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.

Luxury Home, 50' pool, hot tub, grill & pool house

Reunion Paradise! Upscale 5300 SQ FT PLUS Hot Tub, Sauna, Steam Shower, 50' Pool. Quiet & safe when you want to walk, bike or go for a jog at any time. This home is furnished with Ethen Allan tables & chairs, Restoration Hardware and Pottery Barn Bedrooms. Plenty of room in the backyard for a great family reunion. Enough grass space for put up a volleyball. 50' pool, 8 foot deep end, 3.5' shallow end (over 1/2 the pool) Spill over hot tub to enjoy watching the stars or family in the pool.

The Historic Palmer Inn Estate and Guest House

The Historic Palmer Inn Estate is rich in Currituck History and respected by locals. Whether you are searching for a spectacular waterfront backdrop for a wedding or event, a family vacation or a long weekend with a large group this property has it all. Featuring a stunning main house it also has a light and airy guest house on the property. Famous sound views and lots of land to spread out, this property is a must see. About a half hour to both the OBX and the VA line the location is amazing.

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!

Family friendly 5 bedroom beach getaway!

Spacious home perfect for your multi-family beach vacation. 2 large master bedrooms with King beds, a double bunk bed room, 2 twin beds and 1st floor queen room and bathroom. Enjoy the private hot tub located on the top deck and drink or lounge by the large in ground pool. Home is located in Monterey shores which gives access to a gym, basketball and tennis courts, and park. Just a short walk to the beach and the sound with community pier and boat ramp for your kayaks and paddle boards.

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.

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.

Oceanfront! Private Pool,Views,Elevator,Amenities!

This spectacular Ocean Front house in Buck Island has it all! The wonderful Buck Island amenities, gorgeous beaches, private driveway and walkway to the beach! This gorgeous house with amazing views, all master suites, huge custom kitchen, private heated pool, hot tub, game room and elevator will be sure to be a family favorite for years to come.