A stone tower with a staircase leading up to it.

Middletown Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Middletown vacation rentals

A two-story house with a front porch, a chimney, and a small garden with pumpkins.

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

Charming "Cream of the Crop" Cape ~❤️of Middletown
Middletown
10.0 out of 10, Exceptional, (158 reviews)
"Perfect little house in a great historic location."
United States
Donald K.
$296 nightly
The price is $314
Oct 19 - Oct 20
Total with taxes and fees
Charming "Cream of the Crop" Cape ~❤️of Middletown
A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

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

Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
Middletown
9.6 out of 10, Exceptional, (116 reviews)
"Beautiful property! Owner is very quick to communicate and did a fantastic job making it a very relaxing place to stay!"
United States
Cindy B.
$267 nightly
The price is $283
Oct 26 - Oct 27
Total with taxes and fees
Vintage cabin in the ❤️ of Middletown , MD. Pet friendly and prime location.
A bedroom with a bed, a dresser, a ceiling fan, and a window with blinds.

3. Cozy Downtown Cabin - Family Friendly

Cozy Downtown Cabin - Family Friendly
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful property. I will definitely stay there again."
United States
Roger
$241 nightly
The price is $255
Oct 13 - Oct 14
Total with taxes and fees
Cozy Downtown Cabin - Family Friendly
A bedroom with a bed, a bedside table with a lamp, a window with a view, and a decorative wall piece.

4. Cozy, dog-friendly, downtown

Cozy, dog-friendly, downtown
Frederick
10.0 out of 10, Exceptional, (36 reviews)
"Great location, clean place. "
United States
Warren B.
$210 nightly
The price is $223
Oct 13 - Oct 14
Total with taxes and fees
Cozy, dog-friendly, downtown
A storefront with a large glass window, a wooden door, and a brick sidewalk.

5. Huge 1br apt, baby-friendly, dogs, walkable downtown

Huge 1br apt, baby-friendly, dogs, walkable downtown
Downtown Frederick
10.0 out of 10, Exceptional, (13 reviews)
"Great location for a peaceful solo night away -- thanks!"
United States
Kristina S.
Huge 1br apt, baby-friendly, dogs, walkable downtown
A modern kitchen with white cabinets, a wooden table, a stainless steel refrigerator, and a wooden ceiling.

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

Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
Jefferson
10.0 out of 10, Exceptional, (74 reviews)
"Lovely home. Great location! Host was amazingly helpful!"
United States
Tory D.
$294 nightly
The price is $312
Oct 18 - Oct 19
Total with taxes and fees
Welcome to the Rusty Rose-Restored Farmhouse feel in the heart of Jefferson, MD
A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

7. ❤️ Secluded 1940s Romantic Tiny House on the River

❤️ Secluded 1940s Romantic Tiny House on the River
Shepherdstown
9.6 out of 10, Exceptional, (86 reviews)
"Great little getaway. Our only issue was the intense heat of 100 every day. The AC was heavenly!"
United States
Dennis C.
$96 nightly
The price is $107
Oct 25 - Oct 26
Total with taxes and fees
❤️ Secluded 1940s Romantic Tiny House on the River
A room with a blue wall, a wooden dining table, a blue sofa, a white fireplace, and a window with white curtains.

8. Huge, Downtown, Walkable, Coffee, Breweries, Dogs

Huge, Downtown, Walkable, Coffee, Breweries, Dogs
Downtown Frederick
10.0 out of 10, Exceptional, (4 reviews)
"Very comfortable and convenient stay with responsive hosts. Great amenities for longer stays with the w/d. Will be back!"
United States
Dave T.
Huge, Downtown, Walkable, Coffee, Breweries, Dogs
A kitchen with a dishwasher, a sink, and a stove. There are pots hanging above the sink and a window with a view of greenery outside.

9. Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)

Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
Frederick
10.0 out of 10, Exceptional, (71 reviews)
"Wonderfully remodeled spot, great amenities, extremely close to downtown, was perfect for our trip!"
United States
Andrew F.
$279 nightly
The price is $296
Nov 3 - Nov 4
Total with taxes and fees
Beautiful Remodeled Downtown Frederick Cottage (Pet-Friendly)
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

10. Cozy Getaway near Harper`s Ferry, C&O & Potomac

Cozy Getaway near Harper`s Ferry, C&O & Potomac
Brunswick
9.8 out of 10, Exceptional, (70 reviews)
"Cute downtown area with multiple spots to grab breakfast and convenience store stuff. Easy access to Harper's Ferry and made for a nice restful spot between hikes in nature and around town."
United States
Robert
$170 nightly
The price is $180
Oct 13 - Oct 14
Total with taxes and fees
Cozy Getaway near Harper`s Ferry, C&O & Potomac
A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

11. Modern Condo Right off Market Street

Modern Condo Right off Market Street
Downtown Frederick
9.2 out of 10, Wonderful, (105 reviews)
"The place was conveniently located within walking distance to downtown. Place was clean with parking space in back. Had a great stay."
United States
jeff h.
$316 nightly
The price is $335
Oct 13 - Oct 14
Total with taxes and fees
Modern Condo Right off Market Street
A modern kitchen with grey cabinets, a central island, and pendant lighting.

