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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 favorite
A spacious villa is nestled amidst lush greenery, featuring a combination of stone and wood exteriors. A well-maintained yard is highlighted by a gravel pathway, surrounded by colorful flowers. Large windows reflect the serene surroundings and allow ample natural light into the home.
Villa in Millville
4.96 out of 5 average rating, 51 reviews

Exotic Riverfront Villa, Sunsets, HotTub, Fishing

Enjoy the entire Sai Villa on Maurice River, NJ This classic, carbon neutral Mediterranean style villa, with 3+ acres of nature, sits on the gorgeous Maurice River in Millville. Enjoy amazing sunsets, hot tub, fishing, kayaking & family time, or host private events. A perfect pleasure & wedding spot. You are guaranteed to enjoy the slice of paradise. Sai Villa is close to Cape May, Wildwood Beaches, Atlantic City, NLMP, NYC, Poconos and Maurice River Cruises will add to your 5-Star experience.

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 favorite
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 favorite
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 favorite
A tranquil bayside view is captured, with calm waters reflecting the clear sky. A small outdoor table adorned with a silver bucket and glasses sits on a deck, framed by white railings that lead to the water's edge.
Villa in Bethany Beach
4.8 out of 5 average rating, 15 reviews

Beach Cove Bliss

Bayfront Villa in Bethany Beach – Sleeps 16, Walk to the Beach! Beach Cove Villa #15, a stunning 5-bedroom, 4-bath bay view vacation home in Bethany Beach, Delaware. With 2,700 square feet of beautifully designed space, this coastal getaway is perfect for large families, multi-family groups, or friends traveling together. Just minutes from Bethany Beach boardwalk and sandy shores, this villa offers breathtaking water views from six private decks, plus all the comforts of home.

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

Top guest favorite
The living area features comfortable seating options arranged around a central area rug, with a fireplace adding warmth. A large television is mounted on the wall opposite, while natural light streams through the windows, which are adorned with blinds.
Villa in Ocean City
4.99 out of 5 average rating, 73 reviews

Walk to the Beach! Firepit-Grill-Bikes-Fence-N64!

Escape to the Blue House, a pet-friendly retreat just 6-mins to the beach. - Full kitchen and charcoal grill - Coffee bar (k-cups, espresso, coffee grinder, french press, and pour over) - Fully fenced patio with a fire pit and ping pong - Outdoor shower - 5 Bikes - Northside Park - 2 min walk away - N64 - 48W EV charger - Rrecord Palyer Sleep 10 (8 Adults 2 Children) in our 3 bedrooms - 1 king, 1 queen, 1 full over full bunk bed, and full sofa bed. NOT POSTED ON C.LIST

Popular amenities for villa rentals near Chesapeake Bay

Kitchen
Wifi
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 favorite
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

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

Guest favorite
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 favorite
Villa in Herndon
5 out of 5 average rating, 8 reviews

Dulles Executive Resort 5 Mn from IAD, Herndon VA.

An inviting living area is illuminated by natural light from large windows, revealing a modern layout. A comfortable seating arrangement faces a wall-mounted television, while a dining table with black chairs occupies the foreground. Colorful wall art adds a touch of character.
Villa in Aberdeen
4.56 out of 5 average rating, 9 reviews

Cheerful 4 bedrm Villa with deck, grill, fireplace

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, 35 reviews

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath

Guest favorite
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

Guest favorite
The exterior of the home displays a charming two-story design with a mix of dark and light siding. Large windows allow natural light to enter, while the inviting entrance features a well-maintained front yard with a young tree and a driveway leading to a one-car garage.
Villa in Ocean View
5 out of 5 average rating, 7 reviews

Spacious Retreat Near the Beach.

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

Top guest favorite
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

Top guest favorite
A bright living area is presented, featuring two white sofas and a dark wood coffee table at the center. Large windows allow natural light, showcasing views of the pond outside. A patterned rug complements the space, adding a playful element to the decor.
Villa in Selbyville
5 out of 5 average rating, 8 reviews

Fenwick Island-GOLF CART-Bayfront pool and beach!

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

Guest favorite
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 favorite
The front exterior of the villa features a light-colored facade with stone accents and a symmetrical roof. Two garage doors are visible on the left, complemented by well-maintained landscaping and a walkway leading to the entrance, under a blue sky adorned with fluffy clouds.
Villa in Millville
4.88 out of 5 average rating, 51 reviews

Spacious Villa 3 miles to Bethany Beach Water Acc

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

Top guest favorite
The living area features a dark blue sofa adorned with plaid and nautical-themed cushions. A matching upholstered chair is present, along with a decorative ottoman. Wall art depicting coastal scenes is mounted above, flanked by oars. Two lamps provide ambient lighting beside the sofa.
Villa in Bethany Beach
4.89 out of 5 average rating, 36 reviews

Sea Colony West-Summer Breeze, villa 2bdrm/2bth(8)

Guest favorite
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

A balcony view is presented, overlooking the surrounding landscaped grounds and several white multi-unit buildings. Clear blue skies and wispy clouds can be seen above, while distant views of water and greenery add to the serene atmosphere.
Villa in Clarksville

Condo w/ water views and amazing amenities!

A spacious outdoor pool area is shown, surrounded by lounge chairs and shaded areas. Tall trees provide greenery in the background. A lifeguard chair is positioned next to the pool, with swim lanes visible, inviting guests for leisure and relaxation.
Villa in Bethany Beach

3BR Sea Colony Stay | Full Access to Resort Perks

Two adirondack chairs are positioned on a balcony, facing a golf course with lush green grass and a serene lake. A small table holds two cocktails, complemented by the backdrop of trees and a clear sky.
Villa in Ocean Pines
5 out of 5 average rating, 4 reviews

Lakeview/Golf course front home - 4 Bed/3 baths

Villa rentals with a hot tub

A well-appointed room features a spacious bed with a blue and white striped coverlet. A patterned chair is positioned near a window that offers ocean views. Natural light fills the room, complemented by wooden furnishings and a lamp providing additional illumination.
Villa in Virginia Beach

Virginia Beach Resort 7 Day Stay- Ocean Front

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 …

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

Guest favorite
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 living room offers comfortable seating with two upholstered chairs and a sectional sofa. A glass coffee table is centered on a plush carpet, while a gas fireplace and Smart TV are positioned on the wall. Natural light is welcomed through large front windows.
Villa in Ocean View
4.82 out of 5 average rating, 45 reviews

4 Mi to Bethany Beach: Sunny Escape w/ Porches!

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

Top guest favorite
A private enclosed gazebo houses a 4-5 person Jacuzzi, featuring soft blue lighting and soothing water jets. Large windows provide views of the surroundings, while warm ambient lighting creates a relaxing atmosphere for guests to unwind.
Villa in North Cape May
5 out of 5 average rating, 23 reviews

Private Hot Tub Schooner Villa By the Bay

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

Quick stats about villa rentals near Chesapeake Bay

  • Total rentals

    20 properties

  • Nightly prices starting at

    R861 ZAR 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