Mansion holiday rentals in Chesapeake

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Popular amenities for Chesapeake mansion rentals

Luxury mansion rentals

Guest favourite
Home in East Ocean View
4.88 out of 5 average rating, 78 reviews

Perfect Beach Home w/ Ocean Views! Sleeps 10!

JesilleRating, 5 stars2 weeks ago
We had an amazing stay at Brad’s Norfolk beach house! The views were stunning, and the house was huge, spotless and super comfortable. The beach was clean and perfect for walks with our Golden Doodle, who loved it just as much as we did! We had a blast and can't wait to come back. Highly recommend!
Superhost
Home in East Ocean View
4.95 out of 5 average rating, 42 reviews

5 BR Walk to Beach! Great for Families!

LisaRating, 5 stars1 week ago
The home is very nicely furnished with beautiful decorations and space for all. We had six adults who enjoyed being able to cook, eat and visit in the open floor plan. The back porch and deck are close to neighbors but decorated nicely with a grill and activities. Close walk to the beach.
Guest favourite
Home in Virginia Beach
4.96 out of 5 average rating, 56 reviews

Coastal Living Marina & Beach House

MikeRating, 5 stars7 months ago
Brandon was an awesome host. The location is amazing. Really was great to walk to any nice restaurant, but you weren't located on the main street. Better than I could have imagined.
Superhost
Home in Sandbridge
4.84 out of 5 average rating, 125 reviews

Stunning Views of Back Bay & Seconds to the Beach

SigridRating, 5 stars1 month ago
Great place for families walking distance from the beach. I’ll love to visit in the summer when we can enjoy the beach and everything Virginia Beach has to offer.
Superhost
Condo in Williamsburg
5 out of 5 average rating, 3 reviews

6BDR Williamsburg, VA Resort

KevinRating, 5 stars6 months ago
Great place. Felt at home. Very quiet and peaceful after a long day at the park. Would come back again.
Top Guest favourite
Home in Williamsburg
4.97 out of 5 average rating, 39 reviews

Sleeps 12 • 3.9 Miles to Colonial Williamsburg

Matthew Rating, 5 stars1 month ago
Really big house decorated with very cool antiques. Plenty of room and everything you need to feel at home. The host is amazing so helpful and is prepared for your situation. Highly recommend this country mansion style house.
Superhost
Condo in Sandbridge
4.9 out of 5 average rating, 40 reviews

Waterfront 2 Story Penthouse! 4Bd/3Bth

TiajahRating, 5 stars2 weeks ago
My fiancé and I hosted our engagement party over the weekend and this property made it completely possible! It was clean, extremely spacious, and right next to the beach. We even got to top our stay off with dolphin watching! There were about 15 dolphins close to shore giving us a free show! Overall, our stay was awesome. We couldn’t have asked for anything better.
Guest favourite
Home in Corolla
5 out of 5 average rating, 14 reviews

Saltwater Pool, Outdoor Bar, & 5 Min Walk to Beach

FrankRating, 5 stars7 months ago
Beautiful spot in the Outer Banks! Nice access to the beach and extremely peaceful location.

Pet-friendly mansion rentals

Guest favourite
Home in Portsmouth
4.94 out of 5 average rating, 108 reviews

Wooded Wonderland Miniature Golf Hot tub Pool

JustinRating, 5 stars1 week ago
We rented this property to visit the Virginia Tattoo and the beach and had a great trip!
Guest favourite
Home in East Ocean View
4.97 out of 5 average rating, 98 reviews

PETS Welcome! 4Bed Beach View Privately Managed

AimeeRating, 5 stars1 month ago
Matt's home is beautiful, comfortable and very clean. There was a lot of attention paid to our needs such as laundry detergent, garbage bags, etc. The house was well supplied with the necessities to cook, plenty of towels for both bath and beach, and working appliances....we felt very much at home. We were visiting our daughter who goes to a college nearby, and she took advantage of staying with us and commented on how comfortable the bed was. We look forward to staying at Matt's home again.
Guest favourite
Home in East Ocean View
4.9 out of 5 average rating, 138 reviews

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

AshleyRating, 5 stars2 weeks ago
Space was perfect for us staying as a family of 6. Bedrooms were great and the home offered plenty of space throughout. Awesome backyard, although we did not really use - very close beach access. Had all the amenities we needed for a long weekend!
Guest favourite
Home in East Ocean View
4.95 out of 5 average rating, 77 reviews

Short Walk to Beach + Pool Table + Pets OK!

KarlaRating, 5 stars1 week ago
We enjoyed our time there few days thank you for letting us stay at your place i love the location and the back yard was great. My one and only complaint was there was not enough TVs. But other than that all was good.
Superhost
Home in Cape Charles
4.74 out of 5 average rating, 19 reviews

Spacious, Renovated, *Pet-friendly in Historic CC

ShawnRating, 5 stars5 months ago
Had a group stay here and it was great, will stay again
Superhost
Home in Corolla
4.83 out of 5 average rating, 48 reviews

