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Villa rentals near Chesapeake Bay

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Top-rated villa rentals near Chesapeake Bay

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Two adirondack chairs are positioned on a balcony, facing a golf course with lush green grass and a serene lake. A small table holds two cocktails, complemented by the backdrop of trees and a clear sky.
Villa in Ocean Pines
5 out of 5 average rating, 4 reviews

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.

Top Guest favourite
Villa in Herndon
5 out of 5 average rating, 12 reviews

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.

Top Guest favourite
A spacious living area features light wooden flooring, a comfortable white sofa, and a coffee table. Natural light floods through the windows, illuminating the adjacent kitchen area, which includes modern appliances and a dining space. A ceiling fan and wall-mounted TV enhance the inviting atmosphere.
Villa in Virginia Beach
4.89 out of 5 average rating, 105 reviews

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.

Guest favourite
A charming lakefront home is situated on a well-maintained lawn, featuring a mix of shrubs and trees. The exterior showcases a combination of brick and siding with gabled roofs and an arched window. The driveway leads to a two-car garage.
Villa in Virginia Beach
4.86 out of 5 average rating, 43 reviews

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.

Guest favourite
A serene view of a private beach meets the calm waters of the bay under a clear blue sky. Gentle waves lap at the sandy shore, with a wooden dock extending into the water. Soft grasses frame the beach area, contributing to the tranquil atmosphere.
Villa in Montross
4.85 out of 5 average rating, 113 reviews

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

Superhost
A charming house is set within a lush green landscape, framed by well-maintained gardens featuring various plants and trees. The exterior showcases a blend of siding and screen-enclosed areas, with a spacious lawn inviting outdoor activities.
Villa in Gloucester County
4.78 out of 5 average rating, 45 reviews

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 “

Villa in Sparks Glencoe
4.89 out of 5 average rating, 54 reviews

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).

Superhost
A comfortable living area features a light-colored sofa adorned with colorful cushions. A soft area rug covers the floor, while a modern coffee table sits in front of a large television mounted on a wooden cabinet. A potted plant adds a touch of greenery.
Villa in Pasadena
4.37 out of 5 average rating, 19 reviews

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.

Guest favourite
Villa in Annapolis
4.84 out of 5 average rating, 120 reviews

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. .

Superhost
The living room features ample seating with light-colored tufted sofas and accent chairs. A large smart TV is mounted on the wall above a modern fireplace. Natural light flows in through expansive windows, creating an inviting atmosphere.
Villa in Arlington
4.83 out of 5 average rating, 95 reviews

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!

Superhost
A waterfront scene features a docked boat against a striking sunset, reflecting warm hues of orange and pink on the water's surface. Nearby, a two-story cottage stands with a sloped roof, complemented by a tranquil backdrop of the coastal landscape.
Villa in Chincoteague
4.68 out of 5 average rating, 25 reviews

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!

A spacious living area is furnished with a comfortable dark sofa and a light green armchair. A wooden coffee table centers the room, complemented by a TV on a stand. The room features a fireplace and leads to an open kitchen area visible in the background.
Villa in Williamsburg
4.94 out of 5 average rating, 35 reviews

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

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

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