A stone tower with a staircase leading up to it.

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Middletown cottages

A kitchen with a dishwasher, a sink, and a stove. There are pots hanging above the sink and a window with a view of greenery outside.

1. Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (70 reviews)
"Wonderfully remodeled spot, great amenities, extremely close to downtown, was perfect for our trip!"
United States
Andrew F.
The price is AU$390
includes taxes & fees
5 Oct - 6 Oct
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A living room with a dining table, chairs, a sofa, and a television.

2. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"We loved staying here, and walking into town to.explore. The kitchen was well stocked, and the tub was.perfect for soaking after a long day hiking."
United States
Alexandra Z.
The price is AU$314
includes taxes & fees
29 Sept - 30 Sept
Quaint Mini Cottage in Shepherdstown - Walking Distance

3. Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland

Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
Boonsboro
The price is AU$436
includes taxes & fees
5 Oct - 6 Oct
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
A covered porch with wooden benches, a red mailbox, and a view of a park with trees and a fence.

4. Rural & Historic Detour Escape w/ Horses On-site!

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is AU$607
includes taxes & fees
24 Sept - 25 Sept
Rural & Historic Detour Escape w/ Horses On-site!
A bedroom with a bed, a table, and a view of the outdoors.

5. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (52 reviews)
"Wonderful location. Very peaceful and convenient for everything we wanted to do on our trip. Enjoyed all the deer while sitting outside the cottage reading."
United States
Clinton R.
The price is AU$330
includes taxes & fees
6 Oct - 7 Oct
The Carriage House at Carrot Top Cottage
A hot tub with a view of a forested landscape during sunset.

6. Cottage w/ Hot Tub and 100-Mile Valley Views!

Cottage w/ Hot Tub and 100-Mile Valley Views!
Harpers Ferry
9.8 out of 10, Exceptional, (27 reviews)
"The property was so nice with a beautiful view. We had a great time! Highly recommend this property."
United States
Anonymous traveller
The price is AU$527
includes taxes & fees
29 Sept - 30 Sept
Cottage w/ Hot Tub and 100-Mile Valley Views!
A two-story house with a covered porch and a wooden fence.

7. Amazing dog-friendly cottage. Walk 2 Harpers Ferry

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (33 reviews)
"We enjoyed our stay here so much and when we go back to Harper’s Ferry we hope to stay in the same place again"
United States
Zachary S.
The price is AU$516
includes taxes & fees
27 Sept - 28 Sept
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A modern building with large windows, a deck, and a stone wall.

8. Woodsy Retreat with a Hot Tub and Seasonal Views!

Woodsy Retreat with a Hot Tub and Seasonal Views!
Harpers Ferry
9.8 out of 10, Exceptional, (28 reviews)
"Great house. Comfortable beds, had everything we needed. Loved the hot tube and wood burner. "
United States
Amy P.
The price is AU$476
includes taxes & fees
24 Sept - 25 Sept
Woodsy Retreat with a Hot Tub and Seasonal Views!
A white building with a red roof, a car parked in front, and a grassy yard.

9. Bring Your Own Boat - Meticulously restored house on the Potomac River

Bring Your Own Boat - Meticulously restored house on the Potomac River
Hedgesville
9.6 out of 10, Exceptional, (14 reviews)
"Great little place to stay."
United States
Shannon W.
The price is AU$229
includes taxes & fees
4 Oct - 5 Oct
Bring Your Own Boat - Meticulously restored house on the Potomac River
A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

10. The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
Hamilton
10.0 out of 10, Exceptional, (26 reviews)
"Very relaxing stay! Clean hot tub!! "
United States
Mara H.
The price is AU$535
includes taxes & fees
28 Sept - 29 Sept
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
A hot tub on a deck with a view of a lake and forest.

11. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (40 reviews)
"Clean house. Host was able to accessible. Hot tub worked and clean. Kitchen had everything we needed. Great place to stay and relax"
United States
Lisa h.
The price is AU$675
includes taxes & fees
24 Sept - 25 Sept
Peaceful Lakefront Cottage with Mountain Views!
A covered deck with a table and chairs, overlooking a river and autumn foliage.

12. Art Docko - Lakefront Artist Retreat w/ Hot Tub!

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (28 reviews)
"With bedrooms and sitting rooms on 3 floors, our 3-generation family enjoyed having space to gather together as well as space for time apart. The decks allowed for additional places to enjoy the beautiful surroundings. Lake access was great for swimming and kayaking."
United States
Lindy K.
The price is AU$721
includes taxes & fees
7 Oct - 8 Oct
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A two-story building with a balcony, a porch with outdoor seating, and a stone foundation.

13. Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia

Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia
Bolivar
The price is AU$761
includes taxes & fees
1 Oct - 2 Oct
Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia

14. Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV

Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV
Harpers Ferry
The price is AU$858
includes taxes & fees
7 Oct - 8 Oct
Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV
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

Tru By Hilton Hagerstown

Tru By Hilton Hagerstown

10/10 Excellent
"Loved the Tru concept!! Nice clean rooms. Nice little added touches for traveling, like plenty of hooks in the room, nice towels, and a small shelf in the bathroom. All of the staff were super friendly! Great customer service!"
Debra 1-night trip
Posted 6 hours ago
Tru By Hilton Hagerstown

Find out more about Middletown

Middletown Cottages information

Number of reviews
179
Accommodation
85 Cottages
Lowest Price
AU$229
Highest Price
AU$858

Frequently asked questions

What is there to do in Middletown near my cottage?
After you've unpacked your suitcases, set out and explore the awesome things Middletown has on offer. Orchid Cellar Winery is a top attraction to add to your must-see list.