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Middletown Holiday Rentals

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Holiday Rentals in Middletown

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

10.0 out of 10, Exceptional, (123)
"Visited nice restaurants, brew pubs, antique shops. House was perfect for us. Very clean and well equipped. "
The price is NZ$419
includes taxes & fees
2 July - 3 July
Charming "Cream of the Crop" Cape ~❤️of Middletown

New townhouse

10.0 out of 10, Exceptional, (7)
"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!"
The price is NZ$654
includes taxes & fees
6 July - 7 July
New townhouse

Newly constructed 6 bedroom home

10.0 out of 10, Exceptional, (10)
"Comfortable beds! Garage access. 4 bathrooms- great for a big group. "
The price is NZ$768
includes taxes & fees
25 July - 26 July
Newly constructed 6 bedroom home

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

9.4 out of 10, Exceptional, (109)
"This property is perfectly situated if your goal is to be able to walk through Frederick and enjoy the parks, shopping, and restaurants"
The price is NZ$486
includes taxes & fees
1 July - 2 July
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

*Luxury Condo In Downtown Frederick*

9.0 out of 10, Wonderful, (62)
"The condo is quite spacious, more than expected. We enjoyed the modern touches and private parking is a big plus in downtown Frederick. So close to Carroll Creek and Market St. The hosts are responsive. We highly recommend staying at Gideon Getaways! "
The price is NZ$554
includes taxes & fees
30 June - 1 July
*Luxury Condo In Downtown Frederick*

Downtown Charm: Pets Welcome

10.0 out of 10, Exceptional, (1)
"House was nice and cozy. And short trip to downtown area. Would definately stay here again."
The price is NZ$595
includes taxes & fees
30 June - 1 July
Downtown Charm: Pets Welcome

Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont

10.0 out of 10, Exceptional, (1)
"We truly loved this little cottage and was perfect for our stay while visiting family and friends. We took several walks in the area, enjoyed the quiet and the adorable space. The beds were very comfortable. The cottage was very clean and nicely remodeled. We will hopefully be able to rent here again at our next visit! Owner was very responsive and helpful as well. Only was missing a blowdryer, but I improvised! "
The price is NZ$332
includes taxes & fees
2 July - 3 July
Charming 2-bedroom cottage near Mount Saint Mary’s College in Thurmont

Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

9.8 out of 10, Exceptional, (46)
"Awesome place."
The price is NZ$702
includes taxes & fees
1 July - 2 July
Among the Trees, Minutes from Liberty Mtn. Resort and 10 Miles from Gettysburg

Modern Suite with Private Bath – Stylish & Comfy

The price is NZ$232
includes taxes & fees
25 July - 26 July
Modern Suite with Private Bath – Stylish & Comfy

The Cottage on Royal - Historic Leesburg Home

10.0 out of 10, Exceptional, (10)
"Cute little house perfect for a small town getaway. The house was a perfect fit for my family of 5. We were able to walk to the shops and enjoyed a nice day of shopping. We will be back!"
The price is NZ$702
includes taxes & fees
8 July - 9 July
The Cottage on Royal - Historic Leesburg Home

'Thomson Farm' Classic Home < 10 Mi to Vineyards!

10.0 out of 10, Exceptional, (30)
"Charming country home with spacious kitchen and plenty of room to gather. Each bedroom has own updated bathroom- perfect for large groups. Plenty of parking, too."
The price is NZ$3,057
includes taxes & fees
1 July - 2 July
'Thomson Farm' Classic Home < 10 Mi to Vineyards!

Quaint Royal Cottage @ Historic Leesburg

2.0 star property
10.0 out of 10, Exceptional, (8)
"Location was great! We enjoyed our stay in this old historical home that has been completely updated. Property manager was super communicative and easy to work with. 10 out of 10 would stay here again. "
The price is NZ$721
includes taxes & fees
8 July - 9 July
Quaint Royal Cottage @ Historic Leesburg

Retreat in Historic Downtown Leesburg - Walkable to Everything!

10.0 out of 10, Exceptional, (3)
"The house was immaculate, easy to use and walking distance to everything in downtown Leesburg. We would stay again!"
The price is NZ$903
includes taxes & fees
30 June - 1 July
Retreat in Historic Downtown Leesburg - Walkable to Everything!

Cottage on King | Charming Historic Leesburg Home

9.6 out of 10, Exceptional, (52)
"Walkable to downtown historic Leesburg. Clean and super cute little house. Would stay again! "
The price is NZ$505
includes taxes & fees
1 July - 2 July
Cottage on King | Charming Historic Leesburg Home

Historic Hideaway

10.0 out of 10, Exceptional, (18)
"I love this place. It was clean and the host was very attentive. I wish it was warmer because the downtown area has lot of cool places. I highly recommend this spot! "
The price is NZ$560
includes taxes & fees
13 July - 14 July
Historic Hideaway

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

10.0 out of 10, Exceptional, (48)
"Visiting family over the holidays. Our trip was great. Location was perfect. Rental house accommodations fulfilled our needs, was clean and had everything we needed. Will definitely stay again. "
The price is NZ$422
includes taxes & fees
29 June - 30 June
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

Charming Historic Victorian 4 bedroom B&B in serene Rohrersville with WiFi, AC

The price is NZ$653
includes taxes & fees
6 July - 7 July
Charming Historic Victorian 4 bedroom B&B in serene Rohrersville with WiFi, AC

Buckskin Manor - Historic, Pool, 66 Acre Vineyard

9.6 out of 10, Exceptional, (17)
"The house was lovely and the pool was divine !! We all had a great time and would highly recommend this place for any occasion!"
Buckskin Manor - Historic, Pool, 66 Acre Vineyard

4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Yard Games

10.0 out of 10, Exceptional, (12)
"We loved the night out at this property. A beautiful house in a great spot. The hosts were so accommodating and really friendly. "
The price is NZ$954
includes taxes & fees
30 June - 1 July
4 King Suites w/ Hot Tub, Fire Pit, Ping Pong, Arcade, Yard Games

White House Inn - Historic Home in Harpers Ferry!

10.0 out of 10, Exceptional, (32)
"We very much enjoyed our stay at this property. Walking distance to Harper's ferry attractions and plenty of room for 5 adults to spread out. We anticipate renting this property in the future for more ladies weekends!"
The price is NZ$965
includes taxes & fees
10 July - 11 July
White House Inn - Historic Home in Harpers Ferry!
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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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 Maryland National Golf Club and South Mountain State Park.

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.