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Villa rentals near Chesapeake Bay

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Top-rated villa rentals near Chesapeake Bay

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Superhost
A sandy pathway leads from a wooden fence to a wide, open beach. The calm ocean stretches into the horizon under a clear blue sky, with gentle waves lapping at the shore. Dune grass flanks the sides of the path, creating a natural border.
Villa in Frankford
4.7 out of 5 average rating, 10 reviews

Milo's By the Beach

Welcome to your home away from home at the Delaware Shore! Our home is minutes away from Bethany Beach, and just a short drive from Rehoboth Beach, Dewey Beach, Fenwick Beach, and Ocean City, MD. Along with our beautiful beaches, this area is a golfer's dream with Bear Trap Dunes just 2 1/2 miles away and many other beautiful golf courses nearby. This 2025 coastal 4-bedroom villa hosts 2400+ square ft of great modern living space with a one-car garage and driveway for your parking convenience.

Superhost
A sandy pathway leads from a wooden boardwalk through grassy dunes towards the beach. The open sky is filled with fluffy white clouds, and the calm water of the bay is visible in the distance.
Villa in Norfolk
4.93 out of 5 average rating, 29 reviews

LOVE n the Air! 5StarBeachVilla+CoffeeBar+W/D+WiFi

See YouTube: Zoe Bay Properties 5 Star Beach Villa video tour. VA is for lovers and you'll love our family-friendly spacious beach villa at tip of Willoughby Spit, Willoughby Bay on 1 side of the Spit, Chesapeake Bay the other. Only 3-minute walk to beach. No direct beach views, just marina. Fully stocked kitchen, coffee/ tea bar, gameroom, corn hole and the essentials! 4 BR 2 full BA w/tubs, 65" Smart TV w/ROKU, fast WIFI w/elite streaming. Beach cart/chairs/umbrella. Fire pit, outdoor seating.

Guest favourite
A comfortable living area features a light gray sectional sofa and a glass coffee table. Natural light enters through the window, illuminating the space. A television stands on a wooden cabinet, and a decorative plant adds a touch of greenery.
Villa in Richmond
4.96 out of 5 average rating, 73 reviews

Classic Richmond Retreat - Carytown-Downtown-VCU

Classic Richmond Retreat- Steps from authentic neighborhood restaurants, coffee houses and culture! Stay in this stylish Art Deco style Villa, perfectly located in Richmond’s Museum District! Walk to Carytown, VCU, top restaurants, parks & museums. ✔ Experience the 4 Cs - Cozy, Comfortable, Clean, & Convenient ✔ Prime Location – Steps from downtown attractions ✔ Modern Amenities for a hassle-free stay ✔ Private fenced backyard w/ dining area and porch swing -Off Street Parking

Superhost
The home features a single-story brick facade with green shutters on multiple windows. A gently sloping lawn leads to the entrance, surrounded by landscaped greenery. Tall trees form a backdrop, enhancing the peaceful wooded setting.
Villa in Manassas
4.8 out of 5 average rating, 128 reviews

Newly updated Wooded Estate 4BR/3BA in Manassas,VA

Welcome to this beautiful 2 level single-family private wooded getaway, located in historic district Manassas off Virginia State Route 234. This lovely retreat sits on 2 acres of land, has been renovated inside and out with our guests in mind. Three bedrooms/Two bathrooms on main level and huge finished basement to comfortably sleep 10. Fully equipped kitchen, in-home office, gym, washer and dryer. If you are in town for business or pleasure, this home is everything you will need for your stay.

Superhost
Waterfront views are presented, featuring a marina with multiple docks extending into the water. Colorful buildings line the shore, reflecting a blend of styles. Natural landscaping with shrubs enhances the scene, while clear skies and sunlight create a bright atmosphere.
Villa in Chincoteague
4.79 out of 5 average rating, 19 reviews

Sunset Bay Villa 315-Downtown, Pool, Gym, Sunsets!

