
Waterfront holiday rentals in Chesapeake
Find and book unique waterfront rentals on Airbnb
Top-rated waterfront rentals in Chesapeake
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for waterfront rentals in Chesapeake
Waterfront apartment rentals

Knot One - Balcony View of ICW! - Dog Friendly!
We loved watching the boats in the canal. The room was clean, and quiet. Gia was quick to respond to questions. We would stay again if we are in the area.

Serene Tree House Retreat | Spacious 1br/1bth Home
Everything was great and just as described in the listing.

Better at the Bay
We loved our stay at Karen’s place. The apartment is very comfortable, and the views are spectacular. I wish we had more time to enjoy the offerings. We hope to come back again!

Comfy 1BR w pond view Kingsmill
Great place to stay away from lots of people. Super quiet and neat.

Yorktown on the Waterfront
Anne's place was just spectacular! Perfect for 2 couples as our home-base to explore Williamsburg, Yorktown and Jamestown. The high end furnishings are beautiful. The patio, yard and lake view were wonderful. We enjoyed the theater room each night. Thank you for a great vacation.

The Coastal Studio
Great location with shops and restaurants and the lighthouse within minutes. Beautiful view of the water and sunsets. Perfect for a getaway for two!

Sandbridge Beach Bay Getaway
We loved our stay at Jule’s place. She was incredibly helpful with local recommendations and perfect communication. Her spot was well located for our visit to False Cape State Park. Would absolutely stay here again!

Tree Top Beach Bungalow 3 1/2 blocks fr beach
Cute, clean, and cozy place! Hosts were extremely accommodating. The location is close to the beach but tucked away in a not-so-busy neighborhood, so you can walk to destinations while still having a private and quiet location. Would definitely recommend!
Waterfront house rentals

Steps to Beach at Chics Beach! Sleeps 12 & Garage!
We had a wonderful time and the accommodations were superb! Our hosts were very responsive and willing to assist at a moments notice. The refrigerator stopped working (not very old) and they sent someone within hours and made sure there was refrigeration until the refrigerator could be replaced! I wouldn’t hesitate to stay here in the future. It was a wonderful experience!

PETS Welcome! 4Bed Beach View Privately Managed
Matthew’s home was beautiful and comfortable. As a group of 8 we were a little worried about space. But this spot was perfect!! Walkable distance to the beach in a quiet area. And we had plenty of room both inside and out.

*Semi-Priv Beach*King Bed* Waterfront*EV Charger
Unassuming Exterior, Total Sanctuary Inside From the outside, you’d never guess how special this place is—but the moment you walk in, it feels like a hidden retreat. The space is beautifully designed with a peaceful, minimal aesthetic and full of thoughtful details. Everything was spotless, cozy, and curated for relaxation. What truly stood out were the calming, beautiful views—they added an extra layer of tranquility that made us want to stay longer. Whether sipping coffee in the morning or unwinding at night, the scenery was pure serenity. This is the kind of place that invites you to slow down, exhale, and really enjoy the moment. We’d come back in a heartbeat.

Exclusive Beachfront Home w/ 180° Views & Hot Tub!
I could not wait to write a review about our stay. So much so that we are not even home yet. We had a glorious week at Bay Bliss! Bliss is the perfect description. Anywhere in this beautiful home you can hear the waves of the ocean. There was nothing better than listening to that while falling asleep on the comfiest bed in the master bedroom. Hosts were extremely responsive, helpful with local recommendations and extremely friendly. I have stayed at lot of AirBnb’s and hotels. Honestly, I have never felt so at home and I felt that way from the second I walked in the door. We will definitely be back.

Play by the Bay 1 MIN TO WATER
This spot was everything we needed and more. The hosts are kind and accommodating, really made us feel at home from the jump. The place itself? Even better than the pictures. Clean, cozy, and had that good energy you hope for when you’re staying somewhere new. It honestly felt like a home away from home. Would 100% stay here again without thinking twice. Big thanks to the hosts for making it such a smooth and comfortable experience for my family.

Chesapeake Bay Beach house (Chic’s Beach) 1 block!
This place was perfect for the kids and parents and grandparents. We enjoyed our stay here walking distance to the beach was perfection. It was so peaceful, clean and spacious. We enjoyed the downstairs yard & patio area. We didn’t get to use the bbq grill but next time we stay here we will. Beautiful home. Thank you

Quaint and Comfortable Buckroe Beach Getaway.
We chose this property for a weekend event at the beach my daughter was involved in. It was the perfect location. Easy to get to and from the beach. We probably could have walked it but didn’t. The house is spotless and has everything you might need. My kids loved the snacks that were set out for us and the bunk beds. Unfortunately we did not get to spend much time in the yard but it has a great fire pit area and outdoor dining area. A great little place. I would definitely stay again.

