Villa rentals near Chesapeake Bay

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Top-rated villa rentals near Chesapeake Bay

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Villa in Norfolk
4.9 out of 5 average rating, 48 reviews

Spacious 4 bedrms, pool, close proximity to beach

Gorgeous 4 bedroom 2.5 bath home with inground pool (2018 liner!) on a large lot!. Minutes from beach, bases, and interstate. This home offers bright, natural light throughout, hardwood floors, granite countertops, stainless steel appliances, updated lighting, and storage galore. The master bedroom features a beautiful en suite complete with a tub separate shower and double sinks. The owner had a concrete surround installed at the pool for better enjoyment of this private backyard oasis.

Top 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
4.89 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 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
4.86 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.

Villa in Temple Hills
4.86 out of 5 average rating, 7 reviews

Close to DC Excellent location.

Close to Washington, DC. Entire House 4 bedrooms with full kitchen, 2 Full bath, 2 half bathrooms, living and dining area. The family room has 60 60-inch TV. Free 2 parking spaces. Free high-speed net. Work Space with 2 writing Desks. Master bedroom with a king bed and seating area. Roku Smart TV in the family room. Fully equipped New kitchen ready for you. Washer and dryer in the lower level. Basement has a large suite with a queen bed setting and dining area, and .60 inch TV

Guest favorite
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

The exterior of the vacation rental home features a modern two-story design with a combination of light and dark siding. Prominent windows reflect sunlight, while decorative stone accents adorn the base. A colorful flag adds a welcoming touch, complemented by flower beds along the pathway.
Villa in Lewes
4.8 out of 5 average rating, 5 reviews

Coastal Club Resort Style Community 3 BR, 2.5 BA

Lewes Beach vacation rental home at Coastal Club resort style community:3 BR, 2.5 Baths * Sleeps 8 * New Luxury Villa Home * Delaware Community of the Year award-winner! * The home has 3 BR, (The Master Bedroom Suite is on the main floor and has a Queen bed w premium mattress. There are 2 additional bedrooms upstairs that share a full bathroom.  One of those bedrooms has 1 queen bed and the other bedroom has 2 twins bed. There is also a queen size sleep sofa.

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 “

Superhost
A living room area features a cozy seating arrangement with an orange sofa and an armchair. A dark wood coffee table is placed in front of the seating. A decorative chandelier hangs from the ceiling, providing soft lighting. A fireplace adds warmth, and a large window allows natural light.
Villa in Williamsburg
5 out of 5 average rating, 18 reviews

Marriott Manor Club, Williamsburg 1Bed Villa max 4

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 1 bedroom and a living room to sleep 4, and a fully equipped kitchen. Enjoy access to all the World class amenities. -Free Wi-Fi, Free Parking, NO Resort Fees, NO Cleaning Fees*

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 favorite
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!

Guest favorite
Villa in Annapolis
4.84 out of 5 average rating, 120 reviews

Crow's Nest Cottage: Chesapeake Bay View*HOT TUB*

Escape to Serenity: Chesapeake Bay Oasis. Experience the ultimate Chesapeake Bay retreat - stunning 6-bedroom, 3-bath water-view villa, perfectly suited for family reunions & special gatherings. Enjoy breathtaking bay views, steps from the water's edge, with gated 240’ pier, sandy beach, protected swim area, picnic tables, BBQ grills & children's playground. **6-person Outdoor hot tub - current temp is 102•F**

Superhost
The living room features ample seating with light-colored tufted sofas and accent chairs. A large smart TV is mounted on the wall above a modern fireplace. Natural light flows in through expansive windows, creating an inviting atmosphere.
Villa in Arlington
4.83 out of 5 average rating, 96 reviews

Luxury Arlington Farmhouse ~5 Min from D.C.~

Located in the heart of Arlington, this luxury farmhouse style home provides comfort, style, and convenience that is tastefully crafted for all kinds of travelers. The property provides a variety of amenities with a private patio, fire pit, outdoor dinning, exercise space, pool table, barista coffee bar, and more!

Popular amenities for villa rentals near Chesapeake Bay

Quick stats about villa rentals near Chesapeake Bay

  • Total vacation rentals

    Explore 20 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 1,000 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Chesapeake Bay vacation 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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