Guest Houses in Middletown
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A stone tower with a staircase leading up to it.

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Middletown

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Our top choices for Middletown guest houses

A garden with raised beds, a trellis, and potted plants.

A residential house with a garage, a patio with a table and chairs, and potted plants.

A wooden-floored entrance with a red door, a white-framed window, and a doorbell.

A two-story house with a front porch, a garage, and a well-maintained lawn.

1. INDULGE - FRESH FLOWERS, MANY AMENITIES

INDULGE - FRESH FLOWERS, MANY AMENITIES

Middletown

10.0 out of 10, Exceptional, (59 reviews)

10/10

Exceptional

(59 reviews)

"Great place to stay in rural Maryland and have all you need. Awesome place!"

Thomas C.

The price is CA $164

CA $164

CA $279 total

includes taxes & fees

Nov 15 - Nov 16

INDULGE - FRESH FLOWERS, MANY AMENITIES

A stone building with a sloped roof, a paved pathway leading to a porch, and a large tree in the foreground.

A brick fireplace with two built-in shelves and a mantel, flanked by wooden chairs.

A large estate with multiple buildings, expansive green fields, and a road in the background.

A view of a well-maintained lawn with a gazebo and a fountain, surrounded by a white building with large windows.

2. Inn at Springfield Manor

Inn at Springfield Manor

3.0 star property

Thurmont

9.0 out of 10, Wonderful, (66 reviews)

9.0/10

Wonderful

(66 reviews)

"LOVELY place, lovely people"

Thomas

The price is CA $285

CA $285

CA $302 total

includes taxes & fees

Nov 15 - Nov 16

Inn at Springfield Manor

An outdoor patio with a table and chairs, a red umbrella, and a wooden fence.

A two-story white building with a porch, a sign reading "Harper's Guest House," and a flag.

A kitchen with a coffee maker, a refrigerator, and a countertop.

A room with two armchairs, a small table with a lamp, and sheer curtains.

3. The Bluebird Suite at Harpers Ferry Guest House

The Bluebird Suite at Harpers Ferry Guest House

Harpers Ferry

10.0 out of 10, Exceptional, (77 reviews)

10/10

Exceptional

(77 reviews)

"Wonderful suite in a perfect location - walk to lower town. The room was clean and spacious, with a beautiful bathroom and a nice sized mini-fridge. The hosts left snacks, yogurt, cereal and milk. Coffee maker with pods, creamer and sugar. Great stay for a long weekend - highly recommend!!"

Danielle

The price is CA $210

CA $210

CA $314 total

includes taxes & fees

Nov 17 - Nov 18

The Bluebird Suite at Harpers Ferry Guest House

A modern kitchen with a large window, built-in appliances, and a black door with a wreath.

A residential property with a well-maintained lawn, a red barn, and a covered patio area.

A stone pathway leading to a sign for the Paeonian Springs Historic District.

A rustic outdoor seating area with Adirondack chairs, a fire pit, and a wooden table.

4. Romantic Barn Loft | Wine Country & Weddings

Romantic Barn Loft | Wine Country & Weddings

Paeonian Springs

The price is CA $220

CA $220

CA $356 total

includes taxes & fees

Nov 17 - Nov 18

Romantic Barn Loft | Wine Country & Weddings

A room with two armchairs, a small table with a lamp, and a window with curtains.

A four-poster bed with patterned bedding, a wooden dresser, a chair, and a large rug in a bedroom.

A compact kitchen with a built-in dishwasher, a coffee maker, and a small countertop.

5. The Goldfinch Suite at Harpers Ferry Guest House

The Goldfinch Suite at Harpers Ferry Guest House

Harpers Ferry

10.0 out of 10, Exceptional, (65 reviews)

10/10

Exceptional

(65 reviews)

"Very much enjoyed our stay and recommend it."

Robert A.

The price is CA $210

CA $210

CA $314 total

includes taxes & fees

Nov 17 - Nov 18

The Goldfinch Suite at Harpers Ferry Guest House

A house with a porch, an American flag, a garden with flowers and shrubs, and a gazebo in the background.

A spacious living room with a high ceiling, built-in bench seating, a coffee table, and large windows offering a view of the outdoors.

A spacious living room with a high ceiling, built-in bench seating, a large window overlooking greenery, and a cozy seating area with cushions.

A sign for La Soledad Harper's Ferry, a two-story building with a garage, surrounded by lavender fields and a wooden fence.

6. Riverview Suite at La Soledad

Riverview Suite at La Soledad

Harpers Ferry

9.8 out of 10, Exceptional, (15 reviews)

9.8/10

Exceptional

(15 reviews)

"Check in/ check out was seamless, nicest place to pick in harper's ferry!"

Brendan P.

The price is CA $445

CA $445

CA $608 total

includes taxes & fees

Nov 15 - Nov 16

Riverview Suite at La Soledad

A cozy living room with a grey sofa, a coffee table, and a wooden door leading to another room.

A four-poster bed with a white and gray patterned bedspread, a wooden headboard, and a nightstand with a lamp and decorative item.

A compact kitchenette with a refrigerator, coffee maker, and storage shelves.

A person standing on a hill overlooking a valley with a sunset.

7. 2-Room Chickadee Suite @ Harpers Ferry Guest House

2-Room Chickadee Suite @ Harpers Ferry Guest House

Harpers Ferry

10.0 out of 10, Exceptional, (24 reviews)

10/10

Exceptional

(24 reviews)

"The homey, comfortable atmosphere and the location are stand-outs of this charming, B&B. Great hosts!"

Jason

The price is CA $227

CA $227

CA $341 total

includes taxes & fees

Nov 15 - Nov 16

2-Room Chickadee Suite @ Harpers Ferry Guest House

A hallway with a wooden bench, a table with a lamp, and two framed botanical prints on the wall.

A four-poster bed with a pink quilt, two bedside tables with lamps, and three framed floral artworks on the wall.

8. The Cardinal Suite at Harpers Ferry Guest House

The Cardinal Suite at Harpers Ferry Guest House

Harpers Ferry

10.0 out of 10, Exceptional, (30 reviews)

10/10

Exceptional

(30 reviews)

"Everything was exceptional, very quiet and good location. We really appreciated the EV charging!"

Sue K.

The price is CA $227

CA $227

CA $335 total

includes taxes & fees

Nov 18 - Nov 19

The Cardinal Suite at Harpers Ferry Guest House

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.

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Learn more about Middletown

Nestled in the scenic Middletown Valley, this historic town offers charming Main Street shops and the annual Middletown Heritage Festival each September. Outdoor enthusiasts can explore nearby South Mountain State Park's hiking trails or visit local wineries for tastings with spectacular valley views.

See all hotels in Middletown

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Search Guest Houses in Middletown from CA $163

Change your mind

Treat yourself

Be picky

Top cities in Middletown

Middletown

Check prices for these dates

Our top choices for Middletown guest houses

1. INDULGE - FRESH FLOWERS, MANY AMENITIES

2. Inn at Springfield Manor

3. The Bluebird Suite at Harpers Ferry Guest House

4. Romantic Barn Loft | Wine Country & Weddings

5. The Goldfinch Suite at Harpers Ferry Guest House

6. Riverview Suite at La Soledad

7. 2-Room Chickadee Suite @ Harpers Ferry Guest House

8. The Cardinal Suite at Harpers Ferry Guest House

Learn more about Middletown

Explore a world of travel with Expedia