A stone tower with a staircase leading up to it.

Middletown Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Middletown vacation rentals

A rustic cabin interior with a wooden ceiling, a fireplace, a dining area, and a kitchen with a refrigerator and hanging pots.

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

Middletown

Cindy B.

SAR 772 total

includes taxes & fees

8 Nov - 9 Nov

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

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

Middletown

Shelby W.

SAR 967 total

includes taxes & fees

8 Nov - 9 Nov

A log cabin interior with a wooden bench, a leather sofa, a coffee table, and a bookshelf.

3. Cozy Downtown Cabin - Family Friendly

Middletown

Roger

SAR 941 total

includes taxes & fees

9 Nov - 10 Nov

A compact kitchen with a coffee machine, microwave, and a small cart with kitchen tools.

4. Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

Frederick

Andrew

SAR 812 total

includes taxes & fees

22 Nov - 23 Nov

A rustic cabin with a wooden staircase leading to a porch, surrounded by lush greenery and pink flowers.

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

Shepherdstown

Dennis C.

SAR 369 total

includes taxes & fees

15 Nov - 16 Nov

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

Jefferson

Tory D.

SAR 943 total

includes taxes & fees

8 Nov - 9 Nov

A two-story brick building with a balcony and a porch decorated with lights and Christmas trees.

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

Brunswick

Robert

SAR 617 total

includes taxes & fees

8 Nov - 9 Nov

A glass-top table with a metal frame, a white cushioned chair, and a vase with sunflowers on a windowsill.

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

Downtown Frederick

Dave T.

SAR 947 total

includes taxes & fees

12 Nov - 13 Nov

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)

Frederick

Sara W.

SAR 1,044 total

includes taxes & fees

8 Nov - 9 Nov

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

Brunswick

David R.

SAR 714 total

includes taxes & fees

9 Nov - 10 Nov

A spacious living room with a high ceiling, large windows, a fireplace, and a dining area with a table set for six.

11. Antietam Look Out - Incredible Sunset Views!

Keedysville

Melisa T.

SAR 1,739 total

includes taxes & fees

23 Nov - 24 Nov

A modern kitchen with grey cabinets, a central island, and pendant lighting.

12. Luxury Condo In Downtown Frederick

Downtown Frederick

Jessica

SAR 1,250 total

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a porch decorated with string lights and garlands.

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

Brunswick

Kelly

SAR 855 total

includes taxes & fees

8 Nov - 9 Nov

A living room with a dining table, chairs, a sofa, and a television.

14. Quaint Mini Cottage in Shepherdstown - Walking Distance

Shepherdstown

Abigail

SAR 846 total

includes taxes & fees

11 Nov - 12 Nov

A modern kitchen with white cabinetry, a central island, stainless steel appliances, and pendant lighting.

15. Modern Condo Right off Market Street

Downtown Frederick

John

SAR 1,204 total

includes taxes & fees

9 Nov - 10 Nov

A wooden cabin with a patio area, outdoor seating, and a fire pit.

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

Boonsboro

A D.

A cozy cabin interior with a leather sofa, dining table, and large windows offering a view of the outdoors.

17. Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

Keedysville

Jared

A spacious living room with a large window, a wooden coffee table, and a sofa.

18. Schilling House

Bolivar

SAR 1,178 total

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with two Adirondack chairs and a table overlooking a lake with trees and hills in the background.

19. Charming Cabin in the Woods with River Access

Shepherdstown

bethany c.

A nighttime forest path lit by string lights.

20. 1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

Sharpsburg

Nancy D.

SAR 1,218 total

includes taxes & fees

9 Nov - 10 Nov

View all properties

Find vacation rentals that suit your style

Top Middletown Hotel Reviews

A rooftop terrace with outdoor seating, a fire pit, and a view of the sunset over a mountainous landscape.

SpringHill Suites by Marriott Frederick

Frederick

10/10 Excellent

Anonymous traveler

A Holiday Inn Express hotel with a modern design, featuring a stone facade, multiple windows, and a covered entrance.

Holiday Inn Express & Suites Brunswick - Harpers Ferry Area by IHG

Knoxville

10/10 Excellent

Johnna

A Hampton Inn & Suites hotel with a modern facade, large columns, and a well-lit entrance.

