A stone tower with a staircase leading up to it.

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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 NZ$438
includes taxes & fees
1 Nov - 2 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 NZ$386
includes taxes & fees
1 Nov - 2 Nov
Quaint Mini Cottage in Shepherdstown - Walking Distance
A residential area with houses, roads, and green fields.

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 NZ$572
includes taxes & fees
2 Nov - 3 Nov
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, (55 reviews)
"Lovely little spot right off the AT and easy walk into historic HF. "
United States
Michael
The price is NZ$385
includes taxes & fees
9 Nov - 10 Nov
The Carriage House at Carrot Top Cottage
A covered porch with wooden benches, a red mailbox, and a view of a park with trees and a fence.

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

Rural & Historic Detour Escape w/ Horses On-site!
3.0 star property
Keymar
The price is NZ$761
includes taxes & fees
6 Nov - 7 Nov
Rural & Historic Detour Escape w/ Horses On-site!
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 NZ$284
includes taxes & fees
3 Nov - 4 Nov
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, (35 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 NZ$600
includes taxes & fees
1 Nov - 2 Nov
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A hot tub with a view of a forested landscape during sunset.

8. 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, (29 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 NZ$780
includes taxes & fees
16 Nov - 17 Nov
Cottage w/ Hot Tub and 100-Mile Valley Views!
A modern building with large windows, a deck, and a stone wall.

9. 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 NZ$890
includes taxes & fees
29 Nov - 30 Nov
Woodsy Retreat with a Hot Tub and Seasonal Views!
A hot tub on a deck with a view of a lake and forest.

10. 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 NZ$899
includes taxes & fees
10 Nov - 11 Nov
Peaceful Lakefront Cottage with Mountain Views!
A covered deck with a table and chairs, overlooking a river and autumn foliage.

11. 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.
Art Docko - Lakefront Artist Retreat w/ Hot Tub!
A covered outdoor area with a hot tub, wooden benches, and a view of a snowy landscape with trees and a fence.

12. 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, (27 reviews)
"Fun place to stay!!!"
United States
Theresa R.
The price is NZ$679
includes taxes & fees
1 Nov - 2 Nov
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
A historic building with a brick facade, multiple windows, and a covered porch area.

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 NZ$1,549
includes taxes & fees
12 Nov - 13 Nov
Historic Stone Cottage with Hot Tub and Hammock, Minutes from Downtown Harpers Ferry, West Virginia
A two-story house with a porch, a front door, and a number '190' sign.

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 NZ$1,193
includes taxes & fees
12 Nov - 13 Nov
Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV
A two-story house with a front porch, a garage, and a driveway.

15. 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
The price is NZ$799
includes taxes & fees
5 Nov - 6 Nov
Large Family Home: 5 Mi to Dtwn Hagerstown!
A two-story house with a porch and a front door.

16. 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 NZ$978
includes taxes & fees
2 Nov - 3 Nov
Renovated 3B/3B Home | Downtown | Private Fire Pit
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
Leesburg's Old and Historic District
9.8 out of 10, Exceptional, (6 reviews)
"Great location to town of leesburg and can walk to restaurants and shops. Big kitchen and nice outdoor space. "
United States
Corky F.
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
A stone house with a white picket fence, a front porch, and potted plants.

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

Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
3.0 star property
Leesburg's Old and Historic District
The price is NZ$1,195
includes taxes & fees
22 Nov - 23 Nov
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

The Inn at Charles Town - Hollywood Casino

The Inn at Charles Town - Hollywood Casino

8/10 Good
"The property was clean and well maintained. Breakfast was good and staff were all very nice. More options for breakfast would have been nice."
Rebecca 2-night trip
Posted 1 hour ago
The Inn at Charles Town - Hollywood Casino

Find out more about Middletown

Middletown Cottages information

Number of reviews
363
Accommodation
84 Cottages
Lowest Price
NZ$284
Highest Price
NZ$1,549

Frequently asked questions

What is there to do in Middletown near my cottage?
If you're ready to fill up your itinerary in Middletown, check out Maryland National Golf Club. It's a winner with locals and travellers alike.