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Vacation Homes in Greenwood

Westerly Haven B: Walk to Scott Stadium!

2.0 star property
Jefferson Park Avenue
10.0 out of 10, Exceptional, (5)
"Was a great place. "
United States
Tripp C.
$336 nightly
The price is $384
Nov 23 - Nov 24
Total with taxes and fees
Westerly Haven B: Walk to Scott Stadium!

Room for rent in townhouse, 4 miles to downtown Charlottesville

3.5 star property
Charlottesville
Room for rent in townhouse, 4 miles to downtown Charlottesville

Rugby Road Residential -RRR- near UVa and downtown

Barracks Rugby
10.0 out of 10, Exceptional, (39)
"Great place to stay and well organized !"
United States
Joseph F.
$223 nightly
The price is $255
Nov 24 - Nov 25
Total with taxes and fees
Rugby Road Residential -RRR- near UVa and downtown

The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

Waynesboro
10.0 out of 10, Exceptional, (19)
"Beautiful home, very comfortable, and uniquely fun decor. Highly recommend!"
United States
Melissa
$150 nightly
The price is $166
Dec 18 - Dec 19
Total with taxes and fees
The Loriann , A Boutique Stay in a 1940's Home. New Sleep Number Bed!

Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

Nellysford
10.0 out of 10, Exceptional, (5)
"A lovely little hideaway a stone's throw from the Blue Ridge. Clean, comfortable, and cozy. Very communicative and professional hosts. Highly recommended!"
United States
Tim G.
$265 nightly
The price is $298
Nov 23 - Nov 24
Total with taxes and fees
Tucked Inn: Upper Unit - 151 Getaway/Wine + Brews

Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!

Waynesboro
10.0 out of 10, Exceptional, (7)
"We really enjoyed our stay at the property! With so many rooms, there was space for everyone, and everything was very clean upon our arrival. The hot tub was perfect for a cold night! "
United States
Stephen S.
$456 nightly
The price is $508
Nov 25 - Nov 26
Total with taxes and fees
Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!

Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!

Belmont
9.8 out of 10, Exceptional, (51)
"Cute, clean and cozy place! Close to downtown mall. Candace and Jason are very prompt with communication! "
United States
Seeta P.
$200 nightly
The price is $229
Dec 1 - Dec 2
Total with taxes and fees
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!

The Firefly Springhouse

Staunton
9.8 out of 10, Exceptional, (43)
"Great cottage for 2 and peaceful setting. Host was helpful with great dinner recommendations "
United States
Joseph
$103 nightly
The price is $114
Nov 23 - Nov 24
Total with taxes and fees
The Firefly Springhouse

NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Waynesboro
9.6 out of 10, Exceptional, (44)
"We enjoyed this cozy home during our annual trip to the area. Loved the charming, private backyard. Nearby vineyards and Blue Ridge Parkway were an added bonus. "
United States
Virginia W.
$183 nightly
The price is $204
Nov 30 - Dec 1
Total with taxes and fees
NEW! Cheerful 2 bd bungalow with hot tub. Must see!

Hillside Haven: Modern Retreat, Mountain Views

Faber
10.0 out of 10, Exceptional, (30)
"Fantastic property with all the amenities near UVA, and lots of wineries."
United States
roberto c.
$372 nightly
The price is $418
Dec 1 - Dec 2
Total with taxes and fees
Hillside Haven: Modern Retreat, Mountain Views

The Hawksbill Haus (w/ hot tub)

Waynesboro
9.6 out of 10, Exceptional, (8)
"Home was as described. Location was close enough to stores and attractions. Hot tub was nice."
United States
Catherine D.
$293 nightly
The price is $326
Dec 3 - Dec 4
Total with taxes and fees
The Hawksbill Haus (w/ hot tub)

Secluded 20+ Acre Retreat Near Brew & Wine Trails

Afton
9.8 out of 10, Exceptional, (9)
"Everything was exactly as stated. We loved the house and the close proximity to the 151. We will definitely come back! "
United States
Harold R.
$341 nightly
The price is $383
Nov 24 - Nov 25
Total with taxes and fees
Secluded 20+ Acre Retreat Near Brew & Wine Trails

Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Wintergreen Resort
10.0 out of 10, Exceptional, (24)
"A wonderful property to see mountain views and visit the surrounding area."
United States
Peggy B.
$294 nightly
The price is $330
Dec 3 - Dec 4
Total with taxes and fees
Cozy chalet w/ king beds, fireplace, and hot tub. Close to skiing! Dog-friendly!

Secluded cabin on a horse farm, bordered by the North River

GROTTOES
10.0 out of 10, Exceptional, (70)
"Great place to stay "
United States
William H.
$265 nightly
The price is $292
Nov 23 - Nov 24
Total with taxes and fees
Secluded cabin on a horse farm, bordered by the North River

Hill Street House walk to UVA Stadium/Fry's Spring

Fry's Spring
10.0 out of 10, Exceptional, (35)
"We really enjoyed the space. "
United States
Danielle R.
$335 nightly
The price is $390
Dec 1 - Dec 2
Total with taxes and fees
Hill Street House walk to UVA Stadium/Fry's Spring

Tucked Inn: Lower Unit - NEW Nelson Co Getaway

2.0 star property
Nellysford
$260 nightly
The price is $292
Nov 23 - Nov 24
Total with taxes and fees
Tucked Inn: Lower Unit - NEW Nelson Co Getaway

Green on New - Central Location and Staunton Charm

Staunton
9.4 out of 10, Exceptional, (13)
"Really enjoyed our stay! Very clean and quaint little place. Would stay again. "
United States
JANIE M.
$226 nightly
The price is $253
Dec 7 - Dec 8
Total with taxes and fees
Green on New - Central Location and Staunton Charm

The Hunker Down: Cheerful 2 Bed and Pet Friendly

Staunton
9.0 out of 10, Wonderful, (13)
"We stayed here with our two kids (age 2 and 3) and would stay again! The apartment was incredibly clean with plenty of space and everything we needed. We sleep with white noise machines and had no issues with noise at all. Check in and parking was easy and the hosts were very responsive. "
United States
Michelle S.
$222 nightly
The price is $249
Dec 2 - Dec 3
Total with taxes and fees
The Hunker Down: Cheerful 2 Bed and Pet Friendly

Little Yellow House: Walk to Downtown Staunton

Staunton
10.0 out of 10, Exceptional, (6)
"I loved the location and the extra amenities !"
United States
Miriam
$253 nightly
The price is $283
Nov 23 - Nov 24
Total with taxes and fees
Little Yellow House: Walk to Downtown Staunton

Peaceful Retreat w/ Hot Tub, Fire Pit, Mountain Views

Afton
10.0 out of 10, Exceptional, (19)
"Ashley is an awesome host. I love Creekside! This is my second stay there, and I loved it so much I booked an extra day. Best place to stay in Afton "
United States
Michael C.
$399 nightly
The price is $448
Nov 23 - Nov 24
Total with taxes and fees
Peaceful Retreat w/ Hot Tub, Fire Pit, Mountain Views
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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