Book Holiday Homes in Preston

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Preston

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets

Tilghman Island MD
When you stay at this vacation home in Tilghman, you'll be on the waterfront, within a 15-minute walk of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new windowWaterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Cambridge MD
With a stay at this vacation home in Cambridge, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Spocott Windmill.
Opens in a new windowWaterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock

St. Michaels MD
Located in St. Michaels, this vacation home is on the waterfront, within a 10-minute drive of St Michaels Nature Trail and Higgins Yacht Yard and Marina.
Opens in a new windowMinutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Save an average of 15% on thousands of hotels when you're signed in
“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.

“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.

Easton MD
Located in Easton, this vacation home is within a 5-minute drive of Easton Cycle and Sport and Talbot Massage.
Opens in a new window“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.
Waterfront Sunset Bayview: sleeps 6

Waterfront Sunset Bayview: sleeps 6

Chester MD
With a stay at this vacation home in Chester, you'll be on the waterfront, within a 15-minute drive of Chesapeake Bay and Chesapeake Exploration Center.
Opens in a new windowWaterfront Sunset Bayview: sleeps 6
Stunning Waterfront Hideaway on Michener's Choptank River.  Special Rates*

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

Greensboro MD
With a stay at this vacation home in Greensboro, you'll be on the waterfront, and 28.8 mi (46.4 km) from Dover Downs Casino and 29.5 mi (47.5 km) from Dover ...
Opens in a new windowStunning Waterfront Hideaway on Michener's Choptank River. Special Rates*
Luxury Treehouse with Large Deck

Luxury Treehouse with Large Deck

Harrington DE
When you stay at this vacation home in Greenwood, you'll be 11 minutes by car from Abbott's Mill Nature Center.
Opens in a new windowLuxury Treehouse with Large Deck
Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

St Michaels MD
With a stay at this vacation home in St. Michaels (Downtown St. Michaels), you'll be within a 5-minute walk of Muskrat Park and Higgins Yacht Yard and ...
Opens in a new windowDollhouse in Central Historic St Michaels
"Endless Summer" Waterfront on the Chesapeake Bay!

"Endless Summer" Waterfront on the Chesapeake Bay!

Woolford MD
When you stay at this vacation home in Woolford, you'll be 14 minutes by car from Blackwater National Wildlife Refuge.
Opens in a new window"Endless Summer" Waterfront on the Chesapeake Bay!
Don't see what you're looking for?
See all available properties in Preston
View all properties
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
203 Holiday Homes
Lowest Price
AU$168
Highest Price
AU$928
Popular accommodation
Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets, Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW, Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock, “It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches., Waterfront Sunset Bayview: sleeps 6, Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*, Luxury Treehouse with Large Deck, Dollhouse in Central Historic St Michaels, "Endless Summer" Waterfront on the Chesapeake Bay!

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$416 per night from 26 May to 27 May
AU$416
26 May - 27 May
includes taxes & fees
Located in Cambridge, Hyatt Regency Chesapeake Bay is on the waterfront, a 4-minute drive from Bay Country Shop and 5 minutes from Eastern Shore Hospital ...
Opens in a new windowHyatt 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$928 per night from 31 May to 1 June
AU$928
31 May - 1 June
includes taxes & fees
A stay at Inn at Perry Cabin places you in the heart of St. Michaels, within a 15-minute walk of Perry Cabin Park and Saint Michaels Town Hall.
Opens in a new windowInn at Perry Cabin
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

2.5 out of 5
8708 Alicia Drive Easton MD
Fully refundableReserve now, pay when you stay
The price is AU$168 per night from 17 May to 18 May
AU$168
17 May - 18 May
includes taxes & fees
With a stay at Best Western Plus Easton Inn & Suites in Easton, you'll be within a 5-minute drive of Easton Cycle and Sport and Talbot Massage.
Opens in a new windowBest Western Plus Easton Inn & Suites
Save an average of 15% on thousands of hotels when you're signed in
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$199 per night from 1 June to 2 June
AU$199
1 June - 2 June
includes taxes & fees
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 ...
Opens in a new windowSt Michaels Inn
Don't see what you're looking for?
See all available properties in Preston
View all properties
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.