Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in Middletown

Interior
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Cabin in Middletown

9.6 out of 10, Exceptional, (107)
"We loved it! As cute/sweet as described."
United States
Fran E.
The price is ￥10,949
￥29,014 total
includes taxes & fees
Nov 24 - Nov 25
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
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 ￥22,679
￥47,748 total
includes taxes & fees
Nov 24 - Nov 25
Charming "Cream of the Crop" Cape ~❤️of Middletown
Game room
Bring Your Own Boat - Meticulously restored house on the Potomac River

Cottage in Hedgesville

10.0 out of 10, Exceptional, (9)
"Cute little house that my husband and I enjoyed for the weekend. Great location close to Martinsburg. It had everything we needed for our weekend The host communicated well, we had no issues, and we would definitely stay here again. Thank you!"
United States
Jennifer E.
The price is ￥11,731
￥25,214 total
includes taxes & fees
Nov 24 - Nov 25
Bring Your Own Boat - Meticulously restored house on the Potomac River
Property grounds
❤️ Secluded 1940s Romantic Tiny House on the River

Cabin in Shepherdstown

10.0 out of 10, Exceptional, (64)
"We truly loved this location and definitely will be back!"
United States
Astrid
The price is ￥6,194
￥16,386 total
includes taxes & fees
Dec 1 - Dec 2
❤️ Secluded 1940s Romantic Tiny House on the River
Outdoor spa tub
Aslan's How - Cabin with Valley Views & Hot Tub!

Cabin in Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (8)
"We stayed here for our honeymoon and it was very nice and peaceful "
United States
Robert F.
The price is ￥15,641
￥59,351 total
includes taxes & fees
Nov 24 - Nov 25
Aslan's How - Cabin with Valley Views & Hot Tub!
Fridge, microwave, oven, stovetop
Cozy, dog-friendly, downtown

Apartment in Frederick

10.0 out of 10, Exceptional, (26)
"Super cute and was the PERFECT location! We had a great stay! "
United States
Sarah S.
The price is ￥9,854
￥30,341 total
includes taxes & fees
Nov 24 - Nov 25
Cozy, dog-friendly, downtown
Fridge, microwave, coffee/tea maker, electric kettle
Cozy Pine Tree Nest

Apartment in Frederick

9.4 out of 10, Exceptional, (11)
"Really nice apartment was just what we wanted for a weekend while here to run the JFK 50 miler"
United States
David S.
The price is ￥13,920
￥28,185 total
includes taxes & fees
Dec 10 - Dec 11
Cozy Pine Tree Nest
Fridge, microwave, oven, stovetop
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Cottage in Frederick

10.0 out of 10, Exceptional, (61)
"We thoroughly enjoyed our stay in Frederick. The cottage was comfortable and an easy walk to shops, parks and restaurants. We would definitely stay here for our next trip to Frederick. "
United States
Karen B.
The price is ￥18,018
￥40,321 total
includes taxes & fees
Dec 2 - Dec 3
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Smart TV
Pet-friendly, heart of downtown

Apartment in Frederick

10.0 out of 10, Exceptional, (6)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
The price is ￥9,854
￥30,506 total
includes taxes & fees
Nov 24 - Nov 25
Pet-friendly, heart of downtown
Property grounds
Birch Cabin at Hunting Creek Hideaway

Cabin in Thurmont

9.8 out of 10, Exceptional, (17)
"Cabin was perfect! So cute! We loved it and will definitely stay there again! "
United States
Julie B.
The price is ￥13,373
￥21,636 total
includes taxes & fees
Nov 24 - Nov 25
Birch Cabin at Hunting Creek Hideaway
Dining
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Cabin in Keedysville

9.8 out of 10, Exceptional, (64)
"Very nice property. My family had a fun stay!"
United States
Radha V.
The price is ￥15,641
￥57,268 total
includes taxes & fees
Nov 24 - Nov 25
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!
Smart TV, fireplace
Charming in-law suite. The open-concept living area welcomes you.

Apartment in Blue Ridge Summit

9.4 out of 10, Exceptional, (11)
"Very restful very accommodating and very helpful ownerd"
United States
Donna B.
The price is ￥10,323
￥29,863 total
includes taxes & fees
Nov 30 - Dec 1
Charming in-law suite. The open-concept living area welcomes you.
House (3 Bedrooms) | Interior
6 Mi to Gambrill State Park: Family Gem w/ Patio!

