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Compare 545 Vacation Homes in Grasonville with updated reviews, rates, and availability.

"We only stayed one night but the house was perfect for our needs. The main family room/kitchen area was perfect for all of us to comfortably sit together, and the bedroom layout was great for two families (two “wings”). The hosts were super responsive and accommodating. Would just suggest two hairdryers (one in each bathroom - if there was a second, we did not see it) and shower soap. The bed in the primary bedroom was very comfortable and everything went smoothly. "

SAR 1,976 total

includes taxes & fees

2 Dec - 3 Dec

"This cozy home was perfect for my coaches & I that were in town for a lacrosse tourney @ the Naval Academy. This home is literally less than 100 steps from the gate of the Naval Base and same distance to dowtown Annapolis city docks, diming, shopping and sight-seeing. We will defintely be back! Thanks John!!"

"We thoroughly enjoyed the convenience of walking to shops, restaurants, and waterfront! Residence was charming and clean! Only minor issue was we couldn’t locate the iron- just the ironing board! We still had fun but we’re just a bit wrinkled!😁"

"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."

Nature,Outdoors,Scenery,Water,Waterfront

"We had the most wonderful time at this charming house on Tillman Island! While the pics are great, it is even better in person. The house is perfectly nestled on the waterway, offering stunning views. The backyard pool was a true highlight, and we spent countless hours splashing around, the pool in the sun."

"Everyone loved it!"

Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft

"Wonderful serene location on a tributary to the Bay. Beautiful water views with its own dock and kayaks. 15 minutes to Annapolis. House is very comfortable, freshly and attractively decorated, and well stocked. Manager was extraordinarily helpful. Nine of us had a perfect relaxing long weekend. "

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 "

Waterfront with private pier and great views

"The pictures dont do this rental house justice. It was very clean and wonderfully decorated. The seperate unit was ideal for my daughter and her family. The "

Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

"The house was beautiful. The location was perfect. The owner was very responsive. 5 couples stayed in the house and we would all love to return. Thank you for everything!!"

"Very nicely renovated property in the heart of downtown Annapolis. Highly recommend for groups / families and very kid friendly. Great location to walk to all that Annapolis has to offer. "

SAR 3,338 total

includes taxes & fees

3 Dec - 4 Dec

"The Bennett House not only lived up to its pictures online, the cleanliness, abundance of extra special touches, communication with the host, and more surpassed our expectations. The beds were extra comfy, the kitchen, fully stocked, the bathrooms, adorned with the fluffiest white towels and extra toiletries . . . and I can't say enough about the front porch. Even though clouds cloaked the sky when we arrived and when we left, sunshine streamed through our Annapolis trip because of the Bennett...

"What an amazing place... the sunsets, the house, the pool, the amenities... absolutely everything was perfect! The owner was super helpful! "

The Twin Ponds Lodge sits on over 7 acres of private waterfront property.

"The property was excellent for a large group. We was there for a Sailing Regatta on the lake in front of the house. The perfect house for groups."

Across from the Navy and Marine Corps Stadium!

"Property was great and accommodated 7 of us easily. Quiet location, close to everything for our stay in Annapolis. "

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."

"Loved this location as EVERYTHING is walkable - St John's college, USNA, the capitol and Main Street. One skinny parking place was appreciated and reasonable for a standard size vehicle (not super truck or SUV). Enjoyed the older character of the home and modern conveniences as well as small outdoor space that was very nicely landscaped with flowers. "

Welcome to the waterfront Seize the Bay with a private pier (boat pictured not included in rental).

"Despite the rainy weather from hurricane Debby, our family enjoyed our stay at this house/ property. The property was well appointed and we didn’t need for anything. We loved the porch, the dock and the water views. The house was very clean and there was plenty of space to spread out if needed. It was a peaceful getaway. Our hosts were wonderful and were easy to contact and helpful with information. "

"Rock Hall is the perfect little bay town and this property captures that same appeal. Spacious home with great outdoor space. Lovely neighborhood for walks and bike rides. Everything in home worked perfectly. We are certain to return. "