The Moor House

MeganRating, 5 stars7 months ago
This home is an absolutely FANTASTIC getaway location! My family enjoyed every moment of our vacation. The house was as pictured and as described and then more. It is a quick ride back to the water where we spent most our day. We would finish each day with a dip in the pool and hot tub. The back yard view is fantastic as well. My kids spent so much time fishing off the dock on the canal catching crabs, and white perch fish. We loved all the horse views at all random times of the day. I could go on, and on! The hosts were very responsive to all my questions and so accommodating. I would give this home 10 stars if I could!
Guest favourite
Home in Hampton
4.84 out of 5 average rating, 356 reviews

Family Holiday House. Events and Beaches Nearby

AllisonRating, 5 stars1 week ago
This place was amazing! We gathered for a 70th birthday dinner and there was plenty of room for everyone. The screened in patio was the perfect place to gather, have lots of laughs and make lots of memories. Thank you Jackie! Looking forward to next time!
Guest favourite
Cottage in Corolla
4.88 out of 5 average rating, 189 reviews

Quaint Beach Cottage in 4WD-OBX

RobynRating, 5 stars6 months ago
We stayed in the off season, and the houses nearby were unoccupied. It was wonderfully quiet and peaceful. The house was perfect and Kimberly was very friendly and communicative. We’ll definitely rent this house again!

Mansion rentals with a pool

Guest favourite
Home in Sandbridge
4.99 out of 5 average rating, 70 reviews

The Golden Hour Pool is Open!

AshleyRating, 5 stars7 months ago
We really enjoyed staying at the golden hour! The hosts were very responsive and helpful! They had sound machines in every bedroom which if you have kids is a big deal. The toys and kids activities there were a big hit! The pools are pristine and the whole outdoor area is very nice! Very short walk to beach which was also convenient! They literally thought of everything, if you forgot something chances are they had it! Definitely recommend staying here if you have children and want a nice low key place to stay!
Guest favourite
Home in Corolla
4.91 out of 5 average rating, 22 reviews

LUX Oceanview•Heated Pool•2-Min Walk to Beach

BridgetRating, 5 stars1 week ago
This was a beautiful place with lots of room. The host was super responsive to any questions and also offered up local adventures to enjoy. House was clean and in great shape. I would recommend this vacation home to anyone and would use again. The kitchen was stocked perfect with all plates and cookware you need to host meals for a large family
Top Guest favourite
Home in Gloucester Point
4.99 out of 5 average rating, 178 reviews

York River Vacation Home

FlaviaRating, 5 stars3 weeks ago
Great house in a beautiful location. The space is spotless, very large and comfortable, well equipped and tastefully decorated. We’ll try to come back soon!
Superhost
Home in Corolla
4.83 out of 5 average rating, 35 reviews

N-2-Wishn, Corolla Light, NC- 5BR, 6BA,Water Views

Lee & GrantRating, 5 stars7 months ago
Booking a rare four-week stay came with added pressure to make the right choice. We absolutely did! Mark’s home is spacious and well appointed with a wonderfully functional layout. The sound access is incredible, and beach access is super convenient whether you’re taking a quick stroll or setting up for the day. Mark was a great host in addition to local rental management. We loved making the most of resort amenities and the home’s thoughtfully stocked outdoor items, especially the kayaks. This location in Corolla is a perfect balance of small-town vibes with great food and lots to do. We can’t wait to return!
Guest favourite
Home in Sandbridge
5 out of 5 average rating, 24 reviews

Pool, hot tub, walk to beach, family friendly home

JeromyRating, 5 stars1 month ago
The place had plenty of sleeping spaces which is what we needed it was a great stay. Communication went well and there was plenty to entertain everyone
Top Guest favourite
Home in Corolla
5 out of 5 average rating, 16 reviews

Splash of Lime Carova 4x4 Beach Cottage

Mindy StewartRating, 5 stars5 days ago
Martin’s place was BEAUTIFUL and SO clean! Very roomy and beautifully decorated with all the amazing attention to details! The wild horses that came to visit the property were so beautiful and fascinating to watch! I will absolutely be back and 1000% recommend Martin’s place! Martin was also an incredible host with his attentiveness and even talked me through driving on the beach since it was my very first time ever driving on sand… I was terrified lol But he was able to calm me down via the phone and I got there safe and sound with no issues! Awesome stay!! 😁
Superhost
Home in Corolla
4.69 out of 5 average rating, 13 reviews

Soundfront, Pool, Hot tub, Dog Friendly! Elevator

MattRating, 5 stars1 week ago
Place is great, the beautiful sunsets every evening the sitting outside on porches just watching listening to water. Great location, minutes from everything. The elevator spoiled us loading/unloading luggage and groceries. Natalie is quick to respond to any problems that might arise. Don’t hesitate to book this place will definitely be back.
Superhost
Home in Corolla
4.87 out of 5 average rating, 39 reviews

Private Pool, Close to the Beach and Spacious!

DylanRating, 5 stars2 weeks ago
Overall very nice stay at Stephanie's home. She was excellent at communication leading up to the visit and during the trip as well. Had everything we needed and the beds were really comfortable. The location is very close to the 4x4 entrance to Carova which was super convenient, and the main reason we stayed in this area. But it was also close to restaurants, walking distance to the beach, and lots of activities nearby. The house itself is spacious, and the pool and hot tub were great to have for kids and adults alike. The home is showing some signs of wear and tear (decks, furniture, floors, paint) but honestly that's to be expected in OBX homes. Salt and sun aren't kind to upkeep! Thanks again, will consider Stephanie's home for next trip.

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