Located just a few miles from Assateague Beach & the Chincoteague National Wildlife Refuge. Sunset Bay Villa #315 is walking distance to Historic Downtown Chincoteague, Restaurants, Shopping & Carnival Grounds. Open concept, kitchen, living room & dining room. Enjoy sunset views from the deck off the Living Room & Primary King bedroom. King bedroom features jetted tub & separate shower & double sink. Queen bedroom & pyramid bunk bedroom share hall bath. Great fitness room next to pool area!

Superhost
A living room area features a comfortable gray sofa and armchairs, accented by red and black throw pillows. A flat-screen TV is mounted above a white fireplace. Large windows offer natural light, framed by flowing curtains, with views of the surrounding nature.
Villa in Williamsburg
5 out of 5 average rating, 9 reviews

Marriott Manor Club, Williamsburg 2Bed Villa max 6

Situated in the rolling hills of the Williamsburg, Virginia woodlands within the private community of Ford's Colony. A country estate resort serving as a relaxing retreat. Located in the "Historic Triangle" along with Jamestown and Yorktown. The Guest Villa is spacious with 2 bedrooms and a living room to sleep 6, a fully equipped kitchen, and a screened in furnished patio/balcony. Enjoy access to all the World class amenities. -Free Wi-Fi, Free Parking, NO Resort Fees, NO Cleaning Fees*

Superhost
A tiki-style gazebo with a thatched roof is positioned near the waterfront, overlooking calm waters as the sun sets in the background. Soft, warm colors fill the sky, reflecting on the water's surface, while wooden posts line the shore.
Villa in Chincoteague
4.57 out of 5 average rating, 42 reviews

Beautiful 2BR Snug Harbor Waterfront villa!

It is a beautiful WATERFRONT, newly renovated villa overlooking the Assateague lighthouse, the National Park, the Wildlife Refuge and the spot where the wild ponies hang out! There is a marina right on the premises with motor boat, kayak and SUP rentals as well as organized guided kayak tour, nature boat tours and sunset cruises. The villa has fully stocked kitchen with full size fridge, stove, oven, coffee maker, toaster, pots, pans, utensils etc. Bring the family and enjoy our island!

Guest favourite
A spacious living area features light wooden flooring, a comfortable white sofa, and a coffee table. Natural light floods through the windows, illuminating the adjacent kitchen area, which includes modern appliances and a dining space. A ceiling fan and wall-mounted TV enhance the inviting atmosphere.
Villa in Virginia Beach
4.88 out of 5 average rating, 102 reviews

Beach House Just Blocks From Oceanfront Boardwalk.

This 3 story town-home (similar to a Duplex House) is the perfect getaway to enjoy a day at the beach! Only 5 minutes walk to the Oceanfront Boardwalk, you can enjoy an evening walk or have dinner at one of hundreds of restaurants in the area. First master bedroom and 2 other rooms are at second floor. Second master bedroom is third floor. Also we provide key less entry for all door inside, outside the house. Beach chair, grill, etc.... also available for you during the time you stay.

Guest favourite
A charming lakefront home is situated on a well-maintained lawn, featuring a mix of shrubs and trees. The exterior showcases a combination of brick and siding with gabled roofs and an arched window. The driveway leads to a two-car garage.
Villa in Virginia Beach
4.85 out of 5 average rating, 39 reviews

Executive Lakefront Oasis - Center of Va. Beach

Lakefront home with huge deck over the water. This amazing 4 bedroom 3 bath home just got updated. Minutes from the beach, make this location ideal. Beautiful screened in porch for enjoying the lake views. At night, the landscape lighting in the front and back gives an elegant touch. Close enough to enjoy the beach and you'll appreciate the quite relaxing lake when it's time to wind down and make memories with the family. There's a large park directly across the street for the kids.

Guest favourite
A serene view of a landscaped backyard leads to a calm lake, framed by vibrant green trees and blooming azaleas. A wooden deck with a pergola offers an inviting outdoor space, perfect for relaxation and enjoying the surrounding nature.
Villa in Manassas
4.77 out of 5 average rating, 75 reviews

Entire Lakehouse property / Private DOCK (DC/DMV )

Perfect for WORK AND/OR PLAY !! Amazing waterfront property. Tranquility meets convenience of DC metro area! Secluded w Phenomenal View from every corner! Ideal setting for vacation too ! !This gorgeous Lake house comes w a private Dock ready for your excursion! 4 Bedrooms furnished w sleeper on lower level (or 5th bedroom). NEW updates & furnishings ! Great amenities incl kayaks & pedal boat complimentary or simply just enjoy the amazing sunset from the wrapped around deck!

