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Mansion vacation rentals in Chesapeake

Find and book unique mansions on Airbnb

Top-rated mansion rentals in Chesapeake

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Top guest favorite

A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.

Home in Gloucester Point

4.99 out of 5 average rating, 193 reviews

York River Vacation Home

This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

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, 117 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.

An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.

Home in Portsmouth

4.93 out of 5 average rating, 122 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!

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

4.84 out of 5 average rating, 109 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, 106 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.

The image showcases a spacious open-concept living area with a teal couch and modern dining set. Large windows allow natural light to fill the space. A serene outdoor view features a patio with chairs by a tranquil pond surrounded by rocks and greenery.

Home in Hampton

4.95 out of 5 average rating, 126 reviews

*Grotto Waterfall* Bethel Oasis | 2masters | 5bdrs

Built in 2019, our home was designed to make our guests' stay enjoyable. In 2023 a Grotto waterfall feature was added with surrounding 3-foot pond. There are two master bedrooms with walk-in showers, as well as a lovely play set in the back yard. The 1st floor master closet was converted into a simple nursery with a crib and baby swing. The master bedroom on the 2nd floor has a queen size bed for parents and a space dedicated to toddlers, featuring a princess castle bed.

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, 144 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

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, 372 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.

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!

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, 135 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, 133 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.

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, 102 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.

Vacation rentals for every style

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Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Chesapeake mansion rentals

Free parking on premises

Air conditioning

Luxury mansion rentals

Top guest favorite

The outdoor area features a private pool surrounded by a spacious patio. A wooden deck stands above the pool, offering seating for relaxation. Lush trees and a white fence provide privacy and a natural backdrop, creating a serene atmosphere for enjoyment.

Home in Currituck County

5 out of 5 average rating, 7 reviews

Corova Beaches 5BR w/Heated Pool & Hot Tub!

A spacious brick exterior of a two-story home is displayed, featuring a manicured lawn and mature trees. The façade has several large windows, allowing for natural light. A wide driveway leads to a three-car garage, indicating ample parking space.

Home in Hampton

4.86 out of 5 average rating, 14 reviews

Wonderful 4 bedroom home in up-scale neighborhood!

A stone fire pit is surrounded by several gray Adirondack chairs, offering a cozy gathering space. Lush greenery and colorful flowers frame the area, while the tranquil water view reflects the sunlight, creating a serene outdoor setting.

Home in Phoebus

5 out of 5 average rating, 27 reviews

River Retreat at Stonehurst

The exterior of a two-story beach house features a deep blue facade with white trim and multiple balconies. The spacious porches are adorned with white railings, while gravel landscaping enhances the entrance. The structure is surrounded by greenery, providing a welcoming coastal appearance.

Home in Buckroe Beach

4.93 out of 5 average rating, 106 reviews

Luxurious Alberta Beach House w/ Historical Detail

A charming three-story beach home with a light-colored exterior is framed by a white picket fence and lush landscaping. The inviting front porch features decorative railings and several balcony areas. A line of trees adds to the tranquil streetscape, set against a bright blue sky.

Home in Virginia Beach

4.99 out of 5 average rating, 78 reviews

*NEW* Spacious/Standalone 4BR Beach House

A covered porch features several blue Adirondack chairs, offering a place to relax and enjoy elevated views of the nearby sandy beach and ocean. The living space is well-lit by natural light, with a clear sky and scattered clouds in the background.

Home in East Ocean View

4.93 out of 5 average rating, 44 reviews

Oceanfront 3400 sq ft * Spacious-3 levels!

Top guest favorite

A modern kitchen features white cabinetry and stainless steel appliances, complemented by a central island with four wooden stools. Natural light pours in from adjacent windows, illuminating the open living area visible in the background, which includes a comfortable seating arrangement.

Home in Virginia Beach

4.98 out of 5 average rating, 50 reviews

In the Heart of Virginia Beach perfect for groups!

A two-story white house with black shutters and a wide front porch is showcased. The exterior features a mix of siding and stone, surrounded by a landscaped area. Bright blue skies and scattered clouds provide a serene backdrop.

Home in East Ocean View

4.91 out of 5 average rating, 76 reviews

Pet Friendly! Newly Built! 1 Block to the Beach!

Pet-friendly mansion rentals

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, 103 reviews

Wheelchair Accessible Beach Home in Chicks Beach.

The three-story house features light-colored siding and a welcoming front porch. Green shutters frame the windows, while neatly landscaped greenery surrounds the entrance. A white fence provides additional privacy, contributing to the home's charming curb appeal.

Home in Virginia Beach

4.97 out of 5 average rating, 60 reviews

Serene Beach Retreat - Just Steps from the Sand!

