Castlewood Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Castlewood vacation rentals

A wooden deck with a bench, a grill, and a view of a green landscape.

1. Cozy Cabin Retreat: Peaceful Mountain Views

Dungannon

$247 nightly

Nov 13 - Nov 14

Total with taxes and fees

A living room with a fireplace, a television, a sofa, and a coffee table.

2. The Nest on Mill

Lebanon

Patty W.

$166 nightly

Nov 18 - Nov 19

Total with taxes and fees

3. Cozy Cabin Retreat: Peaceful Mountain Views

Dungannon

Terrina M.

$239 nightly

Nov 12 - Nov 13

Total with taxes and fees

A cozy cabin interior with a wooden floor, a sofa with patterned cushions, a wooden armchair, a table with a vase of flowers, and a window with blinds.

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

Mendota

Russell G.

$132 nightly

Nov 22 - Nov 23

Total with taxes and fees

A house with a covered porch and a staircase leading to the entrance.

5. Charming 2-bedroom house in Wise, Virginia

Wise

Chasity F.

$183 nightly

Nov 22 - Nov 23

Total with taxes and fees

A two-story brick house with a front porch, a small front yard, and a large tree to the right.

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

Abingdon

Krzysztof

$116 nightly

Nov 17 - Nov 18

Total with taxes and fees

A covered porch with white columns, outdoor furniture, and potted plants.

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

Wise

Chasity F.

$137 nightly

Nov 13 - Nov 14

Total with taxes and fees

Two wicker chairs with cushions, a small wooden table, and a floral wreath on a white wall.

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

Bristol

Brandi W.

$191 nightly

Nov 12 - Nov 13

Total with taxes and fees

A cluster of modern cabins with large windows, surrounded by a winding driveway, set in a rural landscape.

9. The Fives - 22482 McCurry Haven Luxury Japandi Cabin

Bristol

Jessica B.

$284 nightly

Nov 12 - Nov 13

Total with taxes and fees

A bedroom with a wooden bed, a ceiling fan, and a window with blinds.

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

Bristol

Chelsea D.

$165 nightly

Nov 12 - Nov 13

Total with taxes and fees

A large house with a prominent porch and a well-maintained lawn.

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

Bristol

Darbey W.

$180 nightly

Nov 12 - Nov 13

Total with taxes and fees

A covered outdoor area with wooden flooring, a wooden fence, and several Adirondack chairs.

12. Coal Town Gem

Haysi

Bob T.

$125 nightly

Nov 12 - Nov 13

Total with taxes and fees

A narrow urban street with buildings featuring brick facades and wooden doors.

13. Micro-Hotel- Downtown Bristol

Bristol

Victoria

$217 nightly

Nov 12 - Nov 13

Total with taxes and fees

A kitchen with a stainless steel refrigerator, wooden cabinets, a sink, and a dining area with a chair and table.

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

Bristol

$217 nightly

Nov 12 - Nov 13

Total with taxes and fees

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

Bristol

Bj B.

$212 nightly

Nov 12 - Nov 13

Total with taxes and fees

A living room with a sectional sofa, a TV, a chandelier, and a kitchen visible through an open doorway.

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

Bristol

Amber F.

$248 nightly

Nov 15 - Nov 16

Total with taxes and fees

A hot tub on a wooden deck with a wooden railing, surrounded by trees.

17. {Doo-Wop Den} 50’s Vibe + Hot Tub

Bristol

Brittney H.

$154 nightly

Nov 30 - Dec 1

Total with taxes and fees

A spacious living room with a large window, a ceiling fan, a Christmas tree, and a fireplace.

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

Bristol

Mike C.

$259 nightly

Nov 12 - Nov 13

Total with taxes and fees

A white two-story house with a red door, surrounded by a forest.

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

Bristol

Jessica

$164 nightly

Nov 12 - Nov 13

Total with taxes and fees

A wooden deck with two plastic chairs and a view of a grassy area with trees.

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

Clintwood

Ernest C.

$183 nightly

Nov 12 - Nov 13

Total with taxes and fees

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Find vacation rentals that suit your style

Top Castlewood Hotel Reviews

An outdoor patio with wooden tables and chairs, string lights, and potted plants.

Western Front Hotel

St. Paul

10/10 Excellent

Ginger

A hallway with a fireplace, framed artwork, and a non-smoking sign.

Holiday Inn Express & Suites Lebanon by IHG

Lebanon

10/10 Excellent

Kim

A hotel room with a bed, a desk, a TV, a microwave, a sink, and a large window with a view of a lake.

Super 8 by Wyndham Lebanon

Lebanon

10/10 Excellent

Tod

A modern hotel lobby with a brown sofa set, a round coffee table, and a patterned carpet.

Sleep Inn & Suites Clintwood

Clintwood

10/10 Excellent

JennG

An outdoor dining area with tables and chairs, a bar area with shelves, and a glass enclosure for the bar.

The Bristol Hotel

Bristol

10/10 Excellent

Karen

A modern hotel lobby with a reception desk, seating area, stone fireplace, and large windows.

Fairfield Inn & Suites Bristol

Bristol

10/10 Excellent

Nicole

A modern hotel lobby with a reception desk, seating area, and a long hallway leading to other rooms.

Spark by Hilton Abingdon I-81 near Fairgrounds

Abingdon

10/10 Excellent

Ron

A lobby with teal and gray sofas, a reception desk, and a view through a glass door.

Comfort Suites Abingdon I-81

Abingdon

10/10 Excellent

I always love staying here but this night I got the hotel room for my parents and my grandmother, who is 99, and suffering from dementia. My grandmother had an episode and wouldn't take her medicine and claiming that my mother kidnapped her. The staff dropped what they were doing and talked to my grandmother. One lady was busy cleaning rooms and when my grandmother started talking to her she stopped what she was doing. She even walked with her to the breakfast room and calmly just talked. My...

Amy

A modern hotel with a clear entrance, a covered parking area, and a well-maintained lawn.

Motel 6 Bristol, VA

Bristol

10/10 Excellent

Stayed one night while driving home. Hotel was right off the Interstate, and was easy to locate. Check in was quick and easy. Picked this hotel because I was travelling with my dog, and Motel 6 allow pets to stay free. Room was frankly much better that I was expecting for the price. Plenty of space, bed was clean and comfortable, and the bathroom was spotless. I've paid a lot more for places that weren't nearly as nice. Absolutely would stay here again.

Guy

A modern hotel with a covered entrance, multiple floors, and a sign indicating it is a Country Inn & Suites.

Country Inn & Suites by Radisson, Abingdon, VA

Abingdon

10/10 Excellent

Beata

An indoor swimming pool with clear blue water, a tiled floor, and a ceiling with blue lighting.

Fairfield Inn & Suites by Marriott Abingdon

Abingdon

10/10 Excellent

Carl

A hotel room with a bed, a desk with a lamp, a flat-screen TV, a microwave, and a wardrobe.

Best Western Of Wise

Wise

10/10 Excellent

Anonymous traveler

A modern building with a stone facade, large windows, and a covered entrance area.

Holiday Inn Express & Suites Abingdon by IHG

Abingdon

10/10 Excellent

Tara

Courtyard by Marriott Bristol

Bristol

10/10 Excellent

lynne

Find out more about Castlewood

Everything you need to know about Castlewood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castlewood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castlewood vacation 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 low season months. For more hustle and bustle, you may prefer to visit Castlewood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Castlewood rentals

At Expedia, we put the best Castlewood vacation 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 vacation.

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 vacation rentals in Castlewood?

Yes, we offer vacation rentals near the most popular attractions in Castlewood, or you can go with a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental in Castlewood?

Affordable, Private, Single Level House Steps From Hard Rock Casino Pet Friendly: This vacation 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 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 larger area, you’ll find The Carter Fold and University of Virginia's College at Wise.

What’s a vacation rental in Castlewood like?

A vacation rental is a private property you can book for a few weeks or just a few days in Castlewood. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll feel right at home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and busy reception areas while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family trip or a small group gathering.

Castlewood Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Castlewood vacation rentals

1. Cozy Cabin Retreat: Peaceful Mountain Views

2. The Nest on Mill

3. Cozy Cabin Retreat: Peaceful Mountain Views

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

5. Charming 2-bedroom house in Wise, Virginia

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

7. 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

9. The Fives - 22482 McCurry Haven Luxury Japandi Cabin

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

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

12. Coal Town Gem

13. Micro-Hotel- Downtown Bristol

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

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

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

17. {Doo-Wop Den} 50’s Vibe + Hot Tub

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

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

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

Find vacation rentals that suit your style

Top Castlewood Hotel Reviews

Western Front Hotel

10/10 Excellent

Find out more about Castlewood

Everything you need to know about Castlewood vacation rentals

Castlewood vacation rentals: An excellent choice for every season

How to find incredible deals on Castlewood rentals

Frequently Asked Questions

Can I find vacation rentals in Castlewood?

What's the top vacation rental in Castlewood?

What’s there to see and do in Castlewood?

What’s a vacation rental in Castlewood like?