Preston, MD

Travel Guide

Preston
Preston
Hyatt Regency Chesapeake Bay
Hyatt Regency Chesapeake Bay
4 out of 5
100 Heron Blvd, Cambridge, MD
The price is AED 732 per night from May 6 to May 7
AED 732
AED 1,006 total
includes taxes & fees
6 May - 7 May
Stay at this 4-star beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (1,002 reviews)
"Great spot."

Reviewed on 8 April 2025

Hyatt Regency Chesapeake Bay
Inn at Perry Cabin
Inn at Perry Cabin
5 out of 5
308 Watkins Ln, St. Michaels, MD
The price is AED 1,769 per night from May 11 to May 12
AED 1,769
AED 2,140 total
includes taxes & fees
11 May - 12 May
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
9.4/10 Exceptional! (340 reviews)
"Our stay here was excellent. The highlight was arguably the check-in, where we were surprised with a birthday welcome, as well as a little onesie for our soon to arrive baby girl. This was a birthday/baby moon trip and we shared this info prior to arrival, and the staff was incredible in providing ..."

Reviewed on 5 April 2025

Inn at Perry Cabin
St Michaels Inn
St Michaels Inn
2.5 out of 5
1228 S Talbot Street, St. Michaels, MD
The price is AED 443 per night from May 5 to May 6
AED 443
AED 487 total
includes taxes & fees
5 May - 6 May
Book a stay at this business-friendly hotel in St. Michaels. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,002 reviews)
"Worthwhile"

Reviewed on 16 April 2025

St Michaels Inn
See all 377 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.
Stylish Home on the Choptank River (with Tidal Beach)
Stylish Home on the Choptank River (with Tidal Beach)
Preston
Book a stay at this family-friendly vacation home in Preston. Enjoy free WiFi, a garden, and patios. Popular attractions Gilpin's Point Landing and Caroline ...
10/10 Exceptional! (32 reviews)
Highly Recommend!
"A beautiful and serene setting mapping the contours of nature, tranquility & relaxation. Steven is an exceptional host."

Reviewed on 18 February 2025

Stylish Home on the Choptank River (with Tidal Beach)
Family and Pet-Friendly, Waterfront with Pier
Family and Pet-Friendly, Waterfront with Pier
Cambridge
Stay at this cottage in Cambridge. Enjoy free WiFi, a garden, and patios. Popular attractions Ragged Island and Spocott Windmill are located nearby.
9.8/10 Exceptional! (219 reviews)
An absolute gem
"The only thing I can say is that the online listing really doesn’t do justice to how amazingly stunning Rob & Clarissa’s place is. My family and I decided last minute that we wanted to spend a weekend on the bay. I never expected it to be so beautiful! We got there late in the evening and we were ..."

Reviewed on 25 March 2025

Family and Pet-Friendly, Waterfront with Pier
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
Stay at this vacation home in Woolford. Enjoy free WiFi, a garden, and patios. Popular attractions Woods Island and Harriet Tubman Underground Railroad National ...
10/10 Exceptional! (7 reviews)
Perfect for family fun!
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s ..."

Reviewed on 4 July 2024

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
See all 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.

Popular places to visit

Gilpin's Point Landing

Explore the great outdoors at Gilpin's Point Landing, a lovely green space in Preston.

Gilpin's Point Landing