
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.

Milo's By the Beach
Welcome to your home away from home at the Delaware Shore! Our home is minutes away from Bethany Beach, and just a short drive from Rehoboth Beach, Dewey Beach, Fenwick Beach, and Ocean City, MD. Along with our beautiful beaches, this area is a golfer's dream with Bear Trap Dunes just 2 1/2 miles away and many other beautiful golf courses nearby. This 2025 coastal 4-bedroom villa hosts 2400+ square ft of great modern living space with a one-car garage and driveway for your parking convenience.

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.

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

Walk to the Beach! Firepit-Grill-Bikes-Fence-N64!
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 - Rrecord Palyer 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

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.

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.

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!

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

River Retreat with Eagle's Eye View

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

New! Bright Arlington Retreat!

Stunning 14 Acre Modern Villa with Sunroom

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

The Deluxe Oasis in the West End of Richmond

Dulles Executive Resort 5 Mn from IAD, Herndon VA.

Cozy, Brand New Villa - Bethany Beach, DE
Luxury villa rentals

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath

Spacious Retreat Near the Beach.

BRAND NEW immaculate villa

Fenwick Island-GOLF CART-Bayfront pool and beach!

Spacious 4 bedrms, pool, close proximity to beach

Italy meets Moroccan oasis with huge pool for 10

Sojourn The Lighthouse Beach Front Resort Villa

Waterfront Retreat & Guest House
Villa rentals with a pool

Capitol Hill elegant, charming room

Sol Villa

Surfers Villa

Sunset Bay 105-Waterfront w/ Boat Slip, Pool & Gym

Quiet Villa with Bowling Alley, Pools, +Mini Golf

8 Bedrooms Historic Mansion

Coral Villa

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

Stay, Play, Relax, and Explore …

Large basement for rent, 4 rooms, glass doors, windows, separate full bathroom, large living room

Welcome this beautiful single family house

Cheerful 2 Bedrooms 2 Baths @ Kings Creek Resort

Room 1 - 2 full beds

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 $76 AUD per night before taxes and fees

Verified guest reviews
Over 960 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
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

Wi-Fi availability
20 of Chesapeake Bay holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Assateague Beach
- Haven Beach
- Buckroe Beach and Park
- Jamestown Settlement
- Grandview Beach
- Bethel Beach
- Outlook Beach
- Kiptopeke Beach
- Piney Point Beach
- Golden Horseshoe Golf Club
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Chrysler Museum of Art
- James River Country Club
- Cape Charles Beachfront
- Wilkins Beach
- Little Creek Beach
- Wallops Beach
- Sarah Constant Beach Park




