Photo by Ronanne Vinson

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Compare 319 Vacation Homes in Chesapeake Beach with updated reviews, rates, and availability.

"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."

"We had lots of room to relax and hang out. The kitchen is very well appointed and we definitely could have cooked if we chose to. We enjoyed walking with nice views of the ocean. We especially enjoyed the osprey hanging out near their nest right off the pier."

"This was a comfortable home, and a nice location. We were staying mostly for business, so didn’t do much in town, but the main restaurant and shopping areas are two short blocks away. We did use the nearby nature trail to walk our dogs. The only concerns others might have with the house, and the reason for four stars instead of five, were: minimal kitchen equipment (few pots/pans etc.), steep narrow stairs to the second floor, and low water pressure in the shower. That said, none of these things...

"Enjoyed the location and proximity to the city. Water view and firepit enjoyable. Disappointed that the dock and kayaks not easily accessible. House needs some tlc (we provided a list of easy repairs/maintenance needed.) Love to know why the ceiling fans and lights go on and off randomly."

The driveway allows for plenty of parking for guests!

"This was our third year celebrating our family Thanksgiving in this home. Three generations coming from three different states. Location offers an easy drive for everyone, and the home is large enough for us spread out yet gather for meals. The host listened to our comments from previous years and addressed all of our concerns. Will be returning again."

Tranquil retreat on the South River - private dock

"Amazing time the view was to die for , host was awesome "

Welcome to Bay Ridge - a 4-bedroom and 4.5-bath luxury home in Eastport - 1-mile to downtown

"From communication to check-in and cleanliness, this VRBO has plenty of room and modern amenities. What put this over the top was that a party member left the wallet at the VRBO, and the renters went and retrieved the wallet and met us to return it. They went above and beyond to help us. It has a good backyard and can park 3-4 cars in the driveway; this VRBO has everything. Easily five stars"

"Perfect for our weekend stay. Checkin was easy and communication with the owner was great! Definitely would stay again. Kentmoor restaurant was awesome. Filled with locals who were friendly and welcoming! Food was great!"

SAR 963 total

includes taxes & fees

6 Jan - 7 January 2025

"House was centrally located in town. We parked the car and walked! Beds were very comfortable it was wonderful to have seperate beds for everyone. Well stocked kitchen. Washer & dryer a plus. We will be back. "

"The Ranch at Royal Oak was a fantastic property. The property was exactly as advertised - gorgeous waterfront estate with a large lawn. Incredibly peaceful. We were looking for a getaway to hit pause and just relax and the ranch Royal Oak was exactly what we needed. Marissa was a great host - incredibly responsive, check in instructions are very clear.and easy to follow. I highly recommend this property for your next getaway."

Start your stay at the waterfront Sunset Serenity with a glass of wine.

"We had such a wonderful Father’s Day weekend, at this lovely property! The views are beautiful, the house was laid out perfectly for our large family, and everyone enjoyed fishing off the dock."

Welcome to the new custom-built Washington's Retreat, with views of the Chesapeake Bay.

"The home was wonderful! So clean and spacious! Very modern beachhouse style home with an amazing view. We loved waking up every morning to see the sunrise. Host was very accommodating and professional. 5/5! Highly recommend this property!"

"We stayed here for four days over July 4th holiday. The house is clean, modern, updated and looked new on the inside. Well equipped with linens, towels, bath products, appliances and accessories. Conveniently located to Herrington Harbor marina for events and weddings. Huge fenced backyard which was great for kids and pets to run around. There were a couple of minor issues with the AC (due to a storm power outage) and the guests before us also didn’t take out their trash so the can was full. But...

Annapolis Vacation Rental | 3BR | 2BA | Steps Required | 1,728 Sq Ft

"I took my family down for the weekend to see the Navy football game. The house was perfect and as described. The outside space was just as nice as inside and the neighbors were friendly too. We will absolutely rent here again. "

3 covered balconies, a ground floor patio, and ceramic and propane grills.

"Wonderful location to downtown Annapolis! Beautiful home, well maintained and plenty of room. The porch overlooking the bay has a table for 10 which provided a wonderful setting for our family. This is our second stay and we’ll absolutely stay again "

"Everything close by!"

"We appreciate the hospitality and responsiveness of our gracious host. We would stay again and look forward to our next visit. Recommend staying to all looking for a tranquil getaway in the Annapolis area."

"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...

Cambridge Vacation Rental | 7BR | 5.5BA | Stairs Required | 10,333 Sq Ft

" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...

Sunroom off the kitchen and living room with a magnificent view of the Chesapeake Bay

"Very nice place we found, great views, very clean, quiet, great place to relax for the weekend. everything went well and we would highly recommend anyone for a stay here. we will be back next year"