
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.

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.

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.

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

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.

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*

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!

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.

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.

Entire Lakehouse property / Private DOCK (DC/DMV )
Perfect for WORK AND/OR PLAY !! Amazing waterfront property. Tranquility meets convenience of 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 around deck!

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.

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

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
Private villa rentals

Luxe Homey Get-Away Beach Cove

Serenity By The Beach!

River Retreat with Eagle's Eye View

Nature Retreat

New! Bright Arlington Retreat!

LOVE n the Air! 5StarBeachVilla+CoffeeBar+W/D+WiFi

3BR Sea Colony Stay | Full Access to Resort Perks

Dulles Executive Resort 5 Mn from IAD, Herndon VA.
Luxury villa rentals

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath

Summer Breeze - NEW 4BR Villa near Bethany Beach

Spacious Retreat Near the Beach.

BRAND NEW immaculate villa

Stunning 14 Acre Modern Villa with Sunroom

Firepit/Beach Shuttle/Pools/Office/Smart TVs

Fenwick Island-GOLF CART-Bayfront pool and beach!

Luxury Arlington Farmhouse ~5 Min from D.C.~
Villa rentals with a pool

Spacious Villa 3 miles to Bethany Beach Water Acc

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

Quiet Villa with Access to Amazing Amenities

Spacious 4 bedrms, pool, close proximity to beach

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

Cozy, Brand New Villa - Bethany Beach, DE

Luxury Bishop's Landing Villa Near Bethany Beach

3BR dog-friendly resort community stay, water view
Villa rentals with a hot tub

Stay, Play, Relax, and Explore …

Welcome this beautiful single family house

Coastal Club * 3BR Luxury Villa Townhouse

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

Cheerful 2 Bedrooms 2 Baths @ Kings Creek Resort

The Deluxe Oasis in the west end of Richmond

Westmore Estate II Contemporary Cave Gorgeous B&B

BOARDWALK RESORT City view Studio
Quick stats about villa rentals near Chesapeake Bay
Total rentals
20 properties
Nightly prices starting at
$70 CAD 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
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- Villa rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Haven Beach
- Assateague Beach
- Buckroe Beach and Park
- Grandview Beach
- Jamestown Settlement
- Bethel Beach
- Outlook Beach
- Kiptopeke Beach
- Piney Point Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Golden Horseshoe Golf Club
- Chrysler Museum of Art
- Cape Charles Beachfront
- James River Country Club
- Wilkins Beach
- Little Creek Beach
- Wallops Beach
- Sarah Constant Beach Park