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Holiday Rentals in Waynesboro City County

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Featured Holiday Rentals in Waynesboro City County

Blair's Vintage Apartment Nestled in Wine Country
Property grounds

Blair's Vintage Apartment Nestled in Wine Country

9.8 out of 10, Exceptional, (17)
"Clean and vitage style type of apartment. Nice for a quiet stay."
The price is €193
includes taxes & fees
30 Sept - 1 Oct
Blair's Vintage Apartment Nestled in Wine Country
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Miscellaneous

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

10.0 out of 10, Exceptional, (244)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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

10.0 out of 10, Exceptional, (327)
"The property is nestled very nicely on the mountain and convenient to the main lodge, restaurants and other attractions. We really enjoyed our stay. The condo was plenty big for the two of us and our dog. It is well-appointed Kudos to the owner, Heather, for thinking of everything to make our stay great. "
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

9.0 out of 10, Wonderful, (293)
"Beautiful location and million dollar views are so true. The condo was clean and comfortable. Will stay again and recommend to everybody. "
The price is €212
includes taxes & fees
30 Sept - 1 Oct
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
Property grounds

Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!

10.0 out of 10, Exceptional, (62)
"Loved our stay - the house, location, and amenities were perfect for us!"
The price is €624
includes taxes & fees
27 Oct - 28 Oct
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table
Property grounds

Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table

10.0 out of 10, Exceptional, (15)
"Nice time exploring the area"
Unwind in Seclusion: Log Cabin Retreat with Wood Burning Stove & Game Table
The Modern Mountain Condo
Property grounds

The Modern Mountain Condo

10.0 out of 10, Exceptional, (28)
"Ideal location for skiing at Wintergreen. "
The price is €209
includes taxes & fees
30 Sept - 1 Oct
The Modern Mountain Condo
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
Fridge, microwave, oven, stovetop

Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

9.6 out of 10, Exceptional, (49)
"We had the best weekend! Loved Lake Monocan and Devil’s Knob Spa. Also visited Three Notched and Devil’s Backbone. Condo worked very well. Beds were so comfortable and we lived kicking back on the patio. Will definitely rent again since it’s so close. Thanks for great communications!"
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Exterior

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

10.0 out of 10, Exceptional, (33)
"Great property and host"
The price is €198
includes taxes & fees
2 Oct - 3 Oct
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Love Ridge Mountain Lodging
Hanging Rock Cabin, 2 Bedrooms, Jetted Tub, Mountain View | Terrace/patio

Love Ridge Mountain Lodging

3.0 star property
10.0 out of 10, Exceptional, (12)
"Amazing stay I had, very peaceful and very quiet. "
The price is €263
includes taxes & fees
30 Sept - 1 Oct
Love Ridge Mountain Lodging
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Pool

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

9.6 out of 10, Exceptional, (136)
"Very clean place and very accommodating host"
The price is €215
includes taxes & fees
30 Sept - 1 Oct
New construction! Top of Wintergreen mountain. 1BD/2BA, sleeps 4, pet-friendly
Isolated cottage with good view close to many winery and Brewers.
Exterior

Isolated cottage with good view close to many winery and Brewers.

9.0 out of 10, Wonderful, (22)
"It was great thank you"
The price is €228
includes taxes & fees
30 Sept - 1 Oct
Isolated cottage with good view close to many winery and Brewers.
Ivy Rose Cottage nestled b/t Cville & Vineyards
Fridge, microwave, oven, stovetop

Ivy Rose Cottage nestled b/t Cville & Vineyards

10.0 out of 10, Exceptional, (60)
"Loved staying here!"
The price is €303
includes taxes & fees
30 Sept - 1 Oct
Ivy Rose Cottage nestled b/t Cville & Vineyards
Mechum Hill Cottage: Central to Crozet & Cville
Outdoor dining

Mechum Hill Cottage: Central to Crozet & Cville

9.6 out of 10, Exceptional, (16)
"Very quiet and peaceful. Large, secluded property. Good base from which to explore area wineries, local beer, food, and hike im the Shenandoah National Park."
The price is €245
includes taxes & fees
30 Sept - 1 Oct
Mechum Hill Cottage: Central to Crozet & Cville
Deer Run - Mountain Getaway
Property grounds

Deer Run - Mountain Getaway

10.0 out of 10, Exceptional, (231)
"We’ve been vacationing here yearly since 2018, it’s like coming home, we absolutely love Deer Run!"
Deer Run - Mountain Getaway
NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort
Property grounds

NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort

NEW! Warren’s Woods! Spacious 5-bedroom house in fantastic Wintergreen Resort
Whimsical Creekside Cabin
Property grounds

Whimsical Creekside Cabin

9.8 out of 10, Exceptional, (29)
"Had a very quiet relaxing stay "
The price is €169
includes taxes & fees
30 Sept - 1 Oct
Whimsical Creekside Cabin
Cozy Cabin with private HOT TUB!
Property grounds

Cozy Cabin with private HOT TUB!

10.0 out of 10, Exceptional, (26)
"Very nice and relaxing...Will definitely reccommend to friends."
Cozy Cabin with private HOT TUB!
Upscale and Family-Friendly in Wintergreen
Indoor spa tub

Upscale and Family-Friendly in Wintergreen

9.6 out of 10, Exceptional, (24)
"We absolutely loved our stay. Great hiking access point and very family/pet friendly. Would love to come stay again!"
Upscale and Family-Friendly in Wintergreen
Rustic Mountain Retreat-Bear Paw
Dining

Rustic Mountain Retreat-Bear Paw

9.8 out of 10, Exceptional, (230)
"Can’t wait to go back"
Rustic Mountain Retreat-Bear Paw
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 Waynesboro City County Hotel Reviews

Holiday Inn Express & Suites Waynesboro East by IHG

Holiday Inn Express & Suites Waynesboro East by IHG

10/10 Excellent
"The hotel staff was friendly. The place is very clean. Breakfast was great! "
Rachel 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Waynesboro East by IHG

Find out more about Waynesboro City County

Find out more about Waynesboro City County

Holiday Homes in Waynesboro City County

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