
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.

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

Dulles Executive Resort | Office Suite | 5m to IAD
✨Dulles Executive Resort offers a luxurious stay focused on comfort and cozy style. This spacious one-bedroom villa with 2 beds and a private office is ideal for business travelers, remote workers, and extended stays. Enjoy high-speed Wi-Fi, a marble kitchenette, a bathroom with a smart bidet like a spa, a private entrance, and parking, all just minutes from Washington Dulles International Airport (IAD) and Reston Town Center. Relax on the patio after work or unwind in the office rocking chair.

Huge Private Wooded Estate 5BR/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.

Private Peninsula Estate, Pool Houses, Crab Shack
This isn't a typical waterfront rental. Durham-Hythe Estate is a private 7.5-acre peninsula compound with over 750 feet of shoreline; designed for groups who want space, privacy, and a true Eastern Shore experience. Grab a cup of coffee or tea and watch the sunrise on the dock! Enjoy Chef-prepared meals while watching the evening sunset. Estate living includes swimming, spa time, cookouts, playing with your dogs in the 4-acre field, crab feasts, and relaxing in the raised rose garden!

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-FencedYard-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

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 “

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.

Cheery & Cozy Beach Villa - Walk to Beach
This Villa Offers All The Items You Want For A Perfect Vacation! Beautiful Spacious 3 BR 2 Bath With Sleep Sofa To Sleep Up To 8 Comfortably. Master BR Has A King Bed With A Private Bath. BR 2 has A Queen Bed and BR 3 Has Twin Bunk Bed. Both Have Windows Facing The Coastal Hwy. The Second Full Bathroom Is In The Hallway. Located At 90th St It Is Convenient To A Supermarket And Within Walking Distance To Popular Restaurants.
Popular amenities for villa rentals near Chesapeake Bay
Private villa rentals

3 Mi to Boardwalk: Bethany Beach House w/ Patio!

Luxe Homey Get-Away Beach Cove

Nature Retreat

Luxe 5-Star Waterfront Retreat - Water-Beach Views

New! Bright Arlington Retreat!

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

Cheerful 4 bedrm Villa with deck, grill, fireplace

Blake House Historic Estate with Private Inn
Luxury villa rentals

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath

Spacious Retreat Near the Beach.

Deer Haven at Bacon Hall

Fenwick Island-GOLF CART-Bayfront pool and beach!

Executive Lakefront Oasis - Center of Va. Beach

Spacious 4 bedrms, pool, close proximity to beach

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

Italy meets Moroccan oasis with huge pool for 10
Villa rentals with a pool

Spacious Villa 3 miles to Bethany Beach Water Acc

Summer Breeze – 4BR Villa. Fall & Winter Gateway

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

Millville by the Sea • 3BR • Pools Access

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

Palm Villa

Quiet Villa with Access to Amazing Amenities

Condo w/ water views and amazing amenities!
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

Coastal Club * 3BR Luxury Villa Townhouse

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

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

Cheerful 2 Bedrooms 2 Baths @ Kings Creek Resort

Private room with work table & chair.
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
- Busch Gardens Williamsburg
- Virginia Beach Oceanfront
- Chincoteague Island
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Cape Charles Beachfront
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- First Landing Beach
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Hampton University
- Town Point Park
- Old Dominion University
- Virginia Living History Museum
- Chrysler Hall
- Neptune's Park
- USS Wisconsin (BB-64)
- Harbor Park




