114 High
Your Home
Our Story
Luxury Stays
The Chestertown Life
Your Host, Katie
114 High
Your Home
Our Story
Luxury Stays
The Chestertown Life
Your Host, Katie
More
  • Your Home
  • Our Story
  • Luxury Stays
  • The Chestertown Life
  • Your Host, Katie
  • Your Home
  • Our Story
  • Luxury Stays
  • The Chestertown Life
  • Your Host, Katie

Our Story

Amish builders remodeling historic home in Chestertown, MD

Passion meets Design

Inspired by beautiful historic Chestertown, 114 High Street was thoughtfully and passionately renovated into two luxury rental units. As you step inside, you'll be captivated by the meticulous attention to detail, blending modern amenities with the charm of historic architecture.  114 High offers more than a stay—it’s a story. Discover the heritage, care, and craftsmanship behind our historic Chestertown vacation rental. 

Stay at 114 High

114 Lower

114 Lower

114 Lower

2 Bedroom / 1 Bathroom

Sleeps 2-4



Features:

Outdoor patio

Bar

Large Kitchen

Front Porch

Laundry (W+D)


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114 Upper

114 Lower

114 Lower

2 Bedroom + Sleeping Loft (3) 

2 Bathrooms + 1 Powder Room

Sleeps 7


Features:

2 Story

Primary Bedroom with Walk-In Closet

Large Kitchen

Wet Bar + Wine Fridge

Laundry (W+D)


Request Booking

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