Holiday Rentals in Castlewood

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Check prices for these dates

Our top choices for Castlewood holiday rentals

1. Cozy Cabin Retreat: Peaceful Mountain Views

Cozy Cabin Retreat: Peaceful Mountain Views
3.0 star property
Dungannon
The price is €246
includes taxes & fees
14 Nov - 15 Nov
Cozy Cabin Retreat: Peaceful Mountain Views

2. The Nest on Mill

The Nest on Mill
Lebanon
10.0 out of 10, Exceptional, (60 reviews)
"Always a great stay. "
United States
Patty W.
The price is €171
includes taxes & fees
18 Nov - 19 Nov
The Nest on Mill

3. Cozy Cabin Retreat: Peaceful Mountain Views

Cozy Cabin Retreat: Peaceful Mountain Views
Dungannon
8.0 out of 10, Very good, (2 reviews)
"This home is beautiful. It is very quiet if you just need some rest. It was super clean and the stocked. We had one small issue and the owner had a wonderful couple to handle it within about an hour."
United States
Terrina M.
The price is €267
includes taxes & fees
13 Dec - 14 Dec
Cozy Cabin Retreat: Peaceful Mountain Views

4. Peaceful Country Stay Covered Porch, Fire-pit and Wildlife

Peaceful Country Stay Covered Porch, Fire-pit and Wildlife
Mendota
10.0 out of 10, Exceptional, (15 reviews)
"No exaggeration, the best host we’ve ever encountered and the place was perfection!!!!!This is an absolute gem of a stay. "
United States
Russell G.
The price is €136
includes taxes & fees
22 Nov - 23 Nov
Peaceful Country Stay Covered Porch, Fire-pit and Wildlife

5. Charming 2-bedroom house in Wise, Virginia

Charming 2-bedroom house in Wise, Virginia
Wise
10.0 out of 10, Exceptional, (15 reviews)
"Such a beautiful place with so many special touches. We love being here and enjoying Wise County. The host creates a beautiful and comfortable space."
United States
Chasity F.
The price is €187
includes taxes & fees
22 Nov - 23 Nov
Charming 2-bedroom house in Wise, Virginia

6. Cozy Home near Abingdon – Close to Town & Trails!

Cozy Home near Abingdon – Close to Town & Trails!
Abingdon
10.0 out of 10, Exceptional, (24 reviews)
"Everything was good."
United States
Krzysztof
The price is €124
includes taxes & fees
16 Nov - 17 Nov
Cozy Home near Abingdon – Close to Town & Trails!

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

Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath
Wise
10.0 out of 10, Exceptional, (14 reviews)
"Very comfortable stay! "
United States
Chasity F.
The price is €139
includes taxes & fees
23 Nov - 24 Nov
Nottingham Turret Rm w Queen Bed, Near UVaWise & Main St, Private Detached Bath

8. Retro Retreat! 2BR, 1 Bath Home with WiFi, AC in wonderful Bristol, VA

Retro Retreat! 2BR, 1 Bath Home with WiFi, AC in wonderful Bristol, VA
Bristol
10.0 out of 10, Exceptional, (2 reviews)
"Very nice place with very nice owners "
United States
Brandi W.
The price is €197
includes taxes & fees
13 Nov - 14 Nov
Retro Retreat! 2BR, 1 Bath Home with WiFi, AC in wonderful Bristol, VA

9. The Fives - 22482 McCurry Haven Luxury Japandi Cabin

The Fives - 22482 McCurry Haven Luxury Japandi Cabin
Bristol
10.0 out of 10, Exceptional, (2 reviews)
"This cabin did not disappoint. Our stay was perfect. Would highly recommend this community and cabin 10/10! The host thought of everything and was very easy to work with. We would definitely stay here again."
United States
Jessica B.
The Fives - 22482 McCurry Haven Luxury Japandi Cabin

10. 2 Mi to Downtown Bristol! Updated ADU w/ Parking

2 Mi to Downtown Bristol! Updated ADU w/ Parking
Bristol
10.0 out of 10, Exceptional, (2 reviews)
"Very lovely spot. The bathroom is amazingly beautiful. It’s a great spot for dogs and host was very friendly and accommodating!"
United States
Chelsea D.
The price is €180
includes taxes & fees
13 Nov - 14 Nov
2 Mi to Downtown Bristol! Updated ADU w/ Parking

11. Tranquil Cottage on the 8-Acre Grounds of the Historic Eastman House

Tranquil Cottage on the 8-Acre Grounds of the Historic Eastman House
Bristol
10.0 out of 10, Exceptional, (2 reviews)
"It’s absolutely charming!!!"
United States
Darbey W.
The price is €217
includes taxes & fees
22 Nov - 23 Nov
Tranquil Cottage on the 8-Acre Grounds of the Historic Eastman House

