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Castleton Holiday Rentals

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50 rentals in Castleton.
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Romantic Cottage with Hot Tub on Spectacular Rural Estate, holiday rental in Castleton

Romantic Cottage with Hot Tub on Spectacular Rural Estate

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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10-Person House on Spectacular Rural Estate w/ Hot Tub, holiday rental in Castleton

10-Person House on Spectacular Rural Estate w/ Hot Tub

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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18-Person House with Pool on Spectacular Rural Estate w/ Hot & Pool, holiday rental in Castleton

18-Person House with Pool on Spectacular Rural Estate w/ Hot & Pool

6 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
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8-Person House on Spectacular Rural Estate w/ Hot Tub, holiday rental in Castleton

8-Person House on Spectacular Rural Estate w/ Hot Tub

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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14-Person House with Pool on Spectacular Rural Estate, holiday rental in Castleton

14-Person House with Pool on Spectacular Rural Estate

7 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Cottage Getaway for Two with Private Hot Tub, holiday rental in Castleton

Cottage Getaway for Two with Private Hot Tub

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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12-PERSON HOUSE on Spectacular Estate with enclosed courtyard and Hot Tub, holiday rental in Castleton

12-PERSON HOUSE on Spectacular Estate with enclosed courtyard and Hot Tub

5 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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The Cabins at Rose River Farm, holiday rental in Castleton

The Cabins at Rose River Farm

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Etlan A-frame With  Front View Of Old Rag Mountain., holiday rental in Castleton

Etlan A-frame With Front View Of Old Rag Mountain.

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Serenity and Adventure on Historic Blue Ridge Farm, holiday rental in Castleton

Serenity and Adventure on Historic Blue Ridge Farm

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Serenity and Adventure on Historic Blue Ridge Farm, holiday rental in Castleton

Serenity and Adventure on Historic Blue Ridge Farm

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Old Rag View Horse Farm with Log Lodge and Treehouse, holiday rental in Castleton

Old Rag View Horse Farm with Log Lodge and Treehouse

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Stunning Old Rag and Shenandoah Vistas from this Gorgeous, Peaceful Retreat, holiday rental in Castleton

Stunning Old Rag and Shenandoah Vistas from this Gorgeous, Peaceful Retreat

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Lazy Bear Lodge VA :), holiday rental in Castleton

Lazy Bear Lodge VA :)

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
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Breathtaking Views and modern amenities on the side of the mountain!, holiday rental in Castleton

Breathtaking Views and modern amenities on the side of the mountain!

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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LeFay Cottage at Little Washington, holiday rental in Castleton

LeFay Cottage at Little Washington

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Surrounded by majestic trees Hilltop is located in the Piedmont of Virginia., holiday rental in Castleton

Surrounded by majestic trees Hilltop is located in the Piedmont of Virginia.

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Walnut Lane - unobstructed views of Skyline Drive, holiday rental in Castleton

Walnut Lane - unobstructed views of Skyline Drive

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Amazing Grace  only minutes to town and local attractions, holiday rental in Castleton

Amazing Grace only minutes to town and local attractions

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Modern Cabin on Old Rag -- Dog-Friendly!, holiday rental in Castleton

Modern Cabin on Old Rag -- Dog-Friendly!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Experience Charming LeFay Cottage at Little Washington, holiday rental in Castleton

Experience Charming LeFay Cottage at Little Washington

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Magnificent Log Home,60 Private Acres--Stunning Mountain Views SUN DANCER, holiday rental in Castleton

Magnificent Log Home,60 Private Acres--Stunning Mountain Views SUN DANCER

6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Perfect for large families 5 bedroom home in the Shenandoah Valley, holiday rental in Castleton

Perfect for large families 5 bedroom home in the Shenandoah Valley

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Views, Views, Views, Hot Tub, Log Fires, Swimming Pool, holiday rental in Castleton

Views, Views, Views, Hot Tub, Log Fires, Swimming Pool

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Unique Converted Horsebarn, holiday rental in Castleton

Unique Converted Horsebarn

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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HB1 at Spring Haven Farm, holiday rental in Castleton

HB1 at Spring Haven Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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AMAZING Mountain Views, holiday rental in Castleton

AMAZING Mountain Views

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing, holiday rental in Castleton

Secluded Mountain Cabin, Lakefront, Hiking, Fishing, Relaxing

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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K-9 Heaven, Dog run  Free, holiday rental in Castleton

K-9 Heaven, Dog run Free

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Modern Sperryville Apartment with a View, holiday rental in Castleton

Modern Sperryville Apartment with a View

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Modern 1850s Luray Farmhouse near Lake Arrowhead, holiday rental in Castleton

Modern 1850s Luray Farmhouse near Lake Arrowhead

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Amazing Grace Getaway, holiday rental in Castleton

Amazing Grace Getaway

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Adorable Rose Cottage in Village of Sperryville, holiday rental in Castleton

Adorable Rose Cottage in Village of Sperryville

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Manor House, Spring Haven Farm, holiday rental in Castleton

Manor House, Spring Haven Farm

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Entire Colonial House next to The Inn., holiday rental in Castleton

Entire Colonial House next to The Inn.

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Nonesuch : Private loft apartment attached to main house 50acres and 4acre pond, holiday rental in Castleton

Nonesuch : Private loft apartment attached to main house 50acres and 4acre pond

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Half of Colonial House with full kitchen  next to The Inn., holiday rental in Castleton

Half of Colonial House with full kitchen next to The Inn.

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Hilltop Hideaway - Located in wine country on 25 private acres, holiday rental in Castleton

Hilltop Hideaway - Located in wine country on 25 private acres

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Perfect for Wedding, Retreat, Workshop or Family Reunion, holiday rental in Castleton

Perfect for Wedding, Retreat, Workshop or Family Reunion

5 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
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Bear Pad- Gorgeous Views!, holiday rental in Castleton

Bear Pad- Gorgeous Views!

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Above the Valley, holiday rental in Castleton

Above the Valley

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mountain Escape- Panorama Views from the Deck, holiday rental in Castleton

Mountain Escape- Panorama Views from the Deck

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cottage in Horse Country, Shenandoah National Park, holiday rental in Castleton

Cottage in Horse Country, Shenandoah National Park

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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House is close to Luray Caverns & Shenandoah Park, holiday rental in Castleton

House is close to Luray Caverns & Shenandoah Park

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Historic Virginia Wine Country Villa w/Pool & Yard, holiday rental in Castleton

Historic Virginia Wine Country Villa w/Pool & Yard

6 bedrooms
7 bathrooms
Sleeps 13
Match: Sleeps
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Cozy Rixeyville Cottage w/Deck, Grill, & Stabling!, holiday rental in Castleton

Cozy Rixeyville Cottage w/Deck, Grill, & Stabling!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Sommersweet Farm, holiday rental in Castleton

Tentrr Signature Site - Sommersweet Farm

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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NEW! Modern Mountain Retreat w/ Deck + Hot Tub!, holiday rental in Castleton

NEW! Modern Mountain Retreat w/ Deck + Hot Tub!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Spacious Mountain Home: Family, Pet & WFH Friendly, holiday rental in Castleton

Spacious Mountain Home: Family, Pet & WFH Friendly

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Mountain Memories, holiday rental in Castleton

Mountain Memories

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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