12. Luxury Condo In Downtown Frederick

Luxury Condo In Downtown Frederick
Downtown Frederick
9.2 out of 10, Wonderful, (98 reviews)
"Very clean, had everything we needed and close to shopping and restaurants. "
United States
Kathy S.
$323 nightly
The price is $342
Oct 13 - Oct 14
Total with taxes and fees
Luxury Condo In Downtown Frederick
A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

13. Beautiful, Historic, Hiking, Biking and C&O Canal

Beautiful, Historic, Hiking, Biking and C&O Canal
Brunswick
10.0 out of 10, Exceptional, (29 reviews)
"really nice place"
United States
David R.
$189 nightly
The price is $200
Oct 13 - Oct 14
Total with taxes and fees
Beautiful, Historic, Hiking, Biking and C&O Canal
A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

14. Antietam Look Out - Incredible Sunset Views!

Antietam Look Out - Incredible Sunset Views!
Keedysville
9.8 out of 10, Exceptional, (45 reviews)
"Beautiful property and just as described and shown in the pictures. "
United States
Kent Y.
$318 nightly
The price is $354
Oct 14 - Oct 15
Total with taxes and fees
Antietam Look Out - Incredible Sunset Views!
A square fire pit with a brick base, surrounded by outdoor furniture including a sofa and chairs.

15. Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit

Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
Boonsboro
9.8 out of 10, Exceptional, (18 reviews)
"Extremely cute and a wonderful place to relax."
United States
A D.
$321 nightly
The price is $332
Oct 14 - Oct 15
Total with taxes and fees
Historic Cottage Retreat-IG Hot Tub-Brick Fire Pit
A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

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

RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
Downtown Frederick
9.2 out of 10, Wonderful, (142 reviews)
"Very old but lovely building. Great parking and patio."
United States
Jennifer W.
$295 nightly
The price is $313
Nov 1 - Nov 2
Total with taxes and fees
RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.
A two-story house with a porch decorated with string lights and garlands.

17. Historic Getaway near C&O Canal, hiking and biking

Historic Getaway near C&O Canal, hiking and biking
Brunswick
9.8 out of 10, Exceptional, (13 reviews)
"Very friendly host who made communications easy. We left our iPad behind and they called us right away. The apartment was large, beds were comfortable, and the bathroom renovation was beautiful with a great shower. It is about a block from the C&O trail plus free parking on the property."
United States
Kelly
$235 nightly
The price is $249
Oct 13 - Oct 14
Total with taxes and fees
Historic Getaway near C&O Canal, hiking and biking
A living room with a dining table, chairs, a sofa, and a television.

18. Quaint Mini Cottage in Shepherdstown - Walking Distance

Quaint Mini Cottage in Shepherdstown - Walking Distance
Shepherdstown
9.8 out of 10, Exceptional, (25 reviews)
"Great location and home base for visiting Shepherdstown, Harpers Ferry, and Sharpsburg. Perfect for a couple."
United States
Virginia W.
$199 nightly
The price is $221
Oct 18 - Oct 19
Total with taxes and fees
Quaint Mini Cottage in Shepherdstown - Walking Distance
A room with large windows, wooden floors, and a ceiling fan.

19. Antietam Creek - Quiet 2 Bedroom Cabin

Antietam Creek - Quiet 2 Bedroom Cabin
Keedysville
9.2 out of 10, Wonderful, (100 reviews)
"We had a lovely get-away! Really enjoyed ourselves."
United States
Erinn
$313 nightly
The price is $332
Oct 13 - Oct 14
Total with taxes and fees
Antietam Creek - Quiet 2 Bedroom Cabin
A brick building with a waterfall feature in front.

20. New townhouse

New townhouse
Frederick
9.6 out of 10, Exceptional, (12 reviews)
"We had a great time. It was perfect for us. I would highly recommend it to others and would not hesitate to return there when back in the area. "
United States
Tereasa G.
$399 nightly
The price is $422
Oct 14 - Oct 15
Total with taxes and fees
New townhouse
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

Clarion Inn Harpers Ferry - Charles Town

Clarion Inn Harpers Ferry - Charles Town

10/10 Excellent
"Friendly and helpful staff. Facilities well maintained."
Patience 2-night trip
Posted less than an hour ago
Clarion Inn Harpers Ferry - Charles Town

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 $248 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.

Explore a world of travel with Expedia

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?

Blue Ridge Beauty Home Dog Friendly, Walk to Rivers, A.T. Trail, & HF. NEW LVP: This vacation home rental near Middletown is located in the mountains and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Middletown?

Expedia has 7 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.