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Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 17 - Oct 19
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28
In four months
Jan 23 - Jan 25

Vacation Rentals in Middletown

Countryside Cabin with Mountain Views near Surreybrooke Gardens
Property grounds

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (121)
"Good location "
Countryside Cabin with Mountain Views near Surreybrooke Gardens
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Interior

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

9.6 out of 10, Exceptional, (104)
"Our weekend cabin stay was wonderful. The safe neighborhood was quite and peaceful. Its location near nature and the city was just perfect. The cozy cabin was clean and comfy. We loved Gambrill State Park and downtown Frederick didn't disappoint as well."
The price is ￥9,586
￥26,731 total
includes taxes & fees
Oct 6 - Oct 7
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
Microwave

Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry

9.4 out of 10, Exceptional, (16)
"Small basement apartment had all we needed and wanted. Wonderful location. "
The price is ￥16,590
￥27,519 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Rustic Walkout Basement Cabin in Historic Harpers Ferry
RIVERKEEPER INN, Waterfront Property on the Potomac River
Terrace/patio

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (128)
"Beautiful location right on the Potomac River."
RIVERKEEPER INN, Waterfront Property on the Potomac River
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

❤️ Secluded 1940s Romantic Tiny House on the River

10.0 out of 10, Exceptional, (61)
"We truly loved this location and definitely will be back!"
The price is ￥5,973
￥15,597 total
includes taxes & fees
Oct 12 - Oct 13
❤️ Secluded 1940s Romantic Tiny House on the River
The Oculus - Huge Cabin with a Hot Tub!
Terrace/patio

The Oculus - Huge Cabin with a Hot Tub!

9.6 out of 10, Exceptional, (24)
"The place was big and very roomy and comfortable. Very clean .. very nice. "
The price is ￥14,747
￥64,651 total
includes taxes & fees
Oct 14 - Oct 15
The Oculus - Huge Cabin with a Hot Tub!
Antietam Creek - Quiet 2 Bedroom Cabin
Interior

Antietam Creek - Quiet 2 Bedroom Cabin

9.4 out of 10, Exceptional, (85)
"I loved the trip to that cabin, one of the most wonderful things"
The price is ￥29,494
￥48,928 total
includes taxes & fees
Oct 7 - Oct 8
Antietam Creek - Quiet 2 Bedroom Cabin
Enchanting Cottage, walk to Downtown Harpers Ferry
Terrace/patio

Enchanting Cottage, walk to Downtown Harpers Ferry

9.6 out of 10, Exceptional, (41)
"This place was perfect for our one-night stay in Harpers Ferry. Its location is in easy walking distance of the main sites. The house is old but charming. "
The price is ￥35,186
￥55,628 total
includes taxes & fees
Nov 5 - Nov 6
Enchanting Cottage, walk to Downtown Harpers Ferry
Blue Ridge Getaway - Sunset Views, A.T. Access
Exterior

Blue Ridge Getaway - Sunset Views, A.T. Access

10.0 out of 10, Exceptional, (59)
"My girlfriend and I had a wonderful weekend escaping the hustle and bustle of the city. The view was spectacular and the property was perfect!"
The price is ￥14,747
￥53,838 total
includes taxes & fees
Oct 8 - Oct 9
Blue Ridge Getaway - Sunset Views, A.T. Access
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Exterior detail

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!

10.0 out of 10, Exceptional, (132)
"Wonderful stay in a historic home within walking distance of so much American history and so many trails. Would definitely stay here again."
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Fridge, microwave, oven, stovetop

Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex

9.8 out of 10, Exceptional, (100)
"This home was absolutely fantastic! Very clean, very close to all things. We had a fantastic time."
The price is ￥28,609
￥86,998 total
includes taxes & fees
Oct 20 - Oct 21
Large Groups, Hot Tub, Near Attractions, Wooded/Country Setting w/Aparment/Annex
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Dining

Cozy Mountain Cabin w/ Steam Shower! Family Friendly.

10.0 out of 10, Exceptional, (75)
"Wonderful view from the sunroom. Peaceful and rejuvenating stay in this welcoming home. "
The price is ￥15,263
￥40,952 total
includes taxes & fees
Oct 6 - Oct 7
Cozy Mountain Cabin w/ Steam Shower! Family Friendly.
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Fridge, microwave, oven, stovetop

Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home

9.4 out of 10, Exceptional, (106)
"Great little farm house in a quaint little town "
The price is ￥23,448
￥43,613 total
includes taxes & fees
Oct 9 - Oct 10
Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Home
Luxury Getaway on The Potomac
8 bedrooms, desk, travel crib, free WiFi

Luxury Getaway on The Potomac

9.8 out of 10, Exceptional, (18)
"We had 15 family members and friends staying there for 4 days. It was very comfortable and the kitchen is quite luxurious! Be aware that it's way out in the country, which was exactly what I wanted!Melissa was very responsive to our questions.Only issue we had was that the kitchen wasn't super clean (empty drawers had crumbs, microwave wasn't clean), but not bad enough to complain."
Luxury Getaway on The Potomac
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Exterior

Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin

9.2 out of 10, Wonderful, (61)
"House was wonderful, and I loved how often Tony checked in! Will absolutely be staying here again!"
The price is ￥22,858
￥40,672 total
includes taxes & fees
Oct 6 - Oct 7
Hot Tub, Deck/Grill, Game Room, WiFi at Cute Cabin
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
Outdoor dining

Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people

8.4 out of 10, Very Good, (24)
"This house"
Cozy Cabin w/ Hot Tub, Arcade & Fire Pit perfect for up to 8 people
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Property grounds

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry

9.2 out of 10, Wonderful, (12)
"Four family members stayed for a four day weekend. The place was spotless when we arrived and all amenities are as described. The location is perfect for visiting Harpers Ferry, Shepherdstown, and Antietam. We had wonderful time."
The price is ￥24,480
￥63,200 total
includes taxes & fees
Oct 6 - Oct 7
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Charming Cabin in the Woods with River Access
Exterior

Charming Cabin in the Woods with River Access

9.6 out of 10, Exceptional, (34)
"Very quiet and cozy property. Well maintained and nice location."
The price is ￥24,038
￥43,374 total
includes taxes & fees
Oct 13 - Oct 14
Charming Cabin in the Woods with River Access
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Terrace/patio

Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!

9.8 out of 10, Exceptional, (23)
"Loved this home in the riverfront! Perfect Fourth of July Getaway for the whole family. "
Stunning Views, Riverfront Privacy, 18-Acre Estate - Near Hikes, Wine/Breweries!
Secluded Cabin a Stone's Throw From the A.T.!
Fridge, microwave, oven, stovetop

Secluded Cabin a Stone's Throw From the A.T.!

10.0 out of 10, Exceptional, (33)
"We enjoyed the beautiful views and the house had everything we wanted."
The price is ￥14,747
￥57,923 total
includes taxes & fees
Oct 14 - Oct 15
Secluded Cabin a Stone's Throw From the A.T.!
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

Quality Inn

Quality Inn

10/10 Excellent
"It was a very great experience. The rooms were clean. The front desk people were very helpful. The breakfast was nice and a lady was cleaning the area and refilling the food. "
Paul 1-night trip
Posted 2 days ago
Quality Inn

Find out more about Middletown

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
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • 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?

Enchanting Cottage, walk to Downtown Harpers Ferry: This vacation home rental near Middletown is located in the city center and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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 Maryland National Golf Club and South Mountain State Park.

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.