
Vacation rentals with breakfast in Chesapeake
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Top-rated breakfast rentals in Chesapeake
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House rentals with breakfast

Three Little Birds-Kayak, fish, bike, enjoy!
I wish I could give Three Little Birds more than five stars! Every little detail exceeded our expectations. My three children and I were very comfortable inside and felt like we were in paradise outside. We enjoyed fishing, birdwatching, reading, and soaking in vitamin D from Virginia's perfect sunshine. The indoor space is private, quiet, well equipped and cozy. The location is convenient to everything. I can honestly say that this was the best overall experience at an Air BnB we have ever had. Bridget and Carley are beyond friendly, helpful, accommodating and overlooked no detail. Thank you!

Military - Active/Retired/Family at Cape Defoe B&B
I stayed at Mark’s place while visiting my daughter, who’s in the Navy, and it was the perfect spot for some peaceful downtime. Even though it’s a shared home, the bedroom and bathroom felt very private and exceptionally clean. I was comfortable the entire time and slept well. The house itself is like walking into an art installation—colorful, unexpected, and full of personality. You never quite know what light or feature will come to life next, which made it fun and memorable. Both hosts are clearly creative souls with a flair for design. The backyard was my favorite part—lush with plants, fountains, and statues, all backing up to the Chesapeake waters. At night, it turns into a magical light show with just the sounds of nature and water features. So peaceful and calming. They even had a little breakfast area set up with bakery items and coffee—such a thoughtful touch. I’d definitely stay again and recommend it to anyone looking for a one-of-a-kind and restful experience.

Private Bedroom & Bath Suite for Females Only
This is a great host family who went above and beyond to make my stay comfortable, enjoyable and safe. They went from being hosts to friends during my stay.

Bells Island, w/pool on the water.
Perfect for our group!

Lee Hall
Renee was a very kind, helpful, and accommodating host, for our family of six. The location is super convenient to Busch Gardens. This was my first time staying at a property which was not one where you get the "entire home". My expectations were met in terms of that, and her descriptions of the property and the experience were accurate. I wish her the best of luck in her future endeavors on Airbnb.

Dog Friendly 4 bedroom Home!
Wonderful place with great walk ability to the beach. Great place for larger groups to stay. Good view of the sunset over the sound and in a nice quiet area.

Lake Retreat
My stay at Ethel's was amazing. The entire room was exactly like the pictures. I felt completely at home. The room was spotless, and the bed was super comfortable. I will reserve her space when I come back to VA. I really enjoyed my stay there. She was very responsive and her instructions for the check in are great.

Vintage Den Rm, Private Entrance,& Space,VB Center
Jerome was very very accommodating and super helpful with me my wife and dog. We were in one of the worst situations we had ever been in and we’re desperate for help and to be cut a break. Jerome and his wife Cristy provided that and beyond. Super communicate, super on top of everything, if there was a problem no matter how small or large they had it rectified posthaste. They even completely cleaned up their rather large backyard just so my dog could have somewhere to run and play. As for the room itself, when we arrived it was very clean and very spacious for it only being a room. He has a very large tv and a roku stick for your access to whatever you would wish to watch. There is lots of storage room for your clothes and whatever else you may need. There is also rather spacious mini fridge. The bed was very comfortable as well. There are also two very large windows that can be opened or closed if you need a breeze. Cristy cleans like a mad-woman so any mess that may be around in the house is cleaned before you even realize it. The bathroom was very clean and they even left us a travel bag of toiletries. They have two very friendly cats that love attention. This is in fact a smoke friendly house, which is an incredibly rare find. Thank you so much Jerome and cristy for all of your hospitality and help during this impossible time that I found myself in.
Apartment rentals with breakfast

The Waverly 100 Inn at Old Beach
The place was exactly like the pictures. The breakfast every weekend was great and the place was so close to the beach too. I will be back for sure!

Breakers 204 Inn at Old Beach
Really enjoyed staying here! Easy to find, walkable to the beach and surrounding shops, clean, and we loved the breakfast provided by the local bakery!

Pinewood 102 Inn at Old Beach
Great location, and super clean!! Dimitri was extremely communicative, and the check in process was seamless. Would 100% recommend this Airbnb.

Avamere 206 Inn at Old Beach
I really enjoyed my stay! It was very close to the beach and within walking distance of amazing restaurants. They were very quick to respond to my messages whenever I needed assistance as well. I would 100% recommend this place to anyone who is looking to stay at the oceanfront.

