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Search results; Over 1,000 places in Middletown

Guest favourite
Room in Middletown
Stay with MaryHospitality,
Peaceful Farmette, Double Bedroom
1–6 Apr
4.97 out of 5 average rating, 155 reviews
Superhost
Home in Middletown
“The Rambler” In beautiful Middletown, MD ⛰
Hosted by Brent
14–19 Apr
4.66 out of 5 average rating, 108 reviews
Guest favourite
Home in Middletown
Mountain Church Cottage
Hosted by Leigh
31 May – 5 Jun
4.97 out of 5 average rating, 31 reviews
Guest favourite
Home in Middletown
Beautiful historical town, 3 bedrooms, countryside
Hosted by Qing
25–30 Jun
4.97 out of 5 average rating, 36 reviews
Guest favourite
Home in Myersville
The Crooked Cottage: a Cozy, Curated Escape
Hosted by Saffron
19–24 Apr
4.97 out of 5 average rating, 143 reviews
Home in Frederick
Spacious & Comfy Private Apartment
Hosted by Gus
21–26 Apr
4.73 out of 5 average rating, 15 reviews
Guest favourite
Room in Frederick
Stay with Kerri
Private BR/BA & Balcony Mtntop Manor 12 mins to DT
8–13 Apr
4.98 out of 5 average rating, 51 reviews
Guest favourite
Home in Frederick
Fully Renovated 6 BR Home Near Gambrill State Park
Hosted by Mina
7–12 Apr
4.94 out of 5 average rating, 36 reviews
Superhost
Home in Frederick
Blue Goose Saloon Private Residence
Hosted by Elizabeth
1–6 Apr
4.89 out of 5 average rating, 71 reviews
Guest favourite
Home in Frederick
Amazing view of the Middletown Valley
Hosted by Greg
15–20 Apr
4.93 out of 5 average rating, 75 reviews
Home in Middletown
Equestrian farmhouse : trail rides, Private field
Hosted by Divyanka
1–6 Apr
Guest favourite
Home in Jefferson
Historic Cottage in Wine Country
Hosted by Mary Ann
9–14 Apr
5.0 out of 5 average rating, 159 reviews
Guest favourite
Home in Jefferson
"Rusty Rose" ~ Restored farmhouse 🖤 of Jefferson
Hosted by Heather
14–19 Apr
4.91 out of 5 average rating, 172 reviews
Guest favourite
Home in Jefferson
Firefly Hill Farmhouse
Hosted by Dianisha
7–12 Apr
5.0 out of 5 average rating, 21 reviews
Guest favourite
Home in Smithsburg
The Great Escape Lodge ~ Exquisite Mountain Views
Hosted by Heather
1–6 Apr
4.99 out of 5 average rating, 70 reviews
Superhost
Home in Keedysville
Keedy’s Country Manor
Hosted by Kelly
6–11 Apr
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Adamstown
Wizard's Escape | Sleeps 15+ | Pool | Escape Room
Hosted by Nate
5–10 May
4.97 out of 5 average rating, 31 reviews
Guest favourite
Home in Lovettsville
The Reverie: 70 acre Potomac Waterfront Retreat
Hosted by Danna
19–24 May
4.96 out of 5 average rating, 135 reviews