St. Leonard, MD

Travel Guide

A beach at sunset with a wooden fence in the background.
A beach at sunset with waves, birds, and a clear sky.
A beach with waves at sunset.
A sunset over a beach with waves and a distant shoreline.
Historic 1825 Chesapeake Farm Stay

Historic 1825 Chesapeake Farm Stay

2 out of 5
1380 Wagner Street St. Leonard MD
The price is AED 464 per night from Nov 10 to Nov 11
AED 464
AED 515 total
10 Nov - 11 Nov
includes taxes & fees
Book a stay at this family-friendly B&B in St. Leonard. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Vera's White Sands Marina and ...
Historic 1825 Chesapeake Farm Stay
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

St Leonard MD
Book a stay at this family-friendly vacation home in St. Leonard. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jefferson Patterson ...
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Rod 'N' Reel Resort

Rod 'N' Reel Resort

4 out of 5
4165 Mears Ave Chesapeake Beach MD
The price is AED 489 per night from Nov 12 to Nov 13
AED 489
AED 542 total
12 Nov - 13 Nov
includes taxes & fees
Book a stay at this business-friendly hotel in Chesapeake Beach. Enjoy an outdoor pool, 2 restaurants, and a marina. Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,000 reviews)
"Beautiful property on the Chesapeake Bay. It was very clean. We went off season highly recommend."

Reviewed on 11 October 2026

Rod 'N' Reel Resort
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.
Welcome to Hickory House on the Chesapeake Bay!

Welcome to Hickory House on the Chesapeake Bay!

Saint Leonard MD
Stay at this vacation home in St. Leonard. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Flag Harbor Marina and Long Beach are located ...
9.6/10 Exceptional! (22 reviews)
"This cozy home was perfect for two and would easily accommodate three. The kitchen had everything we needed, the bathroom was clean, the beds comfortable. It's an easy walk to the closest beach and a longer walk but very short drive to the nearest fossil hunting location (FlaggsPond). Theresa was ..."

Reviewed on 29 September 2026

Welcome to Hickory House on the Chesapeake Bay!
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!

St Leonard MD
Book a stay at this family-friendly vacation home in St. Leonard. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jefferson Patterson ...
Large RENOVATED 6 bedroom 5 bath private home with LOTS of space!
Beach Combing & Relaxation

Beach Combing & Relaxation

St Leonard MD
Stay at this vacation home in St. Leonard. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Matoaka Beach and Flag Harbor Marina are located ...
9.6/10 Exceptional! (33 reviews)
"Easy access to get in, pet friendly, open main room and dining. Just a little note for seniors, there is a regular tub/shower, a little hard to get in and out of."

Reviewed on 1 October 2026

Beach Combing & Relaxation
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.

Stay near popular St. Leonard attractions