Chestnut Springs

Roseland

A waterfall in a forest with autumn leaves.

Things to do

Blue Ridge Parkway Bundle

Blue Ridge Parkway Self-Guided Audio Tour Bundle

CA $34
per traveller
Blue Ridge Parkway Self-Guided Audio Tour Bundle
Shenandoah National Park Self-Guided Driving Audio Tour

Shenandoah National Park Self-Guided Driving Audio Tour

CA $24
per traveller
100% of travellers recommend
Shenandoah National Park Self-Guided Driving Audio Tour
See all activities in Roseland

Chestnut Springs Hotel Deals

New Build! Log Cabin with Hot Tub in Wintergreen

New Build! Log Cabin with Hot Tub in Wintergreen

Wintergreen Resort VA
Book a stay at this family-friendly cabin in Wintergreen. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Wintergreen Resort and Raven's ...
10/10 Exceptional! (21 reviews)
"Our family had a wonderful time during our stay at Chestnut Springs. The home is beautiful and nestled in the hills. There was plenty of room for six adults and five kids ages eight to sixteen. The hot tub was a big hit as was the comfortable furnishings and the wood burning fireplace. The kitchen ..."

Reviewed on Aug 8, 2026

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New Build! Log Cabin with Hot Tub in Wintergreen
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

Wintergreen Resort VA
Stay at this condo in Wintergreen. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Wintergreen Resort and Raven's Roost ...
10/10 Exceptional! (91 reviews)
"Lovely property and attentive host. VERY clean and relaxing. The mattress was a bit uncomfortable and the living room had no lighting (i’m a knitter so that was noticeable to me). There was nothing that would keep me from visiting again. This review is for information only! Truly a great stay!"

Reviewed on Aug 15, 2026

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WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
Fully Loaded 8BR in Wintergreen! Sleeps 23

Fully Loaded 8BR in Wintergreen! Sleeps 23

Wintergreen Resort VA
Book a stay at this family-friendly chalet in Wintergreen. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Wintergreen Resort ...
10/10 Exceptional! (12 reviews)
"Nice house with great views, but several amenities were broken.The house is beautiful, very clean, has great views, a well-supplied kitchen, and an amazing sauna. However, several advertised amenities were unavailable during our stay. The outdoor projector was missing its remote, the arcade game ..."

Reviewed on Aug 8, 2026

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Fully Loaded 8BR in Wintergreen! Sleeps 23
Updated! Sleeps 14 - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill

Updated! Sleeps 14 - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill

Wintergreen Resort VA
Book a stay at this family-friendly vacation home in Wintergreen. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Wintergreen Resort and ...
10/10 Exceptional! (18 reviews)
"House was clean and well appointed. This is a great family house with kid and arcade-type games and various spots to hang out. Communications with the hosts were exceptional. Walking distance to a short nature trail. Perfect for a family with a dog or two! Hosts provided keirig coffee and liquid ..."

Reviewed on Jul 20, 2026

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Updated! Sleeps 14 - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill
Hotel 24 South

Hotel 24 South

3 out of 5
24 South Market Street Staunton VA
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Sep 6 to Sep 7
CA $143
CA $160 total
Sep 6 - Sep 7
includes taxes & fees
Book a stay at this historic hotel in Staunton. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the convenient ...
9.4/10 Exceptional! (1,216 reviews)
"Staff was friendly, location right in downtown made for easy walk to local attractions. While it is an older building it’s well maintained."

Reviewed on Aug 20, 2026

Hotel 24 South
Holiday Inn Staunton Conference Center by IHG

Holiday Inn Staunton Conference Center by IHG

3 out of 5
152 Fairway Lane Staunton VA
The price is CA $142 per night from Sep 20 to Sep 21
CA $142
CA $158 total
Sep 20 - Sep 21
includes taxes & fees
Book a stay at this golf hotel in Staunton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
8.2/10 Very good! (1,005 reviews)
"Not clean enough. Fissapp"

Reviewed on Aug 19, 2026

Holiday Inn Staunton Conference Center by IHG
See all 1,343 properties in Chestnut Springs
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.

Where to stay in Chestnut Springs

Find the best Chestnut Springs areas and neighborhoods for the activities you enjoy most. Learn more about Chestnut Springs
Learn more about Chestnut Springs
Devil's Knob overlook at Wintergreen resort ski town with Blue Ridge parkway mountains with autumn fall foliage and clouds mist fog covering peak high angle view

Laurel Ridge

When in Laurel Ridge, you can plan a visit to Wintergreen Resort and Raven's Roost Overlook, some noteworthy sights in the nearby area.

Chestnut Springs

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