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Mansion vacation rentals in Chesapeake

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Top-rated mansion rentals in Chesapeake

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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, 134 reviews

Stunning Views of Back Bay & Seconds to the Beach

Be our guest and enjoy some of the most spectacular views in all of Virginia Beach. Lounge in the pool and watch the sun set over Back Bay or enjoy exploring Back Bay with fishing and site seeing. With the beach being a block away, you can get your feet wet with surfing or snorkeling or simply relax on the beach with your favorite beverage. Little Island Park, Back Bay Wildlife Refuge & The Baja are just a few minutes away as well. This 6 bedroom home, with 11 beds will be the perfect get away.

A deck area is visible with blue outdoor chairs set against a backdrop of white siding. Stairs lead down to the yard, where a charcoal grill and a beach cart are positioned nearby. Decorative string lights are hung above, enhancing the outdoor space.

Home in Willoughby

4.86 out of 5 average rating, 117 reviews

5 BR + Huge Yard, Great for Groups! Walk to Beach!

Relax in this stylish 4BR, 2-bath home in Virginia. Minutes from Willoughby Beach and Monkey Bottom Park. Perfect for families and groups, this home features 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. Perfectly designed for comfort, relaxation, and coastal living. Book now and feel right at home!

The three-story farmhouse-style home features a charming brick facade and a front porch with blue double doors. Lush greenery surrounds the entrance, while a path leads toward the driveway. Sunlight highlights the roof and front yard, creating a welcoming exterior.

Home in Colonial Place

4.96 out of 5 average rating, 104 reviews

Newport Nook: 5/2.5 Home in Norfolk - Sleeps 10!

5 bed / 2.5 bath - Sleeps 10! Our cozy, farmhouse-style Norfolk home is 5 min from Historic Ghent / ODU. Free Wi-Fi, parking for 4 cars. Coffee, grill, & fire pit provided. Pet-friendly! NO cleaning fee or checkout instructions! Driving Distances: ODU - 5 min Sentara Norfolk General - 5 min CHKD / EVMS - 8 min Norfolk Naval Station - 14 min Virginia Beach Oceanfront - 25 min Monthly: $4,200. Fully furnished rental with all utilities, Wi-Fi, weekly housekeeping, pest & lawn care included.

Home in Virginia Beach

4.93 out of 5 average rating, 208 reviews

Vibe District 4BR Beach House • Sleeps 8

Experience the Best of Virginia Beach in Vibrant Vibe District! *Spacious 4BR, 3.5BA home; accommodates up to 8 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!

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, 133 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!

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, 110 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.

A three-story house features a light gray exterior with a welcoming yellow front door. Flanking the entrance are neatly trimmed shrubs and small trees, complementing the spacious front porch. The surrounding area includes well-maintained neighboring houses and a glimpse of a fenced backyard.

Home in Norfolk

4.91 out of 5 average rating, 152 reviews

5 Min to Downtown & Ghent, 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 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

4.82 out of 5 average rating, 114 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. There are two decks with outdoor seating, modern washer and dryer, games and toys, and much much more. Can't wait to host you!

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.

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 2026

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

4.92 out of 5 average rating, 144 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

Home in Phoebus

4.99 out of 5 average rating, 140 reviews

King Bed - Buckroe Beach + Fort Monroe/Phoebus

Perfect location for everything the Hampton Roads has to offer! The home is a short walk to the Phoebus waterfront, a bike ride to Buckroe Beach or Fort Monroe 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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Houses

A space thats all yours, with room for everyone

Popular amenities for Chesapeake mansion rentals

Free parking on premises

Air conditioning

Luxury mansion rentals

Top guest favorite

A cozy living space features a mix of light-colored armchairs and a brown leather sofa arranged around a coffee table. Large windows create an airy atmosphere while allowing natural light to fill the room. A ceiling fan and decorative mirror add to the inviting ambiance.

Home in Carova Beach

5 out of 5 average rating, 12 reviews

The White Lotus, Luxury Vacation in Carova Beach

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 Carova Beach

5 out of 5 average rating, 7 reviews

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

The blue, three-story house is viewed from the side, showcasing multiple windows with white trim. A well-maintained path lined with stones leads to the entrance. Two individuals walk towards the house, and a cart is positioned neatly beside plants in the foreground.

