Mansion holiday rentals in Chesapeake

New Listing-Dream Shack-Heated Pool thru mid Oct

Dream Shack is ready to give you everything you've dreamt of in your Outer Banks vacation! We just installed a NEW HOT TUB for your enjoyment. This home offers high elevation with views galore, sunrises and sunsets you will never forget! You'll have ocean/sound access, soundside boat ramp access, private heated pool, community tennis and basketball courts, a community pool, and direct access to the bike path. Plenty of beach parking can also be found at the Bonito St Access, just 1/2 mile away.

4BR/4BA perfect for BIG families! Near attractions

We've combined two two-bedroom condo units into a large 2460 sq. ft. four bedroom. Enjoy two king size master suites, queen and twin bed guest units and two kitchens and dining rooms. Four full bathrooms. The two living areas each have fireplaces and each has a sleeper sofa. Prepare those family meals in two well-appointed kitchens each equipped with a refrigerator, microwave, toaster, coffee maker and utensils. Only minutes from area shopping, dining and attractions, including Busch Gardens.

The Great Gatsby: Pink Flamingo Lounge Retreat!

Welcome to Gatsby's Pink Flamingo Lounge for a memorable stay! Unwind on swings, play the organ, and enjoy a variety of games in this spacious 4-bedroom, 2-bath home that comfortably sleeps up to 10 guests. Located near charming downtown Surry, our unique space features a fully fenced backyard for your furry canine companions. Outdoor activities include cornhole, Tubelox, darts, sprinkler and a baby pool. Handicap accessible with a ramp, this is a one-of-a-kind retreat you won't want to miss!

New Sound Front Private Pool Hot Tub Dock Elevator

Welcome to your waterfront getaway perfect for the whole family! This charming property offers stunning sound and marsh views and breathtaking sunsets from multiple decks. Explore the sound in our kayaks and paddle board that can be launched right from the private dock. -5 bedrooms -4.5 bathrooms -2 living areas -Sleeps 16 Blending coastal designs with every amenity you could possibly wish for. *Elevator *Private Pool & Hot tub *Private dock with Sound Access *Outdoor shower & BBQ

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.

Waterfront 4 bedroom home with marina facilities

Stunning river views from this spacious family home. The quiet, peaceful setting is perfect for taking in nature and wildlife. The open floor plan that spills onto the patio is great for entertaining. Wonderful spot to enjoy boating, crabbing, fishing, kayaking - all the Severn River has to offer. Home features first floor BR and BR w/ shower, upstairs 3 BR and 2 full BR. Award-Winning Busch Gardens, Historic Colonial Triangle (Yorktown / Williamsburg / Jamestown) Nearby.

MillerLight

A beautiful 2500 square foot beach house on the sound side of Monterey Shores .Two master suites and three other bedrooms. The house has a pool and jacuzzi on the property along with a club house pool , gym tennis courts, basketball court and activities in the summer. The house has wifi and dish tv. There are plenty of restaurant and shopping nearby.The house is on a cul de sac and very private.

Historic Powhatan Resort- 4 bedroom condo!

Peacefully situated amid 256 acres of rolling woodland hills, and boasting all the character of a distinguished manor house, The Historic Powhatan Resort captures the essence of its Colonial surroundings. Sumptuous, spacious accommodations offer a private balcony. Originally built circa 1735, this restored manor house offers a serene getaway during any season.

Waterfront on the James 4,100 SF near Williamsburg

Large 4,100 square feet , lovely, private, brick, four bedroom waterfront home on the James River, with spectacular views. Beautiful sunrises and wildlife to view daily. Close proximity to Busch Gardens, Chippokes State Park, Jamestown, and Colonial Williamsburg. Only a 30 min drive to historic Smithfield.