Superhost
A serene view of a private beach meets the calm waters of the bay under a clear blue sky. Gentle waves lap at the sandy shore, with a wooden dock extending into the water. Soft grasses frame the beach area, contributing to the tranquil atmosphere.
Villa in Montross
4.84 out of 5 average rating, 109 reviews

Beach Retreat

Relax with the whole family at the Beach Retreat! Enjoy the beautiful Sunrise and Sunsets in the Hot tub overlooking your own private beach! There is plenty to do in the Northern Neck of Virginia! We have Wineries, a Brewery, historical sites, boating, swimming, fires on the beach, bike rides, kayaking, plenty of Summer and Fall Festivals and so many great places to eat on and off the river! The Northern Neck of VA is a hidden gem! Just a 90 minute drive from the DC area

Superhost
A fully equipped kitchen is presented with white cabinetry and a clean countertop. A stainless steel sink is flanked by a coffee maker and toaster. An electric stove with a white finish features four burners, providing essential cooking space for guests.
Villa in Chincoteague
4.7 out of 5 average rating, 10 reviews

Sand Dollar Villa

The Sand Dollar Villa @ The Reef Features two bedrooms upstairs and 1/2 bath. Each bedroom has a Queen Bed Downstairs has a fully equipped kitchen, bathroom with a shower and a sleeper sofa in the living room The Reef Vacation Villas has an indoor pool, bikes, stand up paddle boards, corn hole, and Two passes to MAUI JACKS WATERPARK just a short walk away Stay with us and beat the traffic to the beach since we are located just over a half mile from the beach

Popular amenities for villa rentals near Chesapeake Bay

Kitchen
Wi-Fi
Pool
Free parking on premises
Air conditioning

Private villa rentals

The exterior of a spacious home is surrounded by greenery, featuring large windows that invite natural light. A gravel driveway leads to the entrance, which is accented with steps and a circular front window.
Villa in Ocean Pines
4.43 out of 5 average rating, 72 reviews

Luxe Homey Get-Away Beach Cove

Villa in Lewes
New place to stay

Serenity By The Beach!

Guest favourite
The rear view of the Italianate home showcases a spacious, multi-level structure with a tile roof and wrap-around porch. Green lawns and trees frame the property, providing a serene backdrop. Large windows and multiple seating areas invite outdoor relaxation.
Villa in Claremont
4.92 out of 5 average rating, 53 reviews

River Retreat with Eagle's Eye View

Superhost
A waterfront scene features a docked boat against a striking sunset, reflecting warm hues of orange and pink on the water's surface. Nearby, a two-story cottage stands with a sloped roof, complemented by a tranquil backdrop of the coastal landscape.
Villa in Chincoteague
4.68 out of 5 average rating, 25 reviews

Waterfront cottage with the most peaceful view!

A modern twin house is showcased with a deep blue exterior, framed by lush green trees. The front features a double garage and a well-manicured lawn, highlighting the inviting entrance with white accents and stylish architectural details.
Villa in Lewes
4.71 out of 5 average rating, 7 reviews

Coastal Club * 3br Twin House w 2.5 Baths

The exterior of the townhouse is showcased, featuring a mix of white siding and stone accents. Light-colored shutters frame the windows, and a stylish garage door is positioned to the left. A small landscaped area with potted plants adds charm to the entrance.
Villa in Lewes
5 out of 5 average rating, 8 reviews

Coastal Club * 3BR Luxury Villa Townhouse

Guest favourite
A spacious outdoor patio is surrounded by lush greenery, featuring comfortable seating arrangements and a gas grill. Flagstone flooring connects the area to a vibrant garden, with trees providing shade and creating a serene atmosphere for outdoor gatherings.
Villa in Arlington
4.99 out of 5 average rating, 68 reviews

New! Bright Arlington Retreat!

