Villa rentals near Chesapeake Bay

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Top-rated villa rentals near Chesapeake Bay

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
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
4.93 out of 5 average rating, 57 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.

Guest favourite
Aerial view showcases the lush, green property spanning 7.5 acres with a shoreline along the water. The expansive lawn and trees provide a natural backdrop, while the private dock extends into the water, offering access to the serene Chesapeake Bay.
Villa in Neavitt
4.95 out of 5 average rating, 87 reviews

Private Peninsula Estate, Pool Houses, Crab Shack

This isn't a typical waterfront rental. Durham-Hythe Estate is a private 7.5-acre peninsula compound with over 750 feet of shoreline; designed for groups who want space, privacy, and a true Eastern Shore experience. Grab a cup of coffee or tea and watch the sunrise on the dock! Enjoy Chef-prepared meals while watching the evening sunset. Estate living includes swimming, spa time, cookouts, playing with your dogs in the 4-acre field, crab feasts, and relaxing in the raised rose garden!

Top 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
4.89 out of 5 average rating, 113 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.

Top Guest favourite
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, 91 reviews

Walk to the Beach! Fire Pit-Fenced Yard-N64-Bikes!

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 - Record player - Pet ramp 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

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
4.89 out of 5 average rating, 53 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 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
4.86 out of 5 average rating, 118 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 favourite
Villa in Caret
5 out of 5 average rating, 8 reviews

Romantic 1BR Escape|Cozy, Elevated, Unforgettable

Fern and Forest is a boutique woodland retreat in Caret, Virginia, just minutes from the charming waterfront town of Tappahannock. Nestled along the iconic Coastal Highway, this restored 1960s motel has been reimagined as a luxurious three-suite hideaway. Inspired by the surrounding coastal woodlands and Tidewater heritage, The Oak Suite is a studio apartment that features an ensuite bath, a kitchenette with cooktop, and a cozy gathering space both indoors and out.

Guest favourite
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
4.85 out of 5 average rating, 20 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 townhome 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. 5 minute walk to uncrowded ocean beach. This villa offers breathtaking water views from six private decks, plus all the comforts of home.

Superhost
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
4.8 out of 5 average rating, 49 reviews

Stay, Play, Relax, and Explore …

Plan your visit to the Historical Triangle , 15 minutes from the Revolutionary war museum in Yorktown, with battlefields and victory center nearby Just down the road from Bush Gardens Williamsburg about 20 min York river ,Yorktown or beach front dining all easily accessible . Marina, boat ramp , restaurant directly across the street from the property . That is just some of what we have here and just up the road from here at “Stay Play Relax and Explore “

Top Guest favourite
A bright and airy living room showcases cathedral ceilings and a large arch window, allowing natural light to fill the space. Stylish seating includes a cozy sectional sofa, two armchairs, and a decorative coffee table, complemented by a plush area rug and elegant decor.
Villa in Potomac
5 out of 5 average rating, 46 reviews

Spacious and Beautiful Home with "Hygge"!

Make memories to last a lifetime in a home that marries luxury with a serene ambiance that embraces the Scandinavian Hygge style. Enchanting and elegant, but far from fussy, our home makes the ideal spot for friends and family marking a special occasion. Gather by the fire, play a game of pool, or unwind in the hot tub. Note: this is our home, there will be personal items in the house, but we do make an effort to clear as much as possible away.

Guest favourite
An outdoor dining area is shown, featuring a light blue picnic table surrounded by four matching chairs. A patio umbrella stands upright in the center, offering shade. A tall tree is visible in the background along with a white fence that encloses the space.
Villa in Ocean City
4.93 out of 5 average rating, 45 reviews

Cheery & Cozy Beach Villa - Walk to Beach

This Villa Offers All The Items You Want For A Perfect Vacation! Beautiful Spacious 3 BR 2 Bath With Sleep Sofa To Sleep Up To 8 Comfortably. Master BR Has A King Bed With A Private Bath. BR 2 has A Queen Bed and BR 3 Has Twin Bunk Bed. Both Have Windows Facing The Coastal Hwy. The Second Full Bathroom Is In The Hallway. Located At 90th St It Is Convenient To A Supermarket And Within Walking Distance To Popular Restaurants.

Top Guest favourite
A bright and modern kitchen features sleek white cabinets and quartz countertops. A spacious island with seating for four is complemented by stylish pendant lighting. Stainless steel appliances, including a refrigerator and oven, are neatly integrated, providing an inviting space for meal preparation.
Villa in Ocean View
5 out of 5 average rating, 41 reviews

Luxury Bethany Beach Villa in Bishop's Landing

Attention Guests - you must be at least 27 years of age or older to book this property. A Community Specific Rental Guest Form Agreement will be emailed and is required to be signed, also to include guest names so to register for pool & shuttle passes. Failure to agree to these terms will result in denial of your reservation. Please message or contact the host if you have questions about these terms. Enjoy your vacation!

Popular amenities for villa rentals near Chesapeake Bay

Quick stats about villa rentals near Chesapeake Bay

  • Total holiday rentals

    Explore 10 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at $56 AUD per night before taxes and fees

  • Verified guest reviews

    Over 840 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    10 of Chesapeake Bay holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

  • 4.7 Average rating

    Chesapeake Bay stays receive an average rating of 4.7 out of 5 from guests

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