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Mansion holiday rentals in Chesapeake

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Top-rated mansion rentals in Chesapeake

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Home

4.84 out of 5 average rating, 121 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.

Guest favourite

Home

4.86 out of 5 average rating, 151 reviews

Family Rental Close to Beach

Large Victorian home one block from the center of town in Cape Charles. One of only a handful of rentals with FIVE bedrooms. Features renovated bathrooms w/ oversized showers and endless hot water. Walking distance to beach, park, restaurants, shops and more. Large three-story layout with living room, dining room, kitchen, three porches and nine beds. Kitchen is equipped and linens are included. The house is completely outfitted - with high speed internet, Apple TV, YouTube TV and Sonos Stereo.

Guest favourite

Home

4.91 out of 5 average rating, 45 reviews

Perfect Escape with Ocean Breeze!

A new home constructed in 2021 that is a 5 minute walk to the beach from 25th Street. Located in the heart of Old Beach with numerous restaurants, bars, high end supermarket and the boardwalk all within walking distance from the home. The home consists of 3 bedrooms, a bonus room with a king size bed, and a media room/office with a queen size pullout sofa. The home is professionally designed with detailed amenities for our guests throughout the home. Transcendent Stays is a locally driven group

Guest favourite

Home

5 out of 5 average rating, 16 reviews

Whispering Woods Estate- secluded and spacious

BEST kept secret of VA Beach! This 3 story mansion is on 6 acres with vast gardens, huge pool, outdoor kitchen and seating area, a screened-in porch, pond for fishing, & tons of space for outdoor games. The inside is cozy, spacious, and stocked with games! This oasis is the perfect escape to the country but within proximity to the beach, shops, stores, water park, fantastic restaurants, coffee shops, breweries, amphitheater & PAAC is 4 mins for sports tournaments! This mini “resort” is a dream!

Guest favourite

Home

4.98 out of 5 average rating, 126 reviews

Family Reunion on the Bay

2020 prices through 2025! Unpretentious, clean & family-friendly. Bright open-plan home for easy living. Generous seating throughout. Loads of games, toys. Ideal for extended families. Side-door ramp, 1st-floor ADA bedroom, step-in shower w/seat & grab bar nearby. Backyard fire pit, picnic tables, grill, corn hole. Free firewood, propane, stand-up paddleboard, beach chairs & toys. IMPORTANT NOTES: 1. Absolutely NO PETS ALLOWED! ($750 fine) 2. Only weekly, Sat.-to-Sat. rentals June thru Aug. 30.

Home

4.72 out of 5 average rating, 18 reviews

Beach Front - Hot Tub - Game Room - 3500SQFT

Get ready to have your mind blown by this 3500SQFT house just hops, skips, and jumps away from quiet BEACH! If you're craving peace and privacy in one package, you've hit the jackpot here. Get ready for a wildlife spectacle – dolphins, eagles, crabs (a lot of them) and pelicans showing off their epic moves~ Psst... want to know a secret? Cape Charles is just 10-15 minutes away, and it's a foodie's paradise with restaurants that'll make your taste buds dance like they're at a culinary fiesta!

Guest favourite

Home

4.78 out of 5 average rating, 36 reviews

Magnolia Manor 4 Bedrooms , 2 Baths Cheerful house

Located on over an acre of land ,across the street from the historic James River,this 4 bedroom 2 bath home is centrally located. Christopher Newport University(CNU), Ferguson Center for the Arts, The Mariner’s Museum, James River County Club and Riverside Hospital are all approximately 1 mile away. Bush Gardens and Colonial Williamsburg are approximately 20 minutes away.This home also includes a 2 car detached garage.Highend kitchen appliances as well as a washer and dryer are at the home.

Guest favourite

Home

4.99 out of 5 average rating, 78 reviews

Breathtaking Ocean views at Pinch Me, 8bdrm, 6bath

Get ready to make memories by reserving this gorgeous beach house for your group! New carpet throughout the house and a large kitchen that offers 2 dishwashers and a double oven to keep up with the group! 6 baths and 8 beautiful bedrooms in the home. This home is an excellent choice for your family vacation, reunion, or corporate getaway. Just steps away from the Ocean where you can relax on the wonderful beach of Sandbridge. The private pool and cabana adds more to a delightful vacation!

Guest favourite

Home

4.96 out of 5 average rating, 100 reviews

Cape Charles Retreat - 2 Blocks from Beach/Town

Welcome to Cape Charles Retreat! Come on up to the porch, grab a lemonade and settle into the porch swing for some much deserved rest and relaxation. Cape Charles Retreat is a beautiful 100+ year old American Foursquare located two blocks from the beach, Central Park, and town! Our home has been restored to preserve much of its original charm while adding modern amenities and outfitted with everything you’ll need for a great beach vacation. So grab your bathing suit and come for a visit!

