Preston Holiday Rentals

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Check prices for these dates

Tonight
12 Jul - 13 Jul
Tomorrow
13 Jul - 14 Jul
Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul

Holiday Rentals in Preston

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Boats docked at the marina, offering scenic views of the calm water.

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

9.6 out of 10, Exceptional, (10)
"Vacationed here with our family of 5. Very cute and nice layout. Perfect walk to downtown and the docks. "
The price is HK$2,237
HK$4,135 total
includes taxes & fees
15 Jul - 16 Jul
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Guests can enjoy serene waterfront views from the end of the pier, where two Adirondack chairs await.

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

9.8 out of 10, Exceptional, (127)
"We had a wonderful long weekend here. Perfect weather let us swim and kayak and fish all weekend. House was spacious enough for two families of five plus our dog. The views were perfect!"
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Relax by the serene pool surrounded by lush greenery and a comfortable bench.

Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks

10.0 out of 10, Exceptional, (133)
"Great location and property. And epic crabbing to top it off!"
Modern St Michaels estate -Pier, Pool, Gas fire pit, Bikes, Kayaks
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Relax in a serene park setting surrounded by lush greenery and a central gazebo.

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

9.8 out of 10, Exceptional, (183)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Guests can enjoy a serene waterfront view from this tranquil pier.

Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly

9.4 out of 10, Exceptional, (28)
"We really enjoyed this property. It had everything we would want and plenty of space. It was very clean and quiet. The water, fire-pit, porch and living spaces were wonderful for a nice long-weekend get-away!"
Minutes from Downtown St. Michaels | Private Dock | Kayaks Bikes | Pet Friendly
Family and Pet-Friendly, Waterfront with Pier
Escape to a serene forest retreat with a cozy cabin-style lodge featuring a sheltered front porch and breathtaking natural views.

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (248)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
Waterfront property with private boat ramp and new dock!
Sit and enjoy the view from this shaded patio with a round table and two chairs.

Waterfront property with private boat ramp and new dock!

9.6 out of 10, Exceptional, (9)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Stylish entrance with a wooden staircase and a mailbox.

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

10.0 out of 10, Exceptional, (4)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Beautiful Waterfront Retreat in Cambridge!
Relax in this cozy room with a bar area featuring a large window offering a view of the outdoors.

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (39)
"The house was so cute and the fact that we were able to do early check in was amazing!"
The price is HK$1,936
HK$3,774 total
includes taxes & fees
15 Jul - 16 Jul
Beautiful Waterfront Retreat in Cambridge!
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Enjoy waterfront dining at Snapple, where tables and chairs are arranged under a covered awning with umbrellas for shade.

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

2.0 star property
9.8 out of 10, Exceptional, (9)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
The price is HK$2,198
HK$4,094 total
includes taxes & fees
14 Jul - 15 Jul
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Waterfront Sunset Bayview: sleeps 6
Guests can enjoy serene waterfront views from the end of the pier, where two Adirondack chairs await.

Waterfront Sunset Bayview: sleeps 6

10.0 out of 10, Exceptional, (17)
"Loved the location, the property, and amenities. Would definitely stay again!"
The price is HK$3,917
HK$6,524 total
includes taxes & fees
2 Aug - 3 Aug
Waterfront Sunset Bayview: sleeps 6
St. Michaels Waterfront Home
Relax by the serene lake with a dock and a small boat, surrounded by lush greenery and comfortable Adirondack chairs.

St. Michaels Waterfront Home

9.8 out of 10, Exceptional, (29)
"We had a wonderful stay. Check in and out was very easy. The place was clean and well maintained. Very peaceful spot on the water. "
St. Michaels Waterfront Home
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Boats docked at the marina, surrounded by trees and buildings.

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

10.0 out of 10, Exceptional, (11)
"The home was so well appointed and walking distance to stores, restaurants, quaint museums and beautiful nature. The host was so friendly and helpful with quick responses. We had high winds and lots of rain, but stayed cozy and warm. What a friendly Island of people!!"
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Heated pool, sandy beach, pier, and playground set punch point apart!
Relax in Adirondack chairs along the serene lakeside, with a boat available for recreation.

Heated pool, sandy beach, pier, and playground set punch point apart!

10.0 out of 10, Exceptional, (6)
"Beautifully decorated, peaceful, well appointed home for our girls bday celebration. Highly recommend."
Heated pool, sandy beach, pier, and playground set punch point apart!
RELAX- Eastern Shore Creek Home
Cozy up by the fireplace in this inviting living room with a stunning view of the outdoors.

RELAX- Eastern Shore Creek Home

10.0 out of 10, Exceptional, (2)
"Great property that is well kept. It is a short drive to several wonderful restaurants and an outlet shopping center."
RELAX- Eastern Shore Creek Home
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
Enjoy cooking in this well-equipped kitchen with a central island, sink, stove, and ample storage.

Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18

10.0 out of 10, Exceptional, (76)
"We were very impressed with the property and your place was very clean and had just about everything we needed. The location is wonderful and close to the event that we stayed in Cambridge for. I would definitely recommend this for others and will likely be renting again"
Eagle Haven - Waterfront Estate on the Choptank with Pool and Pier - Sleeps 18
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Relax by the pool with a seating area and grill, perfect for outdoor dining or cooking.

Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning

10.0 out of 10, Exceptional, (8)
"My husband and I spent Christmas on Tilghman Island in this unique house right on the water. It was perfect for us to rest, relax and cook Christmas dinner. We enjoyed it so much we want to visit again when the boats are out. The yard was perfect for our dog to get some exercise. I can see this as a perfect place for family and friends in the summer."
Waterfront Bliss: Ultimate Tilghman Retreat by RedAwning
Charming 3-bedroom Midcentury modern home, retro vibe and stylish furnishings.
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the surrounding area.

Charming 3-bedroom Midcentury modern home, retro vibe and stylish furnishings.

9.6 out of 10, Exceptional, (5)
"We had a great week in Cambridge. The Retro House has everything you need. It’s neat, clean, bright and very easy to stay in. It’s in a quiet neighborhood just short drive from the center of town. This was our second stay in the Retro House, we love it & will be coming back in the spring for another week!"
The price is HK$1,420
HK$3,228 total
includes taxes & fees
21 Jul - 22 Jul
Charming 3-bedroom Midcentury modern home, retro vibe and stylish furnishings.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and microwave, and dine at the wooden table.

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

9.8 out of 10, Exceptional, (40)
"Great location with two parking spots and a small yard. Great for family vacation. "
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Private 9 acre Family Retreat on the Chesapeake Bay
Relax in this spacious living room with a high ceiling, featuring a large sliding glass door leading to an outdoor patio with a view.

Private 9 acre Family Retreat on the Chesapeake Bay

10.0 out of 10, Exceptional, (9)
"House was loaded with activities for all ages. So much to do and see. Host was outstanding! Friendly and extremely accommodating."
Private 9 acre Family Retreat on the Chesapeake Bay
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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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?

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina: This holiday home rental outside of Preston is located in the city centre, and has a garden, a selection of games 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?

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.