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Holiday Homes in Middletown

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Featured Holiday Homes in Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
Terrace/patio

Charming "Cream of the Crop" Cape ~❤️of Middletown

10.0 out of 10, Exceptional, (129)
"The property is wonderful! Very cozy and convenient to local attractions."
The price is NZ$421
includes taxes & fees
8 Sept - 9 Sept
Charming "Cream of the Crop" Cape ~❤️of Middletown
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Fridge, microwave, oven, stovetop

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

10.0 out of 10, Exceptional, (52)
"Very conveniently located for our visit with an amazing bakery and awesome meat market across the street. "
The price is NZ$430
includes taxes & fees
8 Sept - 9 Sept
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
Fridge, microwave, oven, stovetop

Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont

10.0 out of 10, Exceptional, (4)
"Very nice place .Quiet and peaceful"
The price is NZ$376
includes taxes & fees
9 Sept - 10 Sept
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont
Lakefront House w/ Modern Comforts!
Property grounds

Lakefront House w/ Modern Comforts!

8.8 out of 10, Excellent, (3)
"The house is lovely. Very much enjoyed the stay. Looking forward to going back!!"
The price is NZ$599
includes taxes & fees
11 Sept - 12 Sept
Lakefront House w/ Modern Comforts!
Quaint Royal Cottage @ Historic Leesburg
Fridge, microwave, oven, stovetop

Quaint Royal Cottage @ Historic Leesburg

2.0 star property
10.0 out of 10, Exceptional, (8)
"Our stay was perfect for our family attending a Wedding in Leesburg. The Host was a great communicator and his guide about the area was wonderful."
The price is NZ$717
includes taxes & fees
10 Sept - 11 Sept
Quaint Royal Cottage @ Historic Leesburg
Chic Spacious Home 5 Mins To College & Frederick Health
Microwave, oven, stovetop, dishwasher

Chic Spacious Home 5 Mins To College & Frederick Health

10.0 out of 10, Exceptional, (1)
"The homeowners are the nicest people I’ve ever met. Super friendly and responsive. I would stay here every single time. Home is beautiful and placed in the heart of Frederick so everything is a walking distance. And there’s no street parking!!!!! That’s definitely an added plus. "
Chic Spacious Home 5 Mins To College & Frederick Health
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
2 bedrooms, travel cot, WiFi, bed sheets

Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (9)
"Great place and good location."
The price is NZ$524
includes taxes & fees
9 Sept - 10 Sept
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Kalia’s Mountain Momma Getaway
Dining tables

Kalia’s Mountain Momma Getaway

10.0 out of 10, Exceptional, (11)
"Location was nice"
The price is NZ$300
includes taxes & fees
8 Sept - 9 Sept
Kalia’s Mountain Momma Getaway
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

9.4 out of 10, Exceptional, (115)
"This property is perfectly situated if your goal is to be able to walk through Frederick and enjoy the parks, shopping, and restaurants"
The price is NZ$489
includes taxes & fees
14 Sept - 15 Sept
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
Exterior detail

Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81

The price is NZ$191
includes taxes & fees
13 Sept - 14 Sept
Modern 2-Bedroom and 2-Bed Apartment with Private Access Door Minutes from I-81
Chic, pets, walk to downtown
Outdoor dining

Chic, pets, walk to downtown

10.0 out of 10, Exceptional, (13)
"Beautiful home with all desired ammenaties and very professional owners"
The price is NZ$654
includes taxes & fees
19 Sept - 20 Sept
Chic, pets, walk to downtown
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Exterior

Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

10.0 out of 10, Exceptional, (4)
"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"
The price is NZ$721
includes taxes & fees
8 Sept - 9 Sept
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!
Terrace/patio

Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

10.0 out of 10, Exceptional, (36)
"It is a cute house out in the country. Loved being away from town just like our home"
The price is NZ$580
includes taxes & fees
5 Oct - 6 Oct
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Terrace/patio

Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!

10.0 out of 10, Exceptional, (15)
"The house is well maintained and furnished, and the outdoor space is lovely. We had a great weekend in Leesburg and would come again. "
The price is NZ$639
includes taxes & fees
14 Sept - 15 Sept
Cozy home centrally located to historical old-town leesburg w/ HotTub & Firepit!
Historic Hideaway
Fridge, microwave, oven, stovetop

Historic Hideaway

10.0 out of 10, Exceptional, (25)
"Perfect location, great indoor and outdoor vibes! "
Historic Hideaway
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Fridge, microwave, oven, stovetop

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

9.4 out of 10, Exceptional, (103)
"Such a special home…cozy and filled with charm! Amazing views!"
The price is NZ$502
includes taxes & fees
10 Sept - 11 Sept
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Microwave

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

9.8 out of 10, Exceptional, (11)
"Small basement apartment had all we needed and wanted. Wonderful location. "
The price is NZ$306
includes taxes & fees
9 Sept - 10 Sept
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
New townhouse
Interior

New townhouse

9.4 out of 10, Exceptional, (9)
"This property was impeccably clean and so comfortable! The beds were incredibly cozy, and the kitchen was well-stocked. We felt right at home and enjoyed our stay immensely. Beds were comfortable, and kitchen well stocked. The location can't be beat, with so many attractions and wonderful restaurants within a short drive. Tons of nice touches for our arrival; great communication; easy access. We will definitely stay here again!"
The price is NZ$650
includes taxes & fees
14 Sept - 15 Sept
New townhouse
Cozy Fall Retreat With Fire Pit – Near Trails
Dining

Cozy Fall Retreat With Fire Pit – Near Trails

10.0 out of 10, Exceptional, (9)
"This property had everything we could ever need. It was beautiful, clean and totally up to date. I highly recommend this house for your visit!"
The price is NZ$583
includes taxes & fees
10 Sept - 11 Sept
Cozy Fall Retreat With Fire Pit – Near Trails
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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Top Middletown Hotel Reviews

Find out more about Middletown

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
Accommodation
297 Holiday Homes
Lowest Price
NZ$421
Highest Price
NZ$682

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