We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Castleton Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests
Bedrooms
Any
Bathrooms
Any
Amenities
Show more
Suitability
Show more
Property type
Show more
Distinctive Features
Show more
Distance from
1 mi
50 rentals in Castleton.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
10-Person House on Spectacular Rural Estate w/ Hot Tub, vacation rental in Castleton
10-Person House on Spectacular Rural Estate w/ Hot Tub, vacation rental in Castleton
10-Person House on Spectacular Rural Estate w/ Hot Tub, vacation rental in Castleton

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
8-Person House on Spectacular Rural Estate w/ Hot Tub, vacation rental in Castleton
8-Person House on Spectacular Rural Estate w/ Hot Tub, vacation rental in Castleton
8-Person House on Spectacular Rural Estate w/ Hot Tub, vacation rental in Castleton

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Romantic Cottage with Hot Tub on Spectacular Rural Estate, vacation rental in Castleton
Romantic Cottage with Hot Tub on Spectacular Rural Estate, vacation rental in Castleton
Romantic Cottage with Hot Tub on Spectacular Rural Estate, vacation rental in Castleton

Romantic Cottage with Hot Tub on Spectacular Rural Estate

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
18-Person House with Pool on Spectacular Rural Estate w/ Hot & Pool, vacation rental in Castleton
18-Person House with Pool on Spectacular Rural Estate w/ Hot & Pool, vacation rental in Castleton
18-Person House with Pool on Spectacular Rural Estate w/ Hot & Pool, vacation rental in Castleton

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

Rental Home
6 bedrooms
5 bathrooms
Sleeps 18
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
14-Person House with Pool on Spectacular Rural Estate, vacation rental in Castleton
14-Person House with Pool on Spectacular Rural Estate, vacation rental in Castleton
14-Person House with Pool on Spectacular Rural Estate, vacation rental in Castleton

14-Person House with Pool on Spectacular Rural Estate

Rental Home
7 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Cottage Getaway for Two with Private Hot Tub, vacation rental in Castleton
Cottage Getaway for Two with Private Hot Tub, vacation rental in Castleton
Cottage Getaway for Two with Private Hot Tub, vacation rental in Castleton

Cottage Getaway for Two with Private Hot Tub

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
12-PERSON HOUSE on Spectacular Estate with enclosed courtyard and Hot Tub, vacation rental in Castleton
12-PERSON HOUSE on Spectacular Estate with enclosed courtyard and Hot Tub, vacation rental in Castleton
12-PERSON HOUSE on Spectacular Estate with enclosed courtyard and Hot Tub, vacation rental in Castleton

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

Rental Home
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
4 person apartment on Spectacular Rural Estate, vacation rental in Castleton
4 person apartment on Spectacular Rural Estate, vacation rental in Castleton
4 person apartment on Spectacular Rural Estate, vacation rental in Castleton

4 person apartment on Spectacular Rural Estate

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home, vacation rental in Castleton
Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home, vacation rental in Castleton
Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home, vacation rental in Castleton

Stunning Family/Friends Retreat,110 Private Acres, Renovated Historic Home

Rental Home
5 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Mountain View 65 Acre Private Retreat  Pool  Hot tub  Wineries Charlottesville, vacation rental in Castleton
Mountain View 65 Acre Private Retreat  Pool  Hot tub  Wineries Charlottesville, vacation rental in Castleton
Mountain View 65 Acre Private Retreat  Pool  Hot tub  Wineries Charlottesville, vacation rental in Castleton

Mountain View 65 Acre Private Retreat Pool Hot tub Wineries Charlottesville

Rental Home
5 bedrooms
3 bathrooms
Sleeps 19
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Save time - get the best Castleton rentals sent straight to your email!
Etlan A-frame With  Front View Of Old Rag Mountain., vacation rental in Castleton
Etlan A-frame With  Front View Of Old Rag Mountain., vacation rental in Castleton
Etlan A-frame With  Front View Of Old Rag Mountain., vacation rental in Castleton

