
Hotel holiday rentals in Chesapeake Beach
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Top-rated hotel rentals in Chesapeake Beach
Guests agree: these hotel rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for hotel rentals in Chesapeake Beach
Family-friendly hotel rentals

Wyndham Kingsgate * 3BR
Family-friendly resort in a central location to all that Williamsburg has to offer. Very spacious rooms.

*Historic Powhatan Resort- 4 bedroom sleeps 12
Our family, aged, 5-75, had a great stay at the Hilton Powhatan Resort. We had plenty of space! It was basically two separate apartments - one upstairs and one downstairs. Each with two bedrooms (one en-suite), 2 bathrooms, and each had a full kitchen and living room. The downstairs one had a nice outdoor sitting area. The resort itself was great w 3 pools - pool towels provided there. You get 2 parking spots but they have guest spots as well. Everyone was friendly. Countless restaurants and stores within 5 minutes of the resort. No list of instructions for check-out. We loved it! We would definitely stay again.

Wyndham Kingsgate * 2BR
Place was great. Family loved it. Plenty to do. Communication was great and check in and out was a breeze!

*Historic Powhatan Resort- 2 Bedroom Sleeps 6
Loved our stay here and the surrounding area! Such a practical and convenient place to vacation!

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

The Historic Powhatan Resort- 2 bdrm
Beautiful grounds. Place was perfect for our 2 families to stay comfortably for 3 nights with plenty of room. Amenities were great.

Luxurious 1 Bedroom-Live Like the Governor of WBG!
Close to most things you'd want to do in a visit to wmsbg. Very clean and we loved using the indoor heated pool at the aquaticcenter and would love to stay again in warmer weather to enjoy other family friendly amenities

*Historic Powhatan Resort- 2 Bedroom Sleeps 6
Very clean and comfortable- a spacious place to stay.
Hotel rentals with a pool

Wyndham Patriots Place | King Bed Studio
Clean space, plenty of room, easy check in. Only negative is the sales pitch for a timeshare but it’s understandable

Charming 2BR Colonial Condo at Wyndham Kingsgate
This was a nice place! Everything was as described in the description! Had an issue with the bathroom sink but the maintenance crew onsite was able to fix it with no problem! Overall excellent rental and we look forward to renting from this host again.

Charming 3BR Colonial Condo at Wyndham Kingsgate
Everything was as stated on the site. My family and I enjoy the place and the location was great.

Wyndham Patriots Place | 2BR/2BA King Bed Suite
This was the perfect stay for our family of four. The place was spacious and extremely clean. The kitchen was equipped for cooking with pots, pans, and utensils. It also is close to the onsite pool and firepit. It is in a peaceful area away from the main road, and only about a 5 minute drive to Colonial Williamsburg, which was very convenient. Overall we had a great stay and would definitely stay here again if we come back to this area!

Charming 1BR Colonial Condo at Wyndham Kingsgate
This was one of the best vacations we have had. Great pool, amazing arcade games, and a small beach not too far. It was so great! They have old photos on this listing. There is not park but no biggie.

Wyndham Patriots Place | 2BR/2BA King Bed Suite
The location was excellent—conveniently close to restaurants and local attractions. The unit was clean, quiet, and well-equipped with everything we needed for a comfortable stay. While we didn’t use the pool, the overall environment was pleasant and relaxing. There was a small timeshare pitch upon check-in, but it was brief and not overly aggressive. Overall, a great stay and would recommend for travelers looking for convenience and comfort.

Charming 2BR Colonial Condo at Wyndham Kingsgate
The accommodation was as described and provided a great value for a family getaway. The host was communicative and provided helpful instructions. Check-in took a while due to the resort's rules and procedures, but I was able to politely decline the timeshare presentation, and we enjoyed the stay and amenities. It isn't the fanciest or most updated place, but it was comfortable, there was a lot to do on site, and it was in a convenient location for exploring the area. Would stay there again.

Wyndham Kingsgate Resort | 1BR/1BA King Bed Suite
Kingsgate in Williamsburg is a family friendly resort. We always have a great time. This unit was clean, convenient and a great homebase for a weekend of Williamsburg attractions.
Hotel rentals with a patio

Cozy 3BD Suite in Gorgeous Williamsburg!
We had a great family vacation. Kids loved the amenities and it was close to everywhere we wanted to go

Club Wyndham Governor’s Green One-Bedroom Suite
The property was beautiful and exactly as listed. It is an excellent spot for family vacations with plenty to do. We will definitely be returning.

Williamsburg, VA- Governor's Green-3Bd Dlx
Nice, clean place. Plenty of room for 3 adults and 3 kids. Short drive to restaurants. ~15 min to Busch Gardens. Nice property with things for the kids to do.

Hilton Virginia Beach 1BR suite with city view
My first experience with Airbnb exceeded my expectations. The location was ideal, situated right next to the boardwalk and beach. The fully equipped kitchen was a lifesaver, especially when traveling with kids. The host was outstanding and very responsive, ensuring we had everything we needed. Both the room and living area were spotless. I’m already looking forward to returning next year!

Oceanview (Va Beach) Getaway
The place is very nice. Beach is right there walking distance. You can see it from your balcony There are a lot to do and I would definitely go back.

Extra large Studio centrally located in Hampton
Maria was indeed a great host. The loft was perfect for what I needed, and the location was 8-12 minutes to every destinationI selected. I love that I had my own parking space and a lock on my loft door from the inside.

Boutique King Room Near Colonial Williamsburg
Despite saying motel out front this space was superb, fresh, and airy! Would absolutely return!

Charming Three Bedroom Penthouse- City View
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- Chesapeake Bay
- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- First Landing State Park
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- Kingsmill Resort
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- Ocean Breeze Waterpark
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- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
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