
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*

Pasadena vacation home
Make memories in this unique, family-friendly home. The decoration set up in the house was in line with the cleanliness and photos. The cleaning fee of this house is $50, we try to make it the best for our guests to have a clean and comfortable resting environment, but we are not up to the standard of a five-star hotel, please do not book this listing with very high cleanliness requirements, I do not want to delay each other's time.

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!

3 BR 1st floor condo, near beach, resort community
1st FL (no steps), 3BR, 2BA condo unit 112C in Village at Bear Trap Dunes resort. Washer/dryer, well-equipped kitchen, deck, screened porch, terrace, 4 flat screen TVs, WIFI, DVD player, Netflix, grill, golf, indoor/outdoor pools, tot lots, gym, tennis, saunas, hot tub, restaurant/bar, close to beach, beach shuttle. Great for jogging, walking, biking, rollerblading.
Popular amenities for villa rentals near Chesapeake Bay
Private villa rentals

Luxe Homey Get-Away Beach Cove

Serenity By The Beach!

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

Queen Bed Non-Smoking

Condo w/ water views and amazing amenities!

Cheerful 4 bedrm Villa with deck, grill, fireplace

Luxury Bishop's Landing Villa Near Bethany Beach

Close to DC Excellent location.
Luxury villa rentals

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath

Nature Retreat

Luxe 5-Star Waterfront Retreat - Water-Beach Views

Stunning 14 Acre Modern Villa with Sunroom

Coastal Club Resort Style Community 3 BR, 2.5 BA

Coastal Club * 3BR Townhouse, Sleeps 9

Spacious 4 bedrms, pool, close proximity to beach

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

Spacious Retreat Near the Beach.

Quiet Villa with Bowling Alley, Pools, +Mini Golf

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

Fenwick Island-GOLF CART-Bayfront pool and beach!

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

Cozy, Brand New Villa - Bethany Beach, DE
Villa rentals with a hot tub

Welcome this beautiful single family house

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

Extra large master bedroom, 2 brand new bright diamond queen beds, separate bathroom, walk-in closet, picturesque, spacious, bright and elegant

Cheerful 2 Bedrooms 2 Baths @ Kings Creek Resort

Exotic Riverfront Villa, Sunsets, HotTub, Fishing

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 £22 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
Destinations to explore
- Rentals with beach access 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
- Outlook Beach
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- The NorVa
- Nauticus
- Old Dominion University
- First Landing Beach
- Colonial Williamsburg's Merchants Square
- Hampton University
- Mount Trashmore Park
- Children's Museum of Virginia
- Harbor Park
- Town Point Park
- Harrison Opera House
- Cape Henry Light House