Cottage in Frederick

3.0 star property
The price is ￥21,115
￥68,390 total
includes taxes & fees
Nov 25 - Nov 26
6 Mi to Gambrill State Park: Family Gem w/ Patio!
Property grounds
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

Cabin in Waynesboro

9.8 out of 10, Exceptional, (89)
"Love it been coming here for a few years now "
United States
Kristina M.
The price is ￥15,641
￥36,966 total
includes taxes & fees
Nov 30 - Dec 1
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.
Interior
Antietam Look Out - Incredible Sunset Views!

Cabin in Keedysville

9.8 out of 10, Exceptional, (32)
"The property was perfect for our family. It was well equipped with all the kitchen necessities. plenty of space, bedrooms, and bathrooms to accommodate 7 adults and a 1 yr old. Great location for seeing sites. "
United States
Barbara B.
The price is ￥15,641
￥55,526 total
includes taxes & fees
Nov 25 - Nov 26
Antietam Look Out - Incredible Sunset Views!
Interior
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!

Cottage in Hamilton

9.6 out of 10, Exceptional, (8)
"It was a great place to starve whole experience was perfect. "
United States
Jaime B.
The price is ￥35,192
￥61,874 total
includes taxes & fees
Nov 25 - Nov 26
The Cottage at Firefly Cellars, cozy getaway in Loudoun wine country!
3 bedrooms, free WiFi, bed sheets
Log Cabin w/ Hot Tub & Waterfront Patio!

Cabin in Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (11)
"Everything was great! We had a lovely stay."
United States
Beth D.
The price is ￥15,641
￥51,681 total
includes taxes & fees
Dec 1 - Dec 2
Log Cabin w/ Hot Tub & Waterfront Patio!
Smart TV
*Luxury Condo In Downtown Frederick*

Vacation Home in Downtown Frederick

9.0 out of 10, Wonderful, (69)
"Great time. Everything was perfect and place was just what we needed. "
United States
dominick c.
The price is ￥15,954
￥40,951 total
includes taxes & fees
Dec 7 - Dec 8
*Luxury Condo In Downtown Frederick*
Property grounds
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!

Cabin in Harpers Ferry

10.0 out of 10, Exceptional, (15)
"Great location. Great house. Could not have asked for more. "
United States
A. Bland and D. T.
The price is ￥15,641
￥61,269 total
includes taxes & fees
Nov 24 - Nov 25
Wolf Den - Airy Cabin w/ Hot Tub & Valley Views!
Fridge, microwave, oven, stovetop
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI

Chalet in Harpers Ferry

9.4 out of 10, Exceptional, (27)
"The house was very clean upon arrival. We enjoyed spending time in the hot tub and playing pool on a kid’s pool table. It was close the Harper’s Ferry. We also saw deer very close both days we were there, and we loved this!!"
United States
Kelly
The price is ￥30,265
￥52,541 total
includes taxes & fees
Dec 1 - Dec 2
Harpers Ferry Cabin: Hot Tub, Deck, Fire Pit, WiFI
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

Hilton Garden Inn Frederick

Hilton Garden Inn Frederick

10/10 Excellent
"Clean, quiet"
Donna 3-night trip
Posted 3 days ago
Hilton Garden Inn Frederick

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
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  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, we offer vacation rentals near well known points of interest in Middletown, or you can select a secluded option if you're looking for relaxation. Middletown is known for its golf courses and riverfront. Make sure you have time to check out the entertainment choices while you're in the area.

What's the top vacation rental in Middletown?

Terra Alta - Incredible River Views and Hot Tub!: This vacation home rental near Middletown is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private yard, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Middletown?

Expedia has 5 vacation rentals for your stay in Middletown.

What can I see and do in Middletown?

While exploring the area, visit family-friendly sights like Catoctin Wildlife Preserve and Zoo, or get outside and enjoy nature at Baker Park. Other places in town to visit include South Mountain State Park and Maryland National Golf Club.

What are vacation rentals like in Middletown?

Vacation rentals are private accommodations you can book for a couple days or more in Middletown. Vacation rentals offer extras like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a small group gathering.