
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.

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 “

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.

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.

Cheery & Cozy Beach Villa - Walk to Beach
This Villa Offers All The Items You Want For A Perfect Vacation! Beautiful Spacious 3 BR 2 Bath With Sleep Sofa To Sleep Up To 8 Comfortably. Master BR Has A King Bed With A Private Bath. BR 2 has A Queen Bed and BR 3 Has Twin Bunk Bed. Both Have Windows Facing The Coastal Hwy. The Second Full Bathroom Is In The Hallway. Located At 90th St It Is Convenient To A Supermarket And Within Walking Distance To Popular Restaurants.

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

3 Mi to Boardwalk: Bethany Beach House w/ Patio!

Luxe Homey Get-Away Beach Cove

Serenity By The Beach!

Coastal Club * 3BR Luxury Villa Townhouse

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

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

Queen Bed Non-Smoking

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

Spacious Retreat Near the Beach.

Coastal Club * 3br Twin House w 2.5 Baths

Stunning 14 Acre Modern Villa with Sunroom

Fenwick Island-GOLF CART-Bayfront pool and beach!

Spacious 4 bedrms, pool, close proximity to beach
Villa rentals with a pool

Spacious Villa 3 miles to Bethany Beach Water Acc

Summer Breeze – 4BR Villa. Fall & Winter Gateway

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

Quiet Villa with Bowling Alley, Pools, +Mini Golf

Condo w/ water views and amazing amenities!

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

Cozy, Brand New Villa - Bethany Beach, DE

Luxury Bishop's Landing Villa Near Bethany Beach
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 * 3 BR Beach Villa

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

Cheerful 2 Bedrooms 2 Baths @ Kings Creek Resort

Westmore Estate II Contemporary Cave Gorgeous B&B

BOARDWALK RESORT City view Studio
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 $50 NZD 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
- Beach house rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Rentals with an accessible height bed Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Beach condo rentals Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Fitness-friendly rentals Chesapeake Bay
- Smoking-friendly rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- Rentals with an accessible height toilet Chesapeake Bay
- Rentals with outdoor seating Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Holiday home rentals Chesapeake Bay
- Private suite rentals Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Rentals with a home theatre Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Rentals with an EV charger Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farmstay rentals Chesapeake Bay
- Rentals with a fireplace Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Rentals with a fire pit Chesapeake Bay
- Rentals with a washing machine and dryer Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Condo rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guesthouse rentals Chesapeake Bay
- House rentals Chesapeake Bay
- RV rentals Chesapeake Bay
- Rentals with pools 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
- The NorVa
- Chrysler Hall
- Virginia Living History Museum
- Old Dominion University
- Colonial Williamsburg's Merchants Square
- Hampton University
- Town Point Park
- Virginia Zoological Park
- Harbor Park
- USS Wisconsin (BB-64)




