Search Vacation Homes in Massey

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Massey

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (260)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (160)
"The property was great, clean and spacious. The views were remarkable and amenities exactly what we needed while we are working a major event."
Chesapeake Bay House with Dock & Private Beach

3 Mi to Dtwn: Townhome w/ Deck in Dover

3 Mi to Dtwn: Townhome w/ Deck in Dover

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

9.6 out of 10, Exceptional, (14)
"Lovely home; welcoming and comfortable, very helpful and communicative property manager."
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

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

9.4 out of 10, Exceptional, (3)
"Nice and quiet place to stay"
The price is SAR 521
SAR 1,054 total
includes taxes & fees
16 Jun - 17 Jun
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

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

9.6 out of 10, Exceptional, (39)
"This is the second time my husband and I have stayed here. Despite a mixed bag of weather ranging from snow, rain, winds, and sunshine, the visit did not disappoint. We were still able to walk on the beach, view the resident bald eagle, immerse ourselves in the ever changing water views and visit surrounding towns.The house was warm and welcoming."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

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

10.0 out of 10, Exceptional, (77)
"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!

Luxury 2-bedroom house with Water views, Chesapeake City

2.0 star property
Luxury 2-bedroom house with Water views, Chesapeake City

Chesapeake City Quiet Overlook

10.0 out of 10, Exceptional, (18)
"Everyone in our family ages 8, 10, 17, 18, 38, 64, and 71 thought the house and location were perfect and we had a great stay."
Chesapeake City Quiet Overlook

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

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

10.0 out of 10, Exceptional, (12)
"Very friendly and helpful host and a great property. "
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (68)
"Enjoyed the stay and house very comfortable."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

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

9.4 out of 10, Exceptional, (46)
"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

Waterfront House on the Upper Chesapeake Bay

9.0 out of 10, Wonderful, (4)
"My boyfriend and i had a great 2 days! So peaceful bing on the water. Cottage was equipped with everything you would need!"
Waterfront House on the Upper Chesapeake Bay

Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

9.6 out of 10, Exceptional, (34)
"This was the best Christmas yet and on top of that, the home was amazing, great amenities, great view, great time. Thank you to the host! "
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!

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

Dover Home - 2 Mi to Delaware State University!

9.2 out of 10, Wonderful, (10)
"Clean, quiet and convenient spot for our stay in Dover. "
Dover Home - 2 Mi to Delaware State University!

Spacious 4-bedroom house with AC and WiFi in charming Kennedyville

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property was well maintained and convenient to the college"
Spacious 4-bedroom house with AC and WiFi in charming Kennedyville

Your perfect Maryland escape awaits!

10.0 out of 10, Exceptional, (4)
"Our group had another great stay. The house is exactly as pictured and the host is very responsive. Everything was perfect from checkin to departure. We will definitely stay at this house again!! "
Your perfect Maryland escape awaits!

Waterfront Home Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown

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 Private Dock, Boat,fish,Eastern shore, Betterton,Chestertown
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.
Save an average of 15% on thousands of hotels when you're signed in