Search Vacation Homes in Preston

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

Vacation Homes in Preston

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.8 out of 10, Exceptional, (11)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is AED 1,084
AED 1,966 total
includes taxes & fees
24 Jul - 25 Jul
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Outdoor pool

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

10.0 out of 10, Exceptional, (133)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Marina

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"We really enjoyed this property. It had everything we would want and plenty of space. It was very clean and quiet. The water, fire-pit, porch and living spaces were wonderful for a nice long-weekend get-away!"
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Terrace/patio

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

9.8 out of 10, Exceptional, (127)
"We had a wonderful long weekend here. Perfect weather let us swim and kayak and fish all weekend. House was spacious enough for two families of five plus our dog. The views were perfect!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Beautiful Waterfront Retreat in Cambridge!
Interior

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (41)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is AED 1,047
AED 1,935 total
includes taxes & fees
18 Aug - 19 Aug
Beautiful Waterfront Retreat in Cambridge!
Waterfront Sunset Bayview: sleeps 6
Terrace/patio

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (17)
"Loved the location, the property, and amenities. Would definitely stay again!"
Waterfront Sunset Bayview: sleeps 6
St. Michaels Waterfront Home
Property grounds

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (29)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home
Peaceful Queenstown Home w/ Deck & Grill!
Interior

Peaceful Queenstown Home w/ Deck & Grill!

9.6 out of 10, Exceptional, (9)
"Very cozy, a very quiet home"
Peaceful Queenstown Home w/ Deck & Grill!
Luxury Treehouse with Large Deck
Interior

Luxury Treehouse with Large Deck

10.0 out of 10, Exceptional, (4)
"We had a wonderful time and the Treehouse was perfect, very clean, thoughtful owner! Wish we had more time to enjoy!!! "
Luxury Treehouse with Large Deck
Heated pool, sandy beach, pier, and playground set punch point apart!
Beach nearby, sun loungers, beach towels

Heated pool, sandy beach, pier, and playground set punch point apart!

10.0 out of 10, Exceptional, (7)
"Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend."
Heated pool, sandy beach, pier, and playground set punch point apart!
RELAX- Eastern Shore Creek Home - 6 Guests
Smart TV, fireplace

RELAX- Eastern Shore Creek Home - 6 Guests

10.0 out of 10, Exceptional, (2)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
RELAX- Eastern Shore Creek Home - 6 Guests
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
Fridge, microwave, oven, stovetop

Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18

10.0 out of 10, Exceptional, (76)
"We were very impressed with the property and your place was very clean and had just about everything we needed. The location is wonderful and close to the event that we stayed in Cambridge for. I would definitely recommend this for others and will likely be renting again"
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Outdoor dining

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

10.0 out of 10, Exceptional, (8)
"My husband and I spent Christmas on Tilghman Island in this unique house right on the water. It was perfect for us to rest, relax and cook Christmas dinner. We enjoyed it so much we want to visit again when the boats are out. The yard was perfect for our dog to get some exercise. I can see this as a perfect place for family and friends in the summer."
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (45)
"Fit all of our needs. Clean,well furnished, nice kitchen. Stayed there twice and will probably go back."
The price is AED 845
AED 1,020 total
includes taxes & fees
30 Jul - 31 Jul
Waterfront Getaway with Dock
Grasonville Home w/ Private Pool on the Water
Pool

Grasonville Home w/ Private Pool on the Water

10.0 out of 10, Exceptional, (21)
"Location was great for our stay"
Grasonville Home w/ Private Pool on the Water
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

9.8 out of 10, Exceptional, (11)
"Great overnight stay for a wedding nearby. Would highly recommend!"
The price is AED 918
AED 1,557 total
includes taxes & fees
21 Jul - 22 Jul
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
Exterior

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie

10.0 out of 10, Exceptional, (16)
"We loved this home. The location is excellent--close to areas like Easton and St Michael's, but out of the way and secluded. We loved sitting on the lawn by the Dixon Creek and watching the sunset. House is well stocked, and wifi is strong--supported 3 people who had to work. Highly recommend this beautiful home."
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayaks | Pet Frie
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien
Interior

Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien

10.0 out of 10, Exceptional, (4)
"Very relaxing house to stay in. Plenty of room and well stocked kitchen . Close to St. Michaels and Cambridge. We were there for the Eagleman triathlon and we really enjoyed the seclusion. "
Minutes from Downtown Easton and St. Michaels | Private Dock | Kayak | Pet Frien
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.
Outdoor pool

Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

10.0 out of 10, Exceptional, (5)
"This is such a special property. The house, the amenities and then the surprising foodie scene in Easton and St. Michael’s is within minutes. This is our second summer at this property and we are already starting to plan our third!"
Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (40)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Preston Hotel Reviews

Hampton Inn Seaford

Hampton Inn Seaford

10/10 Excellent
"I love it "
Rachela 2-night trip
Posted 18 hours ago
Hampton Inn Seaford