Top Guest favourite
A cheerful living space features light blue walls and a starfish-patterned rug. A navy blue couch is complemented by patterned curtains and decorative poufs. Two windows provide natural light, and a lamp stands on a side table. A wall sign conveys a family-oriented theme.
Villa in Millville
4.92 out of 5 average rating, 13 reviews

Firepit/Beach Shuttle/Pools/Office/Smart TVs

Luxury villa rentals

A spacious living area is furnished with a comfortable dark sofa and a light green armchair. A wooden coffee table centers the room, complemented by a TV on a stand. The room features a fireplace and leads to an open kitchen area visible in the background.
Villa in Williamsburg
4.94 out of 5 average rating, 34 reviews

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath

A spacious bathroom features a freestanding soaking tub and a glass-enclosed shower with textured tiles. Two doors provide easy access, while a large window allows natural light to brighten the room. A vibrant red towel hangs elegantly near the shower.
Villa in Gaithersburg
4.22 out of 5 average rating, 9 reviews

Welcome this beautiful single family house

A serene pond is framed by lush greenery and features a gentle slope leading to the water's edge. Reflections of surrounding trees are visible on the calm surface. The landscape is open, revealing a spacious field beyond the pond.
Villa in Queenstown

Nature Retreat

A spacious deck overlooks the water, featuring potted plants and an umbrella for shade. The marina is visible in the background, showcasing boats docked along the waterfront against a clear blue sky.
Villa in Hampton

Luxe 5-Star Waterfront Retreat - Water-Beach Views

Superhost
A bright living area features a wall-mounted television above a white fireplace. Two cozy chairs are positioned beside a pastel-colored sofa. Natural light enters through large windows, while a sliding glass door provides access to a screened-in porch with additional seating.
Villa in Cape Charles

BRAND NEW immaculate villa

A spacious living area features a comfortable leather sectional sofa with decorative cushions. A round wooden coffee table sits in the center, complemented by accent chairs. A modern spiral staircase leads to an upper level. Natural light filters through large windows, illuminating the stylish decor.
Villa in Sparks Glencoe
4.9 out of 5 average rating, 50 reviews

Stunning 14 Acre Modern Villa with Sunroom

The exterior of the townhouse is showcased, featuring a combination of siding and decorative trim. A spacious lawn surrounds the home, while tall trees provide a natural backdrop. The prominent front porch, supported by white columns, adds character and invites relaxation.
Villa in Lewes

Coastal Club * 3BR Townhouse, Sleeps 9

Villa in Norfolk
4.89 out of 5 average rating, 44 reviews

Spacious 4 bedrms, pool, close proximity to beach

Villa rentals with a pool

Superhost
A light blue two-story building features white railings and a spacious deck. Large windows provide natural light, while air conditioning units are positioned for comfort. A gravel area surrounds the property, enhancing accessibility and outdoor space.
Villa in Chincoteague
4.67 out of 5 average rating, 9 reviews

Sol Villa

Guest favourite
A modern bedroom features a spacious bed with a striped blanket, complemented by colorful wall art. A low wooden shelf with books and decorative items provides storage, while a soft area rug adds warmth to the hardwood floor.
Private room in Washington
4.93 out of 5 average rating, 805 reviews

Capitol Hill elegant, charming room

Guest favourite
A modern kitchen is featured, equipped with high-end appliances including a double oven and gas cooktop. A 15-foot white quartz island provides seating, complemented by sleek white barstools. Large windows allow natural light to brighten the space, creating a welcoming atmosphere.
Villa in Frankford
4.83 out of 5 average rating, 6 reviews

Summer Breeze - NEW 4BR Villa near Bethany Beach

Superhost
A compact bathroom is presented with neutral-colored walls and a tiled floor. A round mirror is mounted above a small pedestal sink, and a toilet is positioned against the wall. A shelf is located above the sink, providing additional storage.
Villa in Chincoteague
4.62 out of 5 average rating, 13 reviews

Surfers Villa

Superhost
The image captures a waterfront view of the condo complex, showcasing a series of boats docked at wooden piers. Calm water reflects the blue sky, while landscaped areas with low-growing plants line the docks. The colorful buildings of the complex are visible in the background.
Villa in Chincoteague
4.85 out of 5 average rating, 20 reviews

