Howardsville Vacation Rentals

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Dec 6 - Dec 7
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Dec 19 - Dec 21

Vacation Rentals in Howardsville

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

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

Wintergreen
10.0 out of 10, Exceptional, (252)
"Stayed 3 nights for a wedding at Wintergreen. Wonderful place with spectacular views "
United States
Michael S.
Best views on Mountain! Breathtaking 5 Star condo!. Available New Years Eve!!
Terrace/patio
New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen

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!

Wow! What A View!

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

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

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

2min to Ski Hot Tub EV Charger Mountain View DogOK

Wintergreen Resort
10.0 out of 10, Exceptional, (17)
"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
Interior
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

2.0 star property
Wintergreen Resort
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 ￥20,970
￥54,948 total
includes taxes & fees
Dec 8 - Dec 9
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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

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

Large and Luxurious Exec 5BR Chalet

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

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

Roseland
9.6 out of 10, Exceptional, (142)
"Great stay in Wintergreen!"
United States
Pete K.
The price is ￥17,086
￥38,899 total
includes taxes & fees
Dec 8 - Dec 9
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!

The newest and largest edition to the Wintergreen Retreat portfolio!

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 - Close to the ski slopes

Wintergreen. Sunset Vista Villa - Close to the ski slopes

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 ￥18,174
￥41,341 total
includes taxes & fees
Dec 8 - Dec 9
Wintergreen. Sunset Vista Villa - Close to the ski slopes
Property grounds
Top of Mountain 2 BR Condo, Short Walk to Highlands Lift and scenic overlooks.

Top of Mountain 2 BR Condo, Short Walk to Highlands Lift and scenic overlooks.

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!

Travelers' Rest--Your Wintergreen Retreat in the Center of it All!

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!

You deserve it all! Awesome Views, Comfy Condo & Elevator!

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

Wintergreen Oasis - PRIVATE POOL & SAUNA

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

Pickleball - 2 Homes - Sleeps 20 - 151 Brew Trail

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 ￥124,486
￥216,699 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Pickleball - 2 Homes - Sleeps 20 - 151 Brew Trail
Outdoor dining
Mountain Views in Wintergreen

Mountain Views in Wintergreen

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

Cottage at Deer Ridge Farm

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

The Modern Mountain Condo

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 ￥15,552
￥37,874 total
includes taxes & fees
Dec 8 - Dec 9
The Modern Mountain Condo
Property grounds
View from the Top

View from the Top

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

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

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

10/10 Excellent
"The host was exceptionally friendly, informative and helpful. I had questions for the host before booking. She answered our questions quickly and was always gracious. When we asked if there was a mixer and specific baking dish, she said that she would order one for us. That was above and beyond our expectations. The condo is lovely, was clean and ready for guests. The furnishings are stylish, clean and comfortable. The beds were comfortable as well. The view!!! We took so many pictures of the beautiful view from the condo. That expansive view inspired us to go hiking. We found two great hiking trails close to the condo. When we got back from the hike, we used the unlimited firewood to have a wonderful fire in the fireplace. We played games and enjoyed watching something together on the tv over the fireplace. On Thanksgiving, we used the kitchen to make a wonderful meal and we dined at the dining table enjoying the view. There is a small market on the mountain if you need any last minute groceries. I encourage you to stay at this condo. Our family had a great time at this condo. Maureen is a wonderful host."
Mary G. 2-night trip
Posted 3 days ago
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

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.