Howardsville Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Howardsville

Miscellaneous
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!

Condo in Wintergreen

10.0 out of 10, Exceptional, (252)
"The condo was absolutely lovely! We had great time in Wintergreen and will definitely go back. "
United States
Dawn C.
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!
Terrace/patio
New Build! Log Cabin with Hot Tub in Wintergreen

Cabin in Chestnut Springs

10.0 out of 10, Exceptional, (4)
"Well appointed kitchen, beautiful cabin!"
United States
Curtis
New Build! Log Cabin with Hot Tub in Wintergreen
Exterior
Wow! What A View!

Condo in Wintergreen Resort

10.0 out of 10, Exceptional, (54)
"Very clean, very comfortable, easy to access - we honestly didn't want to leave."
United States
Josh W.
Wow! What A View!
Outdoor dining
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

Condo in Wintergreen Resort

9.8 out of 10, Exceptional, (8)
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
Fridge, microwave, oven, stovetop
2min to Ski Hot Tub EV Charger Mountain View DogOK

Vacation Home in Wintergreen Resort

10.0 out of 10, Exceptional, (17)
"It was great "
United States
Sergio o.
2min to Ski Hot Tub EV Charger Mountain View DogOK
Interior
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Condo in Wintergreen Resort

2.0 star property
10.0 out of 10, Exceptional, (24)
"The property is extremely clean, well decorated and stocked. We had a fantastic time and absolutely would stay here again. "
United States
Cassie H.
The price is ￥20,943
￥54,878 total
includes taxes & fees
Dec 10 - Dec 11
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

Condo in Roseland

10.0 out of 10, Exceptional, (336)
"Great stay, highly recommended"
United States
Jeffrey E.
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Property grounds
Large and Luxurious Exec 5BR Chalet

Vacation Home in Pedlars Edge

10.0 out of 10, Exceptional, (250)
"Perfect location for family ski trip"
United States
Angie S.
Large and Luxurious Exec 5BR Chalet
Pool
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Condo in Roseland

9.6 out of 10, Exceptional, (142)
"Great stay in Wintergreen!"
United States
Pete K.
The price is ￥17,064
￥38,849 total
includes taxes & fees
Dec 10 - Dec 11
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Smart TV, fireplace, video games, books
The newest and largest edition to the Wintergreen Retreat portfolio!

Vacation Home in Wintergreen Resort

9.8 out of 10, Exceptional, (47)
"Beautiful property, well maintained. Perfect for a large group."
United States
Kenneth H.
The newest and largest edition to the Wintergreen Retreat portfolio!
Interior
Wintergreen. Sunset Vista Villa - Sea of Mountains

Condo in Wintergreen Resort

10.0 out of 10, Exceptional, (91)
"Beautiful property! Had everything we needed and was very clean! Highly recommend!"
United States
Amanda W.
The price is ￥18,150
￥40,765 total
includes taxes & fees
Dec 7 - Dec 8
Wintergreen. Sunset Vista Villa - Sea of Mountains
Property grounds
Top of Mountain 2 BR Condo, Short Walk to Highlands Lift and scenic overlooks.

Condo in Wintergreen Resort

9.8 out of 10, Exceptional, (53)
"Great place to stay in Wintergreen!"
United States
Caroline w.
Top of Mountain 2 BR Condo, Short Walk to Highlands Lift and scenic overlooks.
Outdoor dining
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

Condo in Wintergreen Resort

9.6 out of 10, Exceptional, (29)
"Great place to stay, would book again!"
United States
Jessica P.
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Property grounds
You deserve it all! Awesome Views, Comfy Condo & Elevator!

Condo in Chestnut Springs

9.8 out of 10, Exceptional, (195)
"Nice view along with a spacious layout. Was very nice location. "
United States
Daniel
You deserve it all! Awesome Views, Comfy Condo & Elevator!
Exterior
Wintergreen Oasis - PRIVATE POOL & SAUNA

Vacation Home in Nellysford

9.6 out of 10, Exceptional, (34)
"We enjoyed our stay"
United States
Miriam F.
Wintergreen Oasis - PRIVATE POOL & SAUNA
Exterior
Pickleball - 2 Homes - Sleeps 20 - 151 Brew Trail

Vacation Home in Nellysford

10.0 out of 10, Exceptional, (4)
"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."
United States
Peter T.
The price is ￥124,326
￥216,420 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Pickleball - 2 Homes - Sleeps 20 - 151 Brew Trail
Outdoor dining
Mountain Views in Wintergreen

Vacation Home in Laurel Ridge

10.0 out of 10, Exceptional, (9)
"We had a great trip! The house was beautiful with so much space! We loved using the hot tub at night. The host was helpful and responsive to all my questions. Would be happy to book this house again."
United States
Kara S.
Mountain Views in Wintergreen
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Cottage at Deer Ridge Farm

Vacation Home in Charlottesville

10.0 out of 10, Exceptional, (8)
"We had a wonderfully peaceful stay! The house was beautiful and location was amazing. The house was clean and had everything we needed. We look forward to staying again!"
United States
Julie W.
Cottage at Deer Ridge Farm
Property grounds
The Modern Mountain Condo

Condo in Wintergreen Resort

10.0 out of 10, Exceptional, (33)
"Fantastic stay at the Modern Mountain Condo! The check-in process was a breeze, the location is exactly as pictured and was very clean. Spacious location for a couples getaway. Host was extremely responsive to any questions and provided us great instructions and details about the space. Will stay again in the future! "
United States
Kelsey N.
The price is ￥15,532
￥37,303 total
includes taxes & fees
Dec 7 - Dec 8
The Modern Mountain Condo
Property grounds
View from the Top

Condo in Chestnut Springs

10.0 out of 10, Exceptional, (68)
"Loved the views and loved the resort in our off season visit. This 3rd floor VRBO was perfect for us, clean accommodating and comfortable. Especially like the elevator access from the car level. "
United States
Louise M.
View from the Top
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

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

10/10 Excellent
"From the very second you enter this property you are made to feel welcomed and appreciated. Whether it is from Cynthia, Bill or the incredible Pyrenees Zoe. Taking time out of their day to ensure you have the most amazing time is always done with a smile and a great chat. The house is phenomenal, from the history to the comfort it was absolutely 5 stars. Greeting and feeding the animals most days, spending the afternoons in the covered patio and the evenings downstairs by the fire made this an extremely relaxing and memorable vacation. A short drive to everywhere, we spent time at the historic downtown mall, visited Monticello, and frequented the many wineries surrounding the property, before coming “home” to a warm welcome and incredible vistas. I also highly recommend utilizing Darby Farms for the catering, the food was amazing as was the service. Thankyou, Bill and Cynthia for an incredible home away from home Vacation!! "
Leigh H. 7-night trip
Posted 4 days ago
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious

Find out more about Howardsville

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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?

Large and Luxurious Exec 5BR Chalet: This vacation home rental outside of Howardsville is located on a lake and has a fireplace, a patio, 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. You and your friends and family can relax into your vacation with amenities like a selection of games.

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 Buckingham Historic Village 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.