
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.

Coastal Club * 3BR Luxury Villa Townhouse
Coastal Club Community * 33903 * w/ Resort-Style Amenities * 3 BR, 2.5 BA Sleeps 8 * Luxury Villa Townhouse * Community of the Year * 3 BR, 2.5 Baths * Sleeps 8* Coastal Club Resort Community!! Villa Vacation Home located at Coastal Club In Lewes, Delaware. This wonderful new home offers: 2,300 sq. ft. of finished space, Bedroom Layout: The home has 3 BR, The Master Bedroom Suite in on the main floor and has a king bed . There are 2 additional bedrooms upstairs ,one of those bedrooms has

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.

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*

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.

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

Flamingo Villa
The Flamingo Villa @ The Reef Features two bedrooms upstairs and 1/2 bath. Each bedroom has a Queen Bed Downstairs has a fully equipped kitchen, bathroom with a shower and a sleeper sofa in the living room The Reef Vacation Villas has an indoor pool, bikes, stand up paddle boards, corn hole, and Two passes to MAUI JACKS WATERPARK just a short walk away Stay with us and beat the traffic to the beach since we are located just over a half mile from the beach

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 “

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.

Stunning 14 Acre Modern Villa with Sunroom
Fully unwind in style at this beautifully renovated two-story modern villa. Nestled in the quiet country of Sparks Glencoe, you'll have ample space to stretch out out and enjoy the numerous luxury amenities surrounding you. From leather furniture, unique lighting fixtures, and marble counters, to a show-stopping spiral staircase and spacious back deck, you'll be forever grateful you didn't opt for a hotel (and its inevitable noisy neighbors).

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

Sol Villa

Luxe Homey Get-Away Beach Cove

Serenity By The Beach!

Coastal Club * 3 BR Beach Villa

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

Lighthouse Villa

Surfers Villa

Quiet Villa with Bowling Alley, Pools, +Mini Golf
Luxury villa rentals

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath

Nature Retreat

Luxe 5-Star Waterfront Retreat - Water-Beach Views

Spacious 4 bedrms, pool, close proximity to beach

Italy meets Moroccan oasis with huge pool for 10

Coastal Club * 3BR Villa 2 2.5 Baths

Sojourn The Lighthouse Beach Front Resort Villa

Sea Glass Paradise
Villa rentals with a pool

Crush Villa

Capitol Hill elegant, charming room

Summer Breeze – 4BR Villa. Fall & Winter Gateway

New 3BR Corner Unit | Shuttle & Free Linens

Palm Villa

Quiet Villa with Access to Amazing Amenities

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

Screened Porch, Outdoor Shower: Millville Villa
Villa rentals with a hot tub

Bayside * 4 BR Twin House

Welcome this beautiful single family house

Coastal Club * 3br Twin House w 2.5 Baths

Cheerful 2 Bedrooms 2 Baths @ Kings Creek Resort

Bayside * 4BR Luxury Villa Townhouse

Westmore Estate II Contemporary Cave Gorgeous B&B

BOARDWALK RESORT City view Studio

Private room with bath, share living room& kitchen
Quick stats about villa rentals near Chesapeake Bay

Total holiday rentals
Explore 20 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 1,000 verified reviews to help you choose

Family-friendly holiday rentals
20 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
20 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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- Resort rentals Chesapeake Bay
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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
- Town Point Park
- Nauticus
- Old Dominion University
- First Landing Beach
- Virginia Living History Museum
- Chrysler Hall
- USS Wisconsin (BB-64)
- Hampton University
- Neptune's Park
- Point Lookout State Park




