
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.

Hidden Gem.4/bedroom cozy home fenced in yard
Make yourself at home!Hidden Gem offers a clean welcoming space for guests, located in a quiet established neighborhood. Guests should expect a clean and comfortable stay. Conveniently located near parks,shopping, and dining options. Attractions aren’t too far away Rivers casino.2.9. Virginia Beach Ocean Front.23miles. Waterside district Norfolk 8.5 miles. Town center 17.miles. Busch Gardens 40 miles. Old Dominion University 9.8 miles. Norfolk State University 8.8 miles.Hampton University23miles

East Beach Bungalow, 1 block to the beach!
Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! Easy drive to the Naval Bases. A quick walk to the beach or Bay Oaks Park, this four bedroom, three bath home is perfect for a relaxing getaway. This bungalow is great for groups of 8 or fewer. Brand new appliances, washer/dryer, private off-street parking. This house features an open floor plan. Guests are provided with linens, towels, toiletries and high speed internet (SmartTV).

THE POINT! Private waterfront Oasis!
Enjoy breath taking views & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Oh & bring your fishing poles, river is fully stocked!

History Art and Nature-110 Acres of Ancient Forest
WILLIAMSBURG AREA, SURRY, VA. CELEBRATE AMERICA'S 250TH by living in the historic family home of a Revolutionary War soldier! 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. 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.

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.

Wooded Wonderland Miniature Golf Hot tub Pool
Make yourself at home! This property offers a warm and welcoming environment for guests, 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!

4BR Oasis: Your Home Away
Uncover the allure of our 4-bedroom retreat, steps from dining and entertainment. Thoughtfully designed with a fully equipped kitchen, inviting living spaces, and an amazing master bedroom. Proximity to Buckroe Beach, Busch Gardens, Boo Williams Sportsplex, Hampton Waterplex, and the historic charm of Williamsburg awaits your adventure. Let us tailor your stay with personalized recommendations. Welcome to your expansive haven, where every corner is crafted for your enjoyment!

The Hamptonian - Stylish 4 Bedroom/2 Bath Rancher
Enjoy a stylish experience at this centrally-located, guest-centered home. Within minutes of Langley Air Force base, Boo Williams Sports Complex, and the Hampton Coliseum/Convention Center. The Hamptonian accommodations: Wythe Room: 1 Queen Bed - sleeps (2) Phoebus Room: 2 Twin Beds - sleeps (2) Buckroe Room: 1 Queen Bed - sleeps (2) Coliseum Room: 1 King Bed - sleeps (2) Living Room - 55” Television The Buckroe Room - 42” Television The Coliseum Room - 42” Television

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.

Buckroe Beach Luxury Home Hot Tub, Grill, Gameroom
Welcome to Buckroe Palace, Buckroe Beach's newest family vacation home. This new construction beautifully decorated beach home located within a 5 minute walk to Buckroe Beach, features 4 Bedrooms ( 2 Master Suites), 3.5 bathrooms, 2 kitchens, Master Bedrooms with balcony or porches, and Game room with pool table. Complinemtary bottle(s) of wine and snacks upon arrival, free early check-In when available, Tesla EV Charger available, Beach Friendly!!

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!!

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.
Popular amenities for Chesapeake mansion rentals
Luxury mansion rentals

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

PETS Welcome! 4Bed Beach View Privately Managed

Sanctuary on Sandpiper - Bayfront in Sandbridge

Private Pool at the Oceanfront in a Spacious Home

All 4 One | Beach Living

Bayfront Pool Retreat, Walk to Beach

Luxurious Alberta Beach House w/ Historical Detail

*NEW* Spacious/Standalone 4BR Beach House
Pet-friendly mansion rentals

Spacious Home in Chesapeake | 25 Mins to VA Beach!

The Bird’s Nest

The White Lotus - Oceanview Retreat + Wild Horses

VB Palm View: Furnished Monthly Rental - Sleeps 12

Respass Beach Cove Cottage

Escape to the water!

Sojourn Mi Kai The Crib 4 BR Family House

Spacious 5BR Beach Retreat •Pets OK •Sleeps 10
Mansion rentals with a pool

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

Be The Ocean | 5min Walk to Beach w/ Pool & HotTub

Sea Forevermore: Private Pool, Two Hot Tubs!

Pool Hot Tub • Arcade • Walk to Beach • Sleeps 20

Coral Point - Updated Cozy 4 bedroom w/ Salt Water

MillerLight

NEW! Waterfront, Boat Ramp, Pool, Hot Tub

Ocean Pearl- Canal View and Minutes to the beach
Destinations to explore
- New York City Holiday rentals
- Myrtle Beach Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Charlotte Holiday rentals
- Ocean City Holiday rentals
- North Myrtle Beach Holiday rentals
- Raleigh Holiday rentals
- Virginia Beach Holiday rentals
- Wilmington Holiday rentals
- Newark Holiday rentals
- Jersey City Holiday rentals
- Townhouse rentals Chesapeake
- Beachfront rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with lake access Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Waterfront rentals Chesapeake
- Rentals with beach access Chesapeake
- Beach house rentals Chesapeake
- Rentals with a fireplace Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with pools Chesapeake
- Cottage rentals Chesapeake
- Family-friendly rentals Chesapeake
- Apartment rentals Chesapeake
- Rentals with a firepit Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with an EV charger Chesapeake
- House rentals Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with outdoor seating Chesapeake
- Flat rentals Chesapeake
- Guest house rentals Chesapeake
- Mansion rentals Virginia
- Mansion rentals United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Corolla Beach
- Carova Beach
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Ocean Breeze Waterpark
- Regent University
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- First Landing Beach
- Neptune's Park
- Currituck Beach Lighthouse
- Currituck Club
- The Military Aviation Museum
- Nauticus
- The Mariners' Museum
- Town Point Park





