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Middletown Holiday Rentals

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming 'Cream of the Crop' Cape ~❤️of Middletown

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Poplar Place at the foot of South Mountain!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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INDULGE-FRESH FLOWERS,BAKED GOODS, MEMORY FOAM MATTRESS.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Three Bedroom Short Term Rental House on Historic Linden Hall Farm

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Gorgeous 1840 Log Cabin- Downtown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Myersville-Private 9 ac cabin on the creek, yet close to it all.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Sharpsburg Retreat--Civil War Home Near Antietam Battlefield, C&O Canal Towpath

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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IN THE HEART OF ANTIETAM

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Welcome to this patch of serenity on the river's edge, to this hideaway.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Save time - get the best Middletown rentals sent straight to your email!

Sunny And Cozy Little Lodge With A Spectacular View Of The Blue Ridge Mountains

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Secluded on the River, Historic 1815 house, Romantic Shepherdstown

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 5
Match: Sleeps
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1886 Historic Farmhouse Cottage

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Perfect Get-Away! Rest and relax at our Cozy Country Cottage on 4 acres!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Historic Farmhouse, Pond and Spectacular Views. Cozy, Spacious 4400

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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Historic cozy farmhouse in the ❤️ of Myersville , MD close to Rt 70! Welcome Hom

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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RIVERKEEPER INN, Waterfront Property on the Potomac River

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stone Leaf Farm Private Retreat

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Apartment In Historic Downtown Frederick

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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RETREAT on the CREEK - Businees Travelor or Weekend Getaway. HISTORIC DISTRICT.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to the canal and downtown!!! Beautiful 1880 Fully Renovated townhome

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Antietam Creek - Quiet 2 Bedroom Cabin

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Villa with Majestic Views of Monocacy River. Sleeps 5, 2 Bath, Full Kitchen

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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“Oliver’s Retreat”...1882 Private Downtown Apartment in Historic Frederick

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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'Daley's Doll House'

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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RIVERKEEPER INN, Waterfront Cottage on the Potomac

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious One Bedroom Apartment With Private Entrance

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Creekside Retreat.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful 1815 Stone House, private river area

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Country Home With 3 Plus Bedrooms

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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A view of the Middletown Valley Like No Other

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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* Modern * Convenient * 1 BR * Wireless Internet * Smart TV * Kitchen * Parking*

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Rustic Cottage near the Potomac River

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quite Gem Near Downtown & DC

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Historic House Close to The Potomac River / C&O Canal / Appalachian Trail

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Pine Tree Nest

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Grove Guest Home

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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“Oliver’s Retreat”...Lovely Downtown Apartment

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Dream House on the Potomac River Canyon South Rim

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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beautiful Potomac riverfront

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Catoctin Valley Country Home

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Comfortable Bungalow near the Potomac River

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Contemporary Hideaway near Historic Harpers Ferry!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Tranquil Farm House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Modern Chalet near Historic Harpers Ferry!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - 'Autumn Olive' at Evensong Farm

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
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Tentrr Signature Site - 'Wineberry' at Evensong Farm - Coleman Outfitted Site

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 12
Match: Sleeps
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B25 * 2 BR * Wifi * Smart TV * Kitchen * FREE Parking * Convenient * Beautiful

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Charming downtown Frederick rowhome, free parking!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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*Downtown Frederick Condo*

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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