Preston Holiday Rentals: Short-Term Accommodations for Rent

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

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock : This holiday home rental outside of Preston is located on the beach, 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 garden and a selection of games so that you can immerse yourself in your holiday.

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Holiday Rentals in Preston

"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "

"Stayed for the weekend- parked the car and could walk to everything- perfect. Host was super responsive and the place was super clean!"

"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."

"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "

"Property was fantastic. Quit and peacful. Everything that you need and very clean. "

"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"

"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"

"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "

HK$2,930 total

includes taxes & fees

2 Sept - 3 Sept

"We had a wonderful stay including boating, kayaking, swimming, fishing, campfires and crabs! The house was perfect for our group and the owner was very accommodating."

"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "

"Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon."

"This house is awesome - very large and has room for all! It also has some old charm character and features that were really fun, like two "hidden staircases" the kids loved! Bedroom layouts were smartly planned to accommodate large groups and families. The property is truly gorgeous and huge - trails in the woods, lakes, tons of space for yard games and a swing set with two working swings. Parking was abundant, great basketball court and well stocked with the basics! The indoor pool is literally...

"We once again enjoyed our stay here. Perfect location to every where you’d want to go in St. Michael’s! Loved sitting out front looking at the water and park and enjoying music from our front yard. Highly recommend this cottage."

"Good location, clean house, easy check in and check out process."

"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "

"Gorgeous views and location. "

"Great house, host and location. Stayed with a larger group and plenty of room!"

"We had a wonderful stay at the Point of a View Cottage! The views are spectacular and we also enjoyed how easy it was to walk to places to eat and the local market. Recommendations for places to eat were spot on and also appreciated a message over the weekend notifying us of the local craft market held Sunday morning. Would love to come again one day! "

"Clean and nice place to stay"

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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?

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock: This holiday home rental outside of Preston is located on the beach, 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 garden and a selection of games so that you can immerse yourself in your holiday.

What’s there to see and do in Preston?

Williston Lake and Gilpin's Point Landing 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.

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Preston Holiday Rentals

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Holiday Rentals in Preston

Family and Pet-Friendly, Waterfront with Pier

Historic Downtown St. Michaels Studio | Walk to Waterfront, Dining & Shops

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

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

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

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

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

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

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

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

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

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

Waterfront property with private boat ramp and new dock!

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

Amazing views waterfront 3-bedroom home in Madison

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Walk to Everything House

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