Preston Vacation Rentals

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Vacation Rentals in Preston

Property grounds
Stylish Home on the Choptank River (with Tidal Beach)

Vacation Home in 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)
Outdoor dining
Downtown St. Michaels | Porch + Pet-Friendly

Apartment in Saint Michaels

Downtown St. Michaels | Porch + Pet-Friendly
Property grounds
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Vacation Home in 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
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cottage in 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)
Terrace/patio
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Vacation Home in 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
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

Vacation Home in St. Michaels

9.8 out of 10, Exceptional, (44)
"Wonderful home in excellent location!!"
United States
Sydney S.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Cottage in 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!
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Vacation Home in Cambridge

9.6 out of 10, Exceptional, (19)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
$333 nightly
The price is $353
Dec 8 - Dec 9
Total with taxes and fees
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Fridge, microwave, oven, stovetop
The Middle Point Cabin in Saint Michaels

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

Vacation Home in 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
Exterior
Family and Pet-Friendly, Waterfront with Pier

Cottage in 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
Interior
Beautiful Waterfront Retreat in Cambridge!

Vacation Home in 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.
$355 nightly
The price is $376
Dec 2 - Dec 3
Total with taxes and fees
Beautiful Waterfront Retreat in Cambridge!
Exterior
Dollhouse in Central Historic St Michaels

Vacation Home in St Michaels

9.8 out of 10, Exceptional, (56)
"Great location. House is old and therefore a little quirky, but overall comfortable. "
United States
Karen L.
Dollhouse in Central Historic St Michaels
Fridge, microwave, oven, stovetop
Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!

Vacation Home in 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!
Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

Vacation Home in 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
Outdoor dining
Bayfront Retreat Near St. Michaels | Private Dock • Sunset Views

Vacation Home in 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
Fridge, microwave, oven, stovetop
Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families

Vacation Home in Tilghman Island

10.0 out of 10, Exceptional, (14)
"The space was perfect for our group. We enjoyed the food at Two If By Sea and at the country store - both were in walking distance. "
United States
Bernadette S.
Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Cottage in 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
Private kitchen
The Farm House at Hunting Creek

Vacation Home in 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
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

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Great amenities, excellent spa and service, friendly staff and great food."
Janet 1-night trip
Posted 3 days ago
Hyatt Regency Chesapeake Bay

Find out more about Preston

Everything you need to know about Preston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Preston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Preston vacation 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 low season months. For more hustle and bustle, you may prefer to visit Preston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $353 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Preston rentals

At Expedia, we put the best Preston vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Preston?

Yes, there are vacation rentals near top attractions in Preston, or you can choose a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental in Preston?

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28: Located near Preston, this vacation home rental is located on a river and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 larger area, you’ll find The Third Haven Friends Meeting House and Academy of the Arts.

What’s a vacation rental in Preston like?

Vacation rentals are private properties where you can stay for a couple of days or more in Preston. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.