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Castlewood Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
36 rentals in Castlewood.
Pet-Friendly Castlewood Cabin w/ Deck & Pond Views, holiday rental in Castlewood
Pet-Friendly Castlewood Cabin w/ Deck & Pond Views, holiday rental in Castlewood
Pet-Friendly Castlewood Cabin w/ Deck & Pond Views, holiday rental in Castlewood

Pet-Friendly Castlewood Cabin w/ Deck & Pond Views

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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The following properties within 20 miles of Castlewood match all your filters:
The Nest on Mill, holiday rental in Castlewood
The Nest on Mill, holiday rental in Castlewood
The Nest on Mill, holiday rental in Castlewood

The Nest on Mill

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Riverfront Cabin, holiday rental in Castlewood
Cozy Riverfront Cabin, holiday rental in Castlewood
Cozy Riverfront Cabin, holiday rental in Castlewood

Cozy Riverfront Cabin

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Secluded Mountain Cabin on a Large Estate with Water Fall, Hiking Trails & Creek, holiday rental in Castlewood
Secluded Mountain Cabin on a Large Estate with Water Fall, Hiking Trails & Creek, holiday rental in Castlewood
Secluded Mountain Cabin on a Large Estate with Water Fall, Hiking Trails & Creek, holiday rental in Castlewood

Secluded Mountain Cabin on a Large Estate with Water Fall, Hiking Trails & Creek

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Rockybrook Miller's cabin, holiday rental in Castlewood
Rockybrook Miller's cabin, holiday rental in Castlewood
Rockybrook Miller's cabin, holiday rental in Castlewood

Rockybrook Miller's cabin

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Relaxing Creekside Retreat - Firepit, Outdoor Dining, Creekview, holiday rental in Castlewood
Relaxing Creekside Retreat - Firepit, Outdoor Dining, Creekview, holiday rental in Castlewood
Relaxing Creekside Retreat - Firepit, Outdoor Dining, Creekview, holiday rental in Castlewood

Relaxing Creekside Retreat - Firepit, Outdoor Dining, Creekview

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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New List Cozy 7 guest 2 bed 2 bath townhouse min. fr Abingdon Va Creeper Trail, holiday rental in Castlewood
New List Cozy 7 guest 2 bed 2 bath townhouse min. fr Abingdon Va Creeper Trail, holiday rental in Castlewood
New List Cozy 7 guest 2 bed 2 bath townhouse min. fr Abingdon Va Creeper Trail, holiday rental in Castlewood

New List Cozy 7 guest 2 bed 2 bath townhouse min. fr Abingdon Va Creeper Trail

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Victorian Spa EnSuite * Nottingham PL, King Bed, Jacuzzi Near UVa-Wise & Main St, holiday rental in Castlewood
Victorian Spa EnSuite * Nottingham PL, King Bed, Jacuzzi Near UVa-Wise & Main St, holiday rental in Castlewood
Victorian Spa EnSuite * Nottingham PL, King Bed, Jacuzzi Near UVa-Wise & Main St, holiday rental in Castlewood

Victorian Spa EnSuite * Nottingham PL, King Bed, Jacuzzi Near UVa-Wise & Main St

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Nottingham Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St, holiday rental in Castlewood
Nottingham Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St, holiday rental in Castlewood
Nottingham Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St, holiday rental in Castlewood

Nottingham Place in Wise, King Bedrm, Private Living Rm, Near UVa-Wise & Main St

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St,  Private Detached Bath, holiday rental in Castlewood
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St,  Private Detached Bath, holiday rental in Castlewood
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St,  Private Detached Bath, holiday rental in Castlewood

Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Downtown Bristol Cottage - 4 min to CASINO, holiday rental in Castlewood
Cozy Downtown Bristol Cottage - 4 min to CASINO, holiday rental in Castlewood
Cozy Downtown Bristol Cottage - 4 min to CASINO, holiday rental in Castlewood

Cozy Downtown Bristol Cottage - 4 min to CASINO

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Old World Craftmanship with Modern Amenities, holiday rental in Castlewood
Old World Craftmanship with Modern Amenities, holiday rental in Castlewood
Old World Craftmanship with Modern Amenities, holiday rental in Castlewood

