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Featured Holiday Homes in Preston

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
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
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
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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)
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 30.2 mi (48.6 km) from Lewes Beach and 31.4 mi (50.6 km) from Rehoboth Beach ...
Newly built riverfront home with dock, kayaks, basketball court, & game room
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!
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
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford
Located in Woolford, this vacation home is in a rural location, within a 10-minute drive of Blackwater National Wildlife Refuge and Harriet Tubman State Park ...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

St. Michaels
Located in St. Michaels, this vacation home is on the waterfront, within a 10-minute drive of Saint Michaels Village and St. Michaels Winery.
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock
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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
AU$125
Highest Price
AU$634
Popular accommodation
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals, Walk to Everything House, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, Stylish Home on the Choptank River (with Tidal Beach), Newly built riverfront home with dock, kayaks, basketball court, & game room, Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Top trending hotels in Preston

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
100 Heron Blvd, Cambridge, MD
Fully refundableReserve now, pay when you stay
The price is AU$430 per night from 24 Feb to 25 Feb
AU$430
includes taxes & fees
24 Feb - 25 Feb
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 6 minutes from Dorchester County Visitors ...
Hyatt Regency Chesapeake Bay
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is AU$634 per night from 26 Feb to 27 Feb
AU$634
includes taxes & fees
26 Feb - 27 Feb
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, steps from Perry Cabin Park and 8 minutes by foot from Higgins Yacht Yard and Marina.
Inn at Perry Cabin
St Michaels Inn

St Michaels Inn

2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
Fully refundableReserve now, pay when you stay
The price is AU$137 per night from 9 Mar to 10 Mar
AU$137
includes taxes & fees
9 Mar - 10 Mar
When you stay at St Michaels Inn in St. Michaels, you'll be in the historical district, within a 5-minute drive of St. Michaels Winery and Chesapeake Bay Maritime ...
St Michaels Inn
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Days Inn & Suites by Wyndham Seaford

Days Inn & Suites by Wyndham Seaford

2 out of 5
23450 Sussex Highway, Seaford, DE
Fully refundableReserve now, pay when you stay
The price is AU$125 per night from 2 Mar to 3 Mar
AU$125
includes taxes & fees
2 Mar - 3 Mar
With a stay at Days Inn & Suites by Wyndham Seaford in Seaford, you'll be 32.2 mi (51.8 km) from Rehoboth Beach and 11.9 mi (19.2 km) from Delaware Technical ...
Days Inn & Suites by Wyndham Seaford
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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.