Mansion vacation rentals in Chesapeake

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Popular amenities for Chesapeake mansion rentals

Mansion rentals with a pool

Top guest favorite
A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.
Home in Gloucester Point
4.99 out of 5 average rating, 183 reviews

York River Vacation Home

JulieRating, 5 stars4 days ago
Home and location were absolutely perfect! Exceeded our expectations, highly recommend! Would love to come back again.
Top guest favorite
Cottage in Sandbridge
5 out of 5 average rating, 99 reviews

Sanctuary on Sandpiper - Bayfront in Sandbridge

DavidRating, 5 stars4 weeks ago
We loved our stay! This house exceed our expectations and was exactly what we needed for a nice relaxing long weekend in Sandbridge! The house was clean and full of all the amenities we could have needed. The outdoor space was the perfect place to hang out and when we wanted to go to the beach it was only a few blocks away! Christina's communication was excellent throughout the entire booking processing and our stay, she went above and beyond to make sure we had everything we needed. Would definitely stay here again the next time we are in Sandbridge!
Guest favorite
The image showcases a bayfront retreat with a spacious outdoor area featuring a private pool surrounded by lounge chairs. A wooden deck extends into the water, providing access to the private dock. Lush landscaping and trees frame the view, with a two-story house in the background.
Home in Sandbridge
4.93 out of 5 average rating, 14 reviews

New! Boat Dock /Pool /HotTub/ Waterfront/ Beach

Keya Rating, 5 stars3 weeks ago
I had a fantastic experience staying at Sandbridge Stay. The property was exactly as described—clean, cozy, and well-equipped with everything I needed. The location was perfect, close to beach, but still quiet and peaceful for a good night’s rest.
Top guest favorite
An aerial view of a beach cottage reveals its elevated structure surrounded by natural foliage. A swimming pool is visible on the right, while a spacious deck with hammocks provides an inviting outdoor space. The cottage features a light green exterior with white accents.
Home in Corolla
5 out of 5 average rating, 19 reviews

Splash of Lime Carova 4x4 Beach Cottage

MichaelaRating, 5 stars2 weeks ago
We absolutely loved A Splash of Lime! The house was great for us and our 2 dogs! The kitchen had everything we could have asked for. The pool and hot tub were also a huge plus. Easy walk to the beach and you may even pass a few wild horses on the way! Thank you, Martin, for an excellent vacation home!
Superhost
Home in Virginia Beach
4.86 out of 5 average rating, 134 reviews

Beach Home, Upscale Croatan Resort + Private Pool

DylanRating, 5 stars4 weeks 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 favorite
A spacious balcony features several blue adirondack chairs, offering a view of the surrounding buildings and the outdoor area. Clear skies with a few clouds create a bright atmosphere. The ocean is visible in the distance, providing a scenic backdrop.
Condo in Sandbridge
5 out of 5 average rating, 7 reviews

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

ChristopherRating, 5 stars3 weeks ago
If there was such thing as a super-duper host, Cheryl hits the mark. Her condo was meticulous and clean. She was lucid with her communications and quick to respond. This condo has an awesome view and the balcony had plenty of seating to enjoy with others. We want to thank Cheryl for making our stay a very memorable one. She is a ROCK STAR!!!
Top guest favorite
A private pool is surrounded by a wooden fence, with sun loungers positioned nearby. The pool water is a clear turquoise, inviting relaxation amidst a backdrop of lush greenery and trees, providing a serene outdoor oasis.
Home in Corolla
4.96 out of 5 average rating, 265 reviews

Spotless Treehouse | Pool | HotTub | Pickle | Pets

KyleRating, 5 stars3 weeks ago
Host was very responsive and polite to my questions. It was my first time getting an Airbnb and he was very polite in providing his requirements to make my stay work out. The house itself was very pretty and had all the amenities that were listed. Everything was nicely marked and showed where everything went. Walkable distance to the beach and the pool and hot tub were great. For my first stay, the communication and check-in/check-out process were very easy. And thank you to the host for letting my first Airbnb experience be so amazing and easy.
Superhost
A vibrant outdoor space features a private saltwater pool surrounded by lounge chairs and umbrellas. An orange daybed sits next to the water, while a colorful mural with the text 'SANDBRIDGE, VA' adds a cheerful touch to the backdrop.
Home in Sandbridge
4.85 out of 5 average rating, 48 reviews

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

RobertRating, 5 stars2 days 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.

Luxury mansion rentals

Guest favorite
Home in Hampton
4.95 out of 5 average rating, 120 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 favorite
Home in Virginia Beach
4.98 out of 5 average rating, 54 reviews

Serene Beach Retreat - Just Steps from the Sand!

TerriRating, 5 stars2 weeks ago
We loved our stay at Yun's place. The space was perfect for our group and very comfortable from the beds to the living room chairs and couches! I loved the soaking tub in my room and the fact that everything was spotless. There were plenty of pots and pans and proper utensils in the kitchen, which made cooking a breeze. We loved the location being one short block from the beach and boardwalk! We will definitely be staying at this property again in the future.
Superhost
A bathroom space showcases a freestanding white bathtub on a patterned area rug. Adjacent is a glass-enclosed shower with a modern design. Natural light filters in through a high window, illuminating soft blue walls and a clean, tiled floor.
Home in East Ocean View
4.84 out of 5 average rating, 169 reviews

