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Browse Select Preston Holiday Homes

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.8 out of 10, Exceptional, 6 reviews
"We had a great time. Children and their parents spent a lot of time in the surprisingly large pool. Some adults chose the hot tub and the most active members of our group were paddleboarding and kayaking in the river. Severl people went hiking at Blackwater, and a few of us just sat on the screened in porch."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
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
Waterfront Sunset Bayview: sleeps 6
10.0 out of 10, Exceptional, 2 reviews
"Great place great location. Few things for us would have been perfect . Real coffee, hairdryer, outdoor fire pit or grill with fuel. Kindling Thanks for a wonderful stay"
Waterfront Sunset Bayview: sleeps 6
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Beautiful Waterfront Retreat in Cambridge!
10.0 out of 10, Exceptional, 18 reviews
"This house is incredible! Probably the cleanest rental house I have ever stayed in! The house was well stocked and very comfortable. However, we didn’t spend much time in the house because the outside is the real winner! The Crab House has everything to entertain kids and adults for hours! We spent all day in the yard, taking in the beautiful sights! If you are an early riser, like myself and one son, don’t miss the sunrise. So peaceful! If you are looking for crabs while there, Soft & Salty...
The price is €544
includes taxes & fees
21 Jul - 22 Jul
Beautiful Waterfront Retreat in Cambridge!
Downtown St. Michaels | Bikes | Kayaks | Private Pier
9.8 out of 10, Exceptional, 21 reviews
"Very clean and large property on scenic river. Only disappointing issues included problems launching kayaks over a tall wall and unfriendly TY cable system. Offset by abundance of great restaurants and peaceful and well maintained home."
Downtown St. Michaels | Bikes | Kayaks | Private Pier
Stylish Victorian in Historic District
10.0 out of 10, Exceptional, 12 reviews
"We all had a great time staying the weekend at the Beautiful house on Belvedere Avenue. This is the third year in a row we all stayed here. It was very close to the center of town where we had some great food and stopped at R & R for a drink. Plenty of space in the house to enjoy each others company. Would highly recommend this place to other people visiting Cambridge."
Stylish Victorian in Historic District
Gorgeous Creek Side Ranch-Style Estate With Dock
9.0 out of 10, Wonderful, 2 reviews
"Beautiful, comfortable house on huge creek front lot. Even better than the pictures! Communication was very easy, we loved the yard and landscaping. Great bird watching from the deck or through the huge picture windows. Highly recommend!"
The price is €737
includes taxes & fees
23 Jun - 24 Jun
Gorgeous Creek Side Ranch-Style Estate With Dock
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
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 €433
includes taxes & fees
25 Jun - 26 Jun
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
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
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 €254
includes taxes & fees
26 Jun - 27 Jun
Waterfront Getaway with Dock
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
Grasonville Home w/ Private Pool on the Water
10.0 out of 10, Exceptional, 14 reviews
"We had a wonderful time in Grasonville. The property was very clean and well maintained. Views from the home were serene as most rooms have views of the water which we absolutely loved. Another perk of the home is its proximity to surrounding attractions. Our group felt like we were secluded enough but could easily get something in town if needed. We didn’t need much since the home was well stocked. When we contacted the host about a question, they responded quickly. We would definitely stay...
Grasonville Home w/ Private Pool on the Water
Thorneton Point Estate
9.8 out of 10, Exceptional, 6 reviews
"We had a great time. The pool was a big hit and all the common areas in the house gave us plenty of room to spread out. The game room was super, also. A few things that would make it even greater: about half a dozen cockroaches and other bugs were found in the house; lack of instruction manuals for appliances and sauna; exterior doors very difficult to lack; comforter in bedroom 1 smelled like dogs. Matt was very helpful and responsive to questions"
Thorneton Point Estate
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
10.0 out of 10, Exceptional, 1 review
"This is a great property. It was comfortable, clean and spacious. The amenities of bikes and kayaks and a canoe made our stay very enjoyable. Close to downtown St. Michaels but on a quiet inlet. We really enjoyed our stay. Management company was readily available and highly responsive as well."
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
10.0 out of 10, Exceptional, 2 reviews
"The house was perfect for our annual Father’s Day Weekend. Neat and clean just like the description. The pool and property itself were awesome. Had a minor issue, but Doug (property manager) and Jamie (owner) were on top of it and solved it. Would re-rent without a doubt. Thank you for a beautiful home for me to host my weekend. Rob"
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
Stylish Home on the Choptank River (with Tidal Beach)
10.0 out of 10, Exceptional, 25 reviews
"The home is clean, comfortable, and has a gorgeous outdoor living space right on the water. We even had my son's wedding day party prep photos taken here. We would definitely stay here again."
Stylish Home on the Choptank River (with Tidal Beach)
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
10.0 out of 10, Exceptional, 4 reviews
"It was great! We loved it and would come back. Fyi - we did run out of TP, gas for grill and dishwasher soap."
Minutes from Downtown St. Michaels | Waterfront | Pet Friendly | Private Dock
Cambridge Beach Home on Choptank River w/ Pier!
10.0 out of 10, Exceptional, 12 reviews
"This place was perfect for our group of 9. Super well equipped. There wasn't a single thing we needed that it didn't have. Lovely!"
Cambridge Beach Home on Choptank River w/ Pier!
Cambridge Home w/ Private Dock ~ 4 Mi to Dtwn
9.6 out of 10, Exceptional, 10 reviews
"Great place! Great location"
Cambridge Home w/ Private Dock ~ 4 Mi to Dtwn
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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 property types in Preston

Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
9.8 out of 10, Exceptional, 6 reviews
"We had a great time. Children and their parents spent a lot of time in the surprisingly large pool. Some adults chose the hot tub and the most active members of our group were paddleboarding and kayaking in the river. Severl people went hiking at Blackwater, and a few of us just sat on the screened in porch."
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, 106 reviews
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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
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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