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Featured Holiday Homes in Preston

Walk to Everything House

Walk to Everything House

Saint Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.
Walk to Everything House
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Cambridge
With a stay at this vacation home in Cambridge, you'll be on the waterfront, and 6.3 mi (10.2 km) from Ragged Island and 7.7 mi (12.4 km) from Spocott ...
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals
Stylish Home on the Choptank River (with Tidal Beach)

Stylish Home on the Choptank River (with Tidal Beach)

Preston
Located in Preston, this vacation home is by the sea, within a 15-minute drive of Gilpin's Point Landing and Williston Lake.
Stylish Home on the Choptank River (with Tidal Beach)
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Newly built riverfront home with dock, kayaks, basketball court, & game room

Newly built riverfront home with dock, kayaks, basketball court, & game room

Seaford
With a stay at this vacation home in Seaford, you'll be on the waterfront, and 31.4 mi (50.6 km) from Rehoboth Beach Boardwalk and 11.6 mi (18.6 km) from Delaware ...
Newly built riverfront home with dock, kayaks, basketball court, & game room
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing

Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing

Cambridge
When you stay at this vacation home in Cambridge, you'll be 8 minutes by car from Spocott Windmill.
Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

2 out of 5
Cambridge
Located in Cambridge, this vacation home is within a 15-minute walk of Harriet Tubman Museum and Educational Center and Richardson Maritime Museum.
Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

St. Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Higgins Yacht Yard and Marina and Muskrat Park.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Cambridge
When you stay at this vacation home in Cambridge, you'll be on the waterfront and 12 minutes by car from Spocott Windmill.
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels
With a stay at this vacation home in St. Michaels, you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and Marina.
Dollhouse in Central Historic St Michaels
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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.

Preston 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 Preston vacation homes are the perfect way for you to wing it.

Holiday houses in Preston 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 Preston 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 Preston adventures, obvs.

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

Preston Holiday Homes essential information

Accommodation
165 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Walk to Everything House, Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, Stylish Home on the Choptank River (with Tidal Beach), Newly built riverfront home with dock, kayaks, basketball court, & game room, Hudson Creek Retreat, 5 Acre Waterfront Home, Pool, Pier, Fishing & Crabbing, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!, Dollhouse in Central Historic St Michaels

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^Subject to availability and chosen travel dates.