Keswick Holiday Rentals

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Our top choices for Keswick holiday rentals

9.8 out of 10, Exceptional, (37)
"Charming cabin. We loved the peaceful quiet outdoors. "
United States
Molly C. T.
The price is NZ$638
includes taxes & fees
16 Dec - 17 Dec
Stonemont Farm Cabin - in Keswick by VIneyards!