Albermarle #202 Inn at Old Beach
We had a great stay at The Inn at Old Beach over memorial day weekend! The location of this air bnb was ideal- it was off the busy main strip but still close enough so that you can easily walk to the beach and restaurants. The check in was smooth and easy and the hot tub was a fun addition to the stay.

Newcastle 106 Inn at Old Beach
Very clean, very safe part of town. I highly recommend this spot for any small group!

Oceanfront at Barclay Towers
Peter's place is an oceanfront unit, on the boardwalk. The building was somewhat older, and the pool was somewhat small, but the staff were friendly and accommodating. The Ocean view was spectacular, and the convenience to the beach, restaurants and attractions was excellent. I had looked up reviews on the building online, and became a bit skeptical as to how our stay might turn out. As it turns out, we had a great time on the beach, and relaxing on the balcony. The unit has a flat-screen with cable in the bedroom and livingroom. We would gladly stay again.

Hilltop 104 Inn at Old Beach
This place was fantastic. Loved the walkability factor to the beach. Also, the hot tub and breakfast spread in the morning were a great addition. This is the second time I've stayed here, I will be back!
Bed and breakfast rentals with breakfast

Williamsburg Sampler - Lord Nelson Chamber
My fiancé and I had a wonderful stay at this charming bed and breakfast in Colonial Williamsburg. From start to finish, the experience was top-notch. The host was incredibly communicative and made sure everything was smooth and stress-free. The room was beautifully decorated, spotlessly clean, and had all the amenities I needed for a comfortable stay. The rest of the house was just as lovely—warm, welcoming, and tastefully furnished, with a cozy outdoor space perfect for relaxing. The innkeeper was so kind and hospitable, and the breakfasts each morning were absolutely delicious—clearly made with care and attention to detail. I highly recommend staying here if you’re visiting the area. It’s a perfect blend of comfort, charm, and hospitality.

Williamsburg Manor - Russel House Green Room
Exterior is more beautiful in person! Very convenient location to colonial Williamsburg and shopping. If you are looking for a historical experience feel, this is the place you should stay.

Washington Suite - A Williamsburg White House
Wonderful stay!! My flight was canceled and I needed a place to stay last minute! They were flexible. I got in right away. They had wine and treats ready for guests. It truly was a gem of a stay. I’m so glad my flight got canceled. Best hospitality!! And met incredible people at breakfast. Which btw was also amazing!! Quiche with baked oatmeal and a side of ice cream.

Aldrich House B&B Lewis Room
A TRUE Bed and Breakfast. Great location and great hosts. The home is spectacular and the location is very peaceful.

The Rhododendren-King-Luxury-Ensuite with Shower-G
Absolutely loved our stay! Karen was amazing and so helpful. Our room was one of the cleanest airbnbs I e been in yet! The most comfortable bed and pillows. We slept amazing and felt right at home. The breakfast was so delicious and she was able to accommodate my gf requirements. We will definitely be coming back!

Sunny Queen Room with Breakfast - Cedars B&B
Alex and staff are great hosts, we frequently stay here we love it that much! I’ve taken my boys and their friend or have just stayed with my finance. Already browsing my next stay 💕💕

✶Designer Boutique Bed and Breakfast✶ | Rm #2
This was our second stay at the Pinner House, and we were definitely not disappointed! The place is always spotless, but Kris took extra steps to make sure the home was sanitized and we were the only guests, due to covid-19. We really appreciated the accommodations made on that part. It’s such a beautiful getaway in Suffolk, that you truly feel you’re on vacation! From the fire Kris made in their outdoor fireplace in the evening, to the lovely breakfast prepared for us in the morning, you will not be disappointed with your stay at the Pinner House!

Marl Inn Bed and Breakfast - Yorktown Suite
We stayed in the Patriot Suite and the King Size Bed was AWESOME!!! Amy & Paul were great Host and made you feel like family. We even went to church with them and were highly blessed! Thank you Amy & Paul for everything!!! We highly recommend staying there! Nancy & Randell
Quick stats about vacation rentals with breakfast included in Chesapeake
Total rentals
50 properties
Nightly prices starting at
G$4,196 GYD before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Bethel Beach
- Buckroe Beach
- First Landing State Park
- Kingsmill Resort
- Water Country USA
- Buckroe Beach and Park
- Grandview Beach
- Currituck Beach Lighthouse
- Virginia Beach National Golf Club
- Jamestown Settlement
- Sarah Constant Beach Park
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- Ocean Breeze Waterpark
- Norfolk Botanical Garden
- Bonito St. Public Beach Access
- Grove Beach
- Golden Horseshoe Golf Club
- Little Creek Beach