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Compare 50 Vacation Homes in Massey with updated reviews, rates, and availability.

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

"no kettle no cutting board"

"Great experience all around! "

Betterton Beachhouse - historic Buena Vista, overlooking the Chesapeake Bay

"We had a great time at the house with friends from our apartment building and neighborhood for the long Thanksgiving weekend. Debbie and Bob had everything we needed to cook with, the porch overlooking the Bay was amazing, and the living room, TV room and dining room were all used frequently. We also played games, and had a nice fire in the portable fire pit outside. Weather got coooold but the house was always warm and cozy. It was a really fun stay. The bedrooms were great, too. They've taken...

"Everything was nice enough space for everyone to sleep comfortably."

"Perfect house to rent! Clean, spacious, great neighborhood, beautiful property, & very dog friendly! My husband & I rent a different house in different states every year for our anniversary & never go to the same place twice; however, we may have to reconsider as this place was perfect & we may come back! The hot tub & deck(s) were relaxing, the location is great & very quiet, we had fun playing basketball, & we loved the dock and being able to watch the sun rise & set. We suffered the loss of a...

"Property was as described and according to photos. Children’s toys only consisted of card games, and there was no children’s dinnerware which was listed as provided. Kitchen was not well stocked, as there were no baking supplies and we needed to use the oven. Beds were comfortable and there was ample bedding, pillows, blankets, and towels. There was ample parking. Ceiling fans were amazingly quiet and appreciated in each room. Was difficult to use showers only for children’s baths. Property...

"Great!"

"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. 😊👌👍"

"The house and location on Still Pond Maryland was great!! House was clean and tiddy. Caught perch, catfish and bass off their dock!! Area is beautiful and quiet! "

"We had an unforgettable stay at this property! The house and two bungalows exceeded all expectations. The entertainment/living room is massive—one of the largest I’ve ever seen—and offers incredible views of the river from almost every angle. Watching the sunrise and sunset through the large windows was absolutely breathtaking. The kitchen was impressively well-stocked, making meal prep a breeze. There are two dining areas: one table that seats ten and another that seats six, offering...

Welcome to Veazey Cove! This gorgeous blue pool and hot tub feature overlooking the lake and spacious backyard is a favorite of both kids and adults alike!

"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."

Large deck off the back of the house with lots of seating, beautiful views.

"The Lark's Nest is in a nice location. The home decor is pleasant to the eyes and well-arranged. The host provided us with all the necessities (towels, cooking supplies, cleaning supplies, and toiletries). The cons were dirty ceiling fans, the sofa needed cleaning, and the outside lighting needed to be brightened. A mouse was found in the house. The host was apologetic, accommodated us financially, and sent out an exterminator to handle the rodent issue. Overall, the actual place was a good stay...

"Nice place to stay for quick weekend. Close to everything."

Backyard looking from Ben Cardin trail and the C&D Canal

"This home was amazing. Nicely decorated for the holiday. Labels on kitchen cavinets. Host was easy to communicate with. Fast responses. doors made it easy to find things (huge kitchen). "

"Our group of 15 gathered here for a long weekend in July to attend a family event in the area. The house was WONDERFUL, STYLISH & SPACIOUS. And Chesapeake City itself was a surprise bonus… several gift shops, a cute ice cream shop, coffee & breakfast cafe, dinner restaurants - all within walking distance! Loved: everything about the house… proximity to the quaint town… plenty of hot water… awesome AC upstairs…Brad the owner answered emails very quickly… *minor* issues: the main floor AC...

"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."

Welcome to Chesapeake Point! Get ready for you and your loved ones to enjoy the vacation of your DREAMS!

"The property is beautiful! The house! The view! The water! The yard! Everything was just wonderful about our stay at Chesapeake Point. We just loved every minute of our stay about at Chesapeake Point. The home is well maintained and was immaculate. I have never been in a home that was so clean. We will definitely return! "

Welcome to Harbor View Haven- A luxurious getaway home with gorgeous views!

"My family enjoyed this house so much. The place is perfect for a relaxing gateway with so much peace and nature. Will definitely be back!"

"This property is gorgeous! It was everything I could have hoped for. I was in town for a wedding in Earleville in search of a dog friendly rental. I am so happy I found this place. The cottage is down the long driveway neighboring other cottages/houses. Very cute fenced in entryway. The check-in process was very easy with the door code for entry. The cottage was super cute, plenty of space. The pups and I spent most of our time outside enjoying the view. The yard overlooking the water has a...

"Convenient and safe location. Lots of space to spread out and relax. Very comfortable."

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Other property types in Massey

Bluffside seating overlooking the Chesapeake Bay

"We had a great two days here! House has everything you need. We really enjoyed the hot tub! We were lucky the weather was so warm and we could just sit outside all day looking at the water and end the day with gorgeous sunsets. We would definitely come back!"

"it being off season,very quiet. the people in the surrounding neighborhood were very friendly, we had a great time, ash and christine were awsome host. we will deffinately go back again!"