Preston Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Preston

Property grounds
Stylish Home on the Choptank River (with Tidal Beach)

Stylish Home on the Choptank River (with Tidal Beach)

Preston
10.0 out of 10, Exceptional, (43)
"We enjoyed the beautiful views, nature and clean comfortable house with all amenities. Will definitely book again on our next trip to Eastern shore."
United States
Cheryl H.
Stylish Home on the Choptank River (with Tidal Beach)
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
9.6 out of 10, Exceptional, (19)
"Great well-furnished townhouse in a great location and a super responsive host. What’s not to like?!?!"
United States
Lynn
The price is ￥21,659
￥54,281 total
includes taxes & fees
Nov 18 - Nov 19
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Exterior detail
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

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

Cambridge
10.0 out of 10, Exceptional, (14)
"Really nice property. Relaxing weekend. Stayed here with my daughter for two nights. We had a great time. "
United States
Dara M.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cambridge
10.0 out of 10, Exceptional, (262)
"Our stay was great and Rob and Clarissa were very welcoming!"
United States
Allison L.
Family and Pet-Friendly, Waterfront with Pier
Property grounds
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!

Saint Michaels
9.6 out of 10, Exceptional, (122)
"The house and location was perfect for a girls weekend with my mom and 2 daughters! The 1/2 bathrooms in each bedroom were nice to have upstairs!"
United States
Kimberly L.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Outdoor pool
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

Cambridge
9.8 out of 10, Exceptional, (7)
"The property was perfect for our family get together. We had a baby, toddler, preschooler, elementary and teens, moms, dads and grandparents. There was a place for everyone. Having a pack n’ play available would have been nice, but we procured one elsewhere. The property was large and felt very private, but Cambridge was just a quick drive."
United States
Jacqueline M.
NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock
Terrace/patio
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28

Cambridge
10.0 out of 10, Exceptional, (79)
"Good stay overall"
United States
Bill C.
Year Round Waterfront Estate / Family Reunions / Retreats - Sleeps 28
Smart TV, books, printers
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Woolford
9.6 out of 10, Exceptional, (21)
"The house was very nice, the host was very responsive! The outside was nice, only down side lots of mosquitos but that’s expected. "
United States
Elizabeth M.
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Property grounds
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

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

St Michaels
9.6 out of 10, Exceptional, (146)
"Perfect place to stay for a cousins reunion, Central location to all the shops and restaurants."
United States
Amh S.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Fridge, microwave, oven, stovetop
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

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

St. Michaels
9.8 out of 10, Exceptional, (44)
"This cottage is adorable. Great amenities and great location. We thoroughly enjoyed our time in St Michael’s."
United States
Audra B.
Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife
Outdoor pool, a heated pool
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock

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

Woolford
9.8 out of 10, Exceptional, (74)
"As beautiful as the photos appear, they do NOT do this place justice! Just a beautiful place, incredibly peaceful, well-appointed and equipped for families, groups, or any type of rental. Loved our time here!"
United States
Michael E.
Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Property grounds
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

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

Greenwood
9.8 out of 10, Exceptional, (29)
"Great place to stay with a family. Very nicely decorated and clean. "
United States
Meg E.
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
Exterior
Modern Flat in the Heart of St. Michaels – Walk Everywhere

Modern Flat in the Heart of St. Michaels – Walk Everywhere

Saint Michaels
10.0 out of 10, Exceptional, (53)
"Beautiful, clean and well appointed in the perfect spot in downtown Saint Michael’s. Highly recommended!!"
United States
Jeffrey G.
Modern Flat in the Heart of St. Michaels – Walk Everywhere
Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

St Michaels
9.6 out of 10, Exceptional, (125)
"Beautiful little cottage! Location is perfect."
United States
John B.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Private beach
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

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

Sherwood
10.0 out of 10, Exceptional, (19)
"Gorgeous views and location. "
United States
Ryan D.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Terrace/patio
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW

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

Cambridge
9.8 out of 10, Exceptional, (133)
"Beautiful property with gorgeous view. The owner was helpful and accommodating. Everything was clean and the amenities were superb. An evening of kayaking on the water was amazing. Great location for the half Ironman as well! "
United States
Lynn R.
Waterfront Family Retreat with gorgeous views and a large Deepwater Dock. 5' MLW
Sun loungers, beach towels
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND

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

Sherwood
10.0 out of 10, Exceptional, (37)
"We went to Sherwood to celebrate a family event. The house was perfect - lots of room for everyone. Check-in was simple, house was in excellent condition and the owners made every effort to accommodate our needs (some extra equipment for little kids). We enjoyed the pool and the beautiful setting. Great stay!"
United States
James S.
Heated Pool- CHESAPEAKE MANSION - 12,000 SQFT/30 ACRES/HUGE POLYWOOD PLAYGROUND
Outdoor dining
Downtown St. Michaels | Porch + Pet-Friendly

Downtown St. Michaels | Porch + Pet-Friendly

Saint Michaels
Downtown St. Michaels | Porch + Pet-Friendly
Smart TV, fireplace
RELAX- Eastern Shore Creek Home - 6 Guests

RELAX- Eastern Shore Creek Home - 6 Guests

Grasonville
10.0 out of 10, Exceptional, (5)
"We had a real enjoyable and comfortable stay in this beautiful home. The hosts were very responsive and the amenities were much appreciated. The home made this special trip even more memorable."
United States
Sherry N.
RELAX- Eastern Shore Creek Home - 6 Guests
Interior
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River

Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River

East New Market
10.0 out of 10, Exceptional, (14)
"Great House, perfect for a group retreat in a peaceful location. The pool is fantastic on a hot day and the house has good AC to keep you cool.Would happily stay again"
United States
Ed L.
Warwick Farms Waterfront Retreat! Solitude and relaxation on the Warwick River
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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Top Preston Hotel Reviews

Days Inn & Suites by Wyndham Seaford

Days Inn & Suites by Wyndham Seaford

10/10 Excellent
"The thing that stood out for us was being allowed to check in early with no problems. We also had a clean and comfortable room."
Carolyn 2-night trip
Posted 2 days ago
Days Inn & Suites by Wyndham Seaford

Find out more about Preston

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Frequently asked questions

Can I find vacation rentals in Preston?

Yes, there are vacation rentals near top attractions in Preston, or you can choose a more remote option if you'd like a relaxing place to stay.

What's the top vacation rental in Preston?

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock: This vacation home rental near Preston is located on a river and has an outdoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade game room.

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 larger area, you’ll find The Third Haven Friends Meeting House and Avalon Theatre.

What’s a vacation rental in Preston like?

Vacation rentals are private properties where you can stay for a couple of days or more in Preston. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for small groups.