Preston Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Preston

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, 4 reviews
"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 105 reviews
"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Walk to Everything House
Fridge, microwave, oven, stovetop
Walk to Everything House
10.0 out of 10, Exceptional, 64 reviews
"The house was perfectly located in town in St. Michael’s with off street parking as a bonus. Despite the weather being cold and rainy, we had a lovely time in charming St. Michaels. It was a delightful spot for our annual girls weekend."
Walk to Everything House
Beautiful Waterfront Retreat in Cambridge!
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, 17 reviews
"We enjoyed our trip, the house was fully equipped and had all the comforts you could need. The water view, watching the birds, the kayak, the dock at sunrise, were our favorite things. We look forward to coming back sometime soon."
The price is $292
$505 total
includes taxes & fees
Jun 16 - Jun 17
Beautiful Waterfront Retreat in Cambridge!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, 109 reviews
"We had a wonderful trip to St. Michaels. This house is in the perfect location and has everything you need for a great stay!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, 155 reviews
"Very nice home! It was decorated with many antiques and gave you a feeling of another time but with all the modern amenities for a wonderful time."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, 198 reviews
"We love staying at Magee Cottage. It has all you need to relax and enjoy such a comfortable home on the water. This is our second stay and we’ll hurry back in a few months for more of the good life!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, 127 reviews
"The house looked better than the pictures. It was very cozy and had everything we needed. It’s probably the best location for walking around town. Water pressure in the shower was decent, and the beds were comfortable."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
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, 27 reviews
"The house was perfect for our needs. It has a cute, fenced in yard so our 2 dogs could hang outside. It had everything we needed for a wonderful weekend birthday celebration!"
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Dollhouse in Central Historic St Michaels
Exterior
Dollhouse in Central Historic St Michaels
9.8 out of 10, Exceptional, 38 reviews
"Cute little place close to town. Perfect for what we wanted."
Dollhouse in Central Historic St Michaels
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Pool
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, 1 review
"This was the most peaceful and perfect property. I felt like I was on vacation and able to relax! We would definitely return if we are in the area again."
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Property grounds
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
10.0 out of 10, Exceptional, 1 review
"Property and location couldn't be better! Host was very accommodating and quick to respond. Will definitely go back!"
The price is $215
$442 total
includes taxes & fees
Jun 16 - Jun 17
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Waterfront, cozy cottage with private pool on 27 acres of privacy
Beach nearby
Waterfront, cozy cottage with private pool on 27 acres of privacy
9.8 out of 10, Exceptional, 85 reviews
"We came for the Ironman 140.6 and we lucked out finding this lovely cottage! It was the perfect location, the property was beautful, and the house was very clean and had everything we needed. Dave and Cindy were so kind and helpful! They welcomed us to the property, gave us restaurant recommendations, let us pick some figs, and were very helpful when I left something behind. We would love to stay again!"
Waterfront, cozy cottage with private pool on 27 acres of privacy
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, 31 reviews
"One of the best properties I have stayed at. With all the amenities, you never need to leave the home. We enjoyed the views, the quietness of the area, and the wildlife. We nicknamed two beautiful ducks…Sonny and Cher! The house is very clean, the checkin checkout procedures were very easy. The host communicated all the details plus additional suggestions. We are definitely returning very soon."
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
10.0 out of 10, Exceptional, 5 reviews
"We had a lovely stay at The Blue Heron. We had a retreat scheduled with friends that we had to relocate last minute due to snow in western Maryland. We stumbled upon this listing, and the home was perfect for our needs. Plenty of beds, fully stocked kitchen, several rooms and couches for those who wanted to read, others to play games, and others to watch football playoffs on tv. The best part of the house was the dining room table that could seat up to 18 (?). It was nice to be able to not have...
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, 25 reviews
"We loved the proterty! House was set up with pleanty of room for 4 of us. It was clean and comfortable. Out back was very private. Would definitely stay here again. We had a blast!"
The price is $220
$267 total
includes taxes & fees
Jun 26 - Jun 27
Waterfront Getaway with Dock
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Lake
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, 67 reviews
"Wonderful house. Well stocked with supplies. Great open floor plan along with a couple separate spaces on the main floor. Our group had 7 adults and our eight grandchildren six and under. Pool has gated access which was a key feature with all our little ones. The owner provided much info regarding things to do in the area. The bedroom spaces worked out great with our mix. We really enjoyed the crab traps and the dock for fishing. It was mostly casting practice but the kids loved it. We enjoyed...
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Fridge, microwave, oven, stovetop
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
9.6 out of 10, Exceptional, 4 reviews
"Nice place for a getaway."
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
Outdoor pool
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
9.8 out of 10, Exceptional, 51 reviews
"We have enjoyed our stay at the property, everything was very nice and spacious away from everything, just the way we wanted. Our only issue was the landscaping work being done for 2 days of our stay, my son has allergies on cut grass and he ended up staying indoor for the most of those days."
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
Breathtaking Waterfront Estate
Pool
Breathtaking Waterfront Estate
10.0 out of 10, Exceptional, 65 reviews
"The home was spacious and beautifully decorated. Games and bikes and outside fire were perfect for family time. Beautiful scenery and privacy. A perfect stay."
Breathtaking Waterfront Estate
Don't see what you're looking for?
See all available properties in Preston
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.

Other types of properties in Preston you may be interested in

Hyatt Regency Chesapeake Bay
Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, 1,001 reviews
"I loved the sunset, the cleaner, the clean smoke and marihuana free air and the food options. I loved everything about this place. It is a perfect place for a retirement. "
The price is $176
$241 total
includes taxes & fees
Jul 8 - Jul 9
Hyatt Regency Chesapeake Bay
St Michaels Inn
Front of property
St Michaels Inn
2.5 star property
8.2 out of 10, Very Good, 1,000 reviews
"The check-in was fine. The gentleman was very friendly at the desk. The room was average. It appeared clean initially, but the shower did not drain And it smelled when you took a shower because the drain was backing up. Also, there was no stopper in the sink and there was a smell coming from the drain. When I turned down the bed at night, there was a blood stain on the sheets, which was really unappealing to see the least. They didn’t not have a phone in the room to contact the front desk. I had...
The price is $150
$165 total
includes taxes & fees
Jul 7 - Jul 8
St Michaels Inn
Holiday Inn Express Hotel & Suites Harrington-Dover area, DE, an IHG Hotel
Exterior
Holiday Inn Express Hotel & Suites Harrington-Dover area, DE, an IHG Hotel
2.5 star property
9.0 out of 10, Wonderful, 894 reviews
"bed was not comfortable "
The price is $87
$97 total
includes taxes & fees
Jun 16 - Jun 17
Holiday Inn Express Hotel & Suites Harrington-Dover area, DE, an IHG Hotel
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.

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 $215 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.

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?

Beautiful Waterfront Retreat in Cambridge!: You might like this vacation home rental near Preston. It is located on the waterfront and has a selection of games, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

What’s there to see and do in Preston?

Explore the area and family-friendly sights such as Chesapeake Bay Maritime Museum, or get out into nature at a spot like Bill Burton Fishing Pier State Park. In the larger area, you’ll find Avalon Theatre and Great Marsh Park.

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.

Recent reviews of Preston properties
Expedia verified reviews

The Wildset

The Wildset

5/5 Excellent
Memorable
"Everything about The Wildest was a treat. We would definitely stay there again!"
A verified traveler stayed at The Wildset
Posted 17 hours ago
The Wildset