Howardsville Holiday Rentals

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Holiday Rentals in Howardsville

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

10.0 out of 10, Exceptional, (62)
"Loved our stay - the house, location, and amenities were perfect for us!"
The price is AU$1,102
includes taxes & fees
27 Oct - 28 Oct
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

10.0 out of 10, Exceptional, (243)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10.0 out of 10, Exceptional, (327)
"The property is nestled very nicely on the mountain and convenient to the main lodge, restaurants and other attractions. We really enjoyed our stay. The condo was plenty big for the two of us and our dog. It is well-appointed Kudos to the owner, Heather, for thinking of everything to make our stay great. "
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Wintergreen. Sunset Vista Villa - Sea of Mountains

10.0 out of 10, Exceptional, (80)
"Everything was perfect "
The price is AU$410
includes taxes & fees
2 Oct - 3 Oct
Wintergreen. Sunset Vista Villa - Sea of Mountains

Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table

10.0 out of 10, Exceptional, (15)
"Nice time exploring the area"
Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table

Aftonshire Cottage - Heart of Afton's Wine Region

9.8 out of 10, Exceptional, (10)
"Better than advertised. Kitchen has everything needed. Perfect for two couples. Comfy firm beds. Beautiful views- enjoyed watching the horses out back and the roaming deer. The brewery across the street has a fantastic scratch kitchen food truck - and great staff. Would love to book again in the near future. "
Aftonshire Cottage - Heart of Afton's Wine Region

3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes

10.0 out of 10, Exceptional, (62)
"House was very nice. Great set up for family."
3 Ridges Vista. Stunning mountain views, renovated home, 2 mins to ski slopes

Loveshack, a charming tiny house on a 5 acre farm

9.6 out of 10, Exceptional, (7)
"My wife and I had a great weekend getaway. Property was great. Close to restaurants and hiking. Great hosts."
Loveshack, a charming tiny house on a 5 acre farm

Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

9.6 out of 10, Exceptional, (48)
"We had the best weekend! Loved Lake Monocan and Devil’s Knob Spa. Also visited Three Notched and Devil’s Backbone. Condo worked very well. Beds were so comfortable and we lived kicking back on the patio. Will definitely rent again since it’s so close. Thanks for great communications!"
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

9.6 out of 10, Exceptional, (136)
"Very clean place and very accommodating host"
The price is AU$385
includes taxes & fees
28 Sept - 29 Sept
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

9.8 out of 10, Exceptional, (52)
"This was our second stay in Wintergreen. First time at this property. The condo was beautifully decorated, had all the necessities and the view was breathtaking. "
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

Lotus View Retreat in Yogaville, Chalet with WiFi and AC

10.0 out of 10, Exceptional, (4)
"The view really is that beautiful! It's rural and peaceful! The check-in and check-out was easy and the owners pleasant to work with. The house is very comfortable and open."
The price is AU$419
includes taxes & fees
28 Sept - 29 Sept
Lotus View Retreat in Yogaville, Chalet with WiFi and AC

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

8.0 out of 10, Very good, (1)
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Mechum Hill Cottage: Central to Crozet & Cville

9.6 out of 10, Exceptional, (16)
"Very quiet and peaceful. Large, secluded property. Good base from which to explore area wineries, local beer, food, and hike im the Shenandoah National Park."
The price is AU$433
includes taxes & fees
28 Sept - 29 Sept
Mechum Hill Cottage: Central to Crozet & Cville

Insane Mountain Views - New Listing

10.0 out of 10, Exceptional, (33)
"If you’re traveling with a large group or multiple families- this is the property for you.There’s too many things to comment on with this beautiful home. The views- breathtaking. The rooms private, luxurious l, and accommodating and the location was very convenient "
Insane Mountain Views - New Listing

Wow! What A View!

10.0 out of 10, Exceptional, (53)
"Property was gorgeous with amazing mountain views! Comfortable beds, beautiful kitchen and large living room for relaxing. Great location. Can’t wait to stay here again!"
Wow! What A View!

Wintergreen Mountain Views - Diamond in the Slopes - Close to Breweries & Hiking

10.0 out of 10, Exceptional, (3)
"Exterior of the building is a bit dated, but this unit has a fresh and updated feel to it. Everything we needed was provided. Quiet and very clean. Host was easy to work with. I'll definitely check to see if this unit is available the next time I'm visiting.Note: As mentioned in the description, there are a lot of steps to go down (and then back up)."
Wintergreen Mountain Views - Diamond in the Slopes - Close to Breweries & Hiking

The Modern Mountain Condo

10.0 out of 10, Exceptional, (28)
"Ideal location for skiing at Wintergreen. "
The price is AU$370
includes taxes & fees
29 Sept - 30 Sept
The Modern Mountain Condo

Pickleball | 2 Homes | Sleeps 20 | 151 Brew Trail

10.0 out of 10, Exceptional, (3)
"Awesome property and location. We had a group with 11 adults and 8 kids. It was perfect for entertaining kids and adults. We will definitely book again."
The price is AU$1,613
includes taxes & fees
12 Oct - 13 Oct
Pickleball | 2 Homes | Sleeps 20 | 151 Brew Trail

Bear Tracks Cottage: New Hot Tub + Fire Pit

2.0 star property
10.0 out of 10, Exceptional, (23)
"Great for taking advantage of all Nelson County's attractions. "
The price is AU$675
includes taxes & fees
2 Oct - 3 Oct
Bear Tracks Cottage: New Hot Tub + Fire Pit
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

Find out more about Howardsville

Everything you need to know about Howardsville 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 Howardsville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Howardsville holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Howardsville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Howardsville 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 Howardsville holiday rentals we have selected for you start as low as AU$370 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Howardsville rentals

At Expedia, we put the best Howardsville 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 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 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 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 holiday rentals in Howardsville?

Yes, there are holiday rentals close to the most popular sights in Howardsville, 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 Howardsville has to offer?

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!: This holiday home rental outside of Howardsville is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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 wider area.

What are holiday rentals like in Howardsville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Howardsville. Holiday rentals offer extras like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for family trips.