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

Rental Home
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming Cottage in Horse Country Near Blue Ridge, vacation rental in Castleton
Charming Cottage in Horse Country Near Blue Ridge, vacation rental in Castleton
Charming Cottage in Horse Country Near Blue Ridge, vacation rental in Castleton

Charming Cottage in Horse Country Near Blue Ridge

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Entite Colonial House , footsteps away from “The INN at Little Washington “., vacation rental in Castleton
Entite Colonial House , footsteps away from “The INN at Little Washington “., vacation rental in Castleton
Entite Colonial House , footsteps away from “The INN at Little Washington “., vacation rental in Castleton

Entite Colonial House , footsteps away from “The INN at Little Washington “.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Serenity and Adventure on Historic Blue Ridge Farm

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Stunning Old Rag and Shenandoah Vistas from this Gorgeous, Peaceful Retreat, vacation rental in Castleton
Stunning Old Rag and Shenandoah Vistas from this Gorgeous, Peaceful Retreat, vacation rental in Castleton
Stunning Old Rag and Shenandoah Vistas from this Gorgeous, Peaceful Retreat, vacation rental in Castleton

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Serenity and Adventure on Historic Blue Ridge Farm, vacation rental in Castleton
Serenity and Adventure on Historic Blue Ridge Farm, vacation rental in Castleton
Serenity and Adventure on Historic Blue Ridge Farm, vacation rental in Castleton

Serenity and Adventure on Historic Blue Ridge Farm

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Quiet Downtown Home # 1 in Culpeper, vacation rental in Castleton
Quiet Downtown Home # 1 in Culpeper, vacation rental in Castleton
Quiet Downtown Home # 1 in Culpeper, vacation rental in Castleton

Quiet Downtown Home # 1 in Culpeper

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Old Rag View Horse Farm with Log Lodge and Treehouse, vacation rental in Castleton
Old Rag View Horse Farm with Log Lodge and Treehouse, vacation rental in Castleton
Old Rag View Horse Farm with Log Lodge and Treehouse, vacation rental in Castleton

Old Rag View Horse Farm with Log Lodge and Treehouse

Rental Home
6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Country home that overlooks Rappahannock River, vacation rental in Castleton
Country home that overlooks Rappahannock River, vacation rental in Castleton
Country home that overlooks Rappahannock River, vacation rental in Castleton

Country home that overlooks Rappahannock River

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
The Camelot at Windsor Lodge, LLC, vacation rental in Castleton
The Camelot at Windsor Lodge, LLC, vacation rental in Castleton
The Camelot at Windsor Lodge, LLC, vacation rental in Castleton

The Camelot at Windsor Lodge, LLC

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Close to everything and Away from it all., vacation rental in Castleton
Close to everything and Away from it all., vacation rental in Castleton
Close to everything and Away from it all., vacation rental in Castleton

Close to everything and Away from it all.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Surrounded by majestic trees Hilltop is located in the Piedmont of Virginia., vacation rental in Castleton
Surrounded by majestic trees Hilltop is located in the Piedmont of Virginia., vacation rental in Castleton
Surrounded by majestic trees Hilltop is located in the Piedmont of Virginia., vacation rental in Castleton

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
LeFay Cottage at Little Washington, vacation rental in Castleton
LeFay Cottage at Little Washington, vacation rental in Castleton
LeFay Cottage at Little Washington, vacation rental in Castleton

LeFay Cottage at Little Washington

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Amazing Grace  only minutes to town and local attractions, vacation rental in Castleton
Amazing Grace  only minutes to town and local attractions, vacation rental in Castleton
Amazing Grace  only minutes to town and local attractions, vacation rental in Castleton