YES Queen! The Bridgerton House
5 Stars – A Truly Magical Stay! This home was an absolute gem! The hosts were incredibly responsive and kind, making everything from check-in to check-out seamless. The yard was stunning—bursting with colorful flowers, wildlife, and peaceful lake views that made it feel like a private retreat. Inside, the house was spotless, thoughtfully organized, and stocked with everything one could possibly need to feel completely at home. The décor was absolutely beautiful, with an eye for detail that created such a warm, welcoming atmosphere. I would return in a heartbeat—highly recommend!
Waterfront apartment rentals

Bay Breeze At Ocean View Beach Home
Gorgeous ocean views, great location, the balcony was the favorite spot the entire stay! Comfortable furniture, nice little cozy condo! Highly recommend the stay if you’re in the area!

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.

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.

Oceanfront Gem VaB Studio Exceptional Views
This was our second time staying at one of Rebecca and Sean’s VA Beach condos — and the experience did not disappoint! This is just a perfect location, at the very end of the Boardwalk, with a private grassy lawn and outdoor seating just for the condo residents. Lots of restaurants in the surrounding blocks. Our favorite thing is the view — you look right out onto the ocean from the patio, and you can see the beach and the sunrise from the comfortable bed each morning. We spent unhurried hours sitting on the patio in the evenings enjoying the sound of lapping waves and the night sky. This cozy studio was just right for the two of us. Highly recommend. I’ve no doubt we’ll stay there again in the future!

Paradise at the Beach
I cannot say enough positive things about our stay at Kattia's home. My teenage daughter and I were there for the weekend, as she was participating in a volleyball tournament. Kattia provided very clear instructions on how to access the building, obtain the parking pass, etc. I felt comfortable knowing that we were staying in a building with a secure access code. Kattia also customized our door code to one that we would remember for ease! As soon as we walked in we were greeted by a message from Kattia welcoming us and wishing us luck at the tournament- so thoughtful! The kitchen had all of the amenities that we could possibly need, the bathrooms were clean, everything was labeled, and we watched a movie on what we considered a "big-screen TV"! The location is walkable to stores, restaurants and the beach, and Kattia provided recommendations and was communicative during the entire stay. Kattia is a lovely host who seemed genuinely invested in us having a pleasant stay, and we did!

Oceanfront, beach, boardwalk, fun, dolphin, sunris
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.

Luxury Riverfront Condo w/ sunrise & sunset views
The condo was very clean with all necessary essentials. We loved sitting on the porch watching the wildlife, especially the numerous ospreys. It is centrally located, only a short drive to historic Williamsburg, Jamestown and Yorktown. Plan for about a day at each to fully enjoy everything. The grounds of the resort are lovely and a great place to walk or ride bikes. Rodica was very easy to communicate with and was most helpful with all checking instructions, especially with our late arrival. We would definitely like to return.

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym
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!
Quick stats about waterfront rentals in Chesapeake
Total rentals
70 properties
Nightly prices starting at
₹2,585 before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
Destinations to explore
- Virginia Beach Holiday rentals
- Williamsburg Holiday rentals
- Richmond Holiday rentals
- Shanghai Holiday rentals
- Myrtle Beach Holiday rentals
- Charlotte Holiday rentals
- Outer Banks Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Jersey Shore Holiday rentals
- New York Holiday rentals
- Rentals with lake access Chesapeake
- Rentals with beach access Chesapeake
- Mansion rentals Chesapeake
- Private suite rentals Chesapeake
- Rentals with a kayak Chesapeake
- Rentals with a fireplace Chesapeake
- Beachfront rentals Chesapeake
- Flat rentals Chesapeake
- Cottage rentals Chesapeake
- Rentals with a washing machine and dryer Chesapeake
- Rentals with a hot tub Chesapeake
- Rentals with an EV charger Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with a patio Chesapeake
- Pet-friendly rentals Chesapeake
- Apartment rentals Chesapeake
- House rentals Chesapeake
- Beach house rentals Chesapeake
- Fitness-friendly rentals Chesapeake
- Family-friendly rentals Chesapeake
- Rentals with pools Chesapeake
- Rentals with outdoor seating Chesapeake
- Rentals with a firepit Chesapeake
- Townhouse rentals Chesapeake
- Rentals with breakfast Chesapeake
- Waterfront rentals Virginia
- Waterfront rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Kiptopeke Beach