Mansion vacation rentals in Chesapeake

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Top-rated mansion rentals in Chesapeake

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Guest favorite

A spacious living area features large windows offering expansive views of the water. A cozy fireplace is set against a stone wall, while modern white chairs and a dark sectional provide ample seating. A coffee table sits at the center, adding to the inviting layout.

Home in Norfolk

4.97 out of 5 average rating, 118 reviews

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!

Guest favorite

A private pool is surrounded by a spacious patio, featuring lounge chairs and a shaded gazebo. Lush greenery encircles the pool area, providing a sense of privacy. The clear blue water reflects the sky, inviting relaxation and enjoyment.

Home in Virginia Beach

4.86 out of 5 average rating, 118 reviews

Private Pool at the Oceanfront in a Spacious Home

Private Pool at the Oceanfront in a spacious 2600 sq ft home. 3 blocks from the Virginia Beach Boardwalk, Vibe District. 4 bedrooms in a three-story Private Home. 1st Flr: 2 bathrms, a bedrm with Full-bunk bds, kitchen, dining rm & living rm. 2nd lvl contains a lux Mstr ste with massive jacuzzi, dbl shwr and living rm . 3rd Lvl: 2+ bedrms, bathrms & prvt balconies (queen in 1 room and 2 doubles in the other). Two-car garage and driveway, NOT a duplex. Pool unheated. Modern Tvs and cable!

Guest favorite

A welcoming entrance is presented with a light blue door framed by large windows. Two blue chairs are positioned on the porch, complementing the navy siding and white railing. A mat at the door conveys a hospitable message.

Home in Buckroe Beach

4.92 out of 5 average rating, 117 reviews

Luxurious Alberta Beach House w/ Historical Detail

Step inside and feel the calm coastal energy take over. With over 3,000 square feet of sun-filled space, this home sleeps up to 14 guests, perfect for family gatherings or group getaways. Just a 3-minute stroll brings you to the soft sands and gentle waves of Buckroe Beach, one of the area’s most family-friendly spots. Whether you’re sharing stories on the deck, cooking in the spacious kitchen, or unwinding after a beach day, every moment here invites you to feel free, refreshed, and at home.

Guest favorite

The three-story farmhouse-style home features a charming brick facade and a front porch with blue double doors. Lush greenery surrounds the entrance, while a path leads toward the driveway. Sunlight highlights the roof and front yard, creating a welcoming exterior.

Home in Colonial Place

4.97 out of 5 average rating, 120 reviews

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.

Guest favorite

An aerial view of the property reveals a spacious backyard featuring a swimming pool surrounded by lounge chairs and inflatable pool toys. Lush greenery encircles the area, enhancing the sense of privacy, and the house is seen with its inviting deck and patio area.

Home in Portsmouth

4.93 out of 5 average rating, 151 reviews

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!

Top guest favorite

A spacious living area features light wooden flooring, a comfortable white sofa, and a coffee table. Natural light floods through the windows, illuminating the adjacent kitchen area, which includes modern appliances and a dining space. A ceiling fan and wall-mounted TV enhance the inviting atmosphere.

Villa in Virginia Beach

4.89 out of 5 average rating, 106 reviews

Beach House Just Blocks From Oceanfront Boardwalk.

This 3 story town-home (similar to a Duplex House) is the perfect getaway to enjoy a day at the beach! Only 5 minutes walk to the Oceanfront Boardwalk, you can enjoy an evening walk or have dinner at one of hundreds of restaurants in the area. First master bedroom and 2 other rooms are at second floor. Second master bedroom is third floor. Also we provide key less entry for all door inside, outside the house. Beach chair, grill, etc.... also available for you during the time you stay.

Superhost

The two-story beach house features a light-colored exterior with decorative red lanterns hanging from the front porch. White railings frame the wide porch, while a round entrance window invites light. A manicured lawn adds to the welcoming appeal of the home.

