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Middletown Holiday Rentals

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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Holiday Rentals in Middletown

Our top choices for Middletown holiday rentals

Countryside Cabin with Mountain Views near Surreybrooke Gardens
Property grounds

Countryside Cabin with Mountain Views near Surreybrooke Gardens

10.0 out of 10, Exceptional, (113)
"We LOVED our stay at Surrey Cabin! Quaint, clean, quiet, and the property is breathtaking! The bed was super comfortable and we had everything we needed. We will definitely be coming back! "
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, (101)
"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 HK$508
HK$1,417 total
includes taxes & fees
25 Aug - 26 Aug
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
RIVERKEEPER INN, Waterfront Property on the Potomac River
Terrace/patio

RIVERKEEPER INN, Waterfront Property on the Potomac River

9.4 out of 10, Exceptional, (126)
"We had a fabulous time here! This was a great location. Not only was it close to historic sites, downtown Harper’s Ferry, but we also thoroughly enjoyed the river (as did our dog!). While this is a back unit to the host's home, they were were hospitable, friendly, made an effort to give us privacy and allowed us full use of all the amenities. We were concerned about privacy, but had no issues and would absolutely recommend this place. It was also a great neighborhood for our dog to walk/run...
RIVERKEEPER INN, Waterfront Property on the Potomac River
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, (128)
"Place was nice and clean. Location was good. We enjoyed the quiet. Had a blast!"
Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!
Charming Cabin in the Woods with River Access
Exterior

Charming Cabin in the Woods with River Access

9.8 out of 10, Exceptional, (31)
"Very nice rest time…"
The price is HK$1,274
HK$2,340 total
includes taxes & fees
28 Aug - 29 Aug
Charming Cabin in the Woods with River Access
❤️ Secluded 1940s Romantic Tiny House on the River
Property grounds

❤️ Secluded 1940s Romantic Tiny House on the River

9.8 out of 10, Exceptional, (60)
"We truly loved this location and definitely will be back!"
The price is HK$521
HK$1,055 total
includes taxes & fees
1 Sept - 2 Sept
❤️ Secluded 1940s Romantic Tiny House on the River
Blue Ridge Getaway - Sunset Views, A.T. Access
3 bedrooms, desk, iron/ironing board, free WiFi

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

10.0 out of 10, Exceptional, (55)
"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 HK$782
HK$2,837 total
includes taxes & fees
2 Sept - 3 Sept
Blue Ridge Getaway - Sunset Views, A.T. Access
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Interior

Walk to Harpers Ferry! Dog-friendly. Beautiful Views.

10.0 out of 10, Exceptional, (62)
"Location and house was just as described. Would highly recommend staying here if your looking for a location close to Harper's Ferry."
Walk to Harpers Ferry! Dog-friendly. Beautiful Views.
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
Exterior

Amazing dog-friendly cottage. Walk 2 Harpers Ferry

2.0 star property
9.8 out of 10, Exceptional, (15)
"Very nice property with convenient location! Within walking distance of down town. "
The price is HK$1,446
HK$2,560 total
includes taxes & fees
25 Aug - 26 Aug
Amazing dog-friendly cottage. Walk 2 Harpers Ferry
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

8.8 out of 10, Excellent, (8)
"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."
Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry
Birch Cabin at Hunting Creek Hideaway
Property grounds

Birch Cabin at Hunting Creek Hideaway

9.6 out of 10, Exceptional, (9)
"Cabin was perfect! So cute! We loved it and will definitely stay there again! "
The price is HK$668
HK$1,081 total
includes taxes & fees
26 Aug - 27 Aug
Birch Cabin at Hunting Creek Hideaway
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort
Smart TV

Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort

10.0 out of 10, Exceptional, (15)
"This is an amazing place to stay its not far away from alot of things but gives you the sense of being in the middle of no where. "
Cozy cabin among the trees near Historic Gettysburg / Liberty Mountain Resort
Cottage on King | Charming Historic Leesburg Home
Terrace/patio

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (54)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is HK$1,104
HK$2,402 total
includes taxes & fees
9 Sept - 10 Sept
Cottage on King | Charming Historic Leesburg Home
Fall is right around the corner! Plan your mountain getaway now!
Fridge, microwave, oven, stovetop

Fall is right around the corner! Plan your mountain getaway now!

10.0 out of 10, Exceptional, (304)
"We had a great time.The cabin was very clean and cozy. We loved using the fireplace!"
Fall is right around the corner! Plan your mountain getaway now!
Terra Alta - Incredible River Views and Hot Tub!
Exterior

Terra Alta - Incredible River Views and Hot Tub!

9.6 out of 10, Exceptional, (58)
"We had a great time! The house overlooks the river and we loved the hot tub and fire pit! "
The price is HK$782
HK$3,166 total
includes taxes & fees
1 Sept - 2 Sept
Terra Alta - Incredible River Views and Hot Tub!
Modern Country House on the Shenandoah River
Property grounds

Modern Country House on the Shenandoah River

9.8 out of 10, Exceptional, (39)
"The views are beautiful and the house was the perfect size for a group of 7 friends. We had a great time!"
Modern Country House on the Shenandoah River
Wild And Wonderful Silos
1 bedroom, iron/ironing board, free WiFi, bed sheets

Wild And Wonderful Silos

9.2 out of 10, Wonderful, (5)
"Heated mattress was the best. Thank you! "
The price is HK$1,372
HK$2,318 total
includes taxes & fees
25 Aug - 26 Aug
Wild And Wonderful Silos
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Terrace/patio

Riverside cottage, minutes from historic Harpers Ferry! Private river access!

9.8 out of 10, Exceptional, (120)
"Very nice home with river access. Close to all area attractions."
Riverside cottage, minutes from historic Harpers Ferry! Private river access!
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Exterior

Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.

10.0 out of 10, Exceptional, (140)
"Wonderful house for a great weekend away"
The price is HK$1,516
HK$3,125 total
includes taxes & fees
8 Sept - 9 Sept
Family-friendly, thoughtfully modernized, historic home in Harpers Ferry.
Quaint Mini Cottage in Shepherdstown - Walking Distance
Dining

Quaint Mini Cottage in Shepherdstown - Walking Distance

8.0 out of 10, Very good, (3)
"Great, easy to find location. Nancy was a great communicator A wonderful option for us, as we were in the area for a wedding in Sharpsburg where overnight accommodations were a bit slim. Shepherdstown was a cute town with lots of cute local shops and places to eat. Would stay here again! "
Quaint Mini Cottage in Shepherdstown - Walking Distance
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

Comfort Inn Frederick - Ballenger Creek

Comfort Inn Frederick - Ballenger Creek

10/10 Excellent
"Clean, great location for our visit "
CAROL 2-night trip
Posted 22 hours ago
Comfort Inn Frederick - Ballenger Creek

Frequently asked questions

Can I find a holiday rental in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Middletown has to offer?

Downtown Harpers Ferry! Charming Historic House in Harpers Ferry National Park!: This holiday home rental outside of Middletown is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of private gardens in this rental home to help you unwind.

How many holiday rentals will I find in Middletown?

Expedia has 4 holiday 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 holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you need. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.