular amenities for house rentals in Cape Charles

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 175 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

LocationValueWalkability

4.98 out of 5 average rating, 307 reviews

A green pasture is featured, where a group of five horses graze peacefully. The background showcases a wooded area with tall trees, under a clear blue sky. A small shelter is visible in the distance, complementing the tranquil rural setting.

Home in Accomac

Heartsong Farmhouse , a nature lover's retreat.

ValueLocationPool

4.91 out of 5 average rating, 181 reviews

Home in Cobbs Creek

Million $ Views! Pool! Private Hot Tub! EV Charger

ValueLocationPets

Superhost

Home in Hampton

4.89 out of 5 average rating, 139 reviews

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

FamilyValueComfort

Superhost

A backyard patio offers seating at a rectangular table with four chairs, shaded by a large umbrella. A cozy seating arrangement is visible nearby, featuring bright cushions. The in-ground pool reflects the sky, while the tranquil river and greenery create a serene backdrop.

Home in Hampton

4.9 out of 5 average rating, 111 reviews

The Great River Escape *Hot Tub!

LocationValueView

5.0 out of 5 average rating, 31 reviews

New Build-1st Floor King Suite &Kid Friendly Loft!

LocationValueAmenities

4.86 out of 5 average rating, 37 reviews

A spacious waterfront property is featured, showcasing expansive outdoor areas including a heated pool, playground, and large lawn. A comfortable deck surrounds the pool, while the house is adjacent to well-maintained landscaping and pathways, highlighting the scenic surroundings and inviting outdoor activities.

Home in Reedville

Bayfront | Pool Open & Heated, Hot Tub, Dock, Pets

FamilyValueAmenities

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.

5.0 out of 5 average rating, 50 reviews

East of the Sun Victorian - Private Pool

FamilyLocationBack garden

Weekly house rentals

A three-story brick home is set among manicured greenery, featuring a covered entrance supported by arches. A spacious balcony extends across the upper level, adorned with white railings. Several windows, arranged symmetrically, offer a classic architectural appearance with charming outdoor elements.

5.0 out of 5 average rating, 42 reviews

Chesapeake Bay View

ValueFamilyIndoor spaces

4.91 out of 5 average rating, 22 reviews

Chateau-de-Chuck

ValueLocationNearby

A wooden dock extends over a calm lake, framed by lush greenery. Two black chairs are positioned for relaxation, overlooking the water. A slide is visible in the background, accompanied by green and red kayaks, offering options for water activities.

4.93 out of 5 average rating, 45 reviews

Eden Lake House Cape Charles

FamilyLocationAccuracy

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.

4.97 out of 5 average rating, 35 reviews

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

ValueLocationHospitality

A charming two-story house is presented, featuring light blue siding and a welcoming front porch. Lush greenery surrounds the property, and a stone pathway leads to the entrance. A screened porch can be observed that enhances the outdoor living space.

5.0 out of 5 average rating, 28 reviews

Historic Cape Charles- 1 Block from the Beach!

LocationValueOutdoor spaces

The exterior of a spacious historic home is shown, featuring a light blue façade and a pointed roof. A front porch with white railings and steps is visible, complemented by lush greenery and an American flag. Bright blue skies and ample sunlight enhance the inviting atmosphere.

4.95 out of 5 average rating, 21 reviews

Happy Hours! 7 bedrooms, double lot, huge porch

FamilyLocationBiking

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.

4.9 out of 5 average rating, 89 reviews

Pet friendly comfy family home

LocationFamilyWalkability

A three-story home is showcased with a light blue exterior and white trim. Balconies are present on the upper floors, surrounded by white railings. Lush greenery and colorful flowers adorn the front yard, complemented by a neatly maintained lawn.

5.0 out of 5 average rating, 24 reviews

Legasea by the Bay

FamilyValueBeach

Private house rentals

A modern, multi-level home is surrounded by lush green landscaping. Two golf carts are parked under a blue canopy by the driveway, ready for use. The exterior features a blend of light gray and turquoise siding, with multiple windows enhancing the inviting look.

5.0 out of 5 average rating, 29 reviews

The Strand: Free Golf Carts & Pool, 1 Blk to Beach

FamilyLocationSleep quality

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.

5.0 out of 5 average rating, 15 reviews

The Love Shack

LocationFamilyQuiet

4.96 out of 5 average rating, 94 reviews

Game Barn! Next to Central Park! 2 Blocks 2 Beach/

LocationFamilySleep quality

The exterior of a light blue two-story house is shown, featuring a welcoming front porch with a white railing. A mint green front door is centered, flanked by large windows. Lush greenery lines the walkway, enhancing the inviting appearance of the home.

5.0 out of 5 average rating, 78 reviews

Breakwater Cottage

FamilyLocationBack garden

An aerial view shows a scenic landscape with winding waterways surrounded by lush greenery. A private dock extends into the water, while a charming house is visible on a spacious lawn. Mature trees frame the property, enhancing the tranquil setting.

5.0 out of 5 average rating, 40 reviews

Kings Creek Cottage | Waterfront Retreat

LocationFamilyLaundry

5.0 out of 5 average rating, 16 reviews

Beach Bliss Cottage- Hot Tub, Golf Cart & Firepit

LocationFamilyCheck-in

An inviting front porch features a pastel blue-green siding with a vibrant coral door. Two white adirondack chairs sit beside a small potted plant, while a pink swing offers a warm touch, enhancing the welcoming entrance to the home.

4.93 out of 5 average rating, 94 reviews

The Peach House: close to the shops, beach + park

ValueFamilyLaundry

A renovated Victorian house is displayed, featuring a welcoming front porch with comfortable seating. Lush greenery and flower planters accompany the entrance. Light-colored siding contrasts with a bold red roof, and large windows allow ample natural light to illuminate the inviting space.