Location

Dates

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Vacation rentals in Saint Leonard, Maryland, United States

Hickory House on the Chesapeake Bay! image 1

Hickory House on the Chesapeake Bay! image 2

Hickory House on the Chesapeake Bay! image 4

Hickory House on the Chesapeake Bay! image 6

Bay Views, Private Beach Access and Pet Friendly!

2 bedrooms·1 bath

Saint Leonard • Maryland

4.92(88 reviews)

$647.00 USD total for 3 nights

Oct 26 – 29, 2026

Cozy 5-Bed Retreat, Heated Spa

Elegant brick home with glowing entry and stunning autumn curb appeal

Convenient in-home laundry room with washer, dryer, iron, and folding space

Cozy 5-Bed Retreat, Heated Spa

this is the Blue Room. The Decour is inspired by grand millennial chinoiserie. Daylight above is a remote controlled fandelier for climate comfort.

Cozy 5-Bed Retreat, Heated Spa

5 bedrooms·3½ baths

Port Republic • Maryland

4.78(58 reviews)

$1,680.50 USD total for 3 nights

Oct 26 – 29, 2026

Ivy Cove

3 bedrooms·2 baths

Lusby • Maryland

4.99(130 reviews)

$1,176.60 USD total for 3 nights

Oct 27 – 30, 2026

Relaxing Retreat on the Hudson image 1

Relaxing Retreat on the Hudson image 2

Relaxing Retreat on the Hudson image 3

Relaxing Retreat on the Hudson image 4

Relaxing Retreat on the Hudson image 5

Relaxing Retreat on the Hudson

5 bedrooms·2 baths

Maryland

5(34 reviews)

$950.00 USD total for 3 nights

Oct 27 – 30, 2026

Cozy Cottage By The Beach-Pet Friendly

Cozy Cottage By The Beach-Pet Friendly

Main living space.

Cozy Cottage By The Beach-Pet Friendly

Cozy Cottage By The Beach-Pet Friendly

3 bedrooms·2 baths

North Beach • Maryland

4.96(26 reviews)

$964.05 USD total for 3 nights

Oct 27 – 30, 2026

Welcome to beautiful North Beach!

Cozy fire pit patio with stylish seating and outdoor dining

Cozy fire pit patio with private fenced yard and stylish outdoor seating

Palm Haven in North Beach, MD

One of two bedrooms on the ground floor, this bedroom has a queen sized bed and en-suite bathroom.

Palm Haven in North Beach, MD

4 bedrooms·3 baths

North Beach • Maryland

5(198 reviews)

$816.42 USD $706.75 USD total for 3 nights

Oct 27 – 30, 2026

Majestic Murphy Point

Back yard launch

Front facing the bay

Kitchen/Dining open floor plan

Murphy Point on the Chesapeake Vacation Rental

3 bedrooms·1 bath

North Beach • Maryland

4.8(114 reviews)

$1,380.00 USD total for 3 nights

Oct 27 – 30, 2026

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

Bay Haven in North Beach, MD

3 bedrooms·2 baths

North Beach • Maryland

5(250 reviews)

$575.55 USD $502.96 USD total for 3 nights

Oct 27 – 30, 2026

Black Walnut Cove

Outdoor Seating

La Casita at Black Walnut-Waterfront Escape near Saint Michaels

3 bedrooms·1½ baths

Tilghman Island • Maryland

$1,063.75 USD total for 3 nights

Oct 26 – 29, 2026

*Where Eagles Soar*
Peaceful Waterfront Retreat. image 1

*Where Eagles Soar*
Peaceful Waterfront Retreat. image 2

The perfect place to unwind, share stories, and make memories!

The true heart of the home is our spacious sunken living room. Just one step down from the kitchen and dining area, this space wraps you in cozy comfort and is the ultimate spot to unwind. The water views, gorgeous sunsets, wildlife are unbeatable!

*Where Eagles Soar*
Peaceful Waterfront Retreat. image 5

Where Eagles Soar Peaceful Waterfront Retreat.

2 bedrooms·2 baths

Cobb Island • Maryland

4.97(105 reviews)

$1,014.00 USD total for 3 nights

Oct 30 – Nov 2, 2026