Chestnut Springs Hotels, Roseland

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Check prices for these dates

Tonight
9 Mar - 10 Mar
Tomorrow
10 Mar - 11 Mar
This weekend
13 Mar - 15 Mar
Next weekend
20 Mar - 22 Mar

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Our top choices for Chestnut Springs hotels

Winery

The Crossroads Inn

The Crossroads Inn
5.0 star property
24.8 km from Chestnut Springs
10.0 out of 10, Exceptional, (44 reviews)
"The staff were excellent. Very friendly, great hospitality. We will definitely book again."
United States
Sharon
The Crossroads Inn
House (3 Bedrooms) | Interior

Modern Nellysford Getaway on 40 Private Acres!

Modern Nellysford Getaway on 40 Private Acres!
3.0 star property
9.8 km from Chestnut Springs
The price is AU$865
includes taxes & fees
24 Mar - 25 Mar
Modern Nellysford Getaway on 40 Private Acres!
Front of property

Basecamp151

Basecamp151
2.5 star property
9.5 km from Chestnut Springs
9.2 out of 10, Wonderful, (5 reviews)
"Very nice room, clean and comfortable. "
United States
HELEN Stacy
The price is AU$205
includes taxes & fees
11 Mar - 12 Mar
Basecamp151
Outdoor pool, pool loungers

Afton Mountain Inn

Afton Mountain Inn
3.0 star property
10.6 km from Chestnut Springs
9.6 out of 10, Exceptional, (74 reviews)
"Beautiful inn and surrounding property! "
United States
Donna
The price is AU$302
includes taxes & fees
10 Mar - 11 Mar
Afton Mountain Inn
Porch

The Farmhouse at Veritas

The Farmhouse at Veritas
4.0 star property
12.9 km from Chestnut Springs
9.8 out of 10, Exceptional, (34 reviews)
"Nice location a staff. Dining in the vineyard was excellent."
United States
John
The price is AU$519
includes taxes & fees
16 Mar - 17 Mar
The Farmhouse at Veritas
Exterior

Village Inn

Village Inn
2.0 star property
21.3 km from Chestnut Springs
9.0 out of 10, Wonderful, (203 reviews)
"Clean and quiet. A little dated, but perfect for our needs. We've stayed here twice and would come back again."
United States
Frances
The price is AU$160
includes taxes & fees
10 Mar - 11 Mar
Village Inn
Apartment

Stoney Creek Cottage Wintergreen w EV Charger

Stoney Creek Cottage Wintergreen w EV Charger
2.0 star property
7.7 km from Chestnut Springs
The price is AU$656
includes taxes & fees
10 Mar - 11 Mar
Stoney Creek Cottage Wintergreen w EV Charger
Interior detail

Afton Mountain Vineyards

Afton Mountain Vineyards
2.5 star property
11.6 km from Chestnut Springs
10.0 out of 10, Exceptional, (2 reviews)
"Cozy and comfortable with pond and mountain views. Wine tasting on site and easy access to Wintergreen. We loved our stay and will be back again!"
United States
Jennifer
The price is AU$559
includes taxes & fees
10 Mar - 11 Mar
Afton Mountain Vineyards
Premium bedding, memory-foam beds, desk, laptop workspace

Grey Pine Lodge

Grey Pine Lodge
2.0 star property
14.2 km from Chestnut Springs
9.4 out of 10, Exceptional, (117 reviews)
"Pet friendly great grounds"
United States
Jay
The price is AU$213
includes taxes & fees
10 Mar - 11 Mar
Grey Pine Lodge
Free daily local cuisine breakfast

Harmony Haill Bed and Breakfast

Harmony Haill Bed and Breakfast
2.0 star property
27.7 km from Chestnut Springs
8.0 out of 10, Very good, (2 reviews)
"Harmony Hill was a great place to spend a quiet night after exploring the area. It was very clean, and the hosts Mary and Bill were kind and attentive. Breakfast was abundant and well prepared, and my husband's dietary needs were well attended to. We enjoyed!"
United States
Emily
The price is AU$305
includes taxes & fees
17 Mar - 18 Mar
Harmony Haill Bed and Breakfast
Free daily full breakfast

Quality Inn Waynesboro - Skyline Drive

Quality Inn Waynesboro - Skyline Drive
2.5 star property
16 km from Chestnut Springs
7.0 out of 10, Good, (837 reviews)
"The staff very friendly and breakfast was great! "
United States
Jane
The price is AU$103
includes taxes & fees
8 Apr - 9 Apr
Quality Inn Waynesboro - Skyline Drive
Free daily continental breakfast

Econo Lodge Waynesboro - Skyline Drive

Econo Lodge Waynesboro - Skyline Drive
2.0 star property
16 km from Chestnut Springs
7.0 out of 10, Good, (134 reviews)
"Great location, well managed and professional service "
United States
Vethanayagam
The price is AU$90
includes taxes & fees
8 Apr - 9 Apr
Econo Lodge Waynesboro - Skyline Drive
Lobby sitting area

