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Smithsburg Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
48 rentals in Smithsburg.
Hollow Hideaway is perfect for your holiday stay!, holiday rental in Smithsburg
Hollow Hideaway is perfect for your holiday stay!, holiday rental in Smithsburg
Hollow Hideaway is perfect for your holiday stay!, holiday rental in Smithsburg

Hollow Hideaway is perfect for your holiday stay!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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The Great Escape Lodge - Lovely Catoctin Mountain Views, holiday rental in Smithsburg
The Great Escape Lodge - Lovely Catoctin Mountain Views, holiday rental in Smithsburg
The Great Escape Lodge - Lovely Catoctin Mountain Views, holiday rental in Smithsburg

The Great Escape Lodge - Lovely Catoctin Mountain Views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Secluded Farm Getaway In Smithsburg, holiday rental in Smithsburg
Secluded Farm Getaway In Smithsburg, holiday rental in Smithsburg
Secluded Farm Getaway In Smithsburg, holiday rental in Smithsburg

Secluded Farm Getaway In Smithsburg

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Dry Run Cottage, holiday rental in Smithsburg
Dry Run Cottage, holiday rental in Smithsburg
Dry Run Cottage, holiday rental in Smithsburg

Dry Run Cottage

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Secluded Yet Convenient Romantic, Zen-Paradise with Spa & Breathtaking Views, holiday rental in Smithsburg
Secluded Yet Convenient Romantic, Zen-Paradise with Spa & Breathtaking Views, holiday rental in Smithsburg
Secluded Yet Convenient Romantic, Zen-Paradise with Spa & Breathtaking Views, holiday rental in Smithsburg

Secluded Yet Convenient Romantic, Zen-Paradise with Spa & Breathtaking Views

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!, holiday rental in Smithsburg
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!, holiday rental in Smithsburg
Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!, holiday rental in Smithsburg

Entire Mountain Cottage Near Scenic Hiking Trails, Your Getaway Retreat!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Mountain Cottage Near Scenic State Parks and Hiking Trails Great for Large Group, holiday rental in Smithsburg
Mountain Cottage Near Scenic State Parks and Hiking Trails Great for Large Group, holiday rental in Smithsburg
Mountain Cottage Near Scenic State Parks and Hiking Trails Great for Large Group, holiday rental in Smithsburg

Mountain Cottage Near Scenic State Parks and Hiking Trails Great for Large Group

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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The following properties within 20 miles of Smithsburg match all your filters:
Antietam Toll House~ an historic waterfront cabin, holiday rental in Smithsburg
Antietam Toll House~ an historic waterfront cabin, holiday rental in Smithsburg
Antietam Toll House~ an historic waterfront cabin, holiday rental in Smithsburg

Antietam Toll House~ an historic waterfront cabin

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Rustic Cabin in Thurmont, MD, holiday rental in Smithsburg
Rustic Cabin in Thurmont, MD, holiday rental in Smithsburg
Rustic Cabin in Thurmont, MD, holiday rental in Smithsburg

Rustic Cabin in Thurmont, MD

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Myersville-Private 9 ac cabin on the Middle Creek, yet close to it all., holiday rental in Smithsburg
Myersville-Private 9 ac cabin on the Middle Creek, yet close to it all., holiday rental in Smithsburg
Myersville-Private 9 ac cabin on the Middle Creek, yet close to it all., holiday rental in Smithsburg

Myersville-Private 9 ac cabin on the Middle Creek, yet close to it all.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Historic & Cozy ~ Near Antietam Battle & WhiteTail, holiday rental in Smithsburg
Historic & Cozy ~ Near Antietam Battle & WhiteTail, holiday rental in Smithsburg
Historic & Cozy ~ Near Antietam Battle & WhiteTail, holiday rental in Smithsburg

Historic & Cozy ~ Near Antietam Battle & WhiteTail

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful, Spacious Historic Victorian Near Ski Liberty, holiday rental in Smithsburg
Beautiful, Spacious Historic Victorian Near Ski Liberty, holiday rental in Smithsburg
Beautiful, Spacious Historic Victorian Near Ski Liberty, holiday rental in Smithsburg

