
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.

Luxury Private Estate with 6 Bedrooms in Leesburg
luxury Private Estate in Leesburg. Perfect for family fun near wineries & breweries! with 6Bedrooms, huge owners suite & lux bath w/heated floors, soaking tub. The primary suite has a private living room that leads to a balcony. Huge open kitchen with high-end appliances, double wall-oven, oversized island, granite counters, skylights, heated floors, new sunroom, Bluetooth ceiling speakers. Covered Porch with Brand New Hot Tub. Beautiful outdoors with firepit under the stars. Welcome to Harmony.

The Mulberry Manor House
The Mulberry Manor House is conveniently located outside of Washington DC, close to Dulles International & Reagan International airports. Minutes from I66 & public transportation to DC. In the heart of Horse & Wine Country, close to Manassas National Battlefield Park, in historic Haymarket, minutes from historic Middleburg, & The Plains, & still in close proximity to high end shopping, restaurants, movie theaters, hospitals & all the major modern conveniences that Northern Virgina has to offer.

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

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.

Walk to the Beach! Fire Pit-Fenced Yard-N64-Bikes!
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 - Record player - Pet ramp 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

Dulles Executive Retreat | 1BR + Office | Near IAD
✨ Welcome to Dulles Executive Resort, an elegant retreat designed for business travelers, extended stays, and guests seeking comfort near Washington Dulles International Airport (IAD). Private 1BR with an executive office and half-bath, ideal for work trips or couples celebrating special moments. Sleeps up to 4 with a premium sleeper sofa. Enjoy high-speed Wi-Fi, a marble kitchenette, a spa-style bath, a private entrance, parking, and a peaceful patio minutes from Reston Town Center.

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 “

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.

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**
Popular amenities for villa rentals near Chesapeake Bay
Private villa rentals

Luxe Homey Get-Away Beach Cove

Private Getaway on Spacious Property

Nature Retreat

Luxe 5-Star Waterfront Retreat - Water-Beach Views

Bay Access 3 bedroom Main House in Franklin Manor

Condo w/ water views and amazing amenities!

Cheerful 4 bedrm Villa with deck, grill, fireplace

Ocean-Block Pet Friendly Dewey Beach Retreat
Luxury villa rentals

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath

Spacious Retreat Near the Beach.

Coastal Club * 3BR Luxury Villa Townhouse

Deer Haven at Bacon Hall

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

Fenwick Island-GOLF CART-Bayfront pool and beach!

Executive Lakefront Oasis - Center of Va. Beach

Spacious 4 bedrms, pool, close proximity to beach
Villa rentals with a pool

Bear Trap. First-Floor, Pet-Friendly & Pond Views

5 Mi to Bethany Beach | Pools, Shuttle + Fire Pit

River Run Retreat | Pool + Golf Escape

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

Quiet Villa with Bowling Alley, Pools, +Mini Golf

Palm Villa

Your Dream 4 Bedroom Vacation Villa w. Heated Pool

Lakeview/Golf course front home - 4 Bed/3 baths
Villa rentals with a hot tub

Romantic 1BR Escape|Cozy, Elevated, Unforgettable

Virginia Beach Resort 7 Day Stay- Ocean Front

Welcome this beautiful single family house

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

Cheerful 2 Bedrooms 2 Baths @ Kings Creek Resort

Private Hot Tub Schooner Villa By the Bay

The Deluxe Oasis in the West End of Richmond

Westmore Estate II Contemporary Cave Gorgeous B&B
Quick stats about villa rentals near Chesapeake Bay

Total holiday rentals
Explore 10 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 840 verified reviews to help you choose

Family-friendly holiday rentals
10 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
10 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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- Villa rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Old Dominion University
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- First Landing Beach
- The Mariners' Museum
- Nauticus
- Town Point Park
- Virginia Zoological Park
- Virginia Living History Museum
- Hampton University
- Cape Henry Light House
- Chrysler Hall





