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 vacation homes

Exterior

1. Charming "Cream of the Crop" Cape ~❤️of Middletown

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (155 reviews)
"Great place to stay. Very clean and beautiful. The Host was very nice too and kept us informed. We will definetly stay there again!"
United States
Adair M.
The price is AED 459
AED 1,063 total
includes taxes & fees
27 Sep - 28 Sep
Charming "Cream of the Crop" Cape ~❤️of Middletown
Private kitchen

2. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
"Cute little cabin. Perfect for our 1 night stay for a concert in the area. Im just sad we left the kids at home cause they would have loved it too!"
United States
Laura K.
The price is AED 744
AED 897 total
includes taxes & fees
22 Sep - 23 Sep
Cozy Downtown Cabin - Family Friendly
Coffee/tea maker, fridge, microwave, oven

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, MD
Jefferson
10.0 out of 10, Exceptional, (73 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
The price is AED 569
AED 1,195 total
includes taxes & fees
4 Oct - 5 Oct
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A park with a pond, a bridge, and a church in the background.

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, (140 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
The price is AED 408
AED 1,004 total
includes taxes & fees
22 Sep - 23 Sep
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Dining

5. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (97 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
The price is AED 539
AED 1,225 total
includes taxes & fees
22 Sep - 23 Sep
Luxury Condo In Downtown Frederick
Coffee/tea maker, fridge, microwave, oven

6. Newly constructed 6 bedroom home

Newly constructed 6 bedroom home
Frederick
10.0 out of 10, Exceptional, (22 reviews)
"It was a great place to relax, sleep and come home to after busy days in Frederick area. We would definitely stay here again!"
United States
Janice M.
The price is AED 782
AED 1,826 total
includes taxes & fees
26 Sep - 27 Sep
Newly constructed 6 bedroom home
Microwave, oven, stovetop, dishwasher

7. Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC

Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Rohrersville
10.0 out of 10, Exceptional, (17 reviews)
"Beautiful house in a bucolic setting. Perfect for a family for the night."
United States
Kate M.
The price is AED 1,010
AED 1,670 total
includes taxes & fees
28 Sep - 29 Sep
Charming Historic Victorian 4 bedroom guesthouse in Rohrersville with WiFi, AC
Exterior

8. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (12 reviews)
"We had a great time. It was perfect for us. I would highly recommend it to others and would not hesitate to return there when back in the area. "
United States
Tereasa G.
The price is AED 902
AED 1,860 total
includes taxes & fees
4 Oct - 5 Oct
New townhouse
Room

9. Schilling House

Schilling House
3.0 star property
Bolivar
The price is AED 976
AED 1,228 total
includes taxes & fees
29 Sep - 30 Sep
Schilling House
Property grounds

10. 5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit

5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Sharpsburg
10.0 out of 10, Exceptional, (51 reviews)
"The house was in a great location with the winery and battlefield nearby, and the house was very nice and comfortable."
United States
Nancy D.
5-Minute Walk to Winery & Battlefield 1-Acre Wine Weekend Getaway w/ Fire Pit
Terrace/patio

11. Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath

Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
Bolivar
10.0 out of 10, Exceptional, (61 reviews)
"Enjoyed our stay here. Host was very communicative and the place was very clean."
United States
Delaine F.
The price is AED 511
AED 1,049 total
includes taxes & fees
22 Sep - 23 Sep
Icy mini split added, luxury, walk to Washington St, EV, Movie room, Spa bath
Terrace/patio

12. 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 Ferry
Knoxville
10.0 out of 10, Exceptional, (30 reviews)
"Easy to get in, instructions and expectations were clear, amenities were as expected, and the home was beautiful. "
United States
Katherine Z.
4 King Suites, Hot Tub, Ping Pong, Arcade, Chef's Kitchen – Harpers Ferry
Interior

13. A peaceful, forest retreat with stunning views near historic Harpers Ferry.

A peaceful, forest retreat with stunning views near historic Harpers Ferry.
Harpers Ferry
8.8 out of 10, Excellent, (13 reviews)
"House was clean and loaded with required amenities. We loved the backyard view and the proximity to the lakeside picnic area."
United States
henu m.
The price is AED 661
AED 1,407 total
includes taxes & fees
22 Sep - 23 Sep
A peaceful, forest retreat with stunning views near historic Harpers Ferry.
Interior

14. Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!

Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Harpers Ferry
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful home. Very attentive hosts, great location. We enjoyed every minute at this home. "
United States
Katrina
The price is AED 776
AED 1,716 total
includes taxes & fees
23 Sep - 24 Sep
Brand new home in Historic Harpers Ferry - Barrel Sauna - Fire Pit - Luxury!
Interior

15. 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 Riverfront
Sharpsburg
8.2 out of 10, Very good, (66 reviews)
"Lovely place along the c&o. The host was very accommodating and helpful."
United States
Laura D.
The price is AED 757
AED 1,675 total
includes taxes & fees
21 Oct - 22 Oct
Taylor’s Landing Retreat, 6 Acres, C&O Canal Access, Event-Friendly Riverfront
Interior

16. 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, (6 reviews)
The price is AED 413
AED 823 total
includes taxes & fees
22 Sep - 23 Sep
Charming 3 Bedroom Cottage minutes from Ski Liberty and Gettysburg Pa.
Interior

17. New, Contemporary House in Historic Harpers Ferry

New, Contemporary House in Historic Harpers Ferry
Harpers Ferry
9.6 out of 10, Exceptional, (7 reviews)
"The home was perfect for our visit.We were in and out all weekend but really appreciated the well stocked kitchen supplies, the comfortable beds and the hot water levels. We were able to relax in the spacious living room and spend some time on the little outdoor areas. We would stay again but if the group was much bigger there may be issues as there are only bathrooms on the first floor. "
United States
Erin J.
The price is AED 367
AED 1,343 total
includes taxes & fees
23 Sep - 24 Sep
New, Contemporary House in Historic Harpers Ferry
Outdoor dining

18. Exclusive Wooded Chalet w Magnificent River Views

Exclusive Wooded Chalet w Magnificent River Views
Shepherdstown
10.0 out of 10, Exceptional, (20 reviews)
"Fantastic location, amazing views, clean property, responsive host"
United States
Brian
The price is AED 1,767
AED 2,710 total
includes taxes & fees
14 Oct - 15 Oct
Exclusive Wooded Chalet w Magnificent River Views
3 bedrooms, desk, iron/ironing board, travel crib

19. Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV

Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Harpers Ferry
10.0 out of 10, Exceptional, (19 reviews)
"Overall good property- close location to all attractions"
United States
Trisha P.
The price is AED 588
AED 1,449 total
includes taxes & fees
22 Sep - 23 Sep
Balcony-BBQ-Firepit-Hot tub-King-Full kitchen-TV
Exterior

20. Charming Shepherdstown Home - Walk to Downtown

Charming Shepherdstown Home - Walk to Downtown
Shepherdstown
The price is AED 591
AED 1,037 total
includes taxes & fees
22 Sep - 23 Sep
Charming Shepherdstown Home - Walk to Downtown
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

SpringHill Suites by Marriott Frederick

SpringHill Suites by Marriott Frederick

10/10 Excellent
"Room was great. Tony, well planned, with the extra space and amenities of a suite. Modern and well thought out."
Madelon 1-night trip
Posted 1 hour ago
SpringHill Suites by Marriott Frederick