Villa rentals near Chesapeake Bay

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Top-rated villa rentals near Chesapeake Bay

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Villa in Millville

5 Mi to Bethany Beach | Pools, Shuttle + Fire Pit

Book your Millville by the Sea getaway just about 5 miles from Bethany Beach, with pools, seasonal beach shuttle access, a BBQ grill, and a fire pit for relaxed coastal nights. This family-friendly Delaware beach rental gives you the best of both worlds: easy access to Bethany Beach, boardwalk dining, golf, and resort-style community amenities without staying in the busiest beach blocks. After a day in the sun, unwind with dinner on the grill, time by the fire pit, and room to settle in for a true beach-week escape. A 7-night minimum stay is required, with Saturday check-ins preferred. Other Things to Note: • Millville by the Sea Resort Fee: $175 per stay (required for community access); collected at the time of reservation • HOA registration paperwork must be completed at least 12 days prior to arrival to access community amenities • Community amenities are HOA-managed and hours/availability may vary • Parking accommodates up to 4 vehicles (2 garage + 2 driveway) • Linens and bath towels are provided; please bring your own beach towels

4.0 out of 5 average rating, 3 reviews
Guest favourite
The exterior of the guesthouse showcases a modern design, with a combination of dark siding and wooden accents. A spacious balcony is visible on the upper level, while the ground level features a covered parking area. The entrance is highlighted by large, light-colored doors.
Villa in Northwest Washington

DC Garden House - Modern 4-Person Stay by Metro

This new construction guesthouse is perfect for up to 4 guests, offering privacy, comfort, and convenience in a quiet neighborhood fully connected to the city. Highlights: - Sun-filled bedroom features either a king or two twins - 2 Full Bathrooms - Fully Equipped Kitchen. - Private Parking. Ideal for families, friends, or business travelers, this space combines thoughtful design with a great location near transit and local attractions. Book now for a stay that feels like home away from home!

4.78 out of 5 average rating, 63 reviews
Guest favourite
Villa in Rockville

Capital Bliss Luxury Pool Retreat/ DC Attraction

Enjoy summer vibes with a relaxing getaway minutes from the heart of Washington, DC. Whether visiting for sightseeing, family vacations, work travel, or a long weekend escape, this spacious 4-bedroom, 3.5-bath villa offers comfort and style. Enjoy bright open spaces, warm evenings, and a private retreat atmosphere after exploring museums, monuments, dining, and DC neighborhoods. Relax poolside in a cozy luxury setting designed for memorable stays. No large gatherings or parties permitted.

5.0 out of 5 average rating, 34 reviews
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

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.

4.9 out of 5 average rating, 116 reviews
Top guest favourite
A cozy living room features a light-colored sofa adorned with decorative cushions, complemented by a round glass coffee table. A green accent chair is positioned opposite the sofa. Natural light is softly filtered through sheer curtains, with a vibrant plant adding a touch of greenery.
Villa in Herndon

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.

5.0 out of 5 average rating, 25 reviews
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

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.

4.88 out of 5 average rating, 59 reviews
Guest favourite
A serene view of a landscaped backyard leads to a calm lake, framed by vibrant green trees and blooming azaleas. A wooden deck with a pergola offers an inviting outdoor space, perfect for relaxation and enjoying the surrounding nature.
Villa in Manassas

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

4.8 out of 5 average rating, 88 reviews
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

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

4.85 out of 5 average rating, 127 reviews
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

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 “

4.79 out of 5 average rating, 61 reviews
Villa in Deale

Bay Access 3 bedroom Main House in Franklin Manor

Escape to a beautifully renovated coastal cottage with stunning bay views and unforgettable sunsets, just 20 minutes from Annapolis. Located in a quiet waterfront community, this home offers the perfect blend of relaxation, outdoor adventure, and comfortable living. Enjoy access to two private beaches, fishing piers, a swim platform, playground, baseball field, volleyball court, picnic pavilion, and a mile-long bayfront park—all just steps from your door.

4.67 out of 5 average rating, 6 reviews
Top guest favourite
Villa in Caret

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.

5.0 out of 5 average rating, 16 reviews
Guest favourite
An aerial view captures an expansive property surrounded by water, showcasing vibrant green trees and a swimming pool nestled among the foliage. A long pier extends into the water, emphasizing the natural beauty of the estate and the serene landscape.
Villa in Centreville

Blake House Historic Estate with Private Inn

Blake House represents one of the oldest colonial homes in Maryland, built by British settler, Charles Blake, of London, England, in 1691. The house is nestled within 12 acres of manicured gardens, boasting an abundance of indigenous and foreign flora, and surrounded by direct water access. But the most unique feature of this property is the Crown and Anchor Inn (circa. 1735), originally located in Southern Baltimore and moved to the estate in 1941.

5.0 out of 5 average rating, 61 reviews

Popular amenities for villa rentals near Chesapeake Bay

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 €44 per night before taxes and fees

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  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    10 of Chesapeake Bay holiday rentals include wifi 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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