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Compare 257 Vacation Homes in Keswick with updated reviews, rates, and availability.

Comfy 3-bedroom historic building completely renovated, convenient to everything
2.0 star property
10.0 out of 10, Exceptional, (1)
"Most importantly, Bob is a kind and welcoming host and his property is in a great location Charlottesville. The price is also unmatched, though there could be a few improvements to the guest space. The fridge contained old food, there was no hand soap in one bathroom, and there were no trash bags. Also, there are only two beds, not three (best of my knowledge). If the place becomes more suited to VRBO guest needs, it will become a top spot to stay. Very thankful for Bob's flexibility with coming...
The price is AED 1,028
AED 1,583 total
includes taxes & fees
7 Nov - 8 Nov
Comfy 3-bedroom historic building completely renovated, convenient to everything
The House in the Holla at the foot of Shenandoah National Park
9.8 out of 10, Exceptional, (33)
"Great communication and accommodation!"
The price is AED 477
AED 978 total
includes taxes & fees
6 Nov - 7 Nov
The House in the Holla at the foot of Shenandoah National Park
RiverFront Country Home with Blue Mountain Views
9.8 out of 10, Exceptional, (19)
"Place was awesome. There was a great view from the front porch. There is a gas station less than a half mile away, which is very convenient. We were able to get to either Monticello or Montpelier in less than an hour. The town of Crozet is about 40 minutes away, which also has plenty to do. The location made it easy for us to get to all the places we wanted to go. I would absolutely stay at this place again."
The price is AED 393
AED 720 total
includes taxes & fees
6 Nov - 7 Nov
RiverFront Country Home with Blue Mountain Views
Scenic mountain getaway with a firepit and amazing views
10.0 out of 10, Exceptional, (24)
"Nice/Clean place with great views. Be prepared the drive to the property is a mile of gravel/offroad "
Scenic mountain getaway with a firepit and amazing views
Solar, 2 BR, 1 Bath, UVa, Preston, Downtown, EV charger
9.8 out of 10, Exceptional, (7)
"Wknd in C'ville."
Solar, 2 BR, 1 Bath, UVa, Preston, Downtown, EV charger
Charming 2-bedroom Downtown Retreat in Charlottesville with parking & wifi
2.0 star property
The price is AED 771
AED 1,322 total
includes taxes & fees
6 Nov - 7 Nov
Charming 2-bedroom Downtown Retreat in Charlottesville with parking & wifi
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
10.0 out of 10, Exceptional, (231)
"Everything was perfect... We hope to stay again!"
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!
9.8 out of 10, Exceptional, (35)
"Loved the walkability to Belmont and dowtown, and check in process was a breeze. Just right for our visit and would definately stay again."
The price is AED 496
AED 890 total
includes taxes & fees
20 Nov - 21 Nov
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
10.0 out of 10, Exceptional, (28)
"Cozy and charming."
The price is AED 826
AED 1,190 total
includes taxes & fees
12 Nov - 13 Nov
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Locust Lane| 3 Bedroom, 2.5 Bath | Near DTWN MALL!
2.0 star property
10.0 out of 10, Exceptional, (3)
"I stayed at this property once before when it was owned privately. I’m glad to see the charm of the house has not been lost. The house has been updated and more modernized, but it’s still has the cute and cozy feel with the indoor fire place and outdoor space. My only request would be to add a fire place outdoors. Otherwise I would stay here again and again. Also, the location is great if you’re trying to explore the downtown mall or if you enjoy going to the wineries and breweries like I using...
Locust Lane| 3 Bedroom, 2.5 Bath | Near DTWN MALL!
Lakeside retreat with a firepit, dock, sprawling deck, pool table - dog friendly
9.0 out of 10, Wonderful, (12)
"This house was perfect for our family. The layout of the house afforded everyone comfort."
Lakeside retreat with a firepit, dock, sprawling deck, pool table - dog friendly
Broadhead Mountain Retreat | 2 Bedroom, 2 Bath
9.6 out of 10, Exceptional, (45)
"It's close enough to get to all the UVA events, but remote so you feel like you're getting away. Place is very clean and well appointed."
