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 Downtown Hampton

4.96 out of 5 average rating, 107 reviews

Fully Furnished Home in Hampton 5mins from H Uni

Relax with the whole family at this newly renovated and furnished home. The spacious backyard is a prime spot for family fun. This house can easily sleep 11 people with 7 beds total including a fold-out futon. Enjoy a variety of board games and movies on the TV in every room. Located 10 minutes away from places such as the Hampton Roads Convention Center, Hampton Coliseum, Hampton Virginia Aquaplex, Hampton University, and The American Theatre. *You must be 21 years of age or older to book*

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!

Guest favourite

Home in Norfolk

4.9 out of 5 average rating, 135 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 Coliseum Central

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.

Superhost

Home in Portsmouth

4.8 out of 5 average rating, 86 reviews

Modern 4 bed-room home

Relax with the whole family at this peaceful place to stay. This is 4 bed-room house with 2 bathrooms. It also come with free parking and a private fenced in backyard where you can kick your feet up and relax. Only a 25 minute drive from Virginia Beach and 5 minutes from the new Rivers Casino. If you are a big family looking for a spacious place then this is the place. If you are looking to relax in a peaceful place then book :)

Guest favourite

Home in Buckroe Beach

4.93 out of 5 average rating, 125 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

Guest favourite

Home in Newport News

4.83 out of 5 average rating, 149 reviews

Spacious 4BR Home near Hampton Convention Center

This modern home is perfect for entertainment! Its huge backyard is plenty of space for family fun or events. This house easily sleeps 13 people! Its located 10 minutes from Boo Williams Sportcomplex and Hampton Convention Center so its great for concerts and local festivities! It’s a great home that is surrounded by multiple restaurants as well as near by outlets Peninsula Town Center and Tech center.

Superhost

Home in Willoughby Spit

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!

Guest favourite

Home in Phoebus

4.99 out of 5 average rating, 123 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.

Guest favourite

Home in Norfolk

4.98 out of 5 average rating, 96 reviews

THE POINT! Private waterfront Oasis!

Enjoy breath taking views and a fully equipped home with many amenities. If you are looking for a private and intimate experience of quality time and a relaxing retreat with nature, this is IT!!! Convenient to Virginia Beach Oceanfront, Oceanview Beach in Norfolk, Downtown Norfolk, Rivers Casino, Ocean Breeze water park, Waterside District and a host of popular attractions.