
Mansion holiday rentals in Chesapeake
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Top-rated mansion rentals in Chesapeake
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Popular amenities for Chesapeake mansion rentals
Luxury mansion rentals

*Grotto Waterfall* Bethel Oasis | 2masters | 5bdrs
I reserve the home for the celebration of my nephew returning from Sea. It was a very lovely home and very clean . I enjoyed the spacious rooms and the decor of the home. If ever I’m in the area I will definitely reserve this home again. I recommend this home to all who like space. ⭐️⭐️⭐️⭐️⭐️

Sanctuary on Sandpiper - Bayfront in Sandbridge
What a beautiful place to stay. The house is lovely, the back yard was packed full of entertainment: salt water pool, fire pit, corn hole, fishing in the canal and if that isn’t enough it’s a short walk to the beach. The sunrises on the beach and sunsets on the canal were spectacular. We were a family of 8 and there was plenty of room. Christina was very responsive when we reached out and she put together an amazing house manual that included everything you needed to know from A-Z. Couldn’t be happier!!!

Stunning Views of Back Bay & Seconds to the Beach
Great location and host. The home was the perfect size for my family and friends.

Beachfront 2 Dwellings EV charger
This beach house was so beautiful! The location was amazing. The host was very responsive. The house was extremely clean and well organized. We loved the amazing views of the ocean from all the rooms.

Croatan Beach - Big Kitchen, Hot Tub, 2 Masters
Amazing house with even better location. The walk to the beach is incredibly close. Beautiful spacious house. The backyard is Al equipped to with a beautiful deck to lounge and relax.

*NEW* Spacious/Standalone 4BR Beach House
Great place to stay, had everything we needed.

Oceanfront 3400 sq ft * Spacious-3 levels!
This house was perfect for my family. It is about as close as you can get to the beach. There was plenty of room for everyone. We loved every minute there. The only thing I would change is to add a smart tv in the kids room so they can watch tv while going to bed. We absolutely loved the Mexican restaurant right across the street. Lola’s beach cantina. It has excellent food. Brunch and dinner.

Open house with Ocean views!
Amazing space, super clean, spacious, and comfortable, and literally steps away from the beach! Staci’s place was fully stocked with beach gear (including a boogie board, so fun!) and a closet full of board games. The top deck seating was great with a gorgeous view of the beach. The living room was also so cozy for movie nights. We never wanted to leave!
Pet-friendly mansion rentals

The Chesapeake St Retreat - Pet and Kid Friendly
The house was clean and felt like home. The hostess was great to deal with and very responsive. We had an excellent experience staying hear.

Modern. Spacious. Pets Yes! 2Min Walk to Beach
The house as advertised! Clean and very supplied. The beach was small and the area does not have much options to eat. Neighborhood was ok.

Life doesn't get better than this! Walk to beach
We came into town for the Irish Setter club of America National Specialty. We didn’t want the dogs cooped up in a small hotel room and we all wanted to hang together. Dahlia’s place was perfect! Plenty of room, wonderful back yard for the dogs to run and they loved to be able to go to the beach. The amenities were awesome and we were very happy with our stay! Definite must return again!

Your family beach house
Xiaoming’s home was very well decorated and taken care of. Nice layout with plenty of room inside. Good communication.

Relaxation Station at Old Beach
Lovely,spacious home with private back entrance. Walking distance to everything you’d want to do while at the beach. Would stay again!

Chicks Beach Getaway large yard 500 yards to Beach
Place was beautiful, roomy, clean, and perfect for our stay!! I want to return to this place and location in the near future!

