A stone tower with a staircase leading up to it.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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, (71 reviews)
"The house is very cute and a perfect fit for our needs. We appreciated how clean the house was too! It's conveniently located to some many restaurants and shops. We would gladly stay here again!"
United States
Sara W.
The price is SAR 544
SAR 1,110 total
includes taxes & fees
3 Nov - 4 Nov
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)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
The price is SAR 495
SAR 881 total
includes taxes & fees
19 Oct - 20 Oct
Quaint Mini Cottage in Shepherdstown - Walking Distance
Property grounds

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 SAR 1,018
SAR 1,175 total
includes taxes & fees
20 Oct - 21 Oct
Thoughtfully Design Cottage with Breathtaking Indoor and Outdoor in Maryland
A bedroom with a bed, a table, and a view of the outdoors.

4. The Carriage House at Carrot Top Cottage

The Carriage House at Carrot Top Cottage
Harpers Ferry
9.8 out of 10, Exceptional, (54 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is SAR 523
SAR 829 total
includes taxes & fees
9 Nov - 10 Nov
The Carriage House at Carrot Top Cottage
A two-story house with a front porch, a garage, and a driveway.

5. Large Family Home: 5 Mi to Dtwn Hagerstown!

Large Family Home: 5 Mi to Dtwn Hagerstown!
3.0 star property
Williamsport
10.0 out of 10, Exceptional, (1 review)
"The place was just beautiful "
United States
Derrick
Large Family Home: 5 Mi to Dtwn Hagerstown!
A white building with a red roof, a car parked in front, and a grassy yard.

6. 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 SAR 281
SAR 605 total
includes taxes & fees
19 Oct - 20 Oct
Bring Your Own Boat - Meticulously restored house on the Potomac River
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, (34 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 SAR 731
SAR 1,274 total
includes taxes & fees
3 Nov - 4 Nov
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, (29 reviews)
"Property was a great location for all we wanted to do during our vacation. The beach area was the perfect retreat for some relaxation after long days of hiking. Area is beautiful, house was comfortable (slept like a baby), and we had a great stay. Would definitely stay again."
United States
Rebecca N.
The price is SAR 375
SAR 1,286 total
includes taxes & fees
21 Oct - 22 Oct
Woodsy Retreat with a Hot Tub and Seasonal Views!
A hot tub with a view of a forested landscape during sunset.

9. 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, (28 reviews)
"My husband and I went for a short trip. The communication was great and the house was perfect! We spent most of our time in the hot tub checking out the amazing view."
United States
Keri L.
The price is SAR 435
SAR 1,515 total
includes taxes & fees
29 Oct - 30 Oct
Cottage w/ Hot Tub and 100-Mile Valley Views!
A covered deck with a table and chairs, overlooking a river and autumn foliage.

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

Art Docko - Lakefront Artist Retreat w/ Hot Tub!
Harpers Ferry
10.0 out of 10, Exceptional, (29 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 SAR 555
SAR 1,903 total
includes taxes & fees
21 Oct - 22 Oct
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
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, (42 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 SAR 432
SAR 1,591 total
includes taxes & fees
4 Nov - 5 Nov
Peaceful Lakefront Cottage with Mountain Views!
A two-story house with a porch, a front door, and a number '190' sign.

12. 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 SAR 1,720
SAR 2,001 total
includes taxes & fees
20 Oct - 21 Oct
Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV
A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

13. 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)
"Fun place to stay!!!"
United States
Theresa R.
The price is SAR 844
SAR 1,485 total
includes taxes & fees
22 Oct - 23 Oct
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
A two-story house with a porch, a garage, and a fenced yard.

14. Renovated 3B/3B Home | Downtown | Private Fire Pit

Renovated 3B/3B Home | Downtown | Private Fire Pit
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (42 reviews)
"Great location, would stay again."
United States
Eric D S.
The price is SAR 908
SAR 2,099 total
includes taxes & fees
2 Nov - 3 Nov
Renovated 3B/3B Home | Downtown | Private Fire Pit
A covered porch with wooden benches, a red mailbox, and a view of a park with trees and a fence.

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

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is SAR 612
SAR 1,622 total
includes taxes & fees
19 Oct - 20 Oct
Rural & Historic Detour Escape w/ Horses On-site!
A covered porch with two wicker chairs and a wooden railing.

16. 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 SAR 2,101
SAR 2,674 total
includes taxes & fees
25 Oct - 26 Oct
Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia
A stone house with a white picket fence, a front porch, and potted plants.

17. Cottage w/ Furnished Patio & Garden: Dtwn Leesburg

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
3.0 star property
Leesburg's Old and Historic District
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
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

Hillside Inn & Suite

Hillside Inn & Suite

10/10 Excellent
"This is my hotel of choice when I'm in the Martinsburg area. Parking is plentiful and convenient. The staff are always friendly and accommodating."
Kent 2-night trip
Posted 2 hours ago
Hillside Inn & Suite

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