Villa rentals near Chesapeake Bay

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Top-rated villa rentals near Chesapeake Bay

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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

Coastal Club Community * 33903 * w/ Resort-Style Amenities * 3 BR, 2.5 BA Sleeps 8 * Luxury Villa Townhouse * Community of the Year * 3 BR, 2.5 Baths * Sleeps 8* Coastal Club Resort Community!! Villa Vacation Home located at Coastal Club In Lewes, Delaware. This wonderful new home offers: 2,300 sq. ft. of finished space, Bedroom Layout: The home has 3 BR, The Master Bedroom Suite in on the main floor and has a king bed . There are 2 additional bedrooms upstairs ,one of those bedrooms has

Guest favourite
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
4.81 out of 5 average rating, 141 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.

Top guest favourite
Villa in Herndon
5 out of 5 average rating, 13 reviews

Dulles Executive Resort 5 Mn from IAD, Herndon VA.

✨ A refined executive retreat focused on comfort and high-quality stay. This spacious one-bedroom villa with a private office is perfect for business travelers, remote workers, and extended stays. It offers a discreet winter escape for couples. Enjoy high-speed Wi-Fi, a marble-finished kitchenette, spa-style bathrooms with modern smart bidets, a private entrance, and driveway parking in a quiet neighborhood near IAD and Reston Town Center. Every detail supports a smooth, elevated experience.

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*

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, 106 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
4.86 out of 5 average rating, 44 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
4.85 out of 5 average rating, 113 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

Guest favourite
A spacious living area features a sleeper sofa adorned with soft pillows, positioned near a dining table and a fully equipped kitchen in the background. Natural light streams in through a window, illuminating the cool tile flooring and the inviting staircase.
Villa in Chincoteague
4.95 out of 5 average rating, 21 reviews

Flamingo Villa

The Flamingo 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

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
4.78 out of 5 average rating, 45 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.

Villa in Sparks Glencoe
4.89 out of 5 average rating, 54 reviews

Stunning 14 Acre Modern Villa with Sunroom

Fully unwind in style at this beautifully renovated two-story modern villa. Nestled in the quiet country of Sparks Glencoe, you'll have ample space to stretch out out and enjoy the numerous luxury amenities surrounding you. From leather furniture, unique lighting fixtures, and marble counters, to a show-stopping spiral staircase and spacious back deck, you'll be forever grateful you didn't opt for a hotel (and its inevitable noisy neighbors).

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, 37 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 20 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,000 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    20 of Chesapeake Bay holiday rentals include wifi 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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