Book Holiday Homes in Massey

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Featured Holiday Homes in Massey

Pet-Friendly Home on Chester River w/ Dock!

Pet-Friendly Home on Chester River w/ Dock!

2 out of 5
Chestertown
When you stay at this vacation home in Chestertown, you'll be within a 5-minute drive of Washington College.
Pet-Friendly Home on Chester River w/ Dock!
Chesapeake City Quiet Overlook

Chesapeake City Quiet Overlook

Chesapeake City
Located in Chesapeake City, this vacation home is on the waterfront, within a 10-minute drive of C and D Canal Museum and Lums Pond State Park.
Chesapeake City Quiet Overlook
Luxurious and spacious townhome with all necessary amenities awaits your stay.

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

Middletown
Located in Middletown, this vacation home is within a 5-minute drive of Dutch Country Farmers Market and Appoquinimink Friends Meeting House.
Luxurious and spacious townhome with all necessary amenities awaits your stay.
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Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay

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

Perryville
Located in Perryville, this vacation home is on the waterfront, within a 15-minute drive of Garrett Island Beach and Hollywood Casino.
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

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

Betterton
When you stay at this vacation home in Betterton, you'll be on the waterfront and 7 minutes by foot from Betterton Beach.
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

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

Chestertown
When you stay at this vacation home in Chestertown, you'll be within a 5-minute drive of Washington College.
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Right in the center of everywhere in Dover

Right in the center of everywhere in Dover

Dover
With a stay at this vacation home in Dover, you'll be within a 5-minute drive of Williams Park and Silver Lake Park.
Right in the center of everywhere in Dover
Upper Chesapeake Getaway - Newly Renovated

Upper Chesapeake Getaway - Newly Renovated

Perryville
Located in Perryville, this vacation home is on the waterfront, within a 15-minute drive of Garrett Island Beach and Hollywood Casino.
Upper Chesapeake Getaway - Newly Renovated
Mill Creek River House with hot tub Smyrna Dover riverfront with kayaks

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

Smyrna
Located in Smyrna, this vacation home is on the waterfront, within a 15-minute drive of Bayhealth Emergency Center - Smyrna and Woodland Beach.
Mill Creek River House with hot tub Smyrna Dover riverfront with kayaks
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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
50 Holiday Homes
Lowest Price
AU$134
Highest Price
AU$144
Popular accommodation
Pet-Friendly Home on Chester River w/ Dock!, Chesapeake City Quiet Overlook, Luxurious and spacious townhome with all necessary amenities awaits your stay., 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, Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest , Right in the center of everywhere in Dover, Upper Chesapeake Getaway - Newly Renovated, Mill Creek River House with hot tub Smyrna Dover riverfront with kayaks

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$134 per night from 24 Dec to 25 Dec
AU$134
includes taxes & fees
24 Dec - 25 Dec
With a stay at Bally's Dover Casino Resort in Dover, you'll be a 2-minute walk from Dover Downs Casino and 7 minutes by foot from Dover Mall.
Bally'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$144 per night from 5 Jan to 6 Jan
AU$144
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Comfort Inn & Suites in Dover, you'll be within a 10-minute walk of Delaware Agricultural Museum and Village and Delaware State University.
Comfort Inn & Suites
Wyndham Garden Dover

Wyndham Garden Dover

3 out of 5
561 N Dupont Hwy, Dover, DE
Fully refundableReserve now, pay when you stay
The price is AU$134 per night from 12 Jan to 13 Jan
AU$134
includes taxes & fees
12 Jan - 13 Jan 2025
When you stay at Wyndham Garden Dover in Dover, you'll be in the business district, within a 5-minute drive of Delaware Agricultural Museum and Village and Delaware ...
Wyndham Garden Dover
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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$134 per night from 24 Dec to 25 Dec
AU$134
includes taxes & fees
24 Dec - 25 Dec
With a stay at Red Roof Inn & Suites Dover Downtown in Dover, you'll be a 3-minute walk from Delaware Agricultural Museum and Village and 9 minutes by foot from ...
Red Roof Inn & Suites Dover Downtown
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.