Old World Craftmanship with Modern Amenities

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
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Central Bristol Condo - 3 min from downtown and the casino!, holiday rental in Castlewood
Central Bristol Condo - 3 min from downtown and the casino!, holiday rental in Castlewood
Central Bristol Condo - 3 min from downtown and the casino!, holiday rental in Castlewood

Central Bristol Condo - 3 min from downtown and the casino!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Laptop-Friendly Appalachian Mountain Retreat!, holiday rental in Castlewood
Laptop-Friendly Appalachian Mountain Retreat!, holiday rental in Castlewood
Laptop-Friendly Appalachian Mountain Retreat!, holiday rental in Castlewood

Laptop-Friendly Appalachian Mountain Retreat!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Riverfront Cattle Farm Home in the Mountains, holiday rental in Castlewood
Riverfront Cattle Farm Home in the Mountains, holiday rental in Castlewood
Riverfront Cattle Farm Home in the Mountains, holiday rental in Castlewood

Riverfront Cattle Farm Home in the Mountains

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Beautiful Bristol Bungalow w/ Firepit- 5 mins to downtown & 6 mins to Casino, holiday rental in Castlewood
Beautiful Bristol Bungalow w/ Firepit- 5 mins to downtown & 6 mins to Casino, holiday rental in Castlewood
Beautiful Bristol Bungalow w/ Firepit- 5 mins to downtown & 6 mins to Casino, holiday rental in Castlewood

Beautiful Bristol Bungalow w/ Firepit- 5 mins to downtown & 6 mins to Casino

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Close to town, the college and a beautiful serene surrounding, holiday rental in Castlewood
Close to town, the college and a beautiful serene surrounding, holiday rental in Castlewood
Close to town, the college and a beautiful serene surrounding, holiday rental in Castlewood

Close to town, the college and a beautiful serene surrounding

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Newly renovated 3BR/2BA home in beautiful centrally located neighborhood, holiday rental in Castlewood
Newly renovated 3BR/2BA home in beautiful centrally located neighborhood, holiday rental in Castlewood
Newly renovated 3BR/2BA home in beautiful centrally located neighborhood, holiday rental in Castlewood

Newly renovated 3BR/2BA home in beautiful centrally located neighborhood

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Comfortable spacious vacation get away. Four fireplaces, front porch and patio., holiday rental in Castlewood
Comfortable spacious vacation get away. Four fireplaces, front porch and patio., holiday rental in Castlewood
Comfortable spacious vacation get away. Four fireplaces, front porch and patio., holiday rental in Castlewood

Comfortable spacious vacation get away. Four fireplaces, front porch and patio.

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Fulkerson-Hilton historic homestead, holiday rental in Castlewood
Fulkerson-Hilton historic homestead, holiday rental in Castlewood
Fulkerson-Hilton historic homestead, holiday rental in Castlewood

Fulkerson-Hilton historic homestead

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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5 bedroom Estate near casino & downtown, holiday rental in Castlewood
5 bedroom Estate near casino & downtown, holiday rental in Castlewood
5 bedroom Estate near casino & downtown, holiday rental in Castlewood

5 bedroom Estate near casino & downtown

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Entire Historic Inn 7 bedroom / 6 bath Eco-friendly, holiday rental in Castlewood
Entire Historic Inn 7 bedroom / 6 bath Eco-friendly, holiday rental in Castlewood
Entire Historic Inn 7 bedroom / 6 bath Eco-friendly, holiday rental in Castlewood

Entire Historic Inn 7 bedroom / 6 bath Eco-friendly

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Haysi Nature Getaway w/ Fire Pit & On-Site Creek!, holiday rental in Castlewood
Haysi Nature Getaway w/ Fire Pit & On-Site Creek!, holiday rental in Castlewood
Haysi Nature Getaway w/ Fire Pit & On-Site Creek!, holiday rental in Castlewood

Haysi Nature Getaway w/ Fire Pit & On-Site Creek!

