Search Vacation Homes in Middletown

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Middletown vacation homes

Terrace/patio
Charming "Cream of the Crop" Cape ~❤️of Middletown

Vacation Home in Middletown

10.0 out of 10, Exceptional, (139)
"Love the place will book again"
United States
WAYNE M.
The price is AED 294
AED 833 total
includes taxes & fees
11 Dec - 12 Dec
Charming "Cream of the Crop" Cape ~❤️of Middletown
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Vacation Home in Downtown Frederick

9.4 out of 10, Exceptional, (119)
"We loved being so close to all the action downtown. A perfect getaway for our family to explore the area, visit with family, and eat great food!!! "
United States
Natalie C.
The price is AED 408
AED 1,016 total
includes taxes & fees
14 Dec - 15 Dec
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Smart TV
*Luxury Condo In Downtown Frederick*

Vacation Home in Downtown Frederick

9.0 out of 10, Wonderful, (71)
"Great time. Everything was perfect and place was just what we needed. "
United States
dominick c.
The price is AED 375
AED 954 total
includes taxes & fees
11 Dec - 12 Dec
*Luxury Condo In Downtown Frederick*
Dining
New, Contemporary House in Historic Harpers Ferry

Vacation Home in Harpers Ferry

2.0 star property
10.0 out of 10, Exceptional, (1)
"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 1,358 total
includes taxes & fees
22 Dec - 23 Dec
New, Contemporary House in Historic Harpers Ferry
Fridge, microwave, oven, stovetop
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Vacation Home in Jefferson

9.8 out of 10, Exceptional, (58)
"We loved visiting! Wish we could've stayed longer. The accommodations were great; super comfortable and inviting. Everyone enjoyed themselves. Thanks for having us!"
United States
David F.
The price is AED 459
AED 1,032 total
includes taxes & fees
17 Dec - 18 Dec
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
TV
Historic Queen Anne Family Home w Modern Comforts

Vacation Home in Harpers Ferry

10.0 out of 10, Exceptional, (3)
"The location was great and the host was very east to communicate with."
United States
Liz B.
The price is AED 585
AED 1,388 total
includes taxes & fees
11 Dec - 12 Dec
Historic Queen Anne Family Home w Modern Comforts
Property grounds
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick

Vacation Home in Frederick

10.0 out of 10, Exceptional, (34)
"Two bedroom each with its own bathroom was so nice for our small group. The apartment is walking distance to town and in a quiet neighborhood. Our stay was perfect!"
United States
Jennifer S.
The price is AED 411
AED 950 total
includes taxes & fees
5 Jan - 6 January 2026
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
Terrace/patio
White House Inn - Historic Home in Harpers Ferry!

Vacation Home in Harpers Ferry

10.0 out of 10, Exceptional, (38)
"Very clean and well appointed. Great for a large group. "
United States
Richard
The price is AED 367
AED 1,489 total
includes taxes & fees
17 Dec - 18 Dec
White House Inn - Historic Home in Harpers Ferry!
Terrace/patio
Cottage on King | Charming Historic Leesburg Home

Vacation Home in Leesburg's Old and Historic District

9.6 out of 10, Exceptional, (67)
"Great location and very comfortable house. Beautiful place to stay, we loved sitting on the porch in the morning with coffee"
United States
Fern
The price is AED 585
AED 1,235 total
includes taxes & fees
15 Dec - 16 Dec
Cottage on King | Charming Historic Leesburg Home
Fridge, microwave, oven, stovetop
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

Vacation Home in Myersville

9.4 out of 10, Exceptional, (110)
"Alot of choices for food and snacks within walking distance. "
United States
Cherilyn H.
The price is AED 584
AED 1,086 total
includes taxes & fees
17 Dec - 18 Dec
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Interior
New townhouse

Vacation Home in Frederick

9.4 out of 10, Exceptional, (9)
"This property was impeccably clean and so comfortable! The beds were incredibly cozy, and the kitchen was well-stocked. We felt right at home and enjoyed our stay immensely. Beds were comfortable, and kitchen well stocked. The location can't be beat, with so many attractions and wonderful restaurants within a short drive. Tons of nice touches for our arrival; great communication; easy access. We will definitely stay here again!"
United States
Traci U.
The price is AED 555
AED 1,324 total
includes taxes & fees
15 Dec - 16 Dec
New townhouse
Exterior
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

Vacation Home in Harpers Ferry

10.0 out of 10, Exceptional, (5)
"Great and quiet location with all the amenities. Getting to the parking is a bit tricky but other than that great place to stay with family"
United States
Vinod B.
The price is AED 385
AED 1,237 total
includes taxes & fees
18 Dec - 19 Dec
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!
Microwave, oven, stovetop, dishwasher
3-bedroom townhome in charming Hagerstown with AC, WiFi

Vacation Home in Hagerstown

6.0 out of 10, (1)
"The inside was very clean, outside was a mess. Location was bad, on a busy street and a busy railway."
United States
mark C.
The price is AED 404
AED 790 total
includes taxes & fees
26 Dec - 27 Dec
3-bedroom townhome in charming Hagerstown with AC, WiFi
Outdoor spa tub
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!