12. Coal Town Gem

Coal Town Gem
Haysi
9.6 out of 10, Exceptional, (33 reviews)
"Enjoyed our stay in the small town of Haysi. It gave us easy access to the Breaks Interstate Park. We also enjoyed visiting the gift shop located below the VRBO."
United States
Bob T.
The price is €117
includes taxes & fees
22 Nov - 23 Nov
Coal Town Gem

13. Micro-Hotel- Downtown Bristol

Micro-Hotel- Downtown Bristol
Bristol
9.6 out of 10, Exceptional, (34 reviews)
"Cute and quaint property that is very convenient to the Bristol area. Host was very polite and responsive to any questions for our stay."
United States
Victoria
The price is €262
includes taxes & fees
22 Nov - 23 Nov
Micro-Hotel- Downtown Bristol

14. 1 Mi to Music & State St! Updated Bristol Home

1 Mi to Music & State St! Updated Bristol Home
3.0 star property
Bristol
The price is €206
includes taxes & fees
13 Nov - 14 Nov
1 Mi to Music & State St! Updated Bristol Home

15. 1 Mi to Music & State St! Updated Bristol Home

1 Mi to Music & State St! Updated Bristol Home
Bristol
10.0 out of 10, Exceptional, (1 review)
"Very nice place. Had toys, bowls and beds for my pups. Very cozy and comfortable. Would def rent again if ever in the area."
United States
Bj B.
The price is €231
includes taxes & fees
22 Nov - 23 Nov
1 Mi to Music & State St! Updated Bristol Home

16. No cleanup chores-Fenced yard, arcade, fire pit, close to casino, I81, downtown.

No cleanup chores-Fenced yard, arcade, fire pit, close to casino, I81, downtown.
Bristol
9.4 out of 10, Exceptional, (20 reviews)
"Great house and location! The neighbors backyard was a little scary but other than that, the house met our needs!"
United States
Amber F.
The price is €271
includes taxes & fees
13 Nov - 14 Nov
No cleanup chores-Fenced yard, arcade, fire pit, close to casino, I81, downtown.

17. {Doo-Wop Den} 50’s Vibe + Hot Tub

{Doo-Wop Den} 50’s Vibe + Hot Tub
Bristol
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stay! Everything was great! "
United States
Brittney H.
The price is €162
includes taxes & fees
17 Nov - 18 Nov
{Doo-Wop Den} 50’s Vibe + Hot Tub

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

Beautiful + Spacious 4BR Home Bristol, VA. Close to Bristol TN / VA attractions!
Bristol
9.6 out of 10, Exceptional, (33 reviews)
"The location to our event was very convenient.."
United States
Mike C.
The price is €258
includes taxes & fees
13 Nov - 14 Nov
Beautiful + Spacious 4BR Home Bristol, VA. Close to Bristol TN / VA attractions!

19. * Christmas-Themed Getaway in Bristol (HOT-TUB) *

* Christmas-Themed Getaway in Bristol (HOT-TUB) *
Bristol
9.6 out of 10, Exceptional, (8 reviews)
"Very nice place to stay. Felt safe in the area. Small ... so was perfect for 3 of us."
United States
Jessica
The price is €181
includes taxes & fees
22 Nov - 23 Nov
* Christmas-Themed Getaway in Bristol (HOT-TUB) *

20. The 100 Acre Woods located in the Appalachian mountains Clintwood Va

The 100 Acre Woods located in the Appalachian mountains Clintwood Va
Clintwood
10.0 out of 10, Exceptional, (5 reviews)
"Stay was great everything was satisfactory. Great host"
United States
Ernest C.
The price is €174
includes taxes & fees
13 Nov - 14 Nov
The 100 Acre Woods located in the Appalachian mountains Clintwood Va
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find holiday rentals that suit your style

Find out more about Castlewood

Everything you need to know about Castlewood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Castlewood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castlewood holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castlewood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castlewood. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Castlewood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castlewood holiday rentals we have selected for you start as low as €116 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Castlewood rentals

At Expedia, we put the best Castlewood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castlewood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castlewood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castlewood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Castlewood?

Yes, there are holiday rentals close to the most popular sights in Castlewood, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Castlewood has to offer?

Affordable, Private, Single Level House Steps From Hard Rock Casino Pet Friendly: This holiday home rental outside of Castlewood has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

What’s there to see and do in Castlewood?

While you're exploring the area, Sugar Hollow Park and High Knob are a couple of picturesque spots to get outside and enjoy nature. In the wider area, you’ll find The Carter Fold and University of Virginia's College at Wise.

What’s a holiday rental in Castlewood like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castlewood. Holiday rentals feature extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a family trip or a small group gathering.