
Beachfront vacation rentals in Chesapeake
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Top-rated beachfront rentals in Chesapeake
Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.
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Popular amenities for Chesapeake beachfront rentals
Beachfront home rentals with a pool

Positano Villa
Roger’s beach house was charming. It was an older-style home with many modern updates. Quick and easy walking path to the beach. The pool in the backyard was lovely. It was a little dirty upon arriving and Roger came right over and got it all cleaned up for us during our stay. The neighborhood was a little rough we did have a few uncomfortable encounters with homeless people being two girls alone it was a little unsettling. Overall, I would definitely come back again. The weather was absolutely beautiful for our stay.

NEW! Oceanfront / Sunset Bay, 3 Bd / Pool
What a great getaway! I brought two other moms. We had three children under 12 and the beaches are pristine. Home was exactly as described and very clean and it was just a lovely time. I highly recommend this unit and the location.

Breathtaking Ocean views at Pinch Me, 8bdrm, 6bath
Beautiful home in a wonderful location. Tanya was very friendly and communicative throughout the process.

Paradise at the Beach
Great location for walking to the beach and many restaurant options. The beds are comfy and the living room has good seating options (unlike rentals that have only one couch). Kat was very responsive and attentive to our requests. She was great. FYI, Chicos has good pizza and fun atmosphere, Pocahontas Pancakes has great breakfast options and seems to be very popular there. The Shack is a cool outdoor bar. The Irish Pub had live music and fun atmosphere. We would rent again from Kat.

Stunning Views of Back Bay & Seconds to the Beach
What a beautiful and serene space for a women’s retreat! It is very obvious that the home is very well loved as well as very special. We all discussed coming back again because we enjoyed the space, the comfort and the scenery very much. We thoroughly enjoyed the great blue heron right outside the window each day as well as breathtaking sunsets. It was hard to get back to the grind after such a beautiful sanctuary weekend away.

Beach House with breathtaking sunsets
Rodica’s house was as advertised and a great place to spend a long weekend. I would love to come back in the summer when it’s a little warmer and enjoy the pool. We loved sitting in the back deck watching the sunsets and had great weather.

Sandbridge- Great Escape Saltwater Pool &Boat Ramp
We enjoyed our stay at The Great Escape! Most of our time was spent in the private pool and fishing from the yard into the canal. The walk to the beach was quick and easy. We loved how quiet and safe the neighborhood was. The house had all the amenities we needed- it felt like a home away from home. Kim was a great host supplying us with lots of recommendations and was quick to resolve any problems. We hope to visit again in the future!

Pool, hot tub, walk to beach, family friendly home
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
Beachfront home rentals with a hot tub

Tranquility with Hot Tub! 5 min walk to beach
We thoroughly enjoyed our stay Jan 29-Mar2 at Tranquility with Hot Tub. It was so bright and airy. Everything was super clean and there were plenty of towels and hangers. The king size bed was so comfortable and since we were there a month we washed the sheets & put them back on when we did laundry. Soaps were provided for the washer, dishwasher, and kitchen sink. Dimitri was very thoughtful in running an extremely long extension cord out to the parking area since he knew we had an EV! He also had the walk/steps & drivers side of the car shoveled after the 10.5” snow storm & salt applied. Due to the cold weather we didn’t make use of the deck but that would be a lovely place to have morning coffee or grill out although not private from the neighbors view. We highly recommend staying here & will definitely rent here again when visiting our daughter’s family!

Stylish Beach House, Hot Tub, Pet Friendly
The walk to the beach was so quick and easy. We traveled with two kids 5 and 8 and the walk back and forth had zero complaints :). Kids loved the hot tub and the super cool shower on the first floor. The decor of the home was beautiful. The beach had a magical low tide for kids to play in and the locals were supper friendly. The house is right up on the highway so at night it’s pretty noisy. We just cranked up our white noise machines and on the second night no one noticed. Thank you for opening up your home and letting us create some more great memories.

Boardwalk Resort & Villas - 1BR/1BA - Oceanfront!
We stayed a week at Kerri’s place in Virginia. She went above and beyond our expectations, very communicative and organized. She offered a ton of information and insights before and during our stay. Her place offers a delightful and relaxing getaway experience. The resort's picturesque location by the ocean provides stunning views and a serene atmosphere. The rooms are spacious, well-appointed, and comfortable, ensuring a pleasant stay. The resort amenities such as the pool, spa, and on-site restaurants add to the overall wonderful experience. The staff is friendly, accommodating, and dedicated to providing top-notch service to guests. Whether you're looking to relax by the beach or explore the nearby attractions, Boardwalk Resort is a fantastic choice for a vacation in Virginia. I would definitely recommend and revisit Kerri’s place.