Home

4.92 out of 5 average rating, 182 reviews

Spacious home for up to 10! GREAT for families!

Welcome to the Vibe District in Virginia Beach! Exquisitely designed and spacious for up to 10 guests, you will not find a better location! Featuring 4 bedrooms, 3.5 bathrooms & 2 separate living rooms. This is ideal for a group! ~ Walking distance (just 1 mile) to the convention center ~ Easy walk to the beach- only 2.5 blocks! We provide a beach cart and gear for use! ~ Fully stocked kitchen ~ Full use of washer & dryer ~ High speed WiFi! Book your dream family getaway today!

Guest favourite

Home

5 out of 5 average rating, 8 reviews

James river cottage

Wow!!! Bring the whole family to this spectacular place with lots of room for fun. This very large 3,200 square foot gorgeous home has 5 bedrooms and 12 beds. It boasts a beautiful inlawn suite with a queen bed downstairs with a full bathroom. One of the bedrooms has two bunk beds that sleeps 4. All beds are queen size through the house except the king in the master. And 4 twin size bunk beds. 7 queen, 1 king and 4 twin beds. Also has a great media room with a 75 inch smart tv.

Guest favourite

Home

4.94 out of 5 average rating, 18 reviews

Phillips Lake Retreat

Relax with your family or friend at this peaceful home on the waterfront. Enjoy expansive views of the Hampton River. Immerse yourself in the “low country” lifestyle. Sit on our lovely patio and people watch or sit on our back deck for a full view of the lake. Enjoy the stunning lake view throughout the day and at night. Have up to eight guests with our 4 bedrooms, 2 baths home. A queen size air mattress is available for an additional $35. *You must be 25 years or older to book*

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Popular amenities for Chesapeake mansion rentals

Free parking on premises

Air conditioning

Luxury mansion rentals

Guest favourite

Home

4.93 out of 5 average rating, 14 reviews

Atlantic Sunrise - Bright Renovated 9BR | Private

Holiday home

4.91 out of 5 average rating, 35 reviews

VB Paradise / Private Pool, Hot Tub

Guest favourite

Home

4.97 out of 5 average rating, 94 reviews

PETS Welcome! 4Bed Beach View Privately Managed

Home

4.88 out of 5 average rating, 65 reviews

At Oceanside on the gold coast in the North End!

Guest favourite

Home

4.74 out of 5 average rating, 85 reviews

7+ Bdrm, 5.5 Bath Pool/Hot Tub Sandbridge Beach VA

Guest favourite

Home

4.99 out of 5 average rating, 77 reviews

Beachfront 2 Dwellings EV charger

Guest favourite

Home

5 out of 5 average rating, 60 reviews

*NEW* Spacious/Standalone 4BR Beach House

Guest favourite

Home

4.9 out of 5 average rating, 41 reviews

Silver Strand, Pool, Dock w/ Kayaks, Sunset Views

Pet-friendly mansion rentals

Home

5 out of 5 average rating, 3 reviews

Beachfront Getaway, pet friendly

Guest favourite

Home

4.89 out of 5 average rating, 130 reviews

Modern. Spacious. Pets Yes! 2Min Walk to Beach

Guest favourite

Home

4.94 out of 5 average rating, 67 reviews

Short Walk to Beach + Pool Table + Pets OK!

Home

4.85 out of 5 average rating, 163 reviews

Your family beach house

Guest favourite

Home

4.84 out of 5 average rating, 343 reviews

Family Holiday House. Events and Beaches Nearby

Cottage

4.88 out of 5 average rating, 189 reviews

Quaint Beach Cottage in 4WD-OBX

Home

4.88 out of 5 average rating, 34 reviews

4BR Cape Cod in Riverside by CNU

Guest favourite

Home

4.82 out of 5 average rating, 22 reviews

4 Beds + Game Room + Family & Dog Friendly!

Mansion rentals with a pool

Guest favourite

Home

4.99 out of 5 average rating, 70 reviews

The Golden Hour - Let’s Make Some Memories

Home

4.75 out of 5 average rating, 12 reviews

Beachfront/Pool/Hot Tub/Dog Friendly/Winter Specia

Guest favourite

Home

4.9 out of 5 average rating, 20 reviews

Star of Sandbridge

Home

4.67 out of 5 average rating, 73 reviews

Beach House with breathtaking sunsets

Guest favourite

Home

5 out of 5 average rating, 22 reviews

Pool, hot tub, walk to beach, family friendly home

Home

4.82 out of 5 average rating, 33 reviews

Sandy Beaches OBX *New Pool and Hot Tub 2024*

Guest favourite

Home

4.89 out of 5 average rating, 28 reviews

Copa Cabana-Sandbridge getaway

Guest favourite

Home

4.93 out of 5 average rating, 96 reviews

4BD home w/ game room & pool near Langley & PTC!

Destinations to explore