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, 120 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 charming two-story home is presented with a well-maintained lawn and flower beds. Blue shutters frame the windows, and a covered entryway leads to the front door. A clear pathway guides guests toward the entrance, bordered by greenery and blossoming flowers.

Home in Norfolk

4.87 out of 5 average rating, 112 reviews

Huge Yard, Great for Families! Walk to Beach!

Relax in this stylish 4BR, 2-bath home in Virginia. Just minutes from Willoughby Beach and Monkey Bottom Park. Perfect for families and groups, with 2 queen beds, 3 single beds, and 1 bunk bed. Enjoy a dedicated workspace, in-unit laundry, backyard, and patio for outdoor dining. Conveniently located near restaurants, parks, and beach access. It's ideal for beach getaways or extended stays. Thoughtfully designed for comfort, relaxation, and coastal living. Book now and feel right at home!

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, 104 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!

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, 141 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.

Guest favorite

A modern ranch-style home features a slanted roof and a vibrant red front door. The landscaped front yard includes low shrubs and colorful plants, while a pathway leads to the entrance. Large windows provide natural light, framed by decorative shutters.

Home in Hampton

4.91 out of 5 average rating, 189 reviews

Red Door Rancher - Your Home Away From Home

This beautiful home is a one level, close to the city center, Hampton University, Hampton Coliseum, 3 miles to Buckroe Beach, 9 miles to Ocean View Beach, 30 miles to Williamsburg, Yorktown and Virginia Beach. Spacious, ceiling fans, walking distance from the downtown area and the beautiful water views. Enjoy the American Theatre in Phoebus, explore Fort Monroe and Virginia Air & Space Museum. Limit 10 guests, additional by request only. Additional fee applies.

Guest favorite

A serene bedroom features a spacious bed layered with a colorful quilt adorned with coral and sea star patterns. The headboard is upholstered in a light fabric, complemented by an array of decorative pillows in soft pink and turquoise hues. The wall is decorated with a coral-patterned wallpaper.

Home in Phoebus

4.88 out of 5 average rating, 125 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

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, 183 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!

Superhost

The entryway reveals a cozy living room featuring a gray sectional sofa and a navy blue armchair. A circular coffee table sits in the center, complemented by a softly glowing lamp. Light streaming from the room enhances the inviting atmosphere.

Townhouse in Chic's Beach

4.72 out of 5 average rating, 102 reviews

Wheelchair Accessible Beach Home in Chicks Beach.

This newly renovated Beach home is primarily Wheelchair assessable.This is a ground level unit with a handicap assessable entrance, 4 bedrooms , dining, bathroom.This is a DUPLEX there is another rental above this unit. This home has a private entrance side and Back yard. The beach is only 500 yards away. Beautiful semi-private beach has a real neighborhood feel. PLEASE NOTE: Sunday to Sunday after June 1st to Sept 1st 2025.

Guest favorite

A spacious living area features a large sectional sofa with decorative pillows, positioned around a round wooden coffee table. Natural light enters through multiple windows, illuminating the room. A kitchen is visible in the background, further enhancing the open layout.

Home in Newport News

4.83 out of 5 average rating, 155 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.

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, 129 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.