Holiday rentals in Middletown

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Top-rated holiday rentals in Middletown

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Cabin in Myersville

4.97 out of 5 average rating, 247 reviews

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Amazing place to unwind, de-stress & get away. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting.

13–20 Mar

₹9,452 per night
Guest favourite

Home in Jefferson

5.0 out of 5 average rating, 159 reviews

Historic Cottage in Wine Country

Relax and get away to the countryside! Jefferson is centrally located to enjoy the historic site of Harpers Ferry, explore the shops, art and fine food restaurants of Frederick, or take a scenic drive to award winning wineries and breweries! Cozy, two bedroom cottage is ideal for a family/group of friends. Each bedroom has a bath while living room pull-out sofa can accommodate two additional guests. Fully equipped kitchen, laundry room, outdoor seating and porches. Now with WIFI and Roku

10–17 Feb

₹15,686 per night
Guest favourite

Guest house in Middletown

4.95 out of 5 average rating, 242 reviews

Indulge, Fresh Flowers, Frederick County Haven

2 bedroom, full kitchen and laundry, 1 level guesthouse beside detached garage (separate from main house). The front has a rose garden, birdbath and your own patio. An apple tree is beside the guesthouse. A farm is to the back. Asian cafe, Subway, Dempsey's Grill, Amvets, Main Cup bar and restaurant, Tapia's and 3 ice cream parlors are all a short walk away. More restaurants and grocery store are less than a mile. Farmer's market in season on Thursdays. Fresh flowers and coffee are provided.

2–9 Feb

₹8,842 per night

Popular amenities for Middletown holiday rentals

Stay near Middletown's top sights

The Main Cup18 locals recommend
Fratelli's Italian & Seafood7 locals recommend
Safeway11 locals recommend
Dempseys Grille6 locals recommend
Cinco de Mayo - Middletown4 locals recommend
Middletown Park3 locals recommend

Other great holiday rentals in Middletown

Guest favourite

Cottage in Shepherdstown

4.96 out of 5 average rating, 176 reviews

The GW Hollida Cottage of Shepherdstown

6–13 Sep

₹10,105 per night
Guest favourite

Home in Blue Ridge Summit

5.0 out of 5 average rating, 443 reviews

Colonial Era Spring House

5–12 Sep

₹11,277 per night
Guest favourite

Chalet in Boonsboro

4.94 out of 5 average rating, 521 reviews

Mountain Myst

9–16 Mar

₹27,762 per night
Guest favourite

Flat in Brunswick

4.84 out of 5 average rating, 160 reviews

Cozy Getaway near Harper's Ferry, C&O & Potomac

26 Feb – 5 Mar

₹6,935 per night
Guest favourite

Cabin in Lovettsville

4.94 out of 5 average rating, 140 reviews

Cabin On The Cliffside

7–14 Dec

₹11,416 per night
Guest favourite

Guest house in Lovettsville

4.94 out of 5 average rating, 114 reviews

The Patent House

26 May – 2 Jun

₹8,782 per night
Guest favourite

Guest suite in Shepherdstown

4.96 out of 5 average rating, 563 reviews

Historic Scrabble, Shepherdstown

27 Jun – 4 Jul

₹7,756 per night
Guest favourite

Place to stay in Middletown

4.89 out of 5 average rating, 38 reviews

Vintage Mobile Home and Storage Workshop

7–14 Jan

₹6,792 per night
Guest favourite

Home in Middletown

4.97 out of 5 average rating, 31 reviews

Mountain Church Cottage

25 Oct – 1 Nov

₹11,890 per night
Guest favourite

Home in Middletown

4.97 out of 5 average rating, 36 reviews

Beautiful historical town, 3 bedrooms, countryside

19–26 Jan

₹12,770 per night
Guest favourite

Cabin in Myersville

4.98 out of 5 average rating, 58 reviews

Sleepy Hollow Log Cabin

4–11 Oct

₹11,788 per night
Guest favourite

Cottage in Myersville

4.79 out of 5 average rating, 19 reviews

Cheerful 1 Bedroom cottage farm stay with parking

19–26 Aug

₹8,192 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Maryland
  4. Frederick County
  5. Middletown