Preston Vacation Rentals

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Vacation Rentals in Preston

Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
9.8 out of 10, Exceptional, (25)
"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Property grounds
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (106)
"Wonderful return visit to St Michaels. This time at a fantastic historical home in perfect location. Home was everything you could ask for and more. Park your car and walk anywhere, within a very quiet neighborhood, yet minutes from all St Michaels offers. Highly recommend this Property and host."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Fridge, microwave, oven, stovetop
Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, (16)
"The Hudson House was perfect for our stay. My boys were in awe of the house. The owners have made it so cozy and have paid such close attention to details. There were snacks, amazing notes to help you navigate the house, and games to keep the kids busy. I highly recommend this to anyone looking to have a relaxing weekend right on the water. -Nicole M."
The price is CA $359
CA $639 total
includes taxes & fees
May 21 - May 22
Beautiful Waterfront Retreat in Cambridge!
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Fridge, microwave, stovetop, dishwasher
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.6 out of 10, Exceptional, (4)
"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!
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (126)
"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Fridge, microwave, oven, stovetop
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
10.0 out of 10, Exceptional, (30)
"Great place to recharge for a few days as a family! Beautiful and peaceful in the fall — though my kids are ready to come back and use the pool in warmer weather!!!"
Stunning Waterfront Maryland Eastern Shore Home with In-Ground Pool and Hot Tub
Property grounds
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (103)
"Really enjoyed the house and it’s location, perfect for a couples weekend!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Interior
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
10.0 out of 10, Exceptional, (6)
"My sisters and I (5 total) visited in early November. Kent Island Time was a perfect fit. We were impressed by the cleanliness, spacious rooms, and well-equipped common areas. The best feature was the waterfront location. Even in November, we were able to sit outside on the patio and enjoy a glass of wine as we watched the amazing sunset. We all agreed we would absolutely stay again in the future."
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Pool
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Minutes from Downtown St. Michaels | Pool | Hot Tub | Private Dock
Property grounds
St. Michaels Waterfront Home
10.0 out of 10, Exceptional, (20)
"Beautiful house, perfect for a weekend getaway with young kids. The host was very helpful!"
St. Michaels Waterfront Home
Property grounds
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
10.0 out of 10, Exceptional, (151)
"Quaint yet period correct. Plenty of room with decent kitchen. Especially love location and screaned back porch. Have stayed in house several times and does not disappoint!! Will go again for sure!"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Fridge, microwave, oven, stovetop
The Middle Point Cabin in Saint Michaels
9.8 out of 10, Exceptional, (47)
"Looked just like the pictures. Everything was new clean and comfortable. Enclosed patio was a hit with our cat."
The Middle Point Cabin in Saint Michaels
Fridge, microwave, oven, stovetop
Waterfront Getaway with Dock
10.0 out of 10, Exceptional, (25)
"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 CA $299
CA $356 total
includes taxes & fees
May 20 - May 21
Waterfront Getaway with Dock
Terrace/patio
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (5)
"We loved Waterside Cottage. It was so quite & the crabbing was wonderful which is what we were looking for. Topher was wonderful to work with both before we arrived & on the day of arrival. My husband is already asking if we can book it again next year."
Eastern Shore Waterside Cottage Near St. Michaels
Exterior
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (195)
"We enjoyed our stay very much. It was lovely to sit either on the screened in porch or in the living room and look out onto the water. It happened to be chilly & rainy during our stay but with views of the water, we didn’t even mind that."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Pool
Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F
10.0 out of 10, Exceptional, (1)
"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
Property grounds
Minutes from Downtown St. Michaels | Pool | Hot Tub
Minutes from Downtown St. Michaels | Pool | Hot Tub
Lake
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
9.8 out of 10, Exceptional, (66)
"What a beautiful property! We did a quick couples getaway and couldn’t have had a nicer weekend. The house is a beautiful, wraparound porch country home. Floorplan was really well designed and the decor was spot on. Looking forward to coming back next fall as well!"
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Outdoor pool
Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach
9.8 out of 10, Exceptional, (51)
"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
Pool
Breathtaking Waterfront Estate
10.0 out of 10, Exceptional, (65)
"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
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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

Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers
Hyatt Regency Chesapeake Bay
4.0 star property
8.8 out of 10, Excellent, (1002)
"Gorgeous property. Beautiful views. Well maintained and kept clean. The bed was the best lullaby ever. I slept ever so soundly. Breakfast was bountiful and delicious. The young lady that checked us in was on the surly side and could use some professional development on friendliness and hospitality for people of all cultures. But, the gentleman from Ghana that check me out made up for what she lacked and redeemed my experience. I would definitely stay again. "
The price is CA $243
CA $333 total
includes taxes & fees
May 22 - May 23
Hyatt Regency Chesapeake Bay
Front of property
St Michaels Inn
2.5 star property
8.2 out of 10, Very good, (1000)
"The staff was frieendly and very helpful, and the motel was very nice. The only issue I had with the stay was the high sulfur content of the water. It stank, and that's quite unpleasant."
The price is CA $162
CA $178 total
includes taxes & fees
Jun 3 - Jun 4
St Michaels Inn
Exterior
Best Western Plus Easton Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, (1001)
"We've stayed here before and will stay again, anytime we're in Easton. The hotel is easy to find, comfortable, well kept and the staff are always pleasant."
The price is CA $175
CA $193 total
includes taxes & fees
May 19 - May 20
Best Western Plus Easton Inn & Suites
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Preston. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife: This vacation home near Preston offers a garden, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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
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