A modern kitchen features a large island with four leather bar stools, white cabinetry, and stainless steel appliances. Natural light streams through windows, enhancing the open layout that connects to the living area beyond.

Home in Virginia Beach

4.73 out of 5 average rating, 51 reviews

Movie Room + EV Charging Plug! Small Dogs Welcome!

A spacious bedroom is illuminated by natural light from a large window with soft blue curtains. A cozy seating area features a grey sofa and a round coffee table. The room includes a comfortable bed, dark wood furniture, and decorative wall art, creating a serene environment.

Home in Hampton

4.79 out of 5 average rating, 78 reviews

4BR Oasis: Your Home Away

A spacious living area features a bright blue sofa and two yellow armchairs, arranged around a round woven coffee table. A large brick fireplace is the focal point, while natural light streams through the light-colored curtains adorning the windows.

Home in Virginia Beach

4.95 out of 5 average rating, 40 reviews

Virginia Beach Retreat | Minutes to Beach & Town

A spacious game room features a modern, dark leather sectional couch and a foosball table. A crystalline chandelier hangs from the ceiling, and large windows allow natural light to enhance the space. Colorful play items and an easel are visible in the background.

Home in Norfolk

4.85 out of 5 average rating, 53 reviews

4 Beds + Game Room + Family & Dog Friendly!

A serene backyard space features a wooden pergola overhead, providing shade and a relaxing seating area. Brightly colored adirondack chairs encircle a stone patio, with a well-maintained lawn extending beyond. A nearby shed adds a touch of charm to the outdoor setting.

Home in Virginia Beach

4.83 out of 5 average rating, 167 reviews

Relaxation Station at Old Beach

The modern kitchen features light gray cabinetry and stainless steel appliances. A large center island with bar seating is accented by blue upholstered stools. A dining table with beige chairs is set for a meal, complemented by decorative tableware and floral arrangements.

Home in Hampton

5 out of 5 average rating, 33 reviews

Lux Elegance

Mansion rentals with a pool

Top guest favorite

An outdoor area features a private pool surrounded by sun loungers and large umbrellas. A pergola offers shaded seating. The space is bordered by a white fence, with a calm waterway visible in the background, lined with trees and nearby houses.

Home in Sandbridge

4.98 out of 5 average rating, 85 reviews

The Sandbridge Jewel

A pool cover in shades of green is neatly secured on a paved surface, surrounded by tall trees and a serene landscape. A river view is visible in the background, suggesting a tranquil outdoor environment.

Home in Newport News

5 out of 5 average rating, 10 reviews

Pool River House

The image presents a large outdoor pool surrounded by a deck, sun loungers, and a gazebo. Lush greenery lines the background, complementing the serene waters of Back Bay visible in the distance under a bright blue sky with scattered clouds.

Home in Sandbridge

4.85 out of 5 average rating, 132 reviews

Stunning Views of Back Bay & Seconds to the Beach

A refreshing pool is surrounded by five lounge chairs, positioned on a large deck overlooking the serene bay. Lush greenery lines the water's edge, with kayaks resting on the sandy bank. The clear blue sky reflects on the tranquil water, enhancing the peaceful setting.

Home in Sandbridge

4.69 out of 5 average rating, 84 reviews

Beach House with breathtaking sunsets

Top guest favorite

An aerial view of a beach cottage reveals its elevated structure surrounded by natural foliage. A swimming pool is visible on the right, while a spacious deck with hammocks provides an inviting outdoor space. The cottage features a light green exterior with white accents.

Home in Corolla

5 out of 5 average rating, 22 reviews

Splash of Lime Carova 4x4 Beach Cottage

The outdoor space features a private hot tub adjacent to a sparkling pool, surrounded by sun loungers and pool floats. Multiple decks provide access to different levels of the home, with clear blue skies completing the serene setting.

Home in Corolla

4.94 out of 5 average rating, 18 reviews

Luxury Water Front w Private Pool, Hot Tub & Dock

Top guest favorite

A private backyard pool is surrounded by a spacious patio area featuring multiple lounge chairs. The clear blue water of the pool contrasts with the light-colored concrete. Above, a wrap-around deck is visible, enhancing the outdoor recreational space.

Home in Sandbridge

4.94 out of 5 average rating, 16 reviews

6BR Sandbridge Family Retreat w/ Pool

Top guest favorite

A spacious balcony features several blue adirondack chairs, offering a view of the surrounding buildings and the outdoor area. Clear skies with a few clouds create a bright atmosphere. The ocean is visible in the distance, providing a scenic backdrop.

Condo in Sandbridge

5 out of 5 average rating, 20 reviews

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym

Destinations to explore