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Check prices for these dates

Next weekend
21 Rab. I - 23 Rab. I
In two weeks
28 Rab. I - 30 Rab. I
In one month
11 Rab. II - 13 Rab. II
In two months
9 Jum. I - 11 Jum. I

Compare 61 Vacation Homes in Massey with updated reviews, rates, and availability.

Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (257)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

The price is SAR 506
SAR 1,050 total
includes taxes & fees
18 Mar - 19 Mar
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (11)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Beach

Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

9.8 out of 10, Exceptional, (16)
"From the moment we entered the property the relaxation began!! The location and history of the area was interesting. The rooms were comfortable and homey. The screened porch was the central space and the reading knook was never empty. All enjoyed kayaking and paddle boarding in the calm river water. All agreed we would like to revisit the property again. Communication with the owners was prompt and courteous. Thank you"
The price is SAR 2,115
SAR 4,150 total
includes taxes & fees
18 Mar - 19 Mar
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.
Dover Home - 2 Mi to Delaware State University!
Fridge, microwave, stovetop, dishwasher

Dover Home - 2 Mi to Delaware State University!

9.0 out of 10, Wonderful, (6)
"Very comfortable and convenient to our work site. Clean, beds comfortable, and had basics for cooking and relaxing. We will stay again. "
Dover Home - 2 Mi to Delaware State University!
Newly renovated single family home with attached guest suite
Smart TV

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite
Guest Lodge | Private Pool | Outdoor Dining | Game Room
Exterior

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room
Pet-Friendly Home on Chester River w/ Dock!
Interior

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (4)
"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"
Pet-Friendly Home on Chester River w/ Dock!
3 Mi to Dover Motor Speedway: Pet-Friendly Retreat
Fridge, microwave, stovetop, dishwasher

3 Mi to Dover Motor Speedway: Pet-Friendly Retreat

3 Mi to Dover Motor Speedway: Pet-Friendly Retreat
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Dining

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Saybrook Hall | Pickleball + Pool + Hot Tub
Pool

Saybrook Hall | Pickleball + Pool + Hot Tub

Saybrook Hall | Pickleball + Pool + Hot Tub
Private Peaceful Waterfront House with Pool & Hot Tub
Microwave, oven, stovetop, dishwasher

Private Peaceful Waterfront House with Pool & Hot Tub

8.0 out of 10, Very Good, (4)
"The home was nice - great to fit our group of 12, good room for sitting and dining and sleeping, and a nice open layout with the kitchen opening up to the living room. The host also was quite communicative. Overall, this was a good stay.Cons:The biggest offense lacking was that there were no real kitchen knives (one utensil mostly resembled a knife) which made preparing a meal for 12 quite difficult. There also was not shampoo/conditioner/body wash provided in the bathrooms.The hot tub also...
Private Peaceful Waterfront House with Pool & Hot Tub
Nancy’s Touch, A Waterfront Paradise!
Property grounds

Nancy’s Touch, A Waterfront Paradise!

10.0 out of 10, Exceptional, (159)
"This was a great Property, with a Great View. Wife & her sister, and 98yr old Mother really enjoyed it."
Nancy’s Touch, A Waterfront Paradise!
Waterfront Home & Dock,Remodel Kitchen,Eastern shore, Betterton,Chestertown MD.
Miscellaneous

Waterfront Home & Dock,Remodel Kitchen,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,Remodel Kitchen,Eastern shore, Betterton,Chestertown MD.
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Terrace/patio

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (75)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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
Spring Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal
Fridge, microwave, oven, stovetop

Spring Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal

10.0 out of 10, Exceptional, (65)
"The place was great!!"
Spring Season in Chesapeake City, MD 'Old Lock View' @ C&D Canal
Harbor View Haven | Waterfront w/ HOT TUB + Dock!
Exterior

Harbor View Haven | Waterfront w/ HOT TUB + Dock!

10.0 out of 10, Exceptional, (17)
"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!
Upper Chesapeake Getaway - Newly Renovated
Property grounds

Upper Chesapeake Getaway - Newly Renovated

9.8 out of 10, Exceptional, (14)
"Really peaceful. Nice house!"
Upper Chesapeake Getaway - Newly Renovated
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (10)
"This house is very nice and conveniently close to Washington College. Teddi was responsive to our last minute rental. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
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

Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (257)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun loungers

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (45)
"Great little home away from home. A small orientation list for newcomers would be helpful. Closest groceries, gas and such. Outside of that all and all VERY pleasing. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
Fridge, microwave, oven, stovetop

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

The price is SAR 506
SAR 1,050 total
includes taxes & fees
18 Mar - 19 Mar
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck
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.