Howardsville Vacation Rentals

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Vacation Rentals in Howardsville

Fully Loaded 8BR in Wintergreen! Sleeps 23
2.0 star property
Fully Loaded 8BR in Wintergreen! Sleeps 23
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
10.0 out of 10, Exceptional, (247)
"A beautiful peaceful stay. The views are spectacular. You won't be disappointed, everything you need is provided. Can't wait to book again"
United States
Terri L.
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
9.6 out of 10, Exceptional, (53)
"Property was incredibly clean and well-maintained. Enjoyed this condo!"
United States
Sharon G.
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
New Build! Log Cabin with Hot Tub in Wintergreen
10.0 out of 10, Exceptional, (3)
"Overall great experience. We did take down one smoke detector in down stairs bedroom due to beeping and I did not know where any batteries were. Other than that, everything was great!"
United States
Anonymous traveler
New Build! Log Cabin with Hot Tub in Wintergreen
Charming Historic Carriage House Studio Apartment
10.0 out of 10, Exceptional, (5)
$214 nightly
The price is $245
Nov 9 - Nov 10
Total with taxes and fees
Charming Historic Carriage House Studio Apartment
You deserve it all! Awesome Views, Comfy Condo & Elevator!
9.8 out of 10, Exceptional, (193)
"We stayed in a comfortable condo near the top of the mountain ridge with outstanding views! The location was close to the trails we planned to hike on…including a path that connected to the Appalachian Trail. We enjoyed the Chestnut Springs pool and the restaurants behind the lodge. The manager was helpful and friendly with giving us necessary information. A fantastic weekend vacation! "
United States
Eleanor R.
You deserve it all! Awesome Views, Comfy Condo & Elevator!
The Ultimate Escape. Unpack, Relax, Enjoy
10.0 out of 10, Exceptional, (15)
"Check in was smooth. The cabin was absolutely gorgeous. It was a perfect getaway for our Family. "
United States
Chris h.
The Ultimate Escape. Unpack, Relax, Enjoy
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall
9.8 out of 10, Exceptional, (52)
"Great family getaway. While it rained and conditions were terrible for snowboarding/skiing, we had everything we needed to be comfortable while staying at this condo! "
United States
Jamie M.
Top of Mountain 2 BR Condo, Short Walk to scenic overlooks of the Mtns. in Fall
Lotus View Retreat in Yogaville, Chalet with WiFi and AC
10.0 out of 10, Exceptional, (8)
"We loved our quick stay. Check in and check out were very low-key, easy, and flexible. The cabin was immaculate and well appointed with everything we could need. "
United States
Corey B.
$248 nightly
The price is $267
Nov 6 - Nov 7
Total with taxes and fees
Lotus View Retreat in Yogaville, Chalet with WiFi and AC
Cozy cabin for 2 w/ great mt views & walking trails!
10.0 out of 10, Exceptional, (169)
"Everything about this cabin is perfect. Very peaceful location, we loved it!"
United States
A H.
$156 nightly
The price is $175
Nov 5 - Nov 6
Total with taxes and fees
Cozy cabin for 2 w/ great mt views & walking trails!
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
9.6 out of 10, Exceptional, (4)
"The property is clean and fully stocked. Amazing view!!!!!!! Again, amazing view! "
United States
Johnnie O.
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
9.6 out of 10, Exceptional, (138)
"Beautiful condo with everything you need. We appreciated all the little extras including spices in the kitchen, extra toiletries in case we forgot anything, and pet supplies. We enjoyed the music festival events and the dining options too!"
United States
Kathleen L.
$223 nightly
The price is $250
Nov 16 - Nov 17
Total with taxes and fees
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK
9.4 out of 10, Exceptional, (88)
"Wonderful stay"
United States
Charlotte C.
Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
10.0 out of 10, Exceptional, (333)
"Nice and cozy house with all amenities! We really enjoyed it!"
Netherlands
Ingrid M.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Bear Tracks Cottage: New Hot Tub + Fire Pit
2.0 star property
10.0 out of 10, Exceptional, (27)
"Perfect getaway for my wife and myself. Everything was as expected and advertised and the place was beautiful. Would definitely rent here again!"
United States
Tim S.
$410 nightly
The price is $436
Nov 4 - Nov 5
Total with taxes and fees
Bear Tracks Cottage: New Hot Tub + Fire Pit
Wintergreen. Sunset Vista Villa - Sea of Mountains
10.0 out of 10, Exceptional, (88)
"Excellent property. Extremely well equipped and nicely furnished. Comfortable bedding."
United States
Edward S.
$236 nightly
The price is $265
Nov 4 - Nov 5
Total with taxes and fees
Wintergreen. Sunset Vista Villa - Sea of Mountains
2min to Ski Hot Tub EV Charger Mountain View DogOK
10.0 out of 10, Exceptional, (16)
"Had a wonderful weekend stay! Close to the slopes and great location!"
United States
WR Q.
2min to Ski Hot Tub EV Charger Mountain View DogOK
Wow! What A View!
10.0 out of 10, Exceptional, (53)
"This was our 4th stay and it was great as usual. "
United States
Amy j.
Wow! What A View!
Your Fall Retreat! The View at Crawfords Edge
2.0 star property
10.0 out of 10, Exceptional, (10)
"Very nice house with everything we needed. Beds are very comfortable, nicely updated home and beautiful views. Nespresso machine was a plus. Wood burning fireplace also a big plus to us. "
United States
Laura M.
Your Fall Retreat! The View at Crawfords Edge
One of the Best Views in Wintergreen!
9.8 out of 10, Exceptional, (38)
"Really nice - has to be among the best on the mountain."
United States
Nathan C.
One of the Best Views in Wintergreen!
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.
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Top Howardsville Hotel Reviews

Find out more about Howardsville

Everything you need to know about Howardsville 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 Howardsville 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 Howardsville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Howardsville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Howardsville. 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 Howardsville 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 $175 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 Howardsville rentals

At Expedia, we put the best Howardsville 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 Howardsville 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 Howardsville 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 Howardsville. 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 Howardsville?

Yes, you can find vacation rentals near well known attractions in Howardsville, or you can select a more remote option if you're looking for relaxation.

What are some of the best vacation rentals that Howardsville has to offer?

Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK: This vacation home rental outside of Howardsville is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Howardsville?

While exploring the area, visit family-friendly sights like Dorrier Park, or get outside and enjoy nature at James River. Walton's Mountain Museum and James River State Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Howardsville?

Vacation rentals are privately owned properties you can stay in for a few days or a quick weekend in Howardsville. Vacation rentals offer extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for families.