Search Vacation Homes in Hollymead

Most properties are fully refundable. Because flexibility matters.

Save 10% or more on over 100,000 hotels worldwide as a One Key member.

Search over 2.9 million properties and 550 airlines worldwide.

Compare Vacation Homes in Hollymead with updated reviews, rates, and availability.

Fridge, microwave, oven, stovetop
Cozy bungalow with breathtaking mountain views. Close to wineries and hiking!
10.0 out of 10, Exceptional, (40)
"My husband and I brought our newborn for his first trip away from home, and we picked the perfect home for it! It was very clean and quiet, and it was helpful to have access to a laundry machine. We were close by to Shenandoah and went on a few hikes and tried some great restaurants in the area. We look forward to coming back soon!"
The price is $180
$290 total
includes taxes & fees
May 15 - May 16
Cozy bungalow with breathtaking mountain views. Close to wineries and hiking!
TV, fireplace, table tennis
New Luxury Modern Farmhouse, Downtown C'Ville
10.0 out of 10, Exceptional, (10)
"This house is exactly as pictured and described in the listing. It was very clean, spacious and inviting. It is perfect for a large group. Additionally, we were welcomed with fresh flowers, wine, and baked goods - such a thoughtful touch. The house also already had pretty much everything you need - towels (even makeup ones), coffee, tea, soap, etc. The location of the house is great - everywhere we wanted to go downtown (restaurants etc) were 5 minutes max driving. Additionally, there is ample...
New Luxury Modern Farmhouse, Downtown C'Ville
Interior
Honey House—beautiful detached Modern loft near UVA, Downtown and Monticello
10.0 out of 10, Exceptional, (42)
"We loved this house! We want to stay once a year! Beautifully renovated. Can tell that so much thought was put into each design decision. Owner was welcoming and responsive. We can't wait to come back."
The price is $174
$317 total
includes taxes & fees
May 21 - May 22
Honey House—beautiful detached Modern loft near UVA, Downtown and Monticello
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Exterior
Peaceful mountain farmhouse, close to Shenandoah NP, wineries and more
10.0 out of 10, Exceptional, (15)
"The house was perfect for us. I have two toddlers and they had everything we needed. There were baby gates, booster seats and a pack n play. Would definitely come back."
Peaceful mountain farmhouse, close to Shenandoah NP, wineries and more
Exterior
Quarry House on Quiet Entry Farm | Near Wineries
10.0 out of 10, Exceptional, (60)
"We had a fabulous time relaxing and enjoying the beautiful home and amenities on this property. Highly recommend for a friend weekend. Lots to do with wineries and Charlottesville but most importantly the relaxing space of this home!"
Quarry House on Quiet Entry Farm | Near Wineries
Property grounds
Boutique Room steps from Downtown Mall | Rose Jean - Room #3
10.0 out of 10, Exceptional, (6)
"We loved the room and the close proximity to the downtown mall. Great stay!"
The price is $105
$202 total
includes taxes & fees
May 14 - May 15
Boutique Room steps from Downtown Mall | Rose Jean - Room #3
Exterior
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
10.0 out of 10, Exceptional, (220)
"We had a great time and found the property exactly as described. Beds were comfy and hosts very hospitable. Really enjoyed the fresh farm eggs and beautiful bouquets throughout the home. Would highly recommend"
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Fridge, microwave, oven, stovetop
Wooded Escape Near UVA, Wineries & Skyline Dr
10.0 out of 10, Exceptional, (6)
"The property was immaculate and had everything we needed for a quick escape. Owner was so quick to respond and made our stay so easy. Will come back!"
Wooded Escape Near UVA, Wineries & Skyline Dr
Property grounds
Charming Charlottesville Apt w/ Outdoor Space!
10.0 out of 10, Exceptional, (29)
"This property is ideally located to take advantage of everything the Charlottesville area has to offer."
Charming Charlottesville Apt w/ Outdoor Space!
Outdoor dining
Historic Beauty and Walkable to Everywhere
10.0 out of 10, Exceptional, (31)
"Monica's little place was perfect for our long weekend. It's close to so much and easy to navigate to and from. Street parking was available and the neighborhood was sweet. The space was the perfect size for what we needed."
The price is $131
$266 total
includes taxes & fees
May 15 - May 16
Historic Beauty and Walkable to Everywhere
Fridge, microwave, oven, stovetop
Stadium Cottage | Beautiful Home Steps Away From Scott's Stadium/UVA Grounds
10.0 out of 10, Exceptional, (50)
"Great property. Great area. I would not change a thing."
Stadium Cottage | Beautiful Home Steps Away From Scott's Stadium/UVA Grounds
Fridge, microwave, oven, stovetop
