Mansion holiday rentals in Chesapeake

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Popular amenities for Chesapeake mansion rentals

Luxury mansion rentals

Guest favourite
Home in Hampton
4.95 out of 5 average rating, 121 reviews

*Grotto Waterfall* Bethel Oasis | 2masters | 5bdrs

MarticiaRating, 5 stars1 week ago
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. ⭐️⭐️⭐️⭐️⭐️
Top guest favourite
Cottage in Sandbridge
5 out of 5 average rating, 100 reviews

Sanctuary on Sandpiper - Bayfront in Sandbridge

ChristineRating, 5 stars3 weeks ago
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!!!
Superhost
Home in Sandbridge
4.84 out of 5 average rating, 129 reviews

Stunning Views of Back Bay & Seconds to the Beach

GregRating, 5 stars1 week ago
Great location and host. The home was the perfect size for my family and friends.
Top guest favourite
Home in Buckroe Beach
4.99 out of 5 average rating, 87 reviews

Beachfront 2 Dwellings EV charger

JenniferRating, 5 stars2 weeks ago
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.
Superhost
Home in Virginia Beach
4.65 out of 5 average rating, 131 reviews

Croatan Beach - Big Kitchen, Hot Tub, 2 Masters

HarveyRating, 5 stars1 month ago
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.
Guest favourite
Home in Virginia Beach
5 out of 5 average rating, 72 reviews

*NEW* Spacious/Standalone 4BR Beach House

PhillipRating, 5 stars2 weeks ago
Great place to stay, had everything we needed.
Guest favourite
Home in East Ocean View
4.97 out of 5 average rating, 36 reviews

Oceanfront 3400 sq ft * Spacious-3 levels!

SteviRating, 5 stars3 days ago
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.
Guest favourite
Home in Sandbridge
4.93 out of 5 average rating, 44 reviews

Open house with Ocean views!

CateRating, 5 stars1 week ago
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

Superhost
Home in Norfolk
4.84 out of 5 average rating, 98 reviews

The Chesapeake St Retreat - Pet and Kid Friendly

PaulRating, 5 stars1 day ago
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.
Guest favourite
Home in East Ocean View
4.89 out of 5 average rating, 142 reviews

Modern. Spacious. Pets Yes! 2Min Walk to Beach

VimarisRating, 5 stars3 weeks ago
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.
Superhost
Home in Norfolk
4.9 out of 5 average rating, 39 reviews

Life doesn't get better than this! Walk to beach

MarianneRating, 5 stars4 weeks ago
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!
Superhost
Home in East Ocean View
4.84 out of 5 average rating, 170 reviews

Your family beach house

AllenRating, 5 stars1 week ago
Xiaoming’s home was very well decorated and taken care of. Nice layout with plenty of room inside. Good communication.
Superhost
Home in Virginia Beach
4.82 out of 5 average rating, 164 reviews

Relaxation Station at Old Beach

NatalieRating, 5 stars2 weeks ago
Lovely,spacious home with private back entrance. Walking distance to everything you’d want to do while at the beach. Would stay again!
Superhost
Townhouse in Chic's Beach
4.79 out of 5 average rating, 202 reviews

Chicks Beach Getaway large yard 500 yards to Beach

MargaretRating, 5 stars4 weeks ago
Place was beautiful, roomy, clean, and perfect for our stay!! I want to return to this place and location in the near future!
Top guest favourite
Home in Hampton
5 out of 5 average rating, 25 reviews

Lux Elegance

ChereseRating, 5 stars1 week ago
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! ❤️❤️❤️
Top guest favourite
Home in Corolla
4.96 out of 5 average rating, 266 reviews

Spotless Treehouse | Pool | HotTub | Pickle | Pets

JeffRating, 5 stars2 weeks ago
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

Superhost
Home in Currituck County
5 out of 5 average rating, 4 reviews

Corova Beaches 5BR w/Heated Pool & Hot Tub!

ColinRating, 5 stars2 weeks ago
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!
Superhost
Apartment in Sandbridge
4.86 out of 5 average rating, 7 reviews

New! Oceanfront Penthouse/ 2 Decks/ Pool/Beach/Gym

MelisiaRating, 5 stars2 months ago
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.
Guest favourite
Home in Corolla
5 out of 5 average rating, 30 reviews

Aloha Beaches OBX

DavidRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Gloucester Point
4.99 out of 5 average rating, 183 reviews

York River Vacation Home

JulieRating, 5 stars1 week ago
Home and location were absolutely perfect! Exceeded our expectations, highly recommend! Would love to come back again.
Superhost
Home in Virginia Beach
4.86 out of 5 average rating, 134 reviews

Beach Home, Upscale Croatan Resort + Private Pool

DylanRating, 5 stars1 month ago
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
Top guest favourite
Apartment in Sandbridge
5 out of 5 average rating, 8 reviews

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym

KaylaRating, 5 stars2 weeks ago
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!
Top guest favourite
Home in Corolla
4.98 out of 5 average rating, 64 reviews

Carova beach home w/ ocean view, pool & hot tub!

KelleyRating, 5 stars2 weeks ago
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!
Superhost
Home in Sandbridge
4.85 out of 5 average rating, 48 reviews

Designer 7BR w/ Pool and Hot Tub. Pets welcome!

RobertRating, 5 stars1 week ago
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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