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

Pet-Friendly Home on Chester River w/ Dock!
Chestertown Vacation Rental | 4BR | 4.5BA | 6 Steps Required | 3,232 Sq Ft

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.0 out of 10, Wonderful, (2)
"no kettle no cutting board"
Pet-Friendly Home on Chester River w/ Dock!
Chesapeake City Quiet Overlook
Backyard looking from Ben Cardin trail and the C&D Canal

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (13)
"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). "
Chesapeake City Quiet Overlook
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Interior

Luxurious and spacious townhome with all necessary amenities awaits your stay.

10.0 out of 10, Exceptional, (5)
"Great experience all around! "
Luxurious and spacious townhome with all necessary amenities awaits your stay.
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Beach

Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

9.6 out of 10, Exceptional, (43)
"We enjoyed our Thanksgiving get away at this very cute waterfront cottage. Our stay was a extremely relaxing and enjoyable time. 😊👌👍"
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Betterton Beachhouse - historic Buena Vista, overlooking the Chesapeake Bay

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (36)
"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...
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Master bedroom.. King-size bed and en-suite bathroom.

Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

10.0 out of 10, Exceptional, (8)
"This home had to have been the most perfect VRBO we have stayed in. The home was clean, comfortable, stocked with amenities that made the stay incredibly pleasant and in a fantastic location. We particularly enjoyed the built in speakers in the dining room. I would highly recommend this home for a visit to Chestertown. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Right in the center of everywhere in Dover
Game room

Right in the center of everywhere in Dover

8.0 out of 10, Very Good, (3)
"Everything was nice enough space for everyone to sleep comfortably."
Right in the center of everywhere in Dover
Upper Chesapeake Getaway - Newly Renovated
Living area

Upper Chesapeake Getaway - Newly Renovated

9.8 out of 10, Exceptional, (13)
"This home is beautifully decorated, making it most inviting and pleasant. The view of the bay was magical! Sitting on the sun porch was so wonderful! The kitchen was the most well equipped kitchen I’ve had the pleasure to use! Thank you for an amazing stay!!"
Upper Chesapeake Getaway - Newly Renovated
Mill Creek River House with hot tub Smyrna Dover riverfront with kayaks
View from property

Mill Creek River House with hot tub Smyrna Dover riverfront with kayaks

10.0 out of 10, Exceptional, (14)
"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...
Mill Creek River House with hot tub Smyrna Dover riverfront with kayaks
Your perfect Maryland escape awaits!
Room

Your perfect Maryland escape awaits!

10.0 out of 10, Exceptional, (4)
"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...
Your perfect Maryland escape awaits!
The Riverside Oasis waterfront with hot tub

The Riverside Oasis waterfront with hot tub

10.0 out of 10, Exceptional, (4)
"We arrived to a cozy and warm home decorated beautifully for the holidays. Saturday we went for walks along the water and the kids did some biking. Dinner with our group was enjoyable at the large dining table where everyone had a seat- no need for a kiddy table in this house. Resting our heads down on luxurious bedding and waking up to beautiful water views was a delight. We can’t wait to come back with our clan."
The Riverside Oasis waterfront with hot tub
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool

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
Waterfront Home & Dock, sleeps 8 Max. Eastern shore, Betterton Chestertown MD.
Front of House Facing the Water.

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
Miscellaneous

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10.0 out of 10, Exceptional, (52)
"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...
Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
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!

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!
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Large deck off the back of the house with lots of seating, beautiful views.

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

9.6 out of 10, Exceptional, (10)
"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...
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Home away from home
Room

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!!!
Exterior

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
looking down river from the dock

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (80)
"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."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Chesapeake Point | Waterfront w/ HOT TUB + Beach!
Welcome to Chesapeake Point! Get ready for you and your loved ones to enjoy the vacation of your DREAMS!

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

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Bluffside seating overlooking the Chesapeake Bay

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (75)
"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!"
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Chesapeake City Quiet Overlook
Backyard looking from Ben Cardin trail and the C&D Canal

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (13)
"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). "
Chesapeake City Quiet Overlook
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach

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
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.