Lux Elegance
Well what can I say! We all gathered from Atlanta and Maryland to attend a family members graduation. This property blew our mind and it was well worth our travels and the cost. It was spotless, extremely clean, and very spacious and the aroma was breathtaking with a plethora of amenities. Most important, Ivan the host… was exceptionally hospitable. Not to mention the neighbors were also nice to my family and I. We also traveled with our two little dogs who felt right at home in their two cages. This property is number one on our list for Hampton,Virginia! ❤️❤️❤️

Spotless Treehouse | Pool | HotTub | Pickle | Pets
Absolutely great stay !! Everything was exactly as stated, we were even able to check in early. Matt is an outstanding host, and I'm sure would be easy to contact if a problem were to arise, as he answered all the questions I had prior to our arrival in an extremely timely manner. 5 star A + thanks again for a great stay in your truly unique tree house.
Mansion rentals with a pool

Corova Beaches 5BR w/Heated Pool & Hot Tub!
Our family had a wonderful time and couldn’t have asked for a nicer property. NorthStar was beautifully furnished, clean as a whistle, very well-stocked and is run by a top-notch management company. Grace was proactive and extremely responsive. We will return next summer when the water is warmer. Thanks Grace and all at Oak Realty for a wonderful weekend of memories and allowing us such a nice home to call ours for Memorial Day Weekend 2025!

New! Oceanfront Penthouse/ 2 Decks/ Pool/Beach/Gym
Amazingly beautiful. Place was just as described. Owner responsiveness was unmatched. Reached out to me before arrival just to make sure there were no questions. Secluded area from the crowds yet great places to eat nearby or onsite. Loved this place. Would definitely return.

Aloha Beaches OBX
This was our second year in a row we stayed here, and we love it. It’s right next to the beach, and accommodates or group perfectly. The pool/hot tub are perfect for after the beach. Sarah is super responsive and a great host for any needs we reached out with! We are already looking forward to next year’s trip!

York River Vacation Home
Home and location were absolutely perfect! Exceeded our expectations, highly recommend! Would love to come back again.

Beach Home, Upscale Croatan Resort + Private Pool
Such a wonderful place!! Beverly was more than accommodating and was very responsive to all of our questions🙌🏽 we would love to stay here again in the future

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym
Beautiful location! Walking distance to the beach and fishing pier. Family friendly! The space was comfortable with plenty of room for our party of 8! All the accommodations we needed! Responsive host who was very accommodating and hospitable! Would highly recommend and will stay again if in Virginia Beach!

Carova beach home w/ ocean view, pool & hot tub!
Our stay at this place was absolutely incredible! The highlight was undoubtedly the breathtaking 360-degree views that greeted us every morning and evening. It was truly a slice of paradise! The property’s dog-friendly policy was a big plus for us, allowing our furry friends to join in on the vacation fun! The accommodation was not only pet-friendly but also exceptionally well stocked. From kitchen essentials to beach gear, everything we needed was conveniently available, making our stay comfortable and stress-free. We couldn’t have asked for a better retreat. The combination of stunning views, pet-friendly amenities and thoughtful provisions made our stay unforgettable! We will definitely be staying here again in the future!

Designer 7BR w/ Pool and Hot Tub. Pets welcome!
This rental property was the ideal spot for our family reunion of 16, ages 8 to 78. This was one of the most well-equipped properties we have stayed at. We have stayed at several rental properties in Sandbridge Beach, VA in previous years, and this is our favorite. The kitchen was well equipped and stocked with essentials (coffee, sugar, creamers, paper towels, toilet paper, regular and beach towels, etc.) The kids loved the game room and outdoor pool. The adults enjoyed the hot tub and ping pong room. Two big dining tables easily accommodated our group size (8 adults at one and 8 kids at the other). The beds and pillows were all comfortable. Amy, the Operations Manager, was most helpful and very responsive to any of our questions. We plan to return to this property sometime in the future. Definitely a 5-star experience for everyone in our family.
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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Bethel Beach
- Water Country USA
- First Landing State Park
- Kingsmill Resort
- Buckroe Beach and Park
- Grandview Beach
- Currituck Beach Lighthouse
- Jamestown Settlement
- Sarah Constant Beach Park
- Haven Beach
- Virginia Beach National Golf Club
- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
- Outlook Beach
- Kiptopeke Beach