Amazing Grace only minutes to town and local attractions

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
A quiet, lovely old farm on a beautiful piece of land near Shenandoah Park, vacation rental in Castleton
A quiet, lovely old farm on a beautiful piece of land near Shenandoah Park, vacation rental in Castleton
A quiet, lovely old farm on a beautiful piece of land near Shenandoah Park, vacation rental in Castleton

A quiet, lovely old farm on a beautiful piece of land near Shenandoah Park

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Modern Cabin on Old Rag -- Dog-Friendly!, vacation rental in Castleton
Modern Cabin on Old Rag -- Dog-Friendly!, vacation rental in Castleton
Modern Cabin on Old Rag -- Dog-Friendly!, vacation rental in Castleton

Modern Cabin on Old Rag -- Dog-Friendly!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
The Historic Upscale 'Poorhouse' at Cardinal Springs, vacation rental in Castleton
The Historic Upscale 'Poorhouse' at Cardinal Springs, vacation rental in Castleton
The Historic Upscale 'Poorhouse' at Cardinal Springs, vacation rental in Castleton

The Historic Upscale 'Poorhouse' at Cardinal Springs

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Experience Charming LeFay Cottage at Little Washington, vacation rental in Castleton
Experience Charming LeFay Cottage at Little Washington, vacation rental in Castleton
Experience Charming LeFay Cottage at Little Washington, vacation rental in Castleton

Experience Charming LeFay Cottage at Little Washington

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Come for a VISIT! GREAT RATE: $100/125/nt, vacation rental in Castleton
Come for a VISIT! GREAT RATE: $100/125/nt, vacation rental in Castleton
Come for a VISIT! GREAT RATE: $100/125/nt, vacation rental in Castleton

Come for a VISIT! GREAT RATE: $100/125/nt

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
West Davis Mill, vacation rental in Castleton
West Davis Mill, vacation rental in Castleton
West Davis Mill, vacation rental in Castleton

West Davis Mill

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Spectacular Spirit Dancer 5 bedrooms Luxurious on 60 private acres, vacation rental in Castleton
Spectacular Spirit Dancer 5 bedrooms Luxurious on 60 private acres, vacation rental in Castleton
Spectacular Spirit Dancer 5 bedrooms Luxurious on 60 private acres, vacation rental in Castleton

Spectacular Spirit Dancer 5 bedrooms Luxurious on 60 private acres

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Rainmaker Ranch - Peaceful Blue Ridge Mountain Sunsets, vacation rental in Castleton
Rainmaker Ranch - Peaceful Blue Ridge Mountain Sunsets, vacation rental in Castleton
Rainmaker Ranch - Peaceful Blue Ridge Mountain Sunsets, vacation rental in Castleton

Rainmaker Ranch - Peaceful Blue Ridge Mountain Sunsets

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Magnificent Log Home,60 Private Acres--Stunning Mountain Views SUN DANCER, vacation rental in Castleton
Magnificent Log Home,60 Private Acres--Stunning Mountain Views SUN DANCER, vacation rental in Castleton
Magnificent Log Home,60 Private Acres--Stunning Mountain Views SUN DANCER, vacation rental in Castleton

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

Rental Home
6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
HB1 at Spring Haven Farm, vacation rental in Castleton
HB1 at Spring Haven Farm, vacation rental in Castleton
HB1 at Spring Haven Farm, vacation rental in Castleton

HB1 at Spring Haven Farm

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Unique Converted Horsebarn, vacation rental in Castleton
Unique Converted Horsebarn, vacation rental in Castleton
Unique Converted Horsebarn, vacation rental in Castleton

Unique Converted Horsebarn

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
K-9 Heaven, Dog run  Free, vacation rental in Castleton
K-9 Heaven, Dog run  Free, vacation rental in Castleton
K-9 Heaven, Dog run  Free, vacation rental in Castleton

K-9 Heaven, Dog run Free

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
NEW! Spacious Mtn Home; Horse, Pet & WFH Friendly!, vacation rental in Castleton
NEW! Spacious Mtn Home; Horse, Pet & WFH Friendly!, vacation rental in Castleton
NEW! Spacious Mtn Home; Horse, Pet & WFH Friendly!, vacation rental in Castleton

NEW! Spacious Mtn Home; Horse, Pet & WFH Friendly!

