
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.

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.

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.

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 !! 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

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

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 “

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*

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.

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**

The Deluxe Oasis in the West End of Richmond
Welcome to a spacious 4,000 sq ft luxury home in West Henrico, with a big dual tempreture zone swimming pool and a big hot tub. Designed for comfort and relaxation, the home offers a blend of upscale amenities, peaceful surroundings, and convenient access to shops, restaurants, and local attractions. Ideal for families, business travelers, and quiet getaways. Parties are strictly prohibited.
Popular amenities for villa rentals near Chesapeake Bay
Private villa rentals

Luxe Homey Get-Away Beach Cove

Serenity By The Beach!

Coastal Club * 3 BR Beach Villa

Lighthouse Villa

Surfers Villa

Coastal Club * 3BR Luxury Villa Townhouse

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

Coastal Club Resort Style Community 3 BR, 2.5 BA
Luxury villa rentals

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath

Coastal Club Resort-Style Amenities Community Lewe

Nature Retreat

Luxe 5-Star Waterfront Retreat - Water-Beach Views

Stunning 14 Acre Modern Villa with Sunroom

Italy meets Moroccan oasis with huge pool for 10

Coastal Club * 3BR Villa 2 2.5 Baths

Sojourn The Lighthouse Beach Front Resort Villa
Villa rentals with a pool

Sol Villa

Crush Villa

Capitol Hill elegant, charming room

Quiet Villa with Bowling Alley, Pools, +Mini Golf

Palm Villa

Coral Villa

Quiet Villa with Access to Amazing Amenities

Flamingo Villa
Villa rentals with a hot tub

Virginia Beach Resort 7 Day Stay- Ocean Front

Bayside * 4 BR Twin House

Welcome this beautiful single family house

Coastal Club * 3BR Luxury Villa Townhouse

Coastal Club * 31313 * 3 BR, 2.5 BA * New Luxury V

Coastal Club * 3br Twin House w 2.5 Baths

Cheerful 2 Bedrooms 2 Baths @ Kings Creek Resort

Westmore Estate II Contemporary Cave Gorgeous B&B
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 G$6,274 GYD 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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- Villa rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Nauticus
- Town Point Park
- Old Dominion University
- First Landing Beach
- Virginia Living History Museum
- Chrysler Hall
- USS Wisconsin (BB-64)
- Hampton University
- The NorVa
- Neptune's Park




