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Compare 48 Vacation Homes in Massey with updated reviews, rates, and availability.

Dover Home - 2 Mi to Delaware State University!
8.8 out of 10, Excellent, (3)
"The neighborhood was very nice and quiet.The property suited our needs. The only negative the exhaust fan in the upstairs bathroom does not work. "
Dover Home - 2 Mi to Delaware State University!
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
9.4 out of 10, Exceptional, (32)
"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."
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
Chesapeake City Quiet Overlook
10.0 out of 10, Exceptional, (12)
"This home was absolutely magnificent! Location and scenery were wonderful. Just so much to keep our attention and kept us in awe. This was a family trip with siblings and soooo many wonderful memories were made. We are older now and it means more than ever before. Thank you to our host Jane who kept in touch and was so very attentive. Most gracious. We are already talking about going back. Cannot say enough it thank you from the bottom of our hearts.♥️"
Chesapeake City Quiet Overlook
Sunset River Cottage encapsulates nautical romance.
9.0 out of 10, Wonderful, (12)
"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...
Sunset River Cottage encapsulates nautical romance.
Luxurious and spacious townhome with all necessary amenities awaits your stay.
10.0 out of 10, Exceptional, (2)
"This was one of the most cleanest good smelling place I’ve been to in a long time! I travel a lot too!! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Chesapeake Retreat with hot tub. Charming 2 Bed, 1 Bath Home in Chesapeake City
2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a great time staying here. The inside is so cute and comfortable. Location is great and the host is very quick to respond and accommodate requests. 10/10 "
Chesapeake Retreat with hot tub. Charming 2 Bed, 1 Bath Home in Chesapeake City
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
9.6 out of 10, Exceptional, (35)
"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
10.0 out of 10, Exceptional, (15)
"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!"
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
Circa 1900 Home in the Heart of Historic Downtown Chestertown
10.0 out of 10, Exceptional, (63)
"We enjoyed everything about the property."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Amazing Modern house with a full kitchen and parking
10.0 out of 10, Exceptional, (6)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
Amazing Modern house with a full kitchen and parking
Waterfront Millington Vacation Rental w/ Hot Tub!
Waterfront Millington Vacation Rental w/ Hot Tub!
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
9.8 out of 10, Exceptional, (40)
"Very quaint and cute cottage really enjoyed sleeping on the porch , The sound of the waves because it was windy was so soothing. I felt We were on a sailboat."
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Waterfront Home & Dock, sleeps 8 Max. Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (87)
"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! "
Waterfront Home & Dock, sleeps 8 Max. Eastern shore, Betterton Chestertown MD.
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
10.0 out of 10, Exceptional, (51)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
9.8 out of 10, Exceptional, (9)
"We enjoyed our stay here. The dock and waterfront views were amazing! The kayaking was fun. Just a shame we are in a drought because river was too low to go out on Sun. Furniture not the best for comfort but other amenities were good! "
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Home away from home
7.6 out of 10, Good, (5)
"Nice place to stay for quick weekend. Close to everything."
Home away from home
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
9.6 out of 10, Exceptional, (5)
"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...
Hook Wine & Sinker~sleeps 14 to 16 🚤 includes slip at Inn 🚤water views!!!
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
9.8 out of 10, Exceptional, (80)
"House was even better than the photos showed. We spent evenings out on the dock watvhing the river and beautiful views. The hosts thought of every detail for a perfect stay."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
9.8 out of 10, Exceptional, (15)
"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! "
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Massey

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (44)
"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!"
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (71)
"Just what we needed for the night! Thank you "
The price is SAR 368
SAR 569 total
includes taxes & fees
13 Nov - 14 Nov
First Floor Studio Apartment in Historic Chestertown
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
10.0 out of 10, Exceptional, (51)
"The house is roomy and was clean and well stocked."
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.