Beautiful, Spacious Historic Victorian Near Ski Liberty

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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New Studio Apartment - Next To Appalachian Trail - Near Ski Liberty, holiday rental in Smithsburg
New Studio Apartment - Next To Appalachian Trail - Near Ski Liberty, holiday rental in Smithsburg
New Studio Apartment - Next To Appalachian Trail - Near Ski Liberty, holiday rental in Smithsburg

New Studio Apartment - Next To Appalachian Trail - Near Ski Liberty

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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SPRINGHOUSE  1803 - UNIQUE HISTORIC HOME, holiday rental in Smithsburg
SPRINGHOUSE  1803 - UNIQUE HISTORIC HOME, holiday rental in Smithsburg
SPRINGHOUSE  1803 - UNIQUE HISTORIC HOME, holiday rental in Smithsburg

SPRINGHOUSE 1803 - UNIQUE HISTORIC HOME

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Boonsboro Studio w/ Wood-Burning Fire Pit!, holiday rental in Smithsburg
Boonsboro Studio w/ Wood-Burning Fire Pit!, holiday rental in Smithsburg
Boonsboro Studio w/ Wood-Burning Fire Pit!, holiday rental in Smithsburg

Boonsboro Studio w/ Wood-Burning Fire Pit!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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5 story hotel with luxury comfort, located in the heart of Hagerstown, MD, holiday rental in Smithsburg
5 story hotel with luxury comfort, located in the heart of Hagerstown, MD, holiday rental in Smithsburg
5 story hotel with luxury comfort, located in the heart of Hagerstown, MD, holiday rental in Smithsburg

5 story hotel with luxury comfort, located in the heart of Hagerstown, MD

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Historic Heights Neighborhood Apartment, holiday rental in Smithsburg
Charming Historic Heights Neighborhood Apartment, holiday rental in Smithsburg
Charming Historic Heights Neighborhood Apartment, holiday rental in Smithsburg

Charming Historic Heights Neighborhood Apartment

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Amazing Home Stays Near Fairgrounds, holiday rental in Smithsburg
Amazing Home Stays Near Fairgrounds, holiday rental in Smithsburg
Amazing Home Stays Near Fairgrounds, holiday rental in Smithsburg

Amazing Home Stays Near Fairgrounds

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Eisenhower House (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg
The Eisenhower House (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg
The Eisenhower House (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg

The Eisenhower House (or for retreats book the whole Caboose Farm compound)

Holiday Rental House
1 bedroom
3 bathrooms
Sleeps 16
Match: Sleeps
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The Roosevelt House  (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg
The Roosevelt House  (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg
The Roosevelt House  (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg

The Roosevelt House (or for retreats book the whole Caboose Farm compound)

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Jefferson House (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg
The Jefferson House (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg
The Jefferson House (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg

The Jefferson House (or for retreats book the whole Caboose Farm compound)

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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A Winter Retreat: Jet Tub, Fire Pit, Grill, Yard - Close to Winter Attractions, holiday rental in Smithsburg
A Winter Retreat: Jet Tub, Fire Pit, Grill, Yard - Close to Winter Attractions, holiday rental in Smithsburg
A Winter Retreat: Jet Tub, Fire Pit, Grill, Yard - Close to Winter Attractions, holiday rental in Smithsburg

A Winter Retreat: Jet Tub, Fire Pit, Grill, Yard - Close to Winter Attractions

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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A Beautiful House in a Retreat Center on Mountain, holiday rental in Smithsburg
A Beautiful House in a Retreat Center on Mountain, holiday rental in Smithsburg
A Beautiful House in a Retreat Center on Mountain, holiday rental in Smithsburg

A Beautiful House in a Retreat Center on Mountain

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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5 mins to the Outlets Beautiful Mango Mania Palace, holiday rental in Smithsburg
5 mins to the Outlets Beautiful Mango Mania Palace, holiday rental in Smithsburg
5 mins to the Outlets Beautiful Mango Mania Palace, holiday rental in Smithsburg

5 mins to the Outlets Beautiful Mango Mania Palace

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Peaceful Mountain Top House- Time to Enjoy!, holiday rental in Smithsburg
Peaceful Mountain Top House- Time to Enjoy!, holiday rental in Smithsburg
Peaceful Mountain Top House- Time to Enjoy!, holiday rental in Smithsburg

Peaceful Mountain Top House- Time to Enjoy!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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The Corner on Welty, Townhouse in Waynesboro, holiday rental in Smithsburg
The Corner on Welty, Townhouse in Waynesboro, holiday rental in Smithsburg
The Corner on Welty, Townhouse in Waynesboro, holiday rental in Smithsburg

The Corner on Welty, Townhouse in Waynesboro

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The Adams House (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg
The Adams House (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg
The Adams House (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg

The Adams House (or for retreats book the whole Caboose Farm compound)

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Hill Top Retreat Cottage With Amazing Views, holiday rental in Smithsburg
Hill Top Retreat Cottage With Amazing Views, holiday rental in Smithsburg
Hill Top Retreat Cottage With Amazing Views, holiday rental in Smithsburg

Hill Top Retreat Cottage With Amazing Views

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Cozy Nature-Side Cottage-Refresh, Revive & Enjoy!, holiday rental in Smithsburg
Cozy Nature-Side Cottage-Refresh, Revive & Enjoy!, holiday rental in Smithsburg
Cozy Nature-Side Cottage-Refresh, Revive & Enjoy!, holiday rental in Smithsburg

Cozy Nature-Side Cottage-Refresh, Revive & Enjoy!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Mountaintop breezes!--Amazing  view central to Many battlefields, holiday rental in Smithsburg
Mountaintop breezes!--Amazing  view central to Many battlefields, holiday rental in Smithsburg
Mountaintop breezes!--Amazing  view central to Many battlefields, holiday rental in Smithsburg

Mountaintop breezes!--Amazing view central to Many battlefields

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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1879 Updated Home on Frederick Street, holiday rental in Smithsburg
1879 Updated Home on Frederick Street, holiday rental in Smithsburg
1879 Updated Home on Frederick Street, holiday rental in Smithsburg

1879 Updated Home on Frederick Street

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Scenic Mountain Top Retreat with 28 Beds, holiday rental in Smithsburg
Scenic Mountain Top Retreat with 28 Beds, holiday rental in Smithsburg
Scenic Mountain Top Retreat with 28 Beds, holiday rental in Smithsburg

Scenic Mountain Top Retreat with 28 Beds

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Astonishing Airy Mountain Top Retreat, holiday rental in Smithsburg
Astonishing Airy Mountain Top Retreat, holiday rental in Smithsburg
Astonishing Airy Mountain Top Retreat, holiday rental in Smithsburg

Astonishing Airy Mountain Top Retreat

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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Scenic Mountaintop Villa with Free WiFi & Pool, holiday rental in Smithsburg
Scenic Mountaintop Villa with Free WiFi & Pool, holiday rental in Smithsburg
Scenic Mountaintop Villa with Free WiFi & Pool, holiday rental in Smithsburg

Scenic Mountaintop Villa with Free WiFi & Pool

Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 20
Match: Sleeps
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Luxurious Beautiful Mountain Top Retreat, holiday rental in Smithsburg
Luxurious Beautiful Mountain Top Retreat, holiday rental in Smithsburg
Luxurious Beautiful Mountain Top Retreat, holiday rental in Smithsburg

Luxurious Beautiful Mountain Top Retreat

Holiday Rental House
9 bedrooms
5 bathrooms
Sleeps 25
Match: Sleeps
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One-of-a-kind luxury lodge on 100-acre Appalachian farm, holiday rental in Smithsburg
One-of-a-kind luxury lodge on 100-acre Appalachian farm, holiday rental in Smithsburg
One-of-a-kind luxury lodge on 100-acre Appalachian farm, holiday rental in Smithsburg

One-of-a-kind luxury lodge on 100-acre Appalachian farm

Holiday Rental House
10 bedrooms
8 bathrooms
Sleeps 26
Match: Sleeps
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Mountaintop Retreat Center Villa with Wifi, Basketball Court & Beautiful Trails, holiday rental in Smithsburg
Mountaintop Retreat Center Villa with Wifi, Basketball Court & Beautiful Trails, holiday rental in Smithsburg
Mountaintop Retreat Center Villa with Wifi, Basketball Court & Beautiful Trails, holiday rental in Smithsburg

