Mansion holiday rentals in Chesapeake

Find and book unique mansions on Airbnb

Top-rated mansion rentals in Chesapeake

Guests agree: these mansions are highly rated for location, cleanliness and more.

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Guest favourite

Home in Williamsburg

5 out of 5 average rating, 113 reviews

History Art and Nature-110 Acres of Ancient Forest

WILLIAMSBURG AREA, SURRY, VA. Lightwood Forest is a beautiful historic house nestled in 110 acres of private woodland preserve. Surround yourself with history, antiques, art and nature, and over two miles of private hiking trails winding through the ancient forest. A true hands-on historical experience surrounded by nature. Lightwood Forest is in rural Surry County, on the south side of the James River, a short, free car ferry ride from Williamsburg and Jamestown, which runs 24/7, all year.

Guest favourite

Home in Portsmouth

4.94 out of 5 average rating, 115 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

Make yourself at home! This property offers a warm and welcoming environment for guest, located in a quiet and established neighborhood in the middle of Portsmouth, VA. Guests should expect a clean space equipped with modern technology and appliances. Attractions aren’t too far; 41mi from Busch Gardens, 24 mi from Virginia Beach Ocean Front, 7.3 mi from Waterside District Norfolk, and 2.9 mi from Rivers Casino Portsmouth. Peaceful mornings and a comfortable stay awaits at Wooded Wonderland!

Superhost

Home in Virginia Beach

4.93 out of 5 average rating, 198 reviews

Spacious home for up to 8! GREAT for families!

Experience the heart of Virginia Beach's Vibe District! *Spacious 4BR, 3.5BA home; accommodates up to 10 guests *Two separate living rooms for relaxation and entertainment *Just 2.5 blocks from the beach; beach cart and gear provided *1 mile to the Convention Center; perfect for event attendees *Fully equipped kitchen for home-cooked meals *High-speed WiFi; stay connected during your getaway *Washer & dryer available for your convenience Book your dream family vacation today with us!

Superhost

Home in Virginia Beach

4.95 out of 5 average rating, 37 reviews

Family Retreat | Crib | Minutes to Beach & Town

Welcome to our beautiful coastal home! This spacious 4-bedroom, 2.5-bathroom home is fully equipped with family friendly amenities for those traveling with little ones and is close to Town Center, Apex Center, restaurants, and is only a short drive to the beach. Sink into our plush memory foam beds and cook up a storm in our fully stocked kitchen. Just a short drive to beaches and downtown Norfolk. Monthly rentals available! Please submit inquiry for our special monthly pricing.

Guest favourite

Home in Norfolk

4.9 out of 5 average rating, 136 reviews

5 Min to Ghent & Downtown | Fenced Yard | Firepit

Welcome to Norfolk! This is a large 3 story, 4 BR/3.5 BA house located just outside of the popular Ghent district in and walking distance to many breweries, restaurants & coffee shops! This is a fast growing area of town and for good reason, we’re so exited to host you! 15 min drive to Norfolk International Airport 12 min drive to Naval Base 8 min drive to Downtown/waterside district/freemason historic district 6 min drive to ODU campus 4 min drive to Virginia Zoo

Guest favourite

Home in Hampton

4.84 out of 5 average rating, 362 reviews

Family Holiday House. Events and Beaches Nearby

Large comfy 5BR/3BA home in established neighborhood w/Roku TV & high speed internet! Near Buckroe Beach, Hampton Coliseum Event Center, NASA, Langley Air Base, Boo Williams Sports Arena and Newport News. Also near Virginia Beach, Williamsburg and Busch Gardens There are many parks for recreation. We have a large enclosed porch for lounging. The front entry has an easy wheelchair ramp. Restaurants galore and endless shopping. NEAR AIRPORTS in Newport News and Norfolk.

Guest favourite

Home in Phoebus

4.88 out of 5 average rating, 122 reviews

4 Bedroom House 5 Minutes from Both Beaches

Forget your worries in this spacious and serene space. Locally, you will be a 5 minute drive from Buckroe and Outlook beach, 30 second drive from Hampton University, 10 minute drive from Langley Air Force Base, 6 minute drive from the Hampton Coliseum and 1 minute drive to the best restaurants/breweries in town. In addition, this is a great spot to stay if you want to explore Colonial Williamsburg and Busch Gardens, a 30 minute drive.

Guest favourite

Home in Buckroe Beach

4.93 out of 5 average rating, 126 reviews

Blue on Buckroe: Family Beach Getaway w/ Gameroom!

Welcome to Blue On Buckroe! Your ultimate beach retreat awaits at this charming Buckroe Beach cottage, just steps from the sand! Perfect for families and friends, our location offers easy access to sun, fun, and unforgettable memories. 📍 2-min walk to Buckroe Beach 📍 4-min drive to Phoebus 📍 7-min drive to Hampton University 📍 9-min drive to Fort Monroe 📍 10-min drive to downtown Hampton Follow us on IG! @peakhost

Superhost

Home in Norfolk

4.86 out of 5 average rating, 110 reviews

Huge Yard, Great for Families! Walk to Beach!

Experience the perfect mix of relaxation and style at this tastefully designed 4 BR, 2-bath home in Virginia. With 2 queen beds, 3 single beds, and 1 bunk bed, it’s ideal for families or groups! Enjoy a workspace, laundry, backyard, and patio. Near Willoughby Beach and Monkey Bottom Park, you’ll have easy access to beaches and dining. Book today—we can’t wait to welcome you home!

Top guest favourite

Home in Phoebus

4.99 out of 5 average rating, 124 reviews

King Bed - Buckroe Beach + Fort Monroe/Phoebus

Perfect location for everything the Hampton Roads has to offer! Freedom Cottage is a short walk to the Phoebus waterfront, a bike ride to Buckroe Beach, a short drive to I-64 which can get you to Norfolk or Virginia Beach in 15 to 30 minutes! Feel comfortable just relaxing in this family friendly home with plenty of beds and entertainment for rainy days or simply relaxing.

Superhost

Home in Virginia Beach

4.92 out of 5 average rating, 120 reviews

A Modern 4 Bedroom Beach House near VB Boardwalk

This Beautiful Family Friendly 4 Bedroom 3.5 Bath home is centrally located in The Vibe District of the Virginia Beach Oceanfront. We are just a few blocks from the Virginia Beach Boardwalk, The Virginia Beach Sports Complex, The Convention Center, The Virginia Beach Aquarium, Interstate, Amazing local restaurants, coffee shops, and so much more! We cannot wait to host you!

Guest favourite

Home in Sandbridge

4.99 out of 5 average rating, 101 reviews

The Sandbridge Rose

Only 3 blocks from the beach!! Water views and fun from all angles. Pool and wrap around deck overlooking Whiskey Creek of the Back Bay! Best fishing spot in Sandbridge. Bring your boat and/or jet ski and pull right up to this newly remodeled Beach House on the Bay. Large open concept kitchen/family room. The house, the view, the water, it's all stunning!!