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Villa rentals near Chesapeake Bay

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Top-rated villa rentals near Chesapeake Bay

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Guest favorite
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
4.73 out of 5 average rating, 11 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.

Top guest favorite
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, 76 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

Guest favorite
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, 131 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 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, 103 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, 41 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.

Superhost
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
4.78 out of 5 average rating, 77 reviews

Entire Lakehouse property / Private DOCK (DC/DMV )

Perfect for WORK AND/OR PLAY !! WATERFRONT property. Tranquility AND Convenience ! Major Business hubs, 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 ar

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, 112 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, 74 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

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
4.81 out of 5 average rating, 16 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. 5 minute walk to uncrowded ocean beach. This villa offers breathtaking water views from six private decks, plus all the comforts of home.

Top guest favorite
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, 45 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.

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!

Top guest favorite
Villa in Leesburg
5 out of 5 average rating, 44 reviews

The Garage Mahal w/Hot Tub

Relax inside or outside enjoying a luxurious wine country getaway listening to the sounds of nature and birds in a completely private setting just a few miles from Leesburg, and a 2 mile drive to Stone Tower Winery, Leesburg Animal Park, and Oatlands Historic House. Every detail has been meticulously thought through to add to the comfort of your stay away from life's bustle in pure solitude or with friends and family.

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.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 960 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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