Iris Inn and Cabins

Iris Inn and Cabins
4.5 star property
13 km from Chestnut Springs
9.6 out of 10, Exceptional, (9 reviews)
"Incredible Mountain View at Sunset. Extremely comfortable bed. Delicious breakfast."
United States
Dale
The price is AU$530
includes taxes & fees
10 Mar - 11 Mar
Iris Inn and Cabins
Suite, Private Bathroom (Suite 2) | Exterior

Piedmont Grove

Piedmont Grove
2.0 star property
7 km from Chestnut Springs
9.4 out of 10, Exceptional, (33 reviews)
"Enjoyed our stay"
United States
Charlene
The price is AU$402
includes taxes & fees
10 Mar - 11 Mar
Piedmont Grove
Double Room, 2 Double Beds, Ground Floor

Royal Inn Motel

Royal Inn Motel
2.0 star property
16.3 km from Chestnut Springs
6.2 out of 10, (75 reviews)
"Friendly staff clean and lots of shopping nearby "
United States
JoAnne
The price is AU$122
includes taxes & fees
25 Mar - 26 Mar
Royal Inn Motel
Apartment (2 Bedrooms) | Front of property

Wintergreen Ski Resort Condo w/ Golf Access!

Wintergreen Ski Resort Condo w/ Golf Access!
4.0 star property
1.6 km from Chestnut Springs
10.0 out of 10, Exceptional, (2 reviews)
"Really nice and convenient condo. Great amenities. Would definitely stay again."
United States
Matthew
The price is AU$483
includes taxes & fees
10 Mar - 11 Mar
Wintergreen Ski Resort Condo w/ Golf Access!
House

Waynesboro Home Near Wintergreen Charlottesville

Waynesboro Home Near Wintergreen Charlottesville
2.0 star property
17.5 km from Chestnut Springs
The price is AU$998
includes taxes & fees
10 Mar - 11 Mar
Waynesboro Home Near Wintergreen Charlottesville
Free daily full breakfast

Comfort Inn Waynesboro

Comfort Inn Waynesboro
2.5 star property
14.5 km from Chestnut Springs
8.4 out of 10, Very good, (1,004 reviews)
"Room was clean and staff very friendly "
United States
Kim
The price is AU$128
includes taxes & fees
17 Mar - 18 Mar
Comfort Inn Waynesboro
Property amenity

Residence Inn Marriott Waynesboro

Residence Inn Marriott Waynesboro
3.0 star property
14.6 km from Chestnut Springs
9.2 out of 10, Wonderful, (449 reviews)
"Great huge room. Decent breakfast, staff is nice. Hot tub is out of order indefinitely- which bummed us out since we booked the hotel to be able to soak in the hot tub after skiing. "
United States
Amanda
The price is AU$236
includes taxes & fees
9 Apr - 10 Apr
Residence Inn Marriott Waynesboro
Exterior

Holiday Inn Express & Suites Waynesboro East by IHG

Holiday Inn Express & Suites Waynesboro East by IHG
2.5 star property
14.4 km from Chestnut Springs
9.2 out of 10, Wonderful, (505 reviews)
"Very friendly staff and nice room! "
United States
Jared
The price is AU$169
includes taxes & fees
15 Mar - 16 Mar
Holiday Inn Express & Suites Waynesboro East by IHG
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.
View all properties

Our guide on where to stay in Chestnut Springs

Find the best Chestnut Springs areas for the activities you enjoy most.

Laurel Ridge

Laurel Ridge might not have many top sights, but Wintergreen Resort and Raven's Roost Overlook are two attractions nearby that you can check out.

Top Chestnut Springs Hotel Reviews

avid hotel Staunton by IHG

avid hotel Staunton by IHG

2/10 Terrible
"We arrived at the hotel only to be approached while unpacking the car by a man asking for money. We noticed he went into the hotel. The person checking us in said he was another guest and they were aware of the issue. We asked for a full refund and found another hotel. The management should have escorted this guest off the property. Safety didn't seem to be a concern for them. Don't stay here."
David 1-night trip
Posted 11 hours ago
avid hotel Staunton by IHG

Frequently asked questions

What's it like in Chestnut Springs?
Travellers are sure to enjoy a stay in Wintergreen's Chestnut Springs neighbourhood. Consider a visit to Wintergreen Resort as part of your Chestnut Springs travel plans.
What's the best accommodation in Chestnut Springs?
For your stay in Chestnut Springs, New Build! Log Cabin with Hot Tub in Wintergreen is one of the top choices based on our traveller data. Other good options for your stay in the neighbourhood include 4 BR cabin mins to trails & breweries pets welcome and WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS.
How many hotels are there in Chestnut Springs?
Expedia has 76 hotels and other accommodation options in Chestnut Springs to choose from, making this an ideal home base for exploring the greater Wintergreen area.
If I need to cancel my hotel reservation in Chestnut Springs, will I receive a refund?
Yes! The majority of hotel bookings are fully refundable if you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you might be able to still cancel and receive a refund within a 24-hour period of your booking. Put your dates in and click on "Search", then you can use the "fully refundable" filter to view the top deals on offer in Chestnut Springs.
What can I see and do in this Wintergreen neighbourhood?
Wintergreen Resort is an attraction you might want to check out while you're in Chestnut Springs. While you're out sightseeing in Wintergreen, make sure that you visit other sights such as Raven's Roost Overlook or Humpback Rocks.

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