Mansion vacation rentals in Chesapeake

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Top-rated mansion rentals in Chesapeake

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

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Guest favorite

A historic house is set amidst gentle greenery, featuring a white exterior with multiple chimneys and a welcoming porch. A white picket fence encircles the lush yard, enriched by tall trees and seasonal foliage, creating a serene and inviting environment.

Home in Williamsburg

5 out of 5 average rating, 115 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 favorite

Aerial view of the property showcasing a fenced backyard with a sparkling blue pool surrounded by concrete. A seating area with lounge chairs and various floatation devices is visible beside the pool. Lush greenery from surrounding trees frames the scene, providing a sense of privacy.

Home in Portsmouth

4.93 out of 5 average rating, 121 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

A bright and spacious living area features comfortable seating on a large sofa and armchairs. A flat-screen TV is mounted on the wall across from the seating. Natural light enters through multiple windows, and a decorative plant adds a touch of greenery to the room.

Home in Norfolk

4.85 out of 5 average rating, 106 reviews

The Chesapeake St Retreat - Pet and Kid Friendly

The kid and pet friendly retreat your family will love! This beautiful 2,200 sqft, four bedroom home is PERFECT for your beach get away and is less than a 5-minute walk from the beach. This home features a stylish design, a dining room table that can seat up to 10!, a fenced in back yard for your furry friends, beach chairs, wagon and umbrellas for guest use. There are two decks with outdoor seating, modern washer and dryer, games and toys, and much much more. Can't wait to host you!

Top guest favorite

The waterfront view captures a serene sunset over the canal, with soft golden light reflecting on the water. Lush grasses and reeds line the shore, enhancing the tranquil atmosphere. Nearby homes are silhouetted against the vibrant sky, creating a peaceful retreat.

Cottage in Sandbridge

5 out of 5 average rating, 104 reviews

Sanctuary on Sandpiper - Bayfront in Sandbridge

Relax in this renovated 1950's flat-top beach cottage in gorgeous Sandbridge Beach. This waterfront home, on a canal off the beautiful Back Bay, is an easy five-minute, two-block walk to the ocean and the perfect setting for your family beach vacation. With three king beds, a custom-built bunk room, two full baths, a well-equipped kitchen, a spacious backyard, saltwater pool, and all linens and beach gear included, it's got everything you need to spend quality time away with your family.

Guest favorite

An open-concept living area showcases a comfortable sofa adorned with patterned cushions. Two stylish chairs are positioned nearby, complemented by a colorful area rug. Natural light illuminates the space, highlighting the modern decor and inviting atmosphere.

Home in Norfolk

4.91 out of 5 average rating, 143 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 favorite

A spacious home is depicted with a welcoming front porch featuring a gentle ramp for accessibility. Lush greenery surrounds the exterior, and the peaceful atmosphere is enhanced by the colorful sunset sky. The house showcases a combination of brick and siding with large windows.

Home in Hampton

4.84 out of 5 average rating, 369 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.

Superhost

A cozy loft area features light-colored walls and a plush carpet. Two grey sofas are arranged comfortably, adorned with patterned cushions. A patterned ottoman sits in the center, while a potted plant adds a touch of greenery beside a window that provides natural light.

Home in Virginia Beach

4.95 out of 5 average rating, 184 reviews

Spacious Home for 8-Family Friendly! 2 Living Rms!

30 + day stay! Virginia Beach’s Vibe District is perfect for families and groups. With spacious living areas and cozy beds, it sleeps up to 8 guests. Enjoy a fully stocked kitchen, high-speed Wi-Fi, Smart TV, and in-home laundry. Family-friendly perks include a high chair, Pack 'n Play, and beach gear. Just 2.5 blocks from the beach and 1 mile from the convention center, you’re steps from top dining, cafes, and art galleries. Book now!

Guest favorite

A two-story beach cottage features a bright blue exterior with white trim, showcasing a gabled roof. The front porch is adorned with white railings and two doors, one in vibrant red and the other in soft peach. The surrounding area includes neatly kept grass and nearby houses.

Home in Buckroe Beach

4.93 out of 5 average rating, 134 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

Top guest favorite

A cozy living room features a brown leather sofa and a soft rocking chair, providing comfortable seating. A white coffee table sits in the center, while natural light filters through multiple windows. A door leads to the outside, enhancing the spacious feel of the area.

Home in Phoebus

4.99 out of 5 average rating, 130 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 favorite

Large windows provide stunning views of the lake, reflecting vibrant colors of the sunset. A small potted plant sits on a table beside a white chair, while light from the setting sun casts a warm glow across the interior space.

Home in Norfolk

4.97 out of 5 average rating, 101 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.

Guest favorite

A well-appointed bedroom features a spacious bed with light bedding and decorative pillows. Natural light enters through a window adorned with sheer curtains, illuminating the soft-toned walls. A cozy chair and side table complement the space, which is anchored by a patterned area rug.

Home in Hampton

4.92 out of 5 average rating, 113 reviews

4BD home w/ game room & pool near Langley & PTC!

Welcome Home! Be the next to rent this beautifully renovated, modernized home with beautiful kitchen, amazing bathrooms and generous bedrooms and closets. Come in and relax in this centrally located neighborhood - convenient ten minute trip for shopping, restaurants and military bases. This is the one! DONT FORGET TO ASK ABOUT OUR YACHT RENTAL OPTIONS!!!

Guest favorite

A large beach house is shown with two levels of balconies featuring white railings. The exterior is light-colored, and a blue electric vehicle is parked in the driveway, with the rear door open. Clear skies and surrounding grass complete the scene.

Home in East Ocean View

4.98 out of 5 average rating, 125 reviews

Beach House on the Bay

This large beach house is ideal for a family get together or a group of friends vacationing together. With a beach access less than 50 feet from the driveway, you can enjoy a walk along the beach any time of the day. This house offers picturesque views of the Chesapeake Bay from two oceanside decks.