Middletown Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks

Vacation Rentals in Middletown

Cabin in Middletown

9.6 out of 10, Exceptional, (110)
"Beautiful cabin with an adorable mini oven, great TV, creature comforts of robes and throws. Best sleep I’ve ever had in the quiet."
United States
Sharon H.
$186 nightly
The price is $197
Nov 30 - Dec 1
Total with taxes and fees
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.

Vacation Home in Middletown

10.0 out of 10, Exceptional, (139)
"Love the place will book again"
United States
WAYNE M.
$237 nightly
The price is $251
Nov 30 - Dec 1
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown

Cabin in Shepherdstown

10.0 out of 10, Exceptional, (64)
"We truly loved this location and definitely will be back!"
United States
Astrid
$95 nightly
The price is $105
Dec 8 - Dec 9
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the 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.
$145 nightly
The price is $161
Nov 30 - Dec 1
Total with taxes and fees
Bring Your Own Boat - Meticulously restored house on the Potomac River

Apartment in Frederick

10.0 out of 10, Exceptional, (6)
"Very convenient to everything. Quick walk to shops, breweries, and restaurants."
United States
JENNIFER
$184 nightly
The price is $195
Nov 30 - Dec 1
Total with taxes and fees
Pet-friendly, heart of 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.
$184 nightly
The price is $195
Nov 30 - Dec 1
Total with taxes and fees
Cozy, dog-friendly, downtown

Apartment in Blue Ridge Summit

9.4 out of 10, Exceptional, (11)
"Very restful very accommodating and very helpful ownerd"
United States
Donna B.
$173 nightly
The price is $191
Nov 30 - Dec 1
Total with taxes and fees
Charming in-law suite. The open-concept living area welcomes you.

Cabin in Thurmont

9.8 out of 10, Exceptional, (18)
"Was wonderful..private and peaceful. Perfect getaway. "
United States
Courtney G.
$131 nightly
The price is $138
Dec 2 - Dec 3
Total with taxes and fees
Birch Cabin at Hunting Creek Hideaway

Cottage in Frederick

10.0 out of 10, Exceptional, (62)
"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.
$243 nightly
The price is $258
Dec 2 - Dec 3
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

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.
$339 nightly
The price is $377
Nov 30 - Dec 1
Total with taxes and fees
Aslan's How - Cabin with Valley Views & Hot Tub!

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.
$160 nightly
The price is $170
Dec 7 - Dec 8
Total with taxes and fees
Cozy Pine Tree Nest

Cabin in Waynesboro

9.8 out of 10, Exceptional, (89)
"Love it been coming here for a few years now "
United States
Kristina M.
$203 nightly
The price is $224
Nov 30 - Dec 1
Total with taxes and fees
Antietam Toll House~ an historic waterfront cabin with fully fenced yard.

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.
$297 nightly
The price is $330
Dec 1 - Dec 2
Total with taxes and fees
Log Cabin w/ Hot Tub & Waterfront Patio!

Cottage in Frederick

3.0 star property
$828 nightly
The price is $878
Dec 22 - Dec 23
Total with taxes and fees
6 Mi to Gambrill State Park: Family Gem w/ Patio!

Cabin in Keedysville

9.8 out of 10, Exceptional, (64)
"Very nice property. My family had a fun stay!"
United States
Radha V.
$330 nightly
The price is $367
Dec 4 - Dec 5
Total with taxes and fees
Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Cabin in Keedysville

9.8 out of 10, Exceptional, (33)
"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.
$321 nightly
The price is $357
Dec 3 - Dec 4
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!

Apartment in Brunswick

10.0 out of 10, Exceptional, (16)
"Everything was great. Would stay again! Accurate listing."
United States
Marlin S.
$173 nightly
The price is $183
Nov 30 - Dec 1
Total with taxes and fees
Loft Apt Just off C&O near Harpers Ferry and AT

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.
$237 nightly
The price is $251
Nov 30 - Dec 1
Total with taxes and fees
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD

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.
$348 nightly
The price is $387
Dec 1 - Dec 2
Total with taxes and fees
Mountain Chic Retreat-Harpers Ferry, the AT, Wine country w/ Lake Beach passes!

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.
$236 nightly
The price is $250
Nov 30 - Dec 1
Total with taxes and fees
Gorgeous apt, pets, hot tub & fire pit, walk --> DT Frederick
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.

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Save an average of 15% on thousands of hotels when you're signed in

Top Middletown Hotel Reviews

Find out more about Middletown

Everything you need to know about Middletown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middletown vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Middletown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $105 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Riverside cottage, minutes from historic Harpers Ferry! Private river access!: This vacation home rental near Middletown offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 John Brown Wax Museum, 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.