Howardsville Holiday Rentals

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Holiday Rentals in Howardsville

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

10.0 out of 10, Exceptional, (244)
"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

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 NZ$1,217
includes taxes & fees
14 Oct - 15 Oct
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

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

The Modern Mountain Condo

10.0 out of 10, Exceptional, (29)
"Ideal location for skiing at Wintergreen. "
The price is NZ$410
includes taxes & fees
6 Oct - 7 Oct
The Modern Mountain Condo

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

9.6 out of 10, Exceptional, (50)
"The condo was very clean, cozy and well appointed. The view of the golf course was beautiful and the mountain was quiet that week, which we were in need of some peace and quiet. My wife and I are already talking about our next trip to Wintergreen and we will likely stay here again. "
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

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

9.8 out of 10, Exceptional, (54)
"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

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

Loveshack, a charming tiny house on a 5 acre farm

9.6 out of 10, Exceptional, (9)
"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

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

9.6 out of 10, Exceptional, (137)
"Very clean place and very accommodating host"
The price is NZ$424
includes taxes & fees
2 Nov - 3 Nov
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly

Charming Historic Carriage House Studio Apartment

10.0 out of 10, Exceptional, (2)
"Great location that was peaceful and made us feel right at home! Highly recommend to anyone in the area. Also loved the proximity to walking/running trails. "
The price is NZ$321
includes taxes & fees
27 Oct - 28 Oct
Charming Historic Carriage House Studio Apartment

Lotus View Retreat in Yogaville, Chalet with WiFi and AC

10.0 out of 10, Exceptional, (5)
"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. "
The price is NZ$464
includes taxes & fees
6 Oct - 7 Oct
Lotus View Retreat in Yogaville, Chalet with WiFi and AC

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

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

New Build! Log Cabin with Hot Tub in Wintergreen

10.0 out of 10, Exceptional, (2)
"Well appointed kitchen, beautiful cabin!"
The price is NZ$2,195
includes taxes & fees
9 Oct - 10 Oct
New Build! Log Cabin with Hot Tub in Wintergreen

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 NZ$480
includes taxes & fees
6 Oct - 7 Oct
Mechum Hill Cottage: Central to Crozet & Cville

NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort

NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort

Panoramic Peak: Wintergreen Condo with Views

9.6 out of 10, Exceptional, (31)
"With its breathtaking views, this property is a hidden gem. It is also very well maintained. "
The price is NZ$526
includes taxes & fees
4 Nov - 5 Nov
Panoramic Peak: Wintergreen Condo with Views

Among the Trees: Peace, Trails, Tastings at Dobie Slopeside. Prime location.

10.0 out of 10, Exceptional, (18)
"Our stay was fantastic. All the little details made the stay even better. Hand soap, bathroom and kitchen supplies, extra blankets. Beds were very comfortable too! Will definitely stay here again. "
Among the Trees: Peace, Trails, Tastings at Dobie Slopeside. Prime location.

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

9.8 out of 10, Exceptional, (134)
"Great ski-in / ski-out."
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
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 favorite 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 depends 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 NZ$321 per night. Entering your travel dates in the search wizard you might find 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.