Holiday Rental House
6 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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The Wise Owl, a charming 3-bedroom home in Wise with WiFi, AC, holiday rental in Castlewood
The Wise Owl, a charming 3-bedroom home in Wise with WiFi, AC, holiday rental in Castlewood
The Wise Owl, a charming 3-bedroom home in Wise with WiFi, AC, holiday rental in Castlewood

The Wise Owl, a charming 3-bedroom home in Wise with WiFi, AC

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bristol Firefly Studio: Kitchenette, Private Patio, holiday rental in Castlewood
Bristol Firefly Studio: Kitchenette, Private Patio, holiday rental in Castlewood
Bristol Firefly Studio: Kitchenette, Private Patio, holiday rental in Castlewood

Bristol Firefly Studio: Kitchenette, Private Patio

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Townhome near Hard Rock Casino! 2 Br 2.5BA, New Construction and modern, holiday rental in Castlewood
Charming Townhome near Hard Rock Casino! 2 Br 2.5BA, New Construction and modern, holiday rental in Castlewood
Charming Townhome near Hard Rock Casino! 2 Br 2.5BA, New Construction and modern, holiday rental in Castlewood

Charming Townhome near Hard Rock Casino! 2 Br 2.5BA, New Construction and modern

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Custom Cabin Garage Studio in the Woods with WiFi, holiday rental in Castlewood
Custom Cabin Garage Studio in the Woods with WiFi, holiday rental in Castlewood
Custom Cabin Garage Studio in the Woods with WiFi, holiday rental in Castlewood

Custom Cabin Garage Studio in the Woods with WiFi

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cabin in Disguise Adventure Awaits! 
Hike bike kayak
Free Wi-Fi and Parking, holiday rental in Castlewood
Cabin in Disguise Adventure Awaits! 
Hike bike kayak
Free Wi-Fi and Parking, holiday rental in Castlewood
Cabin in Disguise Adventure Awaits! 
Hike bike kayak
Free Wi-Fi and Parking, holiday rental in Castlewood

Cabin in Disguise Adventure Awaits! Hike bike kayak Free Wi-Fi and Parking

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy House On The Hill W/ Hot Tub, holiday rental in Castlewood
Cozy House On The Hill W/ Hot Tub, holiday rental in Castlewood
Cozy House On The Hill W/ Hot Tub, holiday rental in Castlewood

Cozy House On The Hill W/ Hot Tub

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Nice RV with AC in charming Lebanon, holiday rental in Castlewood
Nice RV with AC in charming Lebanon, holiday rental in Castlewood
Nice RV with AC in charming Lebanon, holiday rental in Castlewood

Nice RV with AC in charming Lebanon

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful + Spacious 4BR Home Bristol, VA. Close to Bristol TN / VA, holiday rental in Castlewood
Beautiful + Spacious 4BR Home Bristol, VA. Close to Bristol TN / VA, holiday rental in Castlewood
Beautiful + Spacious 4BR Home Bristol, VA. Close to Bristol TN / VA, holiday rental in Castlewood

Beautiful + Spacious 4BR Home Bristol, VA. Close to Bristol TN / VA

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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In the Heart of Bristol, holiday rental in Castlewood
In the Heart of Bristol, holiday rental in Castlewood
In the Heart of Bristol, holiday rental in Castlewood

In the Heart of Bristol

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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NEW! Bristol Tiny Round Treehouse 3 miles to Historic Downtown 1 Bed 1 Bath, holiday rental in Castlewood
NEW! Bristol Tiny Round Treehouse 3 miles to Historic Downtown 1 Bed 1 Bath, holiday rental in Castlewood
NEW! Bristol Tiny Round Treehouse 3 miles to Historic Downtown 1 Bed 1 Bath, holiday rental in Castlewood

NEW! Bristol Tiny Round Treehouse 3 miles to Historic Downtown 1 Bed 1 Bath

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A perfect romantic getaway!, holiday rental in Castlewood
A perfect romantic getaway!, holiday rental in Castlewood
A perfect romantic getaway!, holiday rental in Castlewood

A perfect romantic getaway!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Entire Spacious Bristol Getaway with Farmhouse Charm, holiday rental in Castlewood
Entire Spacious Bristol Getaway with Farmhouse Charm, holiday rental in Castlewood
Entire Spacious Bristol Getaway with Farmhouse Charm, holiday rental in Castlewood

Entire Spacious Bristol Getaway with Farmhouse Charm

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Rural Home with Private Walking Trails on 1400 Private  
Acres, holiday rental in Castlewood
Rural Home with Private Walking Trails on 1400 Private  
Acres, holiday rental in Castlewood
Rural Home with Private Walking Trails on 1400 Private  
Acres, holiday rental in Castlewood

Rural Home with Private Walking Trails on 1400 Private Acres

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Showing results 1-36 of 36
Frequently Asked Questions about Castlewood