Hampton Inn & Suites Frederick-Fort Detrick

Frederick

10/10 Excellent

Anonymous traveler

An outdoor patio with a fire pit, seating, and a covered area.

Fairfield Inn & Suites by Marriott Hagerstown

Hagerstown

10/10 Excellent

Claire

A hotel lobby with seating areas, a fireplace, and a reception desk.

Comfort Inn Frederick - Ballenger Creek

Frederick

10/10 Excellent

Steven

A Country Inn & Suites building with a stone entrance, large windows, and a sign above the door.

Country Inn & Suites by Radisson, Frederick, MD

Frederick

10/10 Excellent

Clyde

A two-story house with a dark roof, a visible chimney, and a well-lit entrance.

Antietam Overlook Farm

Keedysville

10/10 Excellent

Anonymous traveler

A hotel room with a bed, a desk, a chair, a small ottoman, a bathroom with a granite countertop sink and mirror.

Travelodge by Wyndham Brunswick near Frederick

Brunswick

10/10 Excellent

Tamara

A circular outdoor seating area with a fire pit, surrounded by chairs and tables, set on a brick patio with trees in the background.

TownePlace Suites by Marriott Frederick

Frederick

10/10 Excellent

Mikael

A hotel with a stone facade, a well-lit entrance, and a sign for Homewood Suites.

Homewood Suites by Hilton Frederick

Frederick

10/10 Excellent

Cathy

An indoor swimming pool with clear water, surrounded by lounge chairs and a sunset view through a large window.

Hampton Inn Hagerstown-I-81

Hagerstown

10/10 Excellent

Anonymous traveler

An outdoor seating area with a fire feature, lounge chairs, and a modern building facade.

Fairfield Inn & Suites by Marriott Frederick

Frederick

10/10 Excellent

Kristen

A pool area with red chairs and a person swimming.

Home2 Suites by Hilton Frederick

Frederick

10/10 Excellent

We had a great stay at this hotel. We were excited to have the pool open as well as self-serve breakfast with modifications. My only complaint would be that the front desk staff we mediocre. There was not a friendly warmth that I've had at many other hotels. I needed towels and I was asked to come pick them up at the front desk. (assuming they were short staffed.) A separate time I asked and they said they would bring them to the room. No one ever came. Other than that we had a great...

Zachary

A two-story house with a porch and a staircase leading to the front door.

Hollerstown Hill Bed and Breakfast

Frederick

10/10 Excellent

Yvette

A circular outdoor seating area with a fire pit, surrounded by wicker chairs and tables, set against a backdrop of trees and a building wall.

Courtyard by Marriott Frederick

Frederick

10/10 Excellent

Shamia

An outdoor patio area with wicker furniture, a stone fire feature, and a covered seating area with string lights.

Home2 Suites by Hilton Charles Town

Charles Town

10/10 Excellent

Tommy

A reception desk with a 'Quality by Choice Hotels' sign, a potted plant, and a door to the right.

Quality Inn Harpers Ferry - Charles Town

Harpers Ferry

10/10 Excellent

HARITHA

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.

Middletown Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middletown vacation rentals

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

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

3. Cozy Downtown Cabin - Family Friendly

4. Patty's Place - Private and Convenient EV-Friendly Apartment near Downtown

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

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

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

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

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

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

11. Antietam Look Out - Incredible Sunset Views!

12. Luxury Condo In Downtown Frederick

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

14. Quaint Mini Cottage in Shepherdstown - Walking Distance

15. Modern Condo Right off Market Street

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

17. Sunny Streams Cabin - Sunset Views w/ a Hot Tub!

18. Schilling House

19. Charming Cabin in the Woods with River Access

20. 1-Acre Hot Tub & Fire Pit Retreat, Steps to Winery and Battlefield

Find vacation rentals that suit your style

Top Middletown Hotel Reviews

SpringHill Suites by Marriott Frederick

10/10 Excellent

Frequently Asked Questions

Can I find a vacation rental in Middletown?

What's the top vacation rental in Middletown?

How many vacation rentals will I find in Middletown?

What can I see and do in Middletown?

What are vacation rentals like in Middletown?