Sunset Bay 105-Waterfront w/ Boat Slip, Pool & Gym

Guest favourite
A picturesque villa is set beside a tranquil pond, with vibrant red roses in the foreground. Lush greenery frames the property, while a grand entrance features classical columns. Soft clouds drift in a blue sky, enhancing the serene atmosphere of the surroundings.
Villa in Williamsburg
4.81 out of 5 average rating, 16 reviews

Quiet Villa with Bowling Alley, Pools, +Mini Golf

Superhost
A functional kitchen is displayed, featuring a white refrigerator, microwave, and coffee maker. Dark wood cabinetry lines the walls, complemented by a light-colored countertop. A door leads outside, allowing natural light to illuminate the space, while a window invites fresh air.
Villa in Chincoteague
4.56 out of 5 average rating, 9 reviews

Coral Villa

An indoor pool is illuminated by bright overhead lights. The clear blue water reflects the light and surrounding windows. Lounge chairs are positioned along the edge of the pool, providing a space for relaxation. Large windows allow natural light to fill the area.
Villa in Williamsburg
4.81 out of 5 average rating, 31 reviews

Quiet Villa with Access to Amazing Amenities

Villa rentals with a hot tub

A charming house is set within a lush green landscape, framed by well-maintained gardens featuring various plants and trees. The exterior showcases a blend of siding and screen-enclosed areas, with a spacious lawn inviting outdoor activities.
Villa in Gloucester County
4.77 out of 5 average rating, 43 reviews

Stay, Play, Relax, and Explore …

The exterior of the twin house showcases a two-story structure with blue siding and white trim. A bright red front door adds a pop of color, while a neatly landscaped yard features green plants and colorful flowers. A garage door is visible, blending with the overall aesthetic.
Villa in Selbyville
4.71 out of 5 average rating, 7 reviews

Bayside * 4 BR Twin House

Guest favourite
The exterior of the villa townhouse is presented, showcasing a charming combination of light grey siding and white trim. Two covered porches are featured, complemented by large windows that allow natural light. The driveway leads to a two-car garage, providing convenient parking.
Villa in Lewes
5 out of 5 average rating, 11 reviews

Coastal Club * 3BR Luxury Villa Townhouse

The exterior of a three-story beach villa is displayed, featuring a well-maintained façade with gray siding and stone accents. The entrance includes a dark front door framed by tall windows. A neatly paved driveway leads to a one-car garage on the left.
Villa in Lewes
5 out of 5 average rating, 4 reviews

Coastal Club * 31313 * 3 BR, 2.5 BA * New Luxury V

A spacious living area features a high ceiling with multiple windows allowing natural light. Comfortable seating includes a blue sofa and an armchair, while a decorative coffee table sits at the center. A fireplace and green plants enhance the serene environment.
Villa in Williamsburg
4.61 out of 5 average rating, 18 reviews

Cheerful 2 Bedrooms 2 Baths @ Kings Creek Resort

A welcoming two-story home features a stone facade and a spacious front porch with white railings. Lush, neatly trimmed shrubbery lines the walkway leading to the entrance. Large windows allow natural light to illuminate the interior, enhancing the overall inviting appearance.
Private room in Falls Church

Room 1 - 2 full beds

A spacious queen bed is positioned against a textured wall, illuminated by two bedside lamps. Framed artwork decorates the nearby walls, adding a touch of elegance. A side table holds glassware, complementing the overall contemporary design.
Private room in Cockeysville
4.76 out of 5 average rating, 29 reviews

Westmore Estate II Contemporary Cave Gorgeous B&B

Superhost
A scenic view showcases a sandy beach adjacent to a paved boardwalk lined with palm trees. Colorful umbrellas are set up at a nearby seating area, framed by neatly arranged flower beds. The ocean is visible in the background, with a pier extending into the water.
Private room in Virginia Beach
5 out of 5 average rating, 3 reviews

BOARDWALK RESORT City view Studio

Quick stats about villa rentals near Chesapeake Bay

  • Total rentals

    20 properties

  • Nightly prices starting at

    $87 NZD before taxes and fees

  • Total number of reviews

    960 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore