Mansion holiday rentals in Chesapeake

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

Cape Charles cottage, family friendly, in town

Welcome to Cape Charles Cottage in the historic district! We are 6 blocks to the beach and 4 blocks to Mason ave (shops, restaurants). The town is very walkable or golf cartable…you can rent ours! We can host up to 10 guests with 4 bedrooms and a bonus room with a daybed w trundle that pulls to side by side twins. One bedroom has an ensuite bathroom and the others share a hall bath with a tub/shower. Kitchen is fully equipped, fenced yard, outdoor shower,fire pit, grill & shed with beach gear.

Large Charming Renovated Cape Victorian for 12

It's rare to find a home large enough to host 12 in Cape Charles, especially with a new kitchen & bathrooms! New Spring 2024: A brand new 6-person golf cart can be added to your stay! This 5 bedroom, 3 bath has it all: 8 beds, 1 block to coffee, 2 blocks to main street, 3 blocks to the park, 5 blocks to the beach, off-street parking, outdoor shower, & a blackstone grill. Brand newly furnished in delicate blues, woven rattan & soft pink highlights, accentuating its French Victoria history.

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.

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.

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!

Spacious home for up to 10! GREAT for families!

Experience the heart of Virginia Beach's Vibe District! *Spacious 4BR, 3.5BA home; accommodates up to 10 guests *Two separate living rooms for relaxation and entertainment *Just 2.5 blocks from the beach; beach cart and gear provided *1 mile to the Convention Center; perfect for event attendees *Fully equipped kitchen for home-cooked meals *High-speed WiFi; stay connected during your getaway *Washer & dryer available for your convenience Book your dream family vacation today with us!

*UPSCALE* Ideal location 4 beach vacay! H20 views!

Location, location, location! Start your day w/ a view of the sunrise over Rudee Inlet & Atlantic Ocean! Amazing *WATER VIEWS* & amenities. Spacious, bright, open, & immaculate. Stunning 2318 sq ft, 4 BR/2.5 BA home is the perfect place for your family/friends to make the most out of your beach vacation. Located in a locals’ favorite neighborhood in Resort Area w/ easy access to beach, water sports, boating & restaurants. Spend the day at the beach & wind down in comfort & luxury.

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.