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Holiday Homes in Middletown

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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Featured Holiday Homes in Middletown and around

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior detail

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (128)
"Place was nice and clean. Location was good. We enjoyed the quiet. Had a blast!"
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Property grounds

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

8.8 out of 10, Excellent, (8)
"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Interior

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

10.0 out of 10, Exceptional, (63)
"Location and house was just as described. Would highly recommend staying here if your looking for a location close to Harper's Ferry."
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (54)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is €236
includes taxes & fees
1 Sept - 2 Sept
Cottage on King | Charming Historic Leesburg Home
Gorgeous apt, pets, outdoor grill & fire pit, walk --> DT Frederick
Property grounds

Gorgeous apt, pets, outdoor grill & fire pit, walk --> DT Frederick

10.0 out of 10, Exceptional, (26)
"This place was very clean and had all necessary amenities. The host communicated well. Walkable to town and the park! "
Gorgeous apt, pets, outdoor grill & fire pit, walk --> DT Frederick
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 €271
includes taxes & fees
6 Sept - 7 Sept
Charming "Cream of the Crop" Cape ~❤️of Middletown
Terra Alta - Incredible River Views and Hot Tub!
Exterior

Terra Alta - Incredible River Views and Hot Tub!

9.6 out of 10, Exceptional, (58)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is €352
includes taxes & fees
11 Sept - 12 Sept
Terra Alta - Incredible River Views and Hot Tub!
Modern Country House on the Shenandoah River
Property grounds

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (39)
"The views are beautiful and the house was the perfect size for a group of 7 friends. We had a great time!"
Modern Country House on the Shenandoah River
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
Property grounds

Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

9.6 out of 10, Exceptional, (185)
"Wonderful location near Antietam NP, Shepardstown, and Hagerstown. Small home but plenty of room. My family enjoyed their stay"
Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath
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, (8)
"Great place and good location."
The price is €270
includes taxes & fees
28 Aug - 29 Aug
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
*Luxury Condo In Downtown Frederick*
Smart TV

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (66)
"The home was exactly as expected and made for a wonderful family/friend reunion! Perfect for socializing and so close to local shops and restaurants."
The price is €288
includes taxes & fees
27 Aug - 28 Aug
*Luxury Condo In Downtown Frederick*
The Madison
Dining

The Madison

10.0 out of 10, Exceptional, (34)
"We stayed for a week to tour college campuses for our son and are also considering moving there. We felt at home at The Madison and in the community. The house is exactly as described and in a great location to experience Frederick. "
The Madison
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Terrace/patio

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (120)
"Very nice home with river access. Close to all area attractions."
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Exterior

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

10.0 out of 10, Exceptional, (140)
"Wonderful house for a great weekend away"
The price is €353
includes taxes & fees
8 Sept - 9 Sept
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Happy Harbor | Mtn + Riverside w/ Game Room + Water Hole!
Terrace/patio

Happy Harbor | Mtn + Riverside w/ Game Room + Water Hole!

9.0 out of 10, Wonderful, (27)
"Our large family loved coming together at this beautiful home! We enjoyed sitting around the large kitchen and beautiful living room while the teens and kids enjoyed the game room and the basketball area. We also loved having a large property to explore"
Happy Harbor | Mtn + Riverside w/ Game Room + Water Hole!
Sunlight 2BR townhouse w/ private parking in Downtown Frederick
Fridge, microwave, oven, stovetop

Sunlight 2BR townhouse w/ private parking in Downtown Frederick

9.2 out of 10, Wonderful, (20)
"The location was perfect for walking just about anywhere we needed to go! Two bedrooms were a plus for me, my husband, and his sister. The half bath downstairs was also appreciated!"
Sunlight 2BR townhouse w/ private parking in Downtown Frederick
Gorgeous 1840 Log Cabin- Downtown
Fridge, microwave, oven, stovetop

Gorgeous 1840 Log Cabin- Downtown

10.0 out of 10, Exceptional, (143)
"Charming, nicely restored log home in a great location for downtown. We would definitely stay here again! "
Gorgeous 1840 Log Cabin- Downtown
A private home in historic Bolivar with a hot tub and yard. Pet friendly!
Smart TV, fireplace

A private home in historic Bolivar with a hot tub and yard. Pet friendly!

9.8 out of 10, Exceptional, (8)
"The house was cute and just the right size for us. It was close to everything we wanted to see and do"
The price is €297
includes taxes & fees
28 Aug - 29 Aug
A private home in historic Bolivar with a hot tub and yard. Pet friendly!
Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Outdoor dining

Camp Patowmack - Riverfront, Hot Tub, and Sauna!

10.0 out of 10, Exceptional, (2)
"We thoroughly enjoyed this property. It is a beautiful cabin located directly on the Potomac river near Harpers Ferry. We would stay here again. It has everything you could possibly need for a quiet escape! "
Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Terrace/patio

Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

9.8 out of 10, Exceptional, (23)
"Great stay for two young families. Lovely home and great location. Would recommend for a group trip to the area."
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
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

Best Western Leesburg Hotel & Conference Center

Best Western Leesburg Hotel & Conference Center

10/10 Excellent
"Quick overnight stop on way to NC. Clean hotel with Friendly staff. We enjoyed complimentary breakfast in morning. "
Jamie 1-night trip
Posted 1 day ago
Best Western Leesburg Hotel & Conference Center

Find out more about Middletown

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
1,233
Accommodation
297 Holiday Homes
Lowest Price
€236
Highest Price
€353

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