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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 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, (72 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 AU$401
includes taxes & fees
12 Nov - 13 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, (27 reviews)
"Absolutely adorable, perfect location and well appointed. Would absolutely stay here again. Highly recommend and maybe if you’re lucky you’ll meet the little black cat who visited us!!"
United States
Abigail
The price is AU$329
includes taxes & fees
9 Nov - 10 Nov
Quaint Mini Cottage in Shepherdstown - Walking Distance
A two-story house with a front lawn and trees in the background.

3. Walk to Stores: Home in Historic Shepherdstown!

Walk to Stores: Home in Historic Shepherdstown!
3.0 star property
Shepherdstown
The price is AU$513
includes taxes & fees
19 Nov - 20 Nov
Walk to Stores: Home in Historic Shepherdstown!
A white building with a red roof, a car parked in front, and a grassy yard.

4. 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$222
includes taxes & fees
16 Nov - 17 Nov
Bring Your Own Boat - Meticulously restored house on the Potomac River
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, (55 reviews)
"Very clean and convenient for seeing Harpers Ferry"
United States
Rich C.
The price is AU$307
includes taxes & fees
9 Nov - 10 Nov
The Carriage House at Carrot Top Cottage
A two-story house with a covered porch and a wooden fence.

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

Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Harpers Ferry
9.8 out of 10, Exceptional, (36 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$466
includes taxes & fees
12 Nov - 13 Nov
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
A modern building with large windows, a deck, and a stone wall.

7. 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 AU$580
includes taxes & fees
19 Nov - 20 Nov
Woodsy Retreat with a Hot Tub and Seasonal Views!
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 AU$617
includes taxes & fees
16 Nov - 17 Nov
Cottage w/ Hot Tub and 100-Mile Valley Views!
A hot tub on a deck with a view of a lake and forest.

9. Peaceful Lakefront Cottage with Mountain Views!

Peaceful Lakefront Cottage with Mountain Views!
Harpers Ferry
9.8 out of 10, Exceptional, (42 reviews)
"The property was absolutely beautiful. The view of the lake was so pretty. Communication with the host was wonderful very informative. Very cozy and the house was beautiful inside."
United States
Tara G.
The price is AU$629
includes taxes & fees
18 Nov - 19 Nov
Peaceful Lakefront Cottage with Mountain 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 AU$699
includes taxes & fees
18 Nov - 19 Nov
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.

11. 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 AU$538
includes taxes & fees
10 Nov - 11 Nov
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
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 AU$807
includes taxes & fees
1 Dec - 2 Dec
Enchanting Victorian Cottage Just Steps From All the Major Sites in Harpers Ferry, WV
A covered porch with wooden benches, a red mailbox, and a view of a park with trees and a fence.

13. 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$624
includes taxes & fees
13 Nov - 14 Nov
Rural & Historic Detour Escape w/ Horses On-site!
A two-story house with a porch and a front door.

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, (44 reviews)
"Great location, would stay again."
United States
Eric D S.
The price is AU$801
includes taxes & fees
9 Nov - 10 Nov
Renovated 3B/3B Home | Downtown | Private Fire Pit
A historic building with a brick facade, multiple windows, and a covered porch area.

15. 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$1,019
includes taxes & fees
1 Dec - 2 Dec
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.

16. 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, (7 reviews)
"Great location to town of leesburg and can walk to restaurants and shops. Big kitchen and nice outdoor space. "
United States
Corky F.
The price is AU$939
includes taxes & fees
22 Nov - 23 Nov
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
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
The price is AU$989
includes taxes & fees
22 Nov - 23 Nov
Cottage w/ Furnished Patio & Garden: Dtwn Leesburg
A two-story house with a front porch, a garage, and a driveway.

18. 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!
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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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.

See all hotels in Middletown
A stone tower with a staircase leading up to it.

Top reviews in Middletown

A rooftop terrace with outdoor seating, a fire pit, and a view of the sunset over a mountainous landscape.
SpringHill Suites by Marriott Frederick

SpringHill Suites by Marriott Frederick

SpringHill Suites by Marriott Frederick
Frederick

10/10 Excellent

Over all good
Australia
Campbell
Reviewed May 9, 2024
SpringHill Suites by Marriott Frederick

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.