Vacation Home in Sharpsburg

10.0 out of 10, Exceptional, (39)
"We had an amazing time - lots of walks and places to see - very historical - winery right next door which was an added bonus - accommodation was everything we needed and more - look out for a friendly cat that paid a few visits - thank you Jordan for a great time and will definitely come back to the area"
United Kingdom
Jo W.
The price is AED 459
AED 1,153 total
includes taxes & fees
14 Dec - 15 Dec
Wine Weekend Getaway: Steps to Winery & Battlefield w/ Mountain Views & Hot Tub!
Outdoor spa tub
Terra Alta - Incredible River Views and Hot Tub!

Vacation Home in Charles Town

9.6 out of 10, Exceptional, (65)
"It was a great house for a weekend getaway. Most of the house was clean. The exterior was a little unkept. A few repairs would be good for the exterior. Everything was functional. The bed was great. Hot tub was clean and well maintained. The grill was like new and worked well. I would stay here again. "
United States
Lance B.
The price is AED 367
AED 1,476 total
includes taxes & fees
22 Dec - 23 Dec
Terra Alta - Incredible River Views and Hot Tub!
2 bedrooms, travel crib, WiFi, bed sheets
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry

Vacation Home in Harpers Ferry

2.0 star property
10.0 out of 10, Exceptional, (15)
"Great spot"
China
Clara
The price is AED 661
AED 1,134 total
includes taxes & fees
21 Dec - 22 Dec
Eclectic & Romantic - Walk to Historic Downtown Harpers Ferry
Property grounds
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

Vacation Home in Harpers Ferry

9.4 out of 10, Exceptional, (19)
"A nice relaxing place to stay in the mountains of WV near many things to do. Check-in and check-out instructions were easy to follow. "
United States
L G.
The price is AED 610
AED 1,574 total
includes taxes & fees
11 Dec - 12 Dec
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Fridge, microwave, oven, stovetop
Leesburg Hideaway- King Bed + Private Backyard

Vacation Home in Leesburg

10.0 out of 10, Exceptional, (30)
"Lovely property, really nicely furnished and clean. Brilliant location for lots of places locally and close enough to walk into Leesburg itself to get ice cream!"
United Kingdom
Rachael B.
Leesburg Hideaway- King Bed + Private Backyard
Terrace/patio
Enchanting Cottage, walk to Downtown Harpers Ferry

Vacation Home in Harpers Ferry

9.6 out of 10, Exceptional, (44)
"We really enjoyed our stay here, the location is perfect for exploring Harpers Ferry, within walking distance to everything. The cottage is well equipped, clean and cozy, perfect for a couples get away, would book again if returning to HF. The owner was very communicated, had well organized info for the stay and was easy to work with"
United States
Brandon L.
The price is AED 553
AED 998 total
includes taxes & fees
11 Dec - 12 Dec
Enchanting Cottage, walk to Downtown Harpers Ferry
Interior
Cozy Peaceful Basement Cabin Vibes

Vacation Home in Ijamsville

10.0 out of 10, Exceptional, (5)
"Good trip."
United States
Jewell F.
The price is AED 918
AED 1,312 total
includes taxes & fees
8 Jan - 9 January 2026
Cozy Peaceful Basement Cabin Vibes
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

Red Roof Inn Leesburg, VA

Red Roof Inn Leesburg, VA

10/10 Excellent
" Needed a room for one night while visiting my daughter at college in Purcellville and to attend a church service at Cornerstone Chapel in Leesburg. This hotel was convenient as well as the most economical in Leesburg having good ratings. It turned out great! Must have recently been updated because it was very clean and comfortable. The staff member at the desk for my late night checkin and early morning checkout had a great attitude, professional at the same time friendly and welcoming! Thank you, Red Roof Inn and thank you to your staff member!"
Linda 1-night trip
Posted 1 day ago
Red Roof Inn Leesburg, VA