
Beachfront holiday rentals in Chesapeake Beach
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Top-rated beachfront rentals in Chesapeake Beach
Guests agree: these beachfront homes are highly rated for location, cleanliness and more.
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Popular amenities for beachfront rentals in Chesapeake Beach
Pet-friendly beachfront home rentals

Villa Positano
We had an amazing time. The house was perfect for us. We really enjoyed the pool and short walk to the beach. We could hear the ocean from the master suite. The upstairs deck had view of the water. Everything about our stay was perfect. The area was nice and was quiet and peaceful. We will definitely go back and stay longer next year. Thank you!!!

3 bedroom private home a block from the beach!
I had a wonderful stay at Kate’s home, it was easily 3 minutes to the beach, she had all the needed cooking utensils and even more! And even had some bathroom essentials that was really appreciated

Beachfront Getaway, Pet Friendly, Mermaid Suite
What an amazing stay! I've never been satisfied with an Airbnb, the photos always are so much nicer than the reality - but Big Blue was actually even better than advertised! Merlyn's communication prior to arrival made things very easy. Accessing the unit was simple, and I felt safe with the self-locking doors. The unit was clean and so comfortable, with many personal touches - I instantly felt at home. I was overjoyed when I arrived and toured the unit. Really exceeded my expectations which was such a different feeling than all the other Airbnb I've rented over the years. The beach access was tidy and pretty, the gym and beach gear a nice touch, and the foot wash station was appreciated after my morning walks with the dog. I really can't say enough great things about my stay here. Hosts were friendly and helpful every step of the way. We mostly spent our time traveling around the area from VA Beach to OBX so I can't speak much about Norfolk/Ocean View. I would def rent Big Blue again.

August Suite | Beach | Balcony | Fire Pit
loved our stay. cozy home with everything you need and FANTASTIC host who meets all yours demands without hesitation.

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.

The Happy Place-Quiet, North End 1 block to ocean!
Our stay was fantastic! The location couldn't be better, just a stone's throw from the beach. The property itself was clean and well-stocked with everything we needed. Mary was prompt and helpful in addressing the one minor issue that came up. We highly recommend this spot for a worry-free beach getaway!

The Seaglass Cottage
Nancy was super kind and friendly during our stay! She gave a great seafood restaurant recommendation that was both delicious, affordable, and right down the road. The cottage is quaint and a charming place to stay for a young couple. We had plenty of space, and the cottage was accurately represented by the photos available. We would definitely stay here again if we are in the area!

Gorgeous Vacation House
The house was super clean when we got there, the temperature of the house was great the entire stay. The pool was certainly clean, but since we went early, June the water was a little bit cold, but it felt really nice and refreshing honestly. There were three beach chairs and a wagon there that were helpful for traveling to the beach. There were available cups plate, utensils, and all the necessities that you would need, they even had shampoo and conditioner bottles there for us. We weren’t aware that there was a code to get into the house so instructions for check-in were a little bit unclear, but all I had to do is message and they responded. Overall, I would recommend staying here because even though the area surrounding isn’t the nicest, I felt safe the entire time at that house!
Beachfront home rentals with a pool

Beautiful Beachfront Condo
My family and I had a great stay at Pam's condo. Condo had plenty of room for our family of 5 and had great views of the ocean from all rooms. The condo was very close to my favorite 2 VB restaurants (Waterman's and Chix on the Beach), which made it nice. I would recommend the trolley to go to the north side of VB as it's about a 2 mile walk from the condo. Great place though and highly recommend Pam's condo.

THE OLD BEACON 1 | Beach Living
Beautiful home within walking distance to everything you need, especially the beach and restaurants. Clean home with cozy feel. My son never wanted to leave the beautiful pool at the property. Would recommended to families!!

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!!!

Ocean & Bay Views - Local Family Owned & Operated
We had a lovely stay at Crystal’s while in town for a graduation. Crystal was proactive with directions, recommendations, and instructions, and she responded quickly to questions. The place was nicely decorated, and well-stocked with kitchen gadgets, beach chairs, games, and other necessities. This is a nice place for a getaway.

VA Beach Oceanfront Studio, Beach, Boardwalk, Pool
Great location, right on the beach. The place was clean and had everything I needed for my stay. Josh and Maegan were very detailed in their instruction I didn’t have to reach out to them for anything.

Oceanfront, beachfront, boardwalk, fun, dolphins
We enjoyed staying at Kelly's place in VB. Its an ideal location for anyone who wants to stay right at the boardwalk. We witnessed amazing sunrises and moonrises. The ocean was right in front of us and from the 6th floor, the view was expansive. A lot of restaurants were also nearby. Kelly was always very communicative, polite and professional. The apartment was clean with the kitchen well stocked with utensils The bedrooms were of a pretty large size. And parking was on the premises. Overall, it was a wonderful experience and holiday for us. We strongly recommend Kelly's place.

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

Salida del Sol, North End Beach
The best spot. Super nice amenities and very clean, great location, right across the street from beach access.
Private beachfront home rentals

The Canary Island … Keep Calm and Fish On
We made wonderful memories at this beautiful place. Would definitely recommend!

North End Beach Cottage Apt - One Block from Beach
Our stay here was fantastic! Very close to the beach which you can walk to, and only a short drive away from the waterfront that has great restaurants and lots to do! The place itself was clean, quiet and the perfect size for 2 people. If you’re looking for something with great amenities for the size, and in a great location this is it!

~Summer Fun~ at "Family Retreat by the Beach"
My family really enjoyed our stay. The home was very clean, beautiful and well stocked with snacks are treats! We received great communication from check in to check out. The location was right across the street from the beach and my grandkids absolutely loved it! We will definitely stay here again😎

Modern 4br beach house - Norfolk
Beautiful home close to the beach with walkable restaurants/ coffee shops/ brewery/ farmers market/ Chesapeake bay. We particularly preferred the bay for calmer waters as we have young children. Beautiful spacious home. Huge fenced in yard. Convenient side spigot for rinsing fear post beach. Helpful responsive hosts. Thanks for having us!!

Beach Bungalow on the Boardwalk
Beautiful home! Very close to the beach and boardwalk. Overall we had a pleasant stay!

The Inlet: Quiet Neighborhood 3 Blocks to Beach
We had a great stay here. Comfortable, clean, close to the beach. Check-in and check-out were easy. Would definitely stay here again!

2 Bedroom w/ King Beds walk to beach - top floor 7
We absolutely loved our stay! We we're here for almost a month. I brought quite a few things I thought we would need, but in reality, we didn't need much of anything! They thought of pretty much everything. The only thing I wish I would've brought for this longer stay was my personal blender because I use it daily. Being steps away from the beach was an added bonus, too! The apartment looks exactly like the pictures! I felt safe here and our vehicles were safe as well. The cameras on the property made me feel safe, too. Pip is an amazing host! Very responsive and incredibly helpful. I would stay here again in heartbeat!

Fully Renovated Sunset House
Christina is a wonderful host and has a lovely home, their home was well stocked with all sorts of supplies. It's been a while since I stayed at rental that was this clean and well updated. their towels and linens are very clean as if brand new, and no mildew smell on the towels, for me that's a big plus. She always responded quickly whenever we reached out. The garage was spotless and what a bonus that they provided beach towels, umbrellas, beach cart etc. thank you Christina, your attention to detail shows and we appreciated your hard work and enjoyed our stay. thanks, Mona
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- Chesapeake Bay
- 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