Home in Willoughby

5 out of 5 average rating, 12 reviews

Beachfront Getaway, pet friendly

Top 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, 127 reviews

Beach House on the Bay

Top guest favorite

The exterior of a three-level modern home is framed by a spacious concrete driveway. The house features a distinct gray siding, white trim, and a welcoming yellow porch door. Landscaping includes fresh shrubs and decorative stones, enhancing the home's curb appeal.

Home in Sandbridge

4.98 out of 5 average rating, 87 reviews

The Sandbridge Jewel

The room features two spacious beds positioned against a grey upholstered headboard. A large window allows natural light to fill the space, with light curtains covering it. A desk with a chair is located to the right, complementing the neutral-toned decor.

Home in Riverside

4.9 out of 5 average rating, 162 reviews

Family Haven Retreat by CNU| 1st FL master

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 Coliseum Central

4.84 out of 5 average rating, 375 reviews

Family Holiday House. Events and Beaches Nearby

An aerial view presents the coastal neighborhood with ocean views in the background. The property features a pool area surrounded by landscaped grounds. Nearby houses exhibit varying architectural styles, with roads visible in the foreground leading towards the beach.

Home in Sandbridge

4.77 out of 5 average rating, 26 reviews

Coral Point - Updated Cozy 4 bedroom w/ Salt Water

Pet-friendly mansion rentals

The front view of the residence features a single-story home with a gray brick exterior and a welcoming entrance. A covered porch is accentuated by a pair of symmetrical windows, and a paved driveway provides access to the carport. The surrounding area is filled with grass and trees.

Home in Elizabeth City

4.75 out of 5 average rating, 53 reviews

Creek Road Quarters

A cozy bedroom is showcased, featuring a spacious bed with decorative bedding and pillows. A small white chair is placed at the foot of the bed. Wall-mounted shelves display various items, while a lamp provides soft lighting next to the bed. The grey walls create a calming backdrop.

Home in Great Bridge

4.89 out of 5 average rating, 53 reviews

The Bird’s Nest

Home in Virginia Beach

4.75 out of 5 average rating, 55 reviews

Movie Room+EV Plug! Sm Dogs OK! Spacious + Central

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, 84 reviews

4BR Oasis: Your Home Away

A spacious living area is presented with light wood flooring and high ceilings. Neutral-colored sofas are arranged around a round coffee table, while a comfortable armchair complements the seating. A tasteful floral arrangement sits on the mantle above the fireplace, enhancing the home's inviting decor.

Home in Virginia Beach

4.92 out of 5 average rating, 24 reviews

The Salty Pearl - Your Perfect Beach Getaway!

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 Carova Beach

5 out of 5 average rating, 24 reviews

Splash of Lime Carova 4x4 Beach Cottage

Home in East Ocean View

4.9 out of 5 average rating, 82 reviews

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

Home in Buckroe Beach

4.91 out of 5 average rating, 69 reviews

4 bedroom,2 bath,dog friendly, 3 blocks from beach

Mansion rentals with a pool

Apartment in Williamsburg

4.91 out of 5 average rating, 11 reviews

4 Bedroom at Greensprings Vacation Resort!

A private pool is situated on a spacious wooden deck, with inviting blue water reflecting the landscape. Lounging chairs are placed nearby, and the ocean view is visible in the background, extending to a sandy shore under a bright blue sky.

Home in Sandbridge

4.67 out of 5 average rating, 12 reviews

Oceanfront | 7BR | Pool | Hot Tub | Sleeps 20

A spacious pool area is highlighted, featuring a clear blue pool surrounded by a decorative fence. Brightly colored lounge chairs are positioned on the patio, with a shaded gazebo and lush greenery visible in the background.

Home in Sandbridge

4.99 out of 5 average rating, 81 reviews

The Golden Hour Pool is Open until October 5th!

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, 200 reviews

York River Vacation Home

A private pool is surrounded by comfortable lounge chairs with decorative cushions. A vibrant pink flamingo float is situated in the clear water. The space is framed by lush trees, and a two-story house is visible in the background.

Home in Corolla

4.93 out of 5 average rating, 14 reviews

Stunning Views | Kayaks | Pet-Friendly | Sunsets

Home in Sandbridge

4.9 out of 5 average rating, 20 reviews

6BR Sandbridge Family Retreat w/ Pool

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

4.95 out of 5 average rating, 21 reviews

Luxury Water Front w Private Pool, Hot Tub & Dock

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, 23 reviews

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

Destinations to explore