Hotel holiday rentals in Chesapeake Beach

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Popular amenities for hotel rentals in Chesapeake Beach

Family-friendly hotel rentals

Guest favourite
Resort in Williamsburg
4.9 out of 5 average rating, 147 reviews

*Historic Powhatan Resort- 2 Bedroom Sleeps 6

TerriRating, 5 stars3 weeks ago
We were very happy with our stay at this time share unit. It was much better than others that we’ve stayed in near Williamsburg. If we’re in the area, we will do our best to stay at this location again.
Hotel room in Williamsburg
4.75 out of 5 average rating, 12 reviews

Wyndham Kingsgate * 3BR

LaurenRating, 5 stars47 months ago
Family-friendly resort in a central location to all that Williamsburg has to offer. Very spacious rooms.
Top guest favourite
Resort in Williamsburg
5 out of 5 average rating, 22 reviews

*Historic Powhatan Resort- 4 bedroom sleeps 12

MirianaRating, 5 stars1 month ago
Our family's stay was wonderful! the accommodations were very clean and spacious. the location on the powhatan resort was just perfect for our family getaway. there were lots of great family activities and it felt very peaceful, beautiful, safe and within perfect traveling distance to colonial Williamsburg and historic Jamestown. tania was thorough with her instructions and when we reached out with a question during our trip she responded promptly. thank you, Tania! our family will definitely be booking again!!
Hotel room in Williamsburg
4.6 out of 5 average rating, 15 reviews

Wyndham Kingsgate * 2BR

DanielRating, 5 stars47 months ago
Place was great. Family loved it. Plenty to do. Communication was great and check in and out was a breeze!
Hotel room in Yorktown
4.96 out of 5 average rating, 25 reviews

Marl Inn Bed and Breakfast - Yorktown Suite

RandellRating, 5 stars9 months ago
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
Superhost
Resort in Williamsburg
4.64 out of 5 average rating, 42 reviews

The Historic Powhatan Resort- 2 bdrm

MikeRating, 5 stars33 months ago
Beautiful grounds. Place was perfect for our 2 families to stay comfortably for 3 nights with plenty of room. Amenities were great.
Guest favourite
Resort in Williamsburg
4.85 out of 5 average rating, 130 reviews

*Historic Powhatan Resort- 2 Bedroom Sleeps 6

RachelRating, 5 stars1 month ago
We really enjoyed our stay. Check in was very easy with clear instructions. Area was very safe and located in a convenient location to attractions, restaurants, and shops. The place was very clean. Mattresses were super comfortable. We felt right at home. Would stay here again.
Hotel room in Williamsburg
4.9 out of 5 average rating, 21 reviews

Wyndham Kingsgate ** 3BR

TonyRating, 5 stars48 months ago
Rob and Julia were super responsive and accommodated our last minute booking. The condo was nice, clean, and spacious for our family of six. The facility overall was well maintained and good with guests. They were particularly conscientious about covid protocols to keep everyone safe. Unfortunately that meant some of the amenities like the gym and restaurant weren't reopened yet but that will surely change in coming months. So if you're looking for a decent, family friendly spot for a few days, this is definitely good option.

Hotel rentals with a pool

Resort in Williamsburg
5 out of 5 average rating, 3 reviews

Kingsgate Resort - 2 Bedroom Deluxe

MeghanRating, 5 stars4 months ago
First time staying at this resort location. Prime spot, easy access to. all amenities. Clean space, proactive responses, and engaging staff. Will stay here again for sure!
Resort in Williamsburg
4.85 out of 5 average rating, 20 reviews

Charming 3BR Colonial Condo at Wyndham Kingsgate

DustinRating, 5 stars3 weeks ago
Amenities were great. Location very close to all the historical sites. Really appreciated the coffee in room.
Hotel room in Virginia Beach
5 out of 5 average rating, 6 reviews

Virginia Beach Resort Timeshare

AmberRating, 5 stars8 months ago
The location of this place, especially at its price, is amazing. Steps from the beach and so many great restaurants, the trolly stops right in front of the building, and there is a jet ski rental just a few mins walk behind the building. I also loved that it was at the end of the strip so there was still a lot to do, it wasn’t quite as busy as it would be further into the strip. We had a few hiccups with the building’s organization, but Brian K was amazing! He was available RIGHT away and took care of everything for me! 5 star host for sure!
Resort in Virginia Beach
4.67 out of 5 average rating, 3 reviews

Beach Quarters Resort - Ocean Front Studio

LisaRating, 5 stars7 months ago
Great location, beautiful oceanfront view! We liked being so close to the boardwalk & many restaurants within walking distance. It was a bonus to be close to the sand sculpture exhibit, which we really enjoyed. We also enjoyed how the beach was lit up at night, one of the few locations on the beach with this feature.
Resort in Williamsburg
4.9 out of 5 average rating, 10 reviews

