Book Holiday Homes in Massey

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Featured Holiday Homes in Massey

Sailor's Sunrise Cottage - Chesapeake Bay

Sailor's Sunrise Cottage - Chesapeake Bay

Perryville
When you stay at this vacation home in Perryville, you'll be on the waterfront, within a 5-minute drive of Craft Haven Marina and Chestnut Point Estates and ...
Opens in a new windowSailor's Sunrise Cottage - Chesapeake Bay
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Chestertown
A stay at this vacation home places you in the heart of Chestertown, steps from Historical Society of Kent County Maryland and Chestertown Historic ...
Opens in a new windowCirca 1900 Home in the Heart of Historic Downtown Chestertown
Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!

Chesapeake City
With a stay at this vacation home in Chesapeake City, you'll be within a 5-minute walk of Chesapeake City Town Hall and Chesapeake City Bridge.
Opens in a new windowElegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!
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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

Middletown
With a stay at this vacation home in Middletown, you'll be within a 5-minute drive of Middletown Historic District and The Everett Annex.
Opens in a new windowSpacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

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

Millington
Located in Millington, this vacation home is on the waterfront, within a 10-minute drive of Crumpton Auction and Crumpton Park.
Opens in a new windowLark's Nest on the Chester River. Spacious, waterfront home with private dock.
Chesapeake Point | Waterfront w/ HOT TUB + Beach!

Chesapeake Point | Waterfront w/ HOT TUB + Beach!

Elkton
Located in Elkton, this vacation home is on the waterfront, within a 15-minute drive of Elkton Golf and Batting Center and Union Hospital.
Opens in a new windowChesapeake Point | Waterfront w/ HOT TUB + Beach!
Chesapeake City Quiet Overlook

Chesapeake City Quiet Overlook

Chesapeake City
With a stay at this vacation home in Chesapeake City, you'll be on the waterfront, a 5-minute walk from Chesapeake City Bridge and a 3-minute drive from Cecil ...
Opens in a new windowChesapeake City Quiet Overlook
Waterfront Lodge packed with Amenities

Waterfront Lodge packed with Amenities

Earleville
Located in Earleville, this vacation home is on the waterfront, a 4-minute drive from Earleville Wildlife Management Area and 9 minutes from Long Point ...
Opens in a new windowWaterfront Lodge packed with Amenities
Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

2 out of 5
Kennedyville
With a stay at this vacation home in Kennedyville, you'll be within a 5-minute drive of Urieville Lake Fish Management Area and Urieville Park.
Opens in a new windowSpacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.
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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.

Massey Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Massey vacation homes are the perfect way for you to wing it.

Holiday houses in Massey let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Massey in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Massey adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Massey with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Massey vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Massey Holiday Homes essential information

Accommodation
76 Holiday Homes
Lowest Price
AU$126
Highest Price
AU$176
Popular accommodation
Sailor's Sunrise Cottage - Chesapeake Bay, Circa 1900 Home in the Heart of Historic Downtown Chestertown, Elegant Retreat With Pool, Screened Porch Just Steps From Shops, Dining & Fun!, Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6, Lark's Nest on the Chester River. Spacious, waterfront home with private dock., Chesapeake Point | Waterfront w/ HOT TUB + Beach!, Chesapeake City Quiet Overlook, Waterfront Lodge packed with Amenities, Spacious 4 bedroom house with 2 and a half baths in Kennedyville, Maryland.

Top trending hotels in Massey

Bally's Dover Casino Resort

Bally's Dover Casino Resort

4 out of 5
1131 N Dupont Hwy, Dover, DE
Fully refundableReserve now, pay when you stay
The price is AU$147 per night from 21 Sept to 22 Sept
AU$147
21 Sept - 22 Sept
includes taxes & fees
With a stay at Bally's Dover Casino Resort in Dover, you'll be just steps from Dover Downs Casino and 7 minutes by foot from Dover International Speedway.
Opens in a new windowBally's Dover Casino Resort
Comfort Inn & Suites

Comfort Inn & Suites

2.5 out of 5
764 Dover Leipsic Road, Dover, DE
Fully refundableReserve now, pay when you stay
The price is AU$151 per night from 28 Sept to 29 Sept
AU$151
28 Sept - 29 Sept
includes taxes & fees
With a stay at Comfort Inn & Suites in Dover, you'll be within a 5-minute drive of Dover Downs Casino and Dover International Speedway.
Opens in a new windowComfort Inn & Suites
Red Roof Inn & Suites Dover Downtown

Red Roof Inn & Suites Dover Downtown

2 out of 5
652 N Dupont Hwy, I-95 To Exit #4-a, Dover, DE
Fully refundableReserve now, pay when you stay
The price is AU$126 per night from 12 Oct to 13 Oct
AU$126
12 Oct - 13 Oct
includes taxes & fees
With a stay at Red Roof Inn & Suites Dover Downtown in Dover, you'll be within a 5-minute drive of Dover Downs Casino and Dover International Speedway.
Opens in a new windowRed Roof Inn & Suites Dover Downtown
Save an average of 15% on thousands of hotels when you're signed in
Holiday Inn Express Hotel & Suites Dover by IHG

Holiday Inn Express Hotel & Suites Dover by IHG

2.5 out of 5
1780 N Dupont Hwy, Dover, DE
Fully refundable
The price is AU$176 per night from 19 Oct to 20 Oct
AU$176
19 Oct - 20 Oct
includes taxes & fees
With a stay at Holiday Inn Express Hotel & Suites Dover by IHG in Dover, you'll be within a 5-minute drive of Dover Downs Casino and Dover International ...
Opens in a new windowHoliday Inn Express Hotel & Suites Dover by IHG
Don't see what you're looking for?
See all available properties in Massey
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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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^Subject to availability and chosen travel dates.