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Compare 172 Vacation Homes in Preston with updated reviews, rates, and availability.

Backroad Getaway - Newly Built 3-bedroom retreat in Greenwood with WiFi

10.0 out of 10, Exceptional, (1)
"We stayed at the property for a hunting weekend. The house was great, and the owners made sure you had everything you needed. If available will definitely rent again."
The price is SAR 526
SAR 815 total
includes taxes & fees
6 Jan - 7 January 2025
Backroad Getaway - Newly Built 3-bedroom retreat in Greenwood with WiFi

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (46)
"This was a comfortable home, and a nice location. We were staying mostly for business, so didn’t do much in town, but the main restaurant and shopping areas are two short blocks away. We did use the nearby nature trail to walk our dogs. The only concerns others might have with the house, and the reason for four stars instead of five, were: minimal kitchen equipment (few pots/pans etc.), steep narrow stairs to the second floor, and low water pressure in the shower. That said, none of these things...
Dollhouse in Central Historic St Michaels

Walk to Everything House

10.0 out of 10, Exceptional, (74)
"House was centrally located in town. We parked the car and walked! Beds were very comfortable it was wonderful to have seperate beds for everyone. Well stocked kitchen. Washer & dryer a plus. We will be back. "
Walk to Everything House

RANCH AT ROYAL OAK- Exclusive waterfront pool pier

10.0 out of 10, Exceptional, (24)
"The Ranch at Royal Oak was a fantastic property. The property was exactly as advertised - gorgeous waterfront estate with a large lawn. Incredibly peaceful. We were looking for a getaway to hit pause and just relax and the ranch Royal Oak was exactly what we needed. Marissa was a great host - incredibly responsive, check in instructions are very clear.and easy to follow. I highly recommend this property for your next getaway."
RANCH AT ROYAL OAK- Exclusive waterfront pool pier

Beautiful Peaceful Home

10.0 out of 10, Exceptional, (2)
"I was deciding between booking a hotel or a home and thankful that we decided on this home for our weekend getaway. After visiting the museums in Cambridge, we were welcomed to our home away from home. Very relaxing, comfortable and spacious for our family. Conveniently located to downtown and nice neighborhood. If looking for a home to stay when in the Cambridge area, this is an excellent choice."
Beautiful Peaceful Home

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

9.8 out of 10, Exceptional, (33)
"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...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

9.6 out of 10, Exceptional, (19)
" October 11-14, 2024, we rented the “Willoughby” for a family reunion. Let me start out by saying this home is amazing. It looks exactly as pictured based on the website photos. It was even better than I expected. If you are considering this property, I highly recommend booking it! Believe me when I say the Willoughby is a rare gem. The location of the home is perfect and extremely private. The grounds are pristine and the view of the water is breathtaking. The home sits on the Hudson...
Waterfront Cambridge Gem w/ Hot Tub, Pool & Dock!

Cottage on Cabin Creek

10.0 out of 10, Exceptional, (102)
"Lovely quaint property for two. Exactly as described loved our stay. "
The price is SAR 939
SAR 1,354 total
includes taxes & fees
31 Dec - 1 January 2025
Cottage on Cabin Creek

Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

9.8 out of 10, Exceptional, (6)
"We enjoyed our time at the house very much. We went out to dinner only once and the rest of the time we ate in. We grilled two nights and made a roast one night. The views and the pool were more than you could imagine."
Waterfront, Private Saltwater Pool & Dock, Near Cambridge, Sleeps 10, Kayaks

Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub

10.0 out of 10, Exceptional, (3)
"8 of us had a great time on Harris Creek in McDaniel, MD. Pulled our boats up to private dock and crabbing in minutes. "
Minutes from Downtown St. Michaels and Tilghman | Private Dock | Hot Tub

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

10.0 out of 10, Exceptional, (1)
"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. "
Minutes from Downtown St. Michaels | Guest House | Pool | Private Dock

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

10.0 out of 10, Exceptional, (4)
"Everything about this property was perfect for our family of 10 ranging in age from 79 to 2.5. The children loved the indoor and outdoor play areas, and it was hard to drag them away from the house for Thanksgiving dinner. The location was excellent for access to St Michael's and other spots on the eastern shore. The owner even helped us find a place to get fresh local oysters and shucking them was a family affair."
Heated pool, sandy beach, pier, and playground set punch point apart!

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

9.6 out of 10, Exceptional, (19)
"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!!!"
Waterfront Home, Large Property with Pool, Discount for Monthly/Seasonal Rentals

Adorable two-bedroom retreat close to Easton, Denton, Centreville

10.0 out of 10, Exceptional, (16)
"Beautiful property with lots of thoughtful details. "
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Cozy 2BR Home near Idlewild Park

10.0 out of 10, Exceptional, (2)
"This property was in a great location for attending the Waterfowl festival. The host thought about each detail and our stay was more than comfortable. "
Cozy 2BR Home near Idlewild Park

Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge

2.0 star property
The price is SAR 451
SAR 1,668 total
includes taxes & fees
6 Jan - 7 January 2025
Relaxing, spacious 5BR house on the Hudson Creek in charming Cambridge

Riverfront Denton Estate on 7 Acres w/ Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (3)
"This large property - inside and outside - was perfect for our family get together. We were a total of 7 adults, 3 children and an infant and there were plenty of bedrooms, bathrooms, dining room space and other areas to hang out in. The pool and fire pit were great for kids and adults, and some of the family enjoyed kayaking. The property adjoining the Choptank River was private and peaceful. The property manager - Julie - went above and beyond to provide us what we needed for a great...
Riverfront Denton Estate on 7 Acres w/ Fire Pit!

4 bdrm, 3 bath, 2,700 sqft house on 1 acre with chickens and fenced in back yard

2.0 star property
10.0 out of 10, Exceptional, (1)
"Kyle was very responsive and a great host! This house is set up to accommodate a large group, but has space for privacy as well. Close to restaurants and shopping, but fully stocked kitchen and linens. Would recommend staying here!! Loved the chickens!!"
4 bdrm, 3 bath, 2,700 sqft house on 1 acre with chickens and fenced in back yard

Minutes from Downtown Easton and St. Michaels | Pool | 1st Floor Bedroom | Pet F

10.0 out of 10, Exceptional, (2)
"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

Beautiful Waterfront Retreat in Cambridge!

10.0 out of 10, Exceptional, (33)
"The perfect Thanksgiving. House was just right for family of three although more people would have been fine too. Lived the crab shack and played lots of pool and ping pong. Kitchen well stocked. Owners were prompt in responding to any questions. We would come back in a heartbeat."
The price is SAR 1,033
SAR 1,927 total
includes taxes & fees
26 Dec - 27 Dec
Beautiful Waterfront Retreat in Cambridge!
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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Other property types in Preston

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland

Dollhouse in Central Historic St Michaels

9.6 out of 10, Exceptional, (46)
"This was a comfortable home, and a nice location. We were staying mostly for business, so didn’t do much in town, but the main restaurant and shopping areas are two short blocks away. We did use the nearby nature trail to walk our dogs. The only concerns others might have with the house, and the reason for four stars instead of five, were: minimal kitchen equipment (few pots/pans etc.), steep narrow stairs to the second floor, and low water pressure in the shower. That said, none of these things...
Dollhouse in Central Historic St Michaels

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

9.8 out of 10, Exceptional, (33)
"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...
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
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.