Preston Holiday Rentals

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Holiday Rentals in Preston

Stylish Home on the Choptank River (with Tidal Beach)

Preston
10.0 out of 10, Exceptional, (43)
"The house was great with a wonderful river view! Easily accommodated 5 adults."
United States
Karen
Stylish Home on the Choptank River (with Tidal Beach)

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

Greenwood
9.8 out of 10, Exceptional, (31)
"Great place to stay with a family. Very nicely decorated and clean. "
United States
Meg E.
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Downtown St. Michaels | Porch + Pet-Friendly

Saint Michaels
Downtown St. Michaels | Porch + Pet-Friendly

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge
10.0 out of 10, Exceptional, (15)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge
10.0 out of 10, Exceptional, (80)
"Great for 10 adults and 4 grandchildren!"
United States
Phil S.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

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

St. Michaels
9.8 out of 10, Exceptional, (45)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels
9.6 out of 10, Exceptional, (124)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
9.6 out of 10, Exceptional, (20)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
The price is AU$535
includes taxes & fees
8 Dec - 9 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

The Middle Point Cabin in Saint Michaels

Neavitt
9.8 out of 10, Exceptional, (56)
"We had a great stay. The cottage is just like the pictures. Nice area…lots of things to do."
United States
Michael
The Middle Point Cabin in Saint Michaels

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge
9.8 out of 10, Exceptional, (7)
"Wow! What an incredible property and house. We were a group of families with small kids, and it was heaven for them playing in the pool, on the dock, on the playground, and in the expansive yard. Lots of beautiful sunsets on the patio for the grown-ups too. We never had to leave. Can't recommend highly enough. "
United States
Lea F.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Family and Pet-Friendly, Waterfront with Pier

Cambridge
10.0 out of 10, Exceptional, (264)
"The property, house and amenities were exactly as described. Absolutely gorgeous views second only to the hospitality extended by Rob and Clarissa!"
United States
Tom K.
Family and Pet-Friendly, Waterfront with Pier

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Just what we were looking for. Appreciated the little touches such as already baited crab traps and the complimentary smores kit. "
United States
Dan K.
The price is AU$585
includes taxes & fees
8 Dec - 9 Dec
Beautiful Waterfront Retreat in Cambridge!

Dollhouse in Central Historic St Michaels

St Michaels
9.8 out of 10, Exceptional, (56)
"We highly enjoyed our stay. It was a great location and we got a lot of use out of the screened in porch. The coffee shop out back was a great visit in the morning. "
United States
Nitarah I.
Dollhouse in Central Historic St Michaels

Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Madison
9.8 out of 10, Exceptional, (7)
"the place was great. easy access to water and toys."
United States
Allen C.
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels
9.6 out of 10, Exceptional, (125)
"Prime location! "
United States
Cindy V.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou

Cambridge
9.2 out of 10, Wonderful, (5)
"Great stay"
United States
Jovan J.
Short drive to Downtown Cambridge | Private Dock | Pool | 16.5 Acres | Guest Hou

Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Tilghman Island
9.8 out of 10, Exceptional, (10)
"Great property!!! Absolutely would recommend!"
United States
John and Michele E.
Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels
9.6 out of 10, Exceptional, (147)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

The Farm House at Hunting Creek

Easton
10.0 out of 10, Exceptional, (4)
"Perfect, little farmhouse! Good distance from St. Michael's, Tilghman Island, and Annapolis.We all loved staying here! Clean, fair amount of amenities, and good communication with the caretaker, Jason. "
United States
Brittany I.
The Farm House at Hunting Creek

Minutes from Downtown Easton and St. Michaels | Pool

Easton
10.0 out of 10, Exceptional, (3)
"House was perfect for 5 adults and infant. Everyone had ample space but could come together. Property was spotless. Pool and dock were wonderful. Landscaping needs attention and it would have been nice to have a fire pit for the evenings. Otherwise a great place and space!!"
United States
Judi K.
Minutes from Downtown Easton and St. Michaels | Pool
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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Top Preston Hotel Reviews

Find out more about Preston

Everything you need to know about Preston holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Preston holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Preston holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Preston holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Preston. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Preston holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Preston holiday rentals we have selected for you start as low as AU$535 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Preston rentals

At Expedia, we put the best Preston holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Preston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Preston holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Preston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Preston?

Yes, there are holiday rentals close to the most popular sights in Preston, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Preston has to offer?

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28: This holiday home rental outside of Preston is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What’s there to see and do in Preston?

Gilpin's Point Landing and Williston Lake are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find The Third Haven Friends Meeting House and Academy of the Arts.

What’s a holiday rental in Preston like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Preston. Holiday rentals provide amenities such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, holiday rentals can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.