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Our top choices for Middletown holiday homes

1. Charming "Cream of the Crop" Cape ~❤️of Middletown
Charming "Cream of the Crop" Cape ~❤️of MiddletownMiddletown
10.0 out of 10, Exceptional, (162 reviews)
The price is €242
includes taxes & fees
15 Nov - 16 Nov

2. Cozy Downtown Cabin - Family Friendly
Cozy Downtown Cabin - Family FriendlyMiddletown
10.0 out of 10, Exceptional, (3 reviews)
The price is €201
includes taxes & fees
25 Nov - 26 Nov

3. Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MDJefferson
10.0 out of 10, Exceptional, (75 reviews)
The price is €236
includes taxes & fees
15 Nov - 16 Nov

4. RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.Downtown Frederick
9.2 out of 10, Wonderful, (149 reviews)
The price is €231
includes taxes & fees
15 Nov - 16 Nov

5. Luxury Condo In Downtown Frederick
Luxury Condo In Downtown FrederickDowntown Frederick
9.2 out of 10, Wonderful, (102 reviews)
The price is €304
includes taxes & fees
2 Dec - 3 Dec

6. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
Historic Cottage Retreat-IG Hot Tub-Brick Fire PitBoonsboro
9.8 out of 10, Exceptional, (19 reviews)
The price is €291
includes taxes & fees
15 Nov - 16 Nov

7. Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, ACRohrersville
10.0 out of 10, Exceptional, (22 reviews)
The price is €386
includes taxes & fees
19 Nov - 20 Nov

8. Dog-Friendly | Hiking| Tubing near Harpers Ferry
Dog-Friendly | Hiking| Tubing near Harpers FerryBrunswick
2.0 out of 10, (1 review)
The price is €194
includes taxes & fees
6 Dec - 7 Dec

9. New townhouse
New townhouseFrederick
9.6 out of 10, Exceptional, (13 reviews)
The price is €352
includes taxes & fees
15 Nov - 16 Nov

10. Newly constructed 6 bedroom home
Newly constructed 6 bedroom homeFrederick
10.0 out of 10, Exceptional, (22 reviews)
The price is €432
includes taxes & fees
22 Nov - 23 Nov

11. 4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers FerryKnoxville
10.0 out of 10, Exceptional, (37 reviews)
The price is €446
includes taxes & fees
16 Nov - 17 Nov

12. Walk to Stores: Home in Historic Shepherdstown!
Walk to Stores: Home in Historic Shepherdstown!Shepherdstown
9.4 out of 10, Exceptional, (6 reviews)
The price is €332
includes taxes & fees
19 Nov - 20 Nov

14. Rural & Historic Detour Escape w/ Horses On-Site!
Rural & Historic Detour Escape w/ Horses On-Site!Detour
9.0 out of 10, Wonderful, (8 reviews)
The price is €383
includes taxes & fees
14 Nov - 15 Nov

15. Hidden Creekside retreat near 5 national parks, including Harpers Ferry
Hidden Creekside retreat near 5 national parks, including Harpers FerryMartinsburg
10.0 out of 10, Exceptional, (14 reviews)
The price is €240
includes taxes & fees
15 Nov - 16 Nov

16. Camp Patowmack - Riverfront, Hot Tub, and Sauna!
Camp Patowmack - Riverfront, Hot Tub, and Sauna!Harpers Ferry
9.6 out of 10, Exceptional, (11 reviews)

17. Custom Train-Themed Lodge on 7 Private Acres with Walking Trails
Custom Train-Themed Lodge on 7 Private Acres with Walking TrailsMartinsburg
9.8 out of 10, Exceptional, (25 reviews)
The price is €229
includes taxes & fees
18 Nov - 19 Nov

18. Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.Highfield-Cascade
10.0 out of 10, Exceptional, (11 reviews)
The price is €223
includes taxes & fees
22 Nov - 23 Nov

19. Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, Winery
Mountain Lake Retreat of Harpers Ferry: Hot Tub, Firepit, Fenced Yard, WineryHarpers Ferry
9.8 out of 10, Exceptional, (16 reviews)
The price is €309
includes taxes & fees
22 Nov - 23 Nov

20. Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly RiverfrontSharpsburg
8.2 out of 10, Very good, (66 reviews)
The price is €388
includes taxes & fees
30 Nov - 1 Dec
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.
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.


































































