
Mansion holiday 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.

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!

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.

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!

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!

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.

Luxurious Alberta Beach House w/ Historical Detail
Express stay is available 2 day stay and up. Step into serenity at this stunning coastal retreat! With 3,000 square feet of sunlit space, this home welcomes up to 14 guests—ideal for family reunions or group adventures. Just a 3-minute walk away, Buckroe Beach awaits with its soft sands and gentle waves. Whether you're sharing stories on the deck, cooking up a feast, or relaxing after a beach day, every moment here invites you to feel free, refreshed, and at home.

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!!

A Modern 4 Bedroom Beach House near VB Boardwalk
This Beautiful Family Friendly 4 Bedroom 3.5 Bath home is centrally located in The Vibe District of the Virginia Beach Oceanfront. Located just a few blocks from the Virginia Beach Boardwalk, The Virginia Beach Sports Complex, The Convention Center, The Virginia Beach Aquarium, Interstate, Amazing local restaurants, coffee shops, and so much more! We cannot wait to host you!
Popular amenities for Chesapeake mansion rentals
Luxury mansion rentals

Smack Attack: New Construction, North End, Pool

Serenity Sound House: Sandbridge Oasis with pool

The Green Garden Cottage

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

Norfolk 4BR Home Walk To Beach 2 Suites

Vibe District 5BR Beach House Walk To Oceanfront

Norfolk Beach Retreat • Pets OK • Pool Table

The White Lotus - Oceanview Retreat + Wild Horses
Pet-friendly mansion rentals

Spacious Family Oasis | 5 BR | Huge Yard & Garage

Beach House Just Blocks From Oceanfront Boardwalk.

Upscale Coastal Retreat • 4BR • Walk to Beach •

Escape to the water!

Hidden Gem.4/bedroom cozy home fenced in yard

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

Oceanfront Penthouse | 4BR Sunrise & Sunset Views

Beach Bound Carova OBX w/Pool-Hot Tub Wild Horses

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

New! Beautiful home on canal.

"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
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- Rentals with a hot tub Chesapeake
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- Family-friendly rentals Chesapeake
- Private suite rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Rentals with breakfast Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with pools Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Cottage rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- House rentals Chesapeake
- Rentals with lake access Chesapeake
- Smoking-friendly rentals Chesapeake
- Rentals with beach access 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
- Chrysler Museum of Art
- Old Dominion University
- Currituck Beach Lighthouse
- Neptune's Park
- Regent University
- Colonial Williamsburg's Merchants Square
- First Landing Beach
- The Mariners' Museum
- Nauticus
- Currituck Club
- Town Point Park
- The Military Aviation Museum