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Modern Sperryville Apartment with a View, vacation rental in Castleton
Modern Sperryville Apartment with a View, vacation rental in Castleton
Modern Sperryville Apartment with a View, vacation rental in Castleton

Modern Sperryville Apartment with a View

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Manor House, Spring Haven Farm, vacation rental in Castleton
Manor House, Spring Haven Farm, vacation rental in Castleton
Manor House, Spring Haven Farm, vacation rental in Castleton

Manor House, Spring Haven Farm

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Adorable Rose Cottage in Village of Sperryville, vacation rental in Castleton
Adorable Rose Cottage in Village of Sperryville, vacation rental in Castleton
Adorable Rose Cottage in Village of Sperryville, vacation rental in Castleton

Adorable Rose Cottage in Village of Sperryville

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Cozy Rixeyville Cottage w/Deck, Grill, & Stabling!, vacation rental in Castleton
Cozy Rixeyville Cottage w/Deck, Grill, & Stabling!, vacation rental in Castleton
Cozy Rixeyville Cottage w/Deck, Grill, & Stabling!, vacation rental in Castleton

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Amazing Grace Getaway, vacation rental in Castleton
Amazing Grace Getaway, vacation rental in Castleton
Amazing Grace Getaway, vacation rental in Castleton

Amazing Grace Getaway

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Respite from Reality, vacation rental in Castleton
Respite from Reality, vacation rental in Castleton
Respite from Reality, vacation rental in Castleton

Respite from Reality

Rental Home
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
This working homestead is a destination not just a place to stay., vacation rental in Castleton
This working homestead is a destination not just a place to stay., vacation rental in Castleton
This working homestead is a destination not just a place to stay., vacation rental in Castleton

This working homestead is a destination not just a place to stay.

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Entire Colonial House next to The Inn. , vacation rental in Castleton
Entire Colonial House next to The Inn. , vacation rental in Castleton
Entire Colonial House next to The Inn. , vacation rental in Castleton

Entire Colonial House next to The Inn.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Half of Colonial House with full kitchen  next to The Inn. , vacation rental in Castleton
Half of Colonial House with full kitchen  next to The Inn. , vacation rental in Castleton
Half of Colonial House with full kitchen  next to The Inn. , vacation rental in Castleton

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Hilltop Hideaway - Located in wine country on 25 private acres , vacation rental in Castleton
Hilltop Hideaway - Located in wine country on 25 private acres , vacation rental in Castleton
Hilltop Hideaway - Located in wine country on 25 private acres , vacation rental in Castleton

Hilltop Hideaway - Located in wine country on 25 private acres

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Bunkhouse at Spring Haven Farm, vacation rental in Castleton
Bunkhouse at Spring Haven Farm, vacation rental in Castleton
Bunkhouse at Spring Haven Farm, vacation rental in Castleton

Bunkhouse at Spring Haven Farm

Rental Home
3 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Perfect for Wedding, Retreat, Workshop or Family Reunion, vacation rental in Castleton
Perfect for Wedding, Retreat, Workshop or Family Reunion, vacation rental in Castleton
Perfect for Wedding, Retreat, Workshop or Family Reunion, vacation rental in Castleton

Perfect for Wedding, Retreat, Workshop or Family Reunion

Rental Home
5 bedrooms
3 bathrooms
Sleeps 18
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
October getaway in Shenandoah!, vacation rental in Castleton
October getaway in Shenandoah!, vacation rental in Castleton
October getaway in Shenandoah!, vacation rental in Castleton

October getaway in Shenandoah!

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
PreviousNext
1
Frequently Asked Questions about Castleton