Search Vacation Homes in Massey

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Compare 71 Vacation Homes in Massey with updated reviews, rates, and availability.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (259)
"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

9.0 out of 10, Wonderful, (2)
"Nice and quiet place to stay"
The price is AED 496
AED 1,032 total
includes taxes & fees
6 May - 7 May
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

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

9.8 out of 10, Exceptional, (13)
"Beautiful house, perfect for our family. The humans loved kayaking and bird watching on the river, the canine loved sitting out on the fenced in deck and relaxing in the nice cool AC"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

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

9.8 out of 10, Exceptional, (16)
"The home was perfect for our family of 10. We spent most of our time on the beautiful screened in porch overlooking the river. The location was within a 5 min drive to all our favorite restaurants. The owners are very accommodating and quick to answer any questions. "
Riverfront Country House on Sassafras River. Kayak and Paddleboard. So peaceful.

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

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

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite

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!

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

10.0 out of 10, Exceptional, (76)
"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!

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

9.4 out of 10, Exceptional, (33)
"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!

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

9.6 out of 10, Exceptional, (44)
"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

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

Upper Chesapeake Getaway - Newly Renovated

9.8 out of 10, Exceptional, (14)
"We loved staying at this property. The house was fully updated and stocked with all of the amenities you could ever imagine. The view is absolutely gorgeous and the sunroom and deck were so fun to use. Would definitely recommend for a getaway vacation!"
Upper Chesapeake Getaway - Newly Renovated

Dover Home - 2 Mi to Delaware State University!

9.2 out of 10, Wonderful, (9)
"Clean, quiet and convenient spot for our stay in Dover. "
Dover Home - 2 Mi to Delaware State University!

Harbor View Haven | Waterfront w/ Hot Tub + Dock!

10.0 out of 10, Exceptional, (17)
"Enjoyed all aspects of this property!"
Harbor View Haven | Waterfront w/ Hot Tub + Dock!

Amazing Modern house with a full kitchen and parking

9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
The price is AED 367
AED 960 total
includes taxes & fees
7 May - 8 May
Amazing Modern house with a full kitchen and parking

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (68)
"Lovely, well kept and tastefully furnished house in a great location."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

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!

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room

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

9.6 out of 10, Exceptional, (37)
"This is the perfect house - great spot right on the bay in Betterton, plenty of space, and everything you need for a relaxing vacation. We had a great time and can't wait to come back again."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

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

10.0 out of 10, Exceptional, (52)
"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.
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Other property types in Massey

Chesapeake Romantic Waterfront Home with Private Pool

8.8 out of 10, Excellent, (5)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake Romantic Waterfront Home with Private Pool

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (259)
"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

9.0 out of 10, Wonderful, (2)
"Nice and quiet place to stay"
The price is AED 496
AED 1,032 total
includes taxes & fees
6 May - 7 May
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.