Howardsville Vacation Rentals

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Our top choices for Howardsville vacation rentals

Tranquil Vacation Rental Nestled in the Shenandoah Mountains of Howardsville, Virginia

Tranquil Vacation Rental Nestled in the Shenandoah Mountains of Howardsville, Virginia
Howardsville
The price is CA $395
CA $462 total
includes taxes & fees
May 26 - May 27
Tranquil Vacation Rental Nestled in the Shenandoah Mountains of Howardsville, Virginia

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

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (154 reviews)
"Very clean and pet-friendly "
United States
Heston
The price is CA $152
CA $343 total
includes taxes & fees
May 25 - May 26
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Private Guest Suite by Wineries/Orchards/Cville

Private Guest Suite by Wineries/Orchards/Cville
Palmyra
10.0 out of 10, Exceptional, (49 reviews)
"The property was exactly as described, very clean and comfy. Beautiful location and the host Made us feel welcome with a little treat in the fridge. Will definitely make this location our go to place when in the area!"
United States
Bonny R.
The price is CA $200
CA $320 total
includes taxes & fees
May 26 - May 27
Private Guest Suite by Wineries/Orchards/Cville

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery
Roseland
10.0 out of 10, Exceptional, (103 reviews)
"This place is such a gem. Stunning property, clean, and comfortable. You can tell the hosts take a lot of pride in this place. Loved it. "
United States
Warren
The price is CA $180
CA $273 total
includes taxes & fees
May 29 - May 30
Cozy Mountain Cabin Nelson 151 near Bold Rock Cidery and DB Brewery

Bluebird Cottage: Near 151 + Appalachian Trail

Bluebird Cottage: Near 151 + Appalachian Trail
Roseland
8.4 out of 10, Very good, (9 reviews)
"This house is perfect for a girls weekend. We did a couple places further out but enjoyed Bold Rock and Devils Backbone. It had everything we needed to enjoy some much needed time to relax at the house also. "
United States
Katherine N.
The price is CA $159
CA $403 total
includes taxes & fees
May 25 - May 26
Bluebird Cottage: Near 151 + Appalachian Trail

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (36 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
The price is CA $158
CA $369 total
includes taxes & fees
May 25 - May 26
Wintergreen Condo -Steps to Ski and restaurants

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.6 out of 10, Exceptional, (44 reviews)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
The price is CA $192
CA $405 total
includes taxes & fees
May 25 - May 26
Panoramic Peak: Wintergreen Condo with Views

Historic Bungalow 30 minutes from Wintergreen

Historic Bungalow 30 minutes from Wintergreen
Roseland
10.0 out of 10, Exceptional, (16 reviews)
"Great stay! Thank you!"
United States
Lauren
The price is CA $178
CA $401 total
includes taxes & fees
May 26 - May 27
Historic Bungalow 30 minutes from Wintergreen

Whole House

Whole House
Amherst
9.8 out of 10, Exceptional, (37 reviews)
"Everything was great. "
United States
Nathan T.
The price is CA $124
CA $206 total
includes taxes & fees
Jun 4 - Jun 5
Whole House

Charming Historic Carriage House Studio Apartment

Charming Historic Carriage House Studio Apartment
Charlottesville
10.0 out of 10, Exceptional, (16 reviews)
"Conveniently located for travelers stopping to visit Monticello. "
United States
Kelly G.
The price is CA $136
CA $319 total
includes taxes & fees
Jun 4 - Jun 5
Charming Historic Carriage House Studio Apartment

Brand new serene luxury cottage just off the Brew Ridge Trail

Brand new serene luxury cottage just off the Brew Ridge Trail
Afton
9.8 out of 10, Exceptional, (8 reviews)
"The property was very clean and awesome! It met the needs of our 2 day stay with our pets. We would stay again!"
United States
Joni K.
The price is CA $119
CA $265 total
includes taxes & fees
Jun 9 - Jun 10
Brand new serene luxury cottage just off the Brew Ridge Trail

Cozy cabin for 2 w/ great mt views & walking trails!

Cozy cabin for 2 w/ great mt views & walking trails!
Schuyler
10.0 out of 10, Exceptional, (183 reviews)
"Everything was amazing "
United States
Richard
The price is CA $200
CA $273 total
includes taxes & fees
Jun 7 - Jun 8
Cozy cabin for 2 w/ great mt views & walking trails!

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (14 reviews)
"Had a great stay, location was perfect! Condo was very nice. "
United States
Alicia K.
The price is CA $112
CA $301 total
includes taxes & fees
May 25 - May 26
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.

RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.
Faber
10.0 out of 10, Exceptional, (55 reviews)
"Great property, peaceful setting, great owner response."
United States
Tim V.
The price is CA $373
CA $476 total
includes taxes & fees
May 25 - May 26
RATED A TOP RIVER CABIN In Virginia. Stunning views! The heart of Nelson County.

Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews
Nellysford
9.8 out of 10, Exceptional, (8 reviews)
"Adorable, clean and quiet stay! The place was nicer than expected. It's obvious the hosts are thoughtful of their guests - we found everything we needed and more. A short drive into Nellysford and tucked away in the trees. "
United States
Katie K.
The price is CA $145
CA $416 total
includes taxes & fees
May 25 - May 26
Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!
Wintergreen Resort
10.0 out of 10, Exceptional, (36 reviews)
"This condo is the perfect location for a weekend ski getaway! We will definitely be staying here again!"
United States
Jennifer H.
The price is CA $143
CA $431 total
includes taxes & fees
May 25 - May 26
Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (8 reviews)
"Great location, everything we needed. Great hosts"
United States
Natalie A.
The price is CA $131
CA $386 total
includes taxes & fees
Jun 4 - Jun 5
Laurelwood Hollow: Walk to Ski & Swim

Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (56 reviews)
"The place was very clean and spacious. The communication from the hosts was helpful. We had a very pleasant stay."
United States
James S.
The price is CA $133
CA $523 total
includes taxes & fees
May 25 - May 26
Spacious + Serene Mtn Top Escape, 4 En Suites

Bear Tracks Cottage: New Hot Tub + Fire Pit

Bear Tracks Cottage: New Hot Tub + Fire Pit
Nellysford
10.0 out of 10, Exceptional, (33 reviews)
"Perfect location for a golf trip to Stoney Creek Golf Club!"
United States
Randy R.
The price is CA $253
CA $602 total
includes taxes & fees
May 26 - May 27
Bear Tracks Cottage: New Hot Tub + Fire Pit

Hillside Haven: Modern Retreat, Mountain Views

Hillside Haven: Modern Retreat, Mountain Views
Faber
10.0 out of 10, Exceptional, (35 reviews)
"This was a wonderful, private, modern place to stay! We were here for a visit to Pippin Hill and this was the perfect place!"
United States
Shiloh F.
The price is CA $247
CA $583 total
includes taxes & fees
May 26 - May 27
Hillside Haven: Modern Retreat, 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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Howardsville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Berry Hill Lake - Private Luxury Family Resort w/ Pool & Hot Tub - Pet Friendly: This vacation home rental outside of Howardsville is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.