
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

Private Peninsula Estate, Pool Houses, Crab Shack
This isn't a typical waterfront rental. Durham-Hythe Estate is a private 7.5-acre peninsula compound with over 750 feet of shoreline; designed for groups who want space, privacy, and a true Eastern Shore experience. Grab a cup of coffee or tea and watch the sunrise on the dock! Enjoy Chef-prepared meals while watching the evening sunset. Estate living includes swimming, spa time, cookouts, playing with your dogs in the 4-acre field, crab feasts, and relaxing in the raised rose garden!

Beautiful 2BR Snug Harbor Waterfront villa!
It is a beautiful WATERFRONT, newly renovated villa overlooking the Assateague lighthouse, the National Park, the Wildlife Refuge and the spot where the wild ponies hang out! There is a marina right on the premises with motor boat, kayak and SUP rentals as well as organized guided kayak tour, nature boat tours and sunset cruises. The villa has fully stocked kitchen with full size fridge, stove, oven, coffee maker, toaster, pots, pans, utensils etc. Bring the family and enjoy our island!

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.

Dulles Executive Retreat | 1BR + Office | Near IAD
✨ Welcome to Dulles Executive Resort, an elegant retreat designed for business travelers, extended stays, and guests seeking comfort near Washington Dulles International Airport (IAD). Private 1BR with an executive office and half-bath, ideal for work trips or couples celebrating special moments. Sleeps up to 4 with a premium sleeper sofa. Enjoy high-speed Wi-Fi, a marble kitchenette, a spa-style bath, a private entrance, parking, and a peaceful patio minutes from Reston Town Center.

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

Cozy, New Villa - Bethany Beach, DE
Cozy, family-friendly Villa located less than 1.5 miles from Bethany Beach. Welcome to the perfect vacation retreat in Ocean View, Delaware! This new villa (built in 2024) offers everything you need for an unforgettable getaway. Located on the first floor with pond views, 3-bedroom, 2-bathroom villa; 1300 square feet of luxurious living space. Enjoy access to the Beach Club community and all of the amenities. Located 1.5-mile from Bethany Beach and 3 great golf courses.

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 townhome 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.

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 “

Couple Retreat|Hot tub, Patio Fireplace, Trails
Fern and Forest is a boutique woodland retreat in Caret, Virginia, just minutes from the charming waterfront town of Tappahannock. Nestled along the iconic Coastal Highway, this restored 1960s motel has been reimagined as a luxurious three-suite hideaway. Inspired by the surrounding coastal woodlands and Tidewater heritage, the Foxtail Suite features three bedrooms with ensuite baths, a full kitchen, and inviting gathering spaces both indoors and out.

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

Bay Access 3 bedroom Main House in Franklin Manor

Close to DC Excellent location.

4 BR Direct Bayfront Spectacular Sunsets, Parking

New! Bright Arlington Retreat!

Cheerful 4 bedrm Villa with deck, grill, fireplace

Luxe Homey Get-Away Beach Cove

Waterfront cottage with the most peaceful view!

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

Deer Haven at Bacon Hall

Kingsmill Resort! Williamsburg, Va! 3Bed 3Bath

Amazing waterfront villa for summer fun

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

Bayside * 5BR Luxury Home

Marriott Manor Club, Williamsburg 2Bed Villa max 6

Private Luxury Spa Getaway

Nature Retreat
Villa rentals with a pool

Beautiful Lindal Cedar Home - Private Pool!

Fenwick Island-GOLF CART-Bayfront pool and beach!

Quiet Villa with Bowling Alley, Pools, +Mini Golf

Spacious Retreat Near the Beach.

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

Palm Villa

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

Luxury Bishop's Landing Villa Near Bethany Beach
Villa rentals with a hot tub

King's Creek Plantation: 3-BR Lockoff, Sleeps 10

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

Cheerful 2 Bedrooms 2 Baths @ Kings Creek Resort

Welcome this beautiful single family house

Virginia Beach Resort 7 Day Stay- Ocean Front

Luxury Estate Suite, Hot Tub, Private Balcony

Westmore Estate II Contemporary Cave Gorgeous B&B

Family Forest Retreat|Hot Tub, Trails & Fireplace
Quick stats about villa rentals near Chesapeake Bay

Total holiday rentals
Explore 10 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $71 AUD per night before taxes and fees

Verified guest reviews
Over 840 verified reviews to help you choose

Family-friendly holiday rentals
10 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
10 of Chesapeake Bay holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chesapeake Bay rentals

4.8 Average rating
Chesapeake Bay stays are highly rated by guests—averaging 4.8 out of 5!
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- Villa rentals United States
- Chincoteague Island
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- First Landing Beach
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Chrysler Museum of Art
- Town Point Park
- Nauticus
- Virginia Living History Museum
- Mount Trashmore Park
- USS Wisconsin (BB-64)
- Chrysler Hall
- Sandy Bottom Nature Park
- The NorVa
- Fort Monroe National Monument





