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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
Exterior detail
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 SAR 1,051
SAR 1,618 total
includes taxes & fees
24 Nov - 25 Nov
Comfy 3-bedroom historic building completely renovated, convenient to everything
The House in the Holla at the foot of Shenandoah National Park
Exterior
The House in the Holla at the foot of Shenandoah National Park
9.8 out of 10, Exceptional, (37)
"Very nice cottage. Wonderful location and view. Cottage was very clean and well set-up. Everything you need is provided. "
The price is SAR 488
SAR 995 total
includes taxes & fees
3 Dec - 4 Dec
The House in the Holla at the foot of Shenandoah National Park
RiverFront Country Home with Blue Mountain Views
Property grounds
RiverFront Country Home with Blue Mountain Views
9.8 out of 10, Exceptional, (23)
"Plenty of space for everyone. Grandchildren loved the playground and the big yard. "
RiverFront Country Home with Blue Mountain Views
Scenic mountain getaway with a firepit and amazing views
Beautiful view
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
Exterior
Solar, 2 BR, 1 Bath, UVa, Preston, Downtown, EV charger
9.8 out of 10, Exceptional, (10)
"Everything we hoped for. Close to downtown mall. "
Solar, 2 BR, 1 Bath, UVa, Preston, Downtown, EV charger
Charming 2-bedroom Downtown Retreat in Charlottesville with parking & wifi
Exterior
Charming 2-bedroom Downtown Retreat in Charlottesville with parking & wifi
2.0 star property
10.0 out of 10, Exceptional, (1)
"This property was very comfortable. It was well appointed and the beds were super comfortable. I would come here again for aired. Thank you. "
The price is SAR 788
SAR 1,352 total
includes taxes & fees
24 Nov - 25 Nov
Charming 2-bedroom Downtown Retreat in Charlottesville with parking & wifi
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
You approach the property from this side.
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!
Cozy living space with kitchenette and work table
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 SAR 507
SAR 910 total
includes taxes & fees
4 Dec - 5 Dec
Best of Downtown and Belmont in cozy unique 2BD! Walk everywhere!
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
The view as you pull in the private driveway to your “Suite”.
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
10.0 out of 10, Exceptional, (30)
"Given this is our fourth visit, it goes without saying we enjoy our time at Chase Cottage. Chase Cottage provides a perfect jumping off location for our winery tours, hiking and historical visits. Tracey is a wealth of information and provides us many inside tips on things to do in the area. We will definitely be returning."
The price is SAR 845
SAR 1,213 total
includes taxes & fees
23 Nov - 24 Nov
“The Suite”. at Chase Cottage - Private Entrance! Luxury accommodations.
Locust Lane| 3 Bedroom, 2.5 Bath | Near DTWN MALL!
Locust Lane| 3 Bedroom, 2.5 Bath | Near DTWN MALL!
2.0 star property
10.0 out of 10, Exceptional, (4)
"We absolutely loved our stay at this lovely property. The location in a quite yet centrally situated neighborhood in Charlottesville allowed for quick access to shopping and dining. The house is beautifully decorated yet cozy with all needed amenities. The 3 bedrooms are a good size and the 2.5 bathrooms meant no one was left waiting. The owner/operator was incredibly responsive and kind. We hope to stay here again."
Locust Lane| 3 Bedroom, 2.5 Bath | Near DTWN MALL!
Lakeside retreat with a firepit, dock, sprawling deck, pool table - dog friendly
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
Beautiful View
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
Secluded Zen River Retreat
9.8 out of 10, Exceptional, (19)
"Absolutely breathtaking scenery. Love the house and beautiful river running through the property. definitely definitely "
The price is SAR 405
SAR 736 total
includes taxes & fees
24 Nov - 25 Nov
Secluded Zen River Retreat
It's beautiful in the winter!
Property grounds
It's beautiful in the winter!
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!
Pryor-Haynes House | 4 Bed, 4.5 Bath
Living Rom Area
Pryor-Haynes House | 4 Bed, 4.5 Bath
9.6 out of 10, Exceptional, (98)
"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
Game room
Skyline Drive, Pool table, arcades, board games near Shenandoah NP & wineries
10.0 out of 10, Exceptional, (9)
"We had a wonderful time at Stephanie's place! The space was clean and beautifully furnished. Stephanie went above and beyond to add personalized touches and treats for us to enjoy! We loved playing the arcade games, ping pong and pool. We also tried out a few of the board games.The location was close to Shenandoah and several local restaurants. We had such a fun time. We will definitely be back! "
The price is SAR 375
SAR 732 total
includes taxes & fees
3 Dec - 4 Dec
Skyline Drive, Pool table, arcades, board games near Shenandoah NP & wineries
NEW!! High Street Inn | 6 Bed, 6 Bath
Lower Main level sitting area
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!
Living area
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 SAR 597
SAR 1,374 total
includes taxes & fees
25 Nov - 26 Nov
Westerly Haven B: Walk to Scott Stadium!
Charming Farmhouse Cottage with Mountain Views
Exterior
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
Charming dog-friendly lakefront villa with private dock, firepit, stunning views
9.4 out of 10, Exceptional, (8)
"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!
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!
The Natchez - quiet front porch & rockers.
Exterior
The Natchez - quiet front porch & rockers.
10.0 out of 10, Exceptional, (111)
"My husband and I LOVED the staycation we got to have at the Natchez Cabin! The cabin was bigger and cozier than we expected and the fireplace and rocking chairs were great highlights of our weekend. We would highly recommend this place for a restful and peaceful break from everyday life! "
The Natchez - quiet front porch & rockers.
Ivy Rose Cottage nestled b/t Cville & Vineyards
Exterior
Ivy Rose Cottage nestled b/t Cville & Vineyards
10.0 out of 10, Exceptional, (30)
"The cottage was charming, the grounds beautiful and peaceful. I wish we could have stayed longer."
The price is SAR 747
SAR 1,369 total
includes taxes & fees
25 Nov - 26 Nov
Ivy Rose Cottage nestled b/t Cville & Vineyards
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.