Broadhead Mountain Retreat | 2 Bedroom, 2 Bath
Secluded Zen River Retreat
9.8 out of 10, Exceptional, (17)
"Absolutely breathtaking scenery. Love the house and beautiful river running through the property. definitely definitely "
The price is AED 643
AED 1,010 total
includes taxes & fees
6 Nov - 7 Nov
Secluded Zen River Retreat
It's beautiful in the winter! Winter Special--20% Discount February 1-March 31.
10.0 out of 10, Exceptional, (22)
"We loved our stay at the Madison house while celebrating my sons wedding that took place at the Market at Grelen The house is so so beautiful!!!!"
It's beautiful in the winter! Winter Special--20% Discount February 1-March 31.
Pryor-Haynes House | 4 Bed, 4.5 Bath
9.6 out of 10, Exceptional, (97)
"Nice house with a lot of Charlottesville charm. Definitely need to Uber to most UVA related activities. Would stay there again as it is nice and fit our needs. We had women fly and drive from very far distances. Would have been a game changer to have some kind of warm welcome touches. A bottle of wine, water, or coffee pods would have felt life changing. Would recommend anyway!"
Pryor-Haynes House | 4 Bed, 4.5 Bath
Skyline Drive, Pool table, arcades, board games near Shenandoah NP & wineries
10.0 out of 10, Exceptional, (8)
"Beautiful property. Fantastic hosts. Loved the games and activities! Highly recommend!"
The price is AED 367
AED 716 total
includes taxes & fees
11 Nov - 12 Nov
Skyline Drive, Pool table, arcades, board games near Shenandoah NP & wineries
NEW!! High Street Inn | 6 Bed, 6 Bath
2.0 star property
NEW!! High Street Inn | 6 Bed, 6 Bath
Westerly Haven B: Walk to Scott Stadium!
2.0 star property
10.0 out of 10, Exceptional, (2)
"We had four adults for a weekend getaway. The property is clean and well stocked. It is right off of I64 and within 15 min of the university and Monticello. Communication with the manager was easy and prompt. Their website is excellent with recommendations for food and activities. The only negative to this property is that it is not handicap accessible. The driveway is very steep and the stairs to the front door and upstairs are very steep. Otherwise, we thoroughly enjoyed our stay."
The price is AED 584
AED 1,340 total
includes taxes & fees
17 Nov - 18 Nov
Westerly Haven B: Walk to Scott Stadium!
Charming Farmhouse Cottage with Mountain Views
8.6 out of 10, Excellent, (15)
"Our 14-member family stayed on the entire property (farmhouse, cabin and cottage) and had a wonderful time. This cottage is small and cozy and has beautiful views of green pastures. 2 fox kits came out to frolic in front of the cottage each morning, their den must be nearby. This cabin is perfect for a lone traveler or a couple."
Charming Farmhouse Cottage with Mountain Views
Charming dog-friendly lakefront villa with private dock, firepit, stunning views
9.2 out of 10, Wonderful, (7)
"Plenty of space, accurate listing. Be sure to read the portion around 3 of the bedrooms with breezeway entry if you have small kids. Great views and easy communication! When we stayed there was construction on both sides (the only downfall of trip)- otherwise, fantastic spot, great fishing and would return!"
Charming dog-friendly lakefront villa with private dock, firepit, stunning 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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Other property types in Keswick

Stonemont Farm Cabin - in Keswick by VIneyards!
9.8 out of 10, Exceptional, (25)
"My wife and I stayed here and it was lovely! Very clean, cozy, and had everything we needed! During the day we visited local wineries and also spent the day at Monticello. We spent the evenings by a warm fire. We highly recommend!"
Stonemont Farm Cabin - in Keswick by VIneyards!
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
9.0 out of 10, Wonderful, (90)
"Perfect mini vacation getaway. "
The price is AED 477
AED 661 total
includes taxes & fees
2 Dec - 3 Dec
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful views!
9.8 out of 10, Exceptional, (74)
"Great location for Monticello and other places to visit. Enjoyed our stay "
Greensview Apt | 2 Bedroom, 2 Bath - Beautiful 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.