106 Properties in Middletown, Maryland, United States of America. June 7, 2026 through June 8, 2026

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Washington Monument State Park

South Mountain State Park

Maryland National Golf Club

Orchid Cellar Winery

Gambrill State Park

Willow Oaks Craft Cider and Wine

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Middletown

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eviivo NORAM

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Country Inn & Suites - by Choice Hotels

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Enjoy the season with activities like ice skating, snowmobiling, or sledding.

Scuba diving or snorkeling

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106 properties

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A deck with a long table set for dining, overlooking a river.

A lakeside cabin with a dock, outdoor seating, and a covered area.

Luxury KING Suites, Lakefront w/ Dock, HotTub, Watercraft

Entire home by Vrbo

Sleeps 16 · 6 bedrooms · 5.5 bathrooms

Hot tub on site

Balcony

Gas grill

Hot tub on site, Balcony, Gas grill

1010 out of 10

Exceptionalexceptional

8 reviews(8 reviews)

$2,300 nightly

The current price is $2,638 total

$2,638 total

Total with taxes and fees

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A modern kitchen with white cabinets, stainless steel appliances, and a black countertop. There are two stools at the island.

A stone pathway leading to a house with a statue in the foreground.

Beautiful Mansion in the Country & Wedding Venue

Entire home by Vrbo

Sleeps 32 · 6 bedrooms · 5.5 bathrooms

Pet-friendly

Private pool

Toys

Pet-friendly, Private pool, Toys

9.89.8 out of 10

Exceptionalexceptional

9 reviews(9 reviews)

$140 off

$1,260 nightly

The current price is $2,587 total

$2,587 total

Total with taxes and fees

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Still Meadow Farm

Entire home by Vrbo

Sleeps 10 · 3 bedrooms · 3 bathrooms

Refrigerator

Dryer

AC, Refrigerator, Dryer

1010 out of 10

Exceptionalexceptional

2 reviews(2 reviews)

$735 nightly

The current price is $1,325 total

$1,325 total

Total with taxes and fees

More information about Still Meadow Farm, opens in a new tab

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Photo gallery for Luxury KING Suites, Lakefront w/ Dock, HotTub, Watercraft

Luxury KING Suites, Lakefront w/ Dock, HotTub, Watercraft

Photo gallery for Beautiful Mansion in the Country & Wedding Venue

Beautiful Mansion in the Country & Wedding Venue

Photo gallery for Still Meadow Farm

Still Meadow Farm