Home in East Ocean View

4.87 out of 5 average rating, 112 reviews

Convenient Beach Home, Beach Access Across Street

Convenient beach house near peaceful East Beach. Beach access across the street. This wonderful home offers 3000 SF, 5 bedrooms, 3.5 bathrooms, 5 off-street parking spaces, tiles, hardwood and laminate floor throughout. Centrally located minutes to Norfolk Outlets Mall, Greenbrier Mall, Town Center, Botanical Garden, Norfolk Airport, and 15 miles from VA Beach ocean front. FOR ADDITIONAL INFORMATION, PLEASE CONTACT THE CO-HOST (Quan-616.340.3328) STR Zoning Permit Number: ZP24-00677

Guest favorite

The kitchen features modern appliances and ample counter space, highlighted by a large island with seating for four. Natural light flows through the windows, while the cabinets provide organized storage. A cozy dining area with a table for six is partially visible to the right.

Home in Virginia Beach

4.94 out of 5 average rating, 132 reviews

Large 5BR in the Vibe District• Ideal for Groups

Welcome to the perfect blend of relaxation and spacious coastal living at this stunning 5-bedroom, 3.5-bath home near the beach. With 5 comfortable bedrooms and Smart TVs in each, it’s perfect for large families or groups. Enjoy a fully equipped kitchen, Wi-Fi, streaming, and a private yard with a gas grill and cornhole boards. Just a short stroll from the beach, you’ll have easy access to sun, sand, and fun. Whether for a weekend or extended stay, this home truly has it all!

Guest favorite

A three-story house features a light gray exterior with a welcoming yellow front door. Flanking the entrance are neatly trimmed shrubs and small trees, complementing the spacious front porch. The surrounding area includes well-maintained neighboring houses and a glimpse of a fenced backyard.

Home in Norfolk

4.92 out of 5 average rating, 171 reviews

5 Min to Downtown & Ghent, Fenced Yard, Firepit

Welcome to Norfolk! This is a large 3 story, 4 BR/3.5 BA house located just outside of the popular Ghent district in and walking distance to many breweries, restaurants & coffee shops! This is a fast growing area of town and for good reason, we’re so exited to host you! 15 min drive to Norfolk International Airport 12 min drive to Naval Base 8 min drive to Downtown/waterside district/freemason historic district 6 min drive to ODU campus 4 min drive to Virginia Zoo

Guest favorite

Home in Virginia Beach

4.87 out of 5 average rating, 203 reviews

Charming Single Family Home by the Chesapeake Bay

Discover your perfect Virginia Beach retreat! This charming, single-family home is nestled in a friendly neighborhood just a mile from the stunning Chesapeake Bay. You're within walking or biking distance of great local breweries, restaurants, and parks, including the Bayside Recreational Center and Bayville Park. This home features a private, fenced-in backyard, perfect for relaxing after a day at the beach or letting small pets run around for an additional fee.

Superhost

A bright and spacious living area features comfortable seating on a large sofa and armchairs. A flat-screen TV is mounted on the wall across from the seating. Natural light enters through multiple windows, and a decorative plant adds a touch of greenery to the room.

Home in Norfolk

4.83 out of 5 average rating, 130 reviews

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!!

Guest favorite

A game room features a billiards table with a green felt surface, accompanied by an air hockey table and retro arcade game console. Natural light filters through the window, and a neutral-toned rug adds warmth to the space.

Home in Hampton

4.92 out of 5 average rating, 125 reviews

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

Welcome Home! Be the next to rent this beautifully renovated, modernized home with beautiful kitchen, amazing bathrooms and generous bedrooms and closets. Come in and relax in this centrally located neighborhood - convenient ten minute trip for shopping, restaurants and military bases. Great for families coming in town for Boo Williams tournaments! This is the one! DONT FORGET TO ASK ABOUT OUR YACHT RENTAL OPTIONS!!!