
Villa rentals near Chesapeake Bay
Find and book unique villas on Airbnb
Top-rated villa rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness and more.

Lakeview/Golf course front home - 4 Bed/3 baths
Golfer's paradise on River Run golf course in Berlin, MD! 8 miles to Ocean City! Located overlooking a lake on the 4th hole in the River Run Golf Community. This well decorated duplex is in an ideal location. The beaches, amusements, restaurants, casino, movies, and shopping outlets are all within 15 minutes. You can enjoy the pool, tennis & golf on site in the River Run community. This duplex has 4 BDRM's & 3 full baths. The maximum occupancy allowed for this rental is eight people. NO PETS.

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.

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 “

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).

Pasadena Holiday Home
Make memories in this unique, family-friendly space. 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.

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. .

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!

Waterfront cottage with the most peaceful view!
Take it easy at this unique and tranquil getaway. This 2 Br waterfront cottage is a part of 4 cottages complex. It is literally just steps away from the water. The view is unbelievable! You can see the National Park and the Wildlife Refuge, the lighthouse and the wild Chincotegaue ponies right across the water!

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath
Luxurious 3 bedroom condo in Kingsmill Resort with 3 full baths, fully equipped kitchen, washer/dryer, sleeps 8! Right next door to Busch Gardens, minutes from Water Country and Colonial Williamsburg, Jamestown, and Yorktown. Picturesque, gated, golf course community with playgrounds, tennis courts, etc.
Popular amenities for villa rentals near Chesapeake Bay
Private villa rentals

Luxe Homey Get-Away Beach Cove

Serenity By The Beach!

Coastal Club Resort-Style Amenities Community Lewe

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

Coral Villa

Queen Bed Non-Smoking

Coastal Club Resort Style Community 3 BR, 2.5 BA

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

Spacious 4 bedrms, pool, close proximity to beach

Nature Retreat

Luxe 5-Star Waterfront Retreat - Water-Beach Views

Italy meets Moroccan oasis with huge pool for 10

Coastal Club * 5BR Luxury House w 3.5 Baths

Amazing waterfront villa for summer fun

Coastal Club * 3BR Lewes Beach Home
Villa rentals with a pool

Sol Villa

Capitol Hill elegant, charming room

Crush Villa

Coastal Club * 3 BR Beach Villa

Coastal Club * 3BR Luxury Villa Townhouse

Lighthouse Villa

Surfers Villa

Coastal Club * 3BR Luxury Villa Townhouse
Villa rentals with a hot tub

Bayside * 4 BR Twin House

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

Welcome this beautiful single family house

Coastal Club * 3br Twin House w 2.5 Baths

Cheerful 2 Bedrooms 2 Baths @ Kings Creek Resort

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 $44 AUD 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 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
Destinations to explore
- Rentals with a sauna Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- House rentals Chesapeake Bay
- RV rentals Chesapeake Bay
- Holiday home rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Rentals with a home theatre Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Rentals with a fire pit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Condo rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Villa rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Buckroe Beach
- Outlook Beach
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- First Landing Beach
- Chrysler Hall
- Virginia Living History Museum
- The NorVa
- Old Dominion University
- Colonial Williamsburg's Merchants Square
- Hampton University
- USS Wisconsin (BB-64)
- Harbor Park
- Town Point Park
- Virginia Zoological Park