Your family beach house

EvangelinaRating, 5 stars2 weeks ago
Xiaoming's home was amazing. There was plenty of space and so much to do there. I was so impressed with how close the beach was and also VA Beach/boardwalk. Xiaoming was amazing with communication and she let us check in early too. The home is beautiful! I'm going to miss the master bedroom porch. You will not be disappointed staying here!
Top guest favorite
A waterfront view of the multi-story beach house perched on stilts above the shore. The structure features a charming blue exterior, large windows, and multiple balcony spaces furnished with blue chairs. Waves can be seen lapping at the base, emphasizing the home's coastal setting.
Home in Buckroe Beach
4.99 out of 5 average rating, 86 reviews

Beachfront 2 Dwellings EV charger

WaqasRating, 5 stars2 weeks ago
This was our second time staying at Gina's place and our time there was amazing as always. This home has everything you could possibly need and the views are absolutely beautiful! We will definitely be back next year.
Guest favorite
Home in Virginia Beach
5 out of 5 average rating, 72 reviews

*NEW* Spacious/Standalone 4BR Beach House

PhillipRating, 5 stars1 week ago
Great place to stay, had everything we needed.
Guest favorite
Home in Virginia Beach
4.98 out of 5 average rating, 44 reviews

In the Heart of Virginia Beach perfect for groups!

JeanneRating, 5 stars3 weeks ago
Beautiful home in great location. Very spacious for a group of 6 adults. The living spaces were perfect for meals and socializing. Everything we could possibly need was provided in the house. The home was spotless. Traci was a wonderful host and always available for any questions
Guest favorite
A sandy pathway leads to the beach, flanked by wooden fences and vegetation. The beach is visible in the distance, marked by a small wooden structure. Bright blue skies and a few wispy clouds provide a clear backdrop.
Home in Sandbridge
4.93 out of 5 average rating, 43 reviews

Open house with Ocean views!

CateRating, 5 stars1 day 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!
Top guest favorite
Home in East Ocean View
4.97 out of 5 average rating, 62 reviews

Pet Friendly! Newly Built! 1 Block to the Beach!

DezareaRating, 5 stars1 week ago
We had a great time staying here for my sister’s homecoming from deployment. Our family of 7 adults and 1 toddler had a great time and were comfortable in our own spaces while still being able to enjoy each others company in the common areas

Pet-friendly mansion rentals

Superhost
The entryway reveals a cozy living room featuring a gray sectional sofa and a navy blue armchair. A circular coffee table sits in the center, complemented by a softly glowing lamp. Light streaming from the room enhances the inviting atmosphere.
Townhouse in Chic's Beach
4.71 out of 5 average rating, 100 reviews

Wheelchair Accessible Beach Home in Chicks Beach.

AmyRating, 5 stars3 weeks ago
Great roomy home just a short walk to the bay. A big kitchen table for meals and family games. We loved this gem!
Guest favorite
The exterior showcases a three-story house with a large front staircase flanked by a landscaped yard. Two spacious balconies with white railings provide outdoor seating. The structure features a light color palette, with multiple windows and a front door framed by large glass panels.
Home in East Ocean View
4.89 out of 5 average rating, 142 reviews

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

VimarisRating, 5 stars2 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
An open living area is featured, illuminated by sunlight filtering through numerous windows. A spacious sectional sofa and armchair are positioned near a television. A dining table with white chairs is adorned with a blue vase containing pink flowers, enhancing the inviting ambiance.
Home in Norfolk
4.9 out of 5 average rating, 39 reviews

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

MarianneRating, 5 stars3 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
A modern kitchen features a large island with four leather bar stools, white cabinetry, and stainless steel appliances. Natural light streams through windows, enhancing the open layout that connects to the living area beyond.
Home in Virginia Beach
4.8 out of 5 average rating, 41 reviews

Movie Room + EV Charging Plug! Small Dogs Welcome!

KristaRating, 5 stars1 week ago
Shemash was great to communicate with - and his home was just as described and worked great for us!
Guest favorite
The exterior features a two-story beach house with a light blue facade and white trim. A spacious porch with white railings and dark chairs offers a welcoming entry. Landscaping includes a neatly manicured yard and pathway leading to the front door.
Home in Virginia Beach
4.91 out of 5 average rating, 22 reviews

Coastal Retreat! 6min Walk to Beach. NEW!

CandaceRating, 5 stars1 month ago
We spent a week here for Easter and it was perfect for our large family including children and dogs. Great location close to the beach! Very clean and comfortable! The driveway is small but nothing to worry about unless you drive a giant vehicle.
Guest favorite
A spacious game room features a modern, dark leather sectional couch and a foosball table. A crystalline chandelier hangs from the ceiling, and large windows allow natural light to enhance the space. Colorful play items and an easel are visible in the background.
Home in Norfolk
4.89 out of 5 average rating, 44 reviews

4 Beds + Game Room + Family & Dog Friendly!

JakeRating, 5 stars2 weeks ago
Absolutely loved the house. Clean and roomy. Thank you for letting us stay in your beautiful home!
Superhost
A serene backyard space features a wooden pergola overhead, providing shade and a relaxing seating area. Brightly colored adirondack chairs encircle a stone patio, with a well-maintained lawn extending beyond. A nearby shed adds a touch of charm to the outdoor setting.
Home in Virginia Beach
4.83 out of 5 average rating, 163 reviews

Relaxation Station at Old Beach

NatalieRating, 5 stars1 week ago
Lovely,spacious home with private back entrance. Walking distance to everything you’d want to do while at the beach. Would stay again!
Top guest favorite
The modern kitchen features light gray cabinetry and stainless steel appliances. A large center island with bar seating is accented by blue upholstered stools. A dining table with beige chairs is set for a meal, complemented by decorative tableware and floral arrangements.
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! ❤️❤️❤️

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