
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.

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!

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!

All 4 One | Beach Living
Come enjoy time at the beach in our seaside oasis! All4One is located on the semi-private beach of Croatan in Virginia Beach. This means that although you are but a bike ride away from the hustle and bustle of the Boardwalk, you also have the beach to yourself in a quiet neighborhood setting- best of both worlds right? We certainly think so! My grandma built this home in the 1960's and my husband and have called it home for over a decade. Come enjoy your stay at the beach at our home!

Convenient Beach Home, Beach Access Across Street
Convenient beach house near peaceful East Beach. Beach access across the street. This wonderful home offers 3000 SF, 5 bedrooms, 3.5 bathrooms, 5 off-street parking spaces, tiles, hardwood and laminate floor throughout. Centrally located minutes to Norfolk Outlets Mall, Greenbrier Mall, Town Center, Botanical Garden, Norfolk Airport, and 15 miles from VA Beach ocean front. FOR ADDITIONAL INFORMATION, PLEASE CONTACT THE CO-HOST (Quan-616.340.3328) STR Zoning Permit Number: ZP24-00677

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.

Family beach home with 1st floor master bedroom
This young age house has a big backyard for kids and dog running around( pet fee is $100 per stay). Decent size patio with bbq grill makes a great hangout spot. 4 bedrooms with 1 king and 3 queen beds, a queen size pull out couch sleeper in the living room. Only 2-1/2 blocks away from the clean sand beach, you can take a walk on the beach and come home for breakfast! Perfect for your family vacation! We are not hosting any party/ event, thank you for understanding!

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!!

Designer Beach House | Pool, Hot Tub, Walk to Sand
Breaker Bay is a fully renovated 5BR, 3BA beach cottage in the heart of Sandbridge. With a private pool, hot tub, spacious deck, and open living space, it’s perfect for families or groups. Just minutes from the sand, it offers the ideal blend of comfort and coastal charm. Wake up to ocean sunrises, unwind with bay sunsets, and enjoy all that this peaceful beach community has to offer. Your perfect coastal getaway starts here.

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.
Popular amenities for Chesapeake mansion rentals
Luxury mansion rentals

Smack Attack: New Construction, North End, Pool

The Green Garden Cottage

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

Vibe District 5BR Beach House Walk To Oceanfront

Sanctuary on Sandpiper - Bayfront in Sandbridge

The White Lotus - Oceanview Retreat + Wild Horses

Ocean View Beach House Walk to Shore

EastBay Getaway 4 BR Pet Friendly Steps to Beach
Pet-friendly mansion rentals

Serenity Sound House: Sandbridge Oasis with pool

Beach House Just Blocks From Oceanfront Boardwalk.

Upscale Coastal Retreat • 4BR • Walk to Beach •

7 mins walk to beach! Waterfront view sunroom.

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

Chicks Beach Getaway large yard 500 yards to Beach

Relaxation Station at Old Beach

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

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

York River Vacation Home

Oceanfront Penthouse | 4BR Sunrise & Sunset Views

8br, Pool, Lzy Rvr, Pier, Pool, Hot Tub (Sandbridge)

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

"Sea Star" 8BR- Pool- Hottub- Oceanfront!

Ocean Pearl- Canal View and Minutes to the beach

5BR Waterfront 350ft Beach POOL OPEN 14 Guest Reno
Destinations to explore
- Norfolk Holiday rentals
- New York City Holiday rentals
- Washington Holiday rentals
- Myrtle Beach Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Outer Banks Holiday rentals
- Charlotte Holiday rentals
- Ocean City Holiday rentals
- Cape Fear River Holiday rentals
- Jersey City Holiday rentals
- House rentals Chesapeake
- Rentals with pools Chesapeake
- Townhouse rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Rentals with breakfast Chesapeake
- Condo rentals Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with lake access Chesapeake
- Waterfront rentals Chesapeake
- Apartment rentals Chesapeake
- Guesthouse rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with a kayak Chesapeake
- Smoking-friendly rentals Chesapeake
- Rentals with beach access Chesapeake
- Private suite rentals Chesapeake
- Family-friendly rentals Chesapeake
- Cottage rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with an EV charger Chesapeake
- Beach house rentals Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with a fireplace Chesapeake
- Beachfront rentals Chesapeake
- Rentals with a fire pit 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
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Old Dominion University
- Chrysler Museum of Art
- Regent University
- First Landing Beach
- Colonial Williamsburg's Merchants Square
- Currituck Beach Lighthouse
- Neptune's Park
- Nauticus
- The Mariners' Museum
- Currituck Club
- Virginia Zoological Park
- Back Bay National Wildlife Refuge-N





