
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.

Spacious 4 bedrms, pool, close proximity to beach
Gorgeous 4 bedroom 2.5 bath home with inground pool (2018 liner!) on a large lot!. Minutes from beach, bases, and interstate. This home offers bright, natural light throughout, hardwood floors, granite countertops, stainless steel appliances, updated lighting, and storage galore. The master bedroom features a beautiful en suite complete with a tub separate shower and double sinks. The owner had a concrete surround installed at the pool for better enjoyment of this private backyard oasis.

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.

Close to DC Excellent location.
Close to Washington, DC. Entire House 4 bedrooms with full kitchen, 2 Full bath, 2 half bathrooms, living and dining area. The family room has 60 60-inch TV. Free 2 parking spaces. Free high-speed net. Work Space with 2 writing Desks. Master bedroom with a king bed and seating area. Roku Smart TV in the family room. Fully equipped New kitchen ready for you. Washer and dryer in the lower level. Basement has a large suite with a queen bed setting and dining area, and .60 inch TV

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

Coastal Club Resort Style Community 3 BR, 2.5 BA
Lewes Beach vacation rental home at Coastal Club resort style community:3 BR, 2.5 Baths * Sleeps 8 * New Luxury Villa Home * Delaware Community of the Year award-winner! * The home has 3 BR, (The Master Bedroom Suite is on the main floor and has a Queen bed w premium mattress. There are 2 additional bedrooms upstairs that share a full bathroom. One of those bedrooms has 1 queen bed and the other bedroom has 2 twins bed. There is also a queen size sleep sofa.

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*

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!

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**

Luxury Arlington Farmhouse ~5 Min from D.C.~
Located in the heart of Arlington, this luxury farmhouse style home provides comfort, style, and convenience that is tastefully crafted for all kinds of travelers. The property provides a variety of amenities with a private patio, fire pit, outdoor dinning, exercise space, pool table, barista coffee bar, and more!
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 * 3BR Luxury Villa Townhouse

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

Coral Villa

Cheerful 4 bedrm Villa with deck, grill, fireplace
Luxury villa rentals

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath

Nature Retreat

Luxe 5-Star Waterfront Retreat - Water-Beach Views

New! Bright Arlington Retreat!

Private Luxury Spa Hot Tub Retreat with Ping Pong

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

Crush Villa

Capitol Hill elegant, charming room

Summer Breeze – 4BR Villa. Fall & Winter Gateway

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

Lighthouse Villa

New 3BR Corner Unit | Shuttle & Free Linens

Coastal Club * 3BR Luxury Villa Townhouse

Palm 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 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
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 ﺩ.ﺇ110 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
Destinations to explore
- Rentals with outdoor seating Chesapeake Bay
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- Villa rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- Buckroe Beach
- First Landing State Park
- 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
- First Landing Beach
- Virginia Living History Museum
- Old Dominion University
- Hampton University
- Chrysler Hall
- Neptune's Park
- USS Wisconsin (BB-64)
- Children's Museum of Virginia