Exclusive Beachfront Home w/ 180° Views & Hot Tub!
Kiána was super responsive and very kind! So thankful she helped us out last minute too! Anything we needed she was there to help! Hail to the redskins!!

Milk 'N' Honey at the 4X4 Carova Beach
Absolutely loved the home and the whole experience! Our only issue was in our arrival and not being aware that high tide would impact when you should attempt getting to the house. More information regarding the tide schedule and if the roads within the houses are accessible would be very helpful. Recommendation to stop at the grocery store before you each the beach access road and what types of things are not supplied at the house would be good, too. Overall we were so very pleased with our stay and Misty was great when we needed her. I would absolutely recommend this house to my friends and family and would love to visit again!

Star of Sandbridge
House was perfect for our group. Plenty of space to hang out inside and out. Everything was as described and there were no issues checking in or out. Would stay again if in the area.

Ocean Sands Resort 1 bedroom Oceanfront Balcony!
Everything went as smooth as expected. It was clean centrally, located, and easy to find . We have already discussed going back in the future. Jessica was friendly and easy to contact when needed, and very responsive. At this location, the staff was amazing. Desmond works at the front desk and gave us an amazing suggestion for dinner and Quinn also works at the front gave me a suggestion for breakfast. Both were amazing and we ended up eating dinner at the restaurant five nights while we were there I believe it was called 21st Street Seafood Company.

Beach Quarters Resort - The Presidential Suite 2
We really enjoyed our stay! The accommodations were perfect for our family of 5. Gorgeous views. The staff were very helpful and responsive.
Pet-friendly beachfront home rentals

Water Oaks at Chic's Beach
I could not recommend this place and these hosts enough! The place was warm and welcoming and I absolutely love the location. A very peaceful neighborhood with easy bay access. The hosts were amazing and responsive. The house had some maintenance problems but at no fault of theirs…just typical house problems and they handled everything extremely well and we were not inconvenienced at all! Also our dog loved the place and they were stocked will all the dog necessities which was very helpful!

Cozy beach cottage! One block to the beach!
We stayed at the cozy beach cottage for a "girls trip" for three busy moms looking for a peaceful retreat for the weekend. The house was just as described - cute, clean, and cozy. We appreciated Kenzi's attention to detail and clear instructions, as well as local restaurant recommendations. This house is one block from the ocean; an easy stroll to watch the sunset from beach. We appreciate that the house had everything we needed and required no tasks for checkout. Thank you Kenzi for allowing us a weekend of rest and relaxation!

Beach Bungalow - 1 Block to Beach - Pets Welcome!
Absolutely loved this spot! The theming was adorable for a beach weekend and the location was perfect - just steps from the beach! Would definitely stay here again

Beachfront Getaway, pet friendly
Our family enjoyed our weekend at Big Blue. It was special because it was my wife's birthday and there was plenty of family with us. We really liked how the 2nd and 3rd floor are duplicates of each other. It's like 2 different apartments , but we had access to both. The kids on the 2nd floor and the adults on the 3rd. Very clean open spaces. The host were responsive and proactive. We hope to make the Willoughby Spit area a regular vacation spot, very lovely.

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

Quiet East Beach Bungalow, 1 block to beach!
A+++ From the front door to the sand is only a football field away! New and pristine house. Host is incredibly responsive. Peaceful and clean beach. Close to shopping and VA beach boardwalk is only 20 minutes. Highly recommended.

Lovely Ocean View Cottage
We had such an enjoyable trip staying at this perfect cottage. The location was amazing-short walk to a tranquil beach that felt like our own little escape. The landscaping and yard were beautiful! The place felt like a peaceful retreat. The cottage itself was cozy, clean, and had everything we needed even a thoughtful welcome basket. It truly was the perfect getaway and just what we needed to recharge. Highly recommend!

Your family beach house
Prefect place and everything we needed. Host couldn’t have been more helpful
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- Virginia Beach Oceanfront
- Carova Beach
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- Chrysler Museum of Art
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