Mountaintop Retreat Center Villa with Wifi, Basketball Court & Beautiful Trails

Holiday Rental House
9 bedrooms
6 bathrooms
Sleeps 27
Match: Sleeps
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Pool, Hot Tub, and Fun for all!, holiday rental in Smithsburg
Pool, Hot Tub, and Fun for all!, holiday rental in Smithsburg
Pool, Hot Tub, and Fun for all!, holiday rental in Smithsburg

Pool, Hot Tub, and Fun for all!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy private in law suite in charming Blue Ridge Summit with AC, WiFi,Smart TV., holiday rental in Smithsburg
Cozy private in law suite in charming Blue Ridge Summit with AC, WiFi,Smart TV., holiday rental in Smithsburg
Cozy private in law suite in charming Blue Ridge Summit with AC, WiFi,Smart TV., holiday rental in Smithsburg

Cozy private in law suite in charming Blue Ridge Summit with AC, WiFi,Smart TV.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Spruce Run Cabin, a wooded retreat on the mountain, holiday rental in Smithsburg
Spruce Run Cabin, a wooded retreat on the mountain, holiday rental in Smithsburg
Spruce Run Cabin, a wooded retreat on the mountain, holiday rental in Smithsburg

Spruce Run Cabin, a wooded retreat on the mountain

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Historic Hagerstown Haven: Walk to Parks, Downtown, holiday rental in Smithsburg
Historic Hagerstown Haven: Walk to Parks, Downtown, holiday rental in Smithsburg
Historic Hagerstown Haven: Walk to Parks, Downtown, holiday rental in Smithsburg

Historic Hagerstown Haven: Walk to Parks, Downtown

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Step in the 90's in Historic Downtown Hagerstown, holiday rental in Smithsburg
Step in the 90's in Historic Downtown Hagerstown, holiday rental in Smithsburg
Step in the 90's in Historic Downtown Hagerstown, holiday rental in Smithsburg

Step in the 90's in Historic Downtown Hagerstown

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Mansion in the Country & Wedding Venue, holiday rental in Smithsburg
Beautiful Mansion in the Country & Wedding Venue, holiday rental in Smithsburg
Beautiful Mansion in the Country & Wedding Venue, holiday rental in Smithsburg

Beautiful Mansion in the Country & Wedding Venue

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 32
Match: Sleeps
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Welcome Home: Comfortable Home for Families, Pets, Remote Workers, holiday rental in Smithsburg
Welcome Home: Comfortable Home for Families, Pets, Remote Workers, holiday rental in Smithsburg
Welcome Home: Comfortable Home for Families, Pets, Remote Workers, holiday rental in Smithsburg

Welcome Home: Comfortable Home for Families, Pets, Remote Workers

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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A place to unwind and recharge. Offer a blend of relaxation, tranquility, warmth, holiday rental in Smithsburg
A place to unwind and recharge. Offer a blend of relaxation, tranquility, warmth, holiday rental in Smithsburg
A place to unwind and recharge. Offer a blend of relaxation, tranquility, warmth, holiday rental in Smithsburg

A place to unwind and recharge. Offer a blend of relaxation, tranquility, warmth

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Washington House (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg
The Washington House (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg
The Washington House (or for retreats book the whole Caboose Farm compound), holiday rental in Smithsburg

The Washington House (or for retreats book the whole Caboose Farm compound)

Holiday Rental House
8 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Private, Relaxing, quite, 3 Bedroom  Unit, sleeps 6 to 8 people, holiday rental in Smithsburg
Private, Relaxing, quite, 3 Bedroom  Unit, sleeps 6 to 8 people, holiday rental in Smithsburg
Private, Relaxing, quite, 3 Bedroom  Unit, sleeps 6 to 8 people, holiday rental in Smithsburg

Private, Relaxing, quite, 3 Bedroom Unit, sleeps 6 to 8 people

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Huge Hagerstown Home w/ Deck ~ 4 Mi to Downtown!, holiday rental in Smithsburg
Huge Hagerstown Home w/ Deck ~ 4 Mi to Downtown!, holiday rental in Smithsburg
Huge Hagerstown Home w/ Deck ~ 4 Mi to Downtown!, holiday rental in Smithsburg

Huge Hagerstown Home w/ Deck ~ 4 Mi to Downtown!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-48 of 48
Frequently Asked Questions about Smithsburg