Preston Holiday Rentals : Search Short-Term Rentals

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

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock! : This holiday home rental outside Preston is located on a lake, and has a fireplace, a balcony 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. You can relax into your holiday with a selection of games and 1 hot tub.

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Holiday Rentals in Preston

"The location couldn't have been more ideal. We were able to walk everywhere...all around town. And there was a beautiful view of the town park and the bay from the house. We were there for Christmas, visiting family, and her house was overflowing, so this was a little home-away-from-home. There were some difficulties. The shower curtain and main bath downstairs needs updating and the kitchen could be better appointed. The stairs to the king bed bedroom are, as others and the owner noted, very...

"The house was just as it was listed!! Our annual family vacation was so much fun here! Plenty of room, very clean, and fully stocked! Peddle boats, kayaks, and pool used daily!! Fire every night!!! Thank you for the wonderful hospitality!!!"

"Nice location down town. House was just as the pictures showed. "

"Host was amazing. Property is perfect. Will be staying here again. "

"Terrific house, beautiful scenery, property management was very responsive and helpful. Would stay again. Thank you. "

"The house was very clean and was great for our home base while visiting family in St. Michael’s. The owner was very response and friendly. The house included all basic amenities and then some! The owner really took the time and care preparing this place for guests. Downtown Cambridge is a short drive and a cute little town with shops and restaurants. We didn’t have a ton of time to explore downtown but plan to on our next stay! "

"This was a winter getaway to a very comfortable house with all the amenities on a quiet tributary of the Chesapeake. A rare vacation for and just what we wanted. Conveniently located near St Michael’s and Easton. Communication was excellent and everything was just as described. Would go back if we get the opportunity. "

"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."

"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...

"This property is a phenomenal place to spend time with family and enjoy beautiful St. Michael’s. The house is well stocked and convenient to town. We’d love to come back. "

"Nice place "

"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "

"We truly loved our stay! The home was super comfortable and well stocked for making Thanksgiving dinner for 6. We loved just looking out at the geese, swans and blue herons ! Really lovely. We’ll be back!"

"Perfect large space on a quiet and pretty area. Really great space. "

"wonderful home and great views. Clean, quiet, plenty of amenities"

"We had a wonderful stay here. The house has a really functional kitchen so we were able to cook a lot of meals here. The pool was perfect for young swimmers (decent sized shallow end) and we loved hanging out on the dock, crabbing and kayaking. With plenty of adult bikes, we took a trip each morning to the playground too. We hope to be back!"

"Overall we had a good time and home and property are lovely. However there were maintenance issues that should have been attended to. I have discussed these items with the rental group and feel they will take to heart the suggestions and act upon them. No need to detail here because I am sure they will tend to them."

"Great house with an outstanding view. We enjoyed our stay and the communication with the management group was great. "

"The original home is unique and gorgeous and the additions, the sunroom facing sunrises and the lodge style master chef kitchen gave us plenty of room to spread out. The large lawn and driveway gave us plenty of areas to walk the dogs and the beach was a daily swim spot for the dogs. The pool was one of the nicest we have had yet. We love the places with nice pools facing the boats out on the water. We will be back again for sure"

Smart TV, fireplace, video games, DVD player

"Very well equipped home at a beautiful location overlooking the water. The pool was a real treat for the kids in our group. The property manager was in regular communication and quickly dealt with one item that needed attention."

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Other types of properties in Preston you may be interested in

Indoor pool, 2 outdoor pools, pool umbrellas, pool loungers

"Great check in and highly personable staff. Dawn Reed and service staff with luggage transfer were excellent. Pool area looked amazing. Mitcherners service and bar food were provided great atmosphere and delicious food."

includes taxes & fees

24 Feb - 25 Feb

Breakfast, lunch, dinner served; sea views

"The property is beautiful and, the atmosphere is relaxing. I loved the fresh floral Christmas decorations."

includes taxes & fees

19 Feb - 20 Feb

"Enjoyed the stay. It was close to town and a lot of great attractions "

includes taxes & fees

19 Feb - 20 Feb

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, apart-hotels, 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 favorite 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 depends 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 per night. Entering your travel dates in the search wizard you might find 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.

Recent reviews of Preston properties

Holiday Inn Express Hotel & Suites Harrington-Dover area, DE, an IHG Hotel

5/5 Excellent

"My second stay here was every bit as good as the first. The staff are all friendly and helpful, the place is spotless. Check in and check out are a breeze. Donna at the front desk is especially pleasant, professional and courteous. "

A verified traveller stayed at Holiday Inn Express Hotel & Suites Harrington-Dover area, DE, an IHG Hotel

Posted 4 days ago

5/5 Excellent

"I historically had good stays at Best Westerns. For this stay, the staff at the desk were friendly, professional and helpful. The room was clean, and the hotel offered complimentary coffee and breakfast. The location was good and had free parking. Overall I had a good experience."

A verified traveller stayed at Best Western Plus Easton Inn & Suites

Posted 4 days ago

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?

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!: This holiday home rental outside Preston is located on a lake, and has a fireplace, a balcony 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. You can relax into your holiday with a selection of games and 1 hot tub.

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 Avalon Theatre.

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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Holiday Rentals in Preston

Plan, book, stay with confidence

Check prices for these dates

Holiday Rentals in Preston

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

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

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Walk to Everything House

Walk to Everything House

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Charming 4-bedroom house in Cambridge. the hart Of Eastern Shore, with WiFi, AC

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

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

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

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

Dollhouse in Central Historic St Michaels

Dollhouse in Central Historic St Michaels

Gorgeous Creek Side Ranch-Style Estate With Dock

Gorgeous Creek Side Ranch-Style Estate With Dock

Turn Winter Blues Into Blissful Views, Book Now!

Turn Winter Blues Into Blissful Views, Book Now!

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

Tranquil Beautiful Waterfront Near Historic St. Michaels & Royal Oak

Breathtaking Waterfront Estate

Breathtaking Waterfront Estate

Short drive to Downtown Cambridge | Pool | Private Dock | Game Room | Stunning V

Short drive to Downtown Cambridge | Pool | Private Dock | Game Room | Stunning V

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

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

Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach

Amazing Waterfront Retreat On The Chesapeake Bay Private Pool Private Beach

Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks

Minutes from Downtown Cambridge | Private Dock | Pool | Kayaks

Other types of properties in Preston you may be interested in

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

Inn at Perry Cabin

Inn at Perry Cabin

St Michaels Inn

St Michaels Inn

Find out more about Preston

Find out more about Preston

Recent reviews of Preston properties

Recent reviews of Preston properties

Holiday Inn Express Hotel & Suites Harrington-Dover area, DE, an IHG Hotel

Frequently asked questions