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Featured Holiday Homes in Preston

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
Tranquil  Beautiful Waterfront  Near Historic St. Michaels & Royal Oak

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

easton
With a stay at this vacation home, you'll be centrally located in Easton, within a 10-minute drive of Saint Michaels Village and St. Michaels Winery.
Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac

Easton
When you stay at this vacation home in Easton, you'll be on the waterfront and 14 minutes by car from Hog Neck Golf Course.
Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac
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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
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Greenwood
Located in Greenwood, this vacation home is in a rural location, within a 15-minute drive of T.S. Smith & Sons and Bridgeville Historical Society Museum.
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
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
Serene Waterfront Minutes from St Michaels.

Serene Waterfront Minutes from St Michaels.

Easton
Located in Easton, this vacation home is on the waterfront, a 5-minute drive from Saint Michaels Village and 6 minutes from St. Michaels Winery.
Serene Waterfront Minutes from St Michaels.
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
The price is AU$623 per night from 29 Apr to 30 Apr
AU$623
includes taxes & fees
29 Apr - 30 Apr
A stay at this vacation home places you in the heart of Cambridge, steps from Long Wharf Park and Choptank River Lighthouse.
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Time Stands Still At the Dock.

Time Stands Still At the Dock.

Tilghman Island
When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Tilghman Watermen’s Museum and Talbot County Library ...
Time Stands Still At the 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
210 Holiday Homes
Lowest Price
AU$154
Highest Price
AU$945
Popular accommodation
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak, Beautiful, Open floor plan, amazing sunset views,Waterside Pool, Pier, 6+ac, Walk to Everything House, Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf, Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC, Serene Waterfront Minutes from St Michaels., Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, Time Stands Still At the 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 6 May to 7 May
AU$430
includes taxes & fees
6 May - 7 May
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$945 per night from 4 May to 5 May
AU$945
includes taxes & fees
4 May - 5 May
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$212 per night from 29 Apr to 30 Apr
AU$212
includes taxes & fees
29 Apr - 30 Apr
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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Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG

Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG

2.5 out of 5
17271 S Dupont Hwy, Harrington, DE
Fully refundable
The price is AU$154 per night from 1 May to 2 May
AU$154
includes taxes & fees
1 May - 2 May
Located in Harrington, Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG is within a 5-minute drive of Harrington Raceway and Casino and Delaware ...
Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG
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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.