Wyndham Patriots Place | 2BR/2BA King Bed Suite

NoelRating, 5 stars8 months ago
Peaceful, quiet neighborhood ! Amenities were nice and the place was sooo affordable for the amount of room & acommodations we were given.
Superhost
Resort in Virginia Beach
5 out of 5 average rating, 5 reviews

Ocean Beach - Studio

JoyRating, 5 stars1 week ago
Stefan always responded to my questions very quickly. The place was amazing. My husband and I had a wonderful stay. Stefan’s place is located right on the boardwalks. You can easily walk to the beach, pools, and nearby bars & restaurants. There are several pools in the condo, including hot tub. I will definitely stay at Stefan’s again next time we visit VAB.
Resort in Virginia Beach
5 out of 5 average rating, 3 reviews

Ocean Beach Club during Neptune Festival!

ArthurRating, 5 stars67 months ago
Beautiful place, right on the beach. Love the pools, right in the heart of VA Beach, and Missy set everything up to make getting in and out simple.
Resort in Williamsburg
4.71 out of 5 average rating, 14 reviews

Charming 3BR Colonial Condo at Wyndham Kingsgate

CiaraRating, 5 stars1 week ago
The host responded timely from the beginning which was greatly appreciated. The entire process was smooth sailing. The space was much more than expected in the best ways for a family of 6 to fit comfortably. I was truly impressed. Very clean, neat and nice decor. Location close to Busch Gardens and several places. Wish we’d stayed longer to enjoy all the amenities. I would definitely want to stay at this location again. A+ for our family. Thank you for allowing us in your beautiful space. A+ from us!!

Hotel rentals with a patio

Top guest favourite
Resort in Williamsburg
4.94 out of 5 average rating, 227 reviews

Kingsmill Resort Hotel room with 2 queen beds

NielsRating, 5 stars1 week ago
Just a few minutes outside Williamsburg, Mari's place is a quiet and attractive place to base a trip to Colonial Williamsburg and other attractions in the area
Guest favourite
Resort in James City County
4.9 out of 5 average rating, 48 reviews

Fairway View King Room.

TaylorRating, 5 stars1 day ago
For a trip to Busch Gardens, this was perfect. Took less than 10 minutes from leaving the unit, to being parked at Busch Gardens. Susie was very proactive with instructions, the unit was clean and pleasantly decorated, some thoughtful snacks and waters were provided, and the surrounding resort grounds were beautiful. As other reviewers have pointed out, the walls are fairly thin and you hear a lot of noise from the surrounding units. Luckily this never was a nuisance for us during our stay, but we feel like it has the potential to be depending on the neighbors. Besides that one concern, our stay was great! We would definitely choose Susie's listing again!
Top guest favourite
Hotel room in Norfolk
4.9 out of 5 average rating, 59 reviews

Cozy Santorini Room at Grandiflora Wine Garden!

MichaelaRating, 5 stars2 weeks ago
Perfectly walkable to delicious restaurants and cafes. A beautiful home with all that you could need. Erin and Jason were so communicative and flexible.
Resort in Williamsburg
4.89 out of 5 average rating, 9 reviews

Charming 1BR Colonial Condo at Wyndham Kingsgate

FrankRating, 5 stars6 months ago
The place was super clean and most comfortable for the price and location. It is cheaper than a hotel/motel but has a refrigerator, a microwave and a stove top. The TVs were top level. Most of all, the comfort level of the 1 BR villa was ever present. Not to mention, the amenities were way and above anything an "Inn" would have available. We highly recommend these accommodations.
Guest favourite
Hotel room in Williamsburg
4.71 out of 5 average rating, 7 reviews

Boutique Double Room Near Colonial Williamsburg

AarickaRating, 5 stars2 weeks ago
We recently stayed at the Roadside Inn with our two girls (4&7) and our dog Ranger for our Spring Break. The location to all of the local attractions (Williamsburg, Jamestowne, Busch Gardens for us) was super convenient for us. My husband and I played cards on the picnic table outside the lobby after our kids went to bed which was nice to be able to see our room door in case anyone woke up! The room was perfectly furnished and newly renovated for the price. We ended up using most of the restaurant recommendations given and all were fantastic! Our stay was overall great, but next time we will get two rooms for a little extra space.
Superhost
Hotel room in Williamsburg
5 out of 5 average rating, 6 reviews

Armistead House - Room 301 (3rd Floor)

MatthewRating, 5 stars6 months ago
This Inn was amazing!! Such great charm in the historic district with modern upgrades. The rooms were massive and cozy! I would love to find out what mattress was there because I have never slept that well! Parking right out from was easy and a quick 5 min walk to all the restaurants. Really enjoyed it and if you are on the fence just do it!!

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