4 bedroom house close by UVA and wineries and barracks Rd shopping center
10.0 out of 10, Exceptional, (5)
"Well stocked kitchen, comfortable beds. Enjoyed pool and ping pong."
4 bedroom house close by UVA and wineries and barracks Rd shopping center
4 bedrooms, desk, iron/ironing board, travel crib
Entire House: 2,200 sq.ft. with Farm Views!
10.0 out of 10, Exceptional, (11)
"Great spot in the Barboursville area of Virginia. Beautiful view of the Blue Ridge Mountains out the front window and very close to Barboursville Winery as well as many others. Perfect place to stay!"
Entire House: 2,200 sq.ft. with Farm Views!
Fireplace, table tennis
*NEW* Lewis Mtn Retreat: Walk to UVA & JPJ
10.0 out of 10, Exceptional, (6)
"GREAT location, cute house, super safe neighborhood. Plenty of sleeping options, kitchen was well equipped and Roku tv’s were easy to use. Owners were very responsive and they provided helpful information about the area. Would stay again!"
The price is $408
$879 total
includes taxes & fees
Jun 12 - Jun 13
*NEW* Lewis Mtn Retreat: Walk to UVA & JPJ
Property grounds
The Catterton House- historic home in wine country
9.8 out of 10, Exceptional, (37)
"So very clean and packed with Virginia memorabilia, this VRBO is wonderful step back in time. One of most beautiful porches we have ever sipped coffee on, with a breath taking view of the valley below and blue ridges in the distance. This will be top of our list for accommodations whenever we are in the Charlottesville area."
The Catterton House- historic home in wine country
Property grounds
Broadhead Mountain Retreat | 2 Bedroom, 2 Bath
9.8 out of 10, Exceptional, (38)
"My friends and I had a wonderful stay at Broadhead Mountain Retreat! We were looking for a weekend getaway in a beautiful quiet location that's not too far from other things to do (tourist attractions, restaurants, shopping, etc) and this fit the bill perfectly. Make sure you get groceries and any other necessities before you head up the mountain to avoid making extra trips up and down the unpaved road. Four wheel drive is a good choice if possible but it's doable without one. Highly recommend!"
Broadhead Mountain Retreat | 2 Bedroom, 2 Bath
2 bedrooms, free WiFi, bed sheets
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!
9.8 out of 10, Exceptional, (28)
"Very small space outside of bedrooms but clean and comfy. Parking space is TIGHT. Walking distance to old town."
The price is $135
$235 total
includes taxes & fees
May 29 - May 30
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!
Smart TV, books
Downtown Mall Cottage just off Main St., breweries/wineries 10-30min drive
9.8 out of 10, Exceptional, (142)
"The property is close to many key locations which makes for a more enjoyable trip."
Downtown Mall Cottage just off Main St., breweries/wineries 10-30min drive
Fridge, microwave, oven, stovetop
Charming Updated 3 Bedroom Home Near Downtown
9.6 out of 10, Exceptional, (29)
"We enjoyed our stay"
The price is $225
$453 total
includes taxes & fees
May 14 - May 15
Charming Updated 3 Bedroom Home Near Downtown
Fridge, microwave, oven, stovetop
Beautiful Ranch Style Home - Minutes from Downtown CVille!
9.6 out of 10, Exceptional, (39)
"Everything was great. Only we were not left any dishwasher detergent. I did call the number you gave me. It only got a voice mail so we hand washed most dishes but had to leave early this AM and left a few cups, etc in dishwasher."
Beautiful Ranch Style Home - Minutes from Downtown CVille!
Don't see what you're looking for?
See all available properties in Hollymead
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.

Other property types in Hollymead

Exterior
Log Cabin on the River
10.0 out of 10, Exceptional, (5)
"We had a wonderful time! The cabin was well appointed and the location was gorgeous."
The price is $225
$326 total
includes taxes & fees
Jun 9 - Jun 10
Log Cabin on the River
Property grounds
Relax at 3100 feet and enjoy the peace and tranquility
9.8 out of 10, Exceptional, (59)
"I spent a week on a self-meditation retreat. The location and the facilities were beautiful. The view is amazing - the pictures are accurate. Tessy and Steve were great hosts - very helpful. I got to walk part of the Appalachian Trail nearby - saw a bear cross the path. There are wineries nearby, though I did not go to any. Great place for a getaway."
Relax at 3100 feet and enjoy the peace and tranquility
Exterior
Cozy modern cabin - the squirrel's nest
9.4 out of 10, Exceptional, (199)
"We had a great time staying at the Squirrel’s Nest. The location is secluded but still only 15 minutes away from Shenandoah. The cabin was warm & cozy and a perfect escape from everyday life. Hot tub was a plus!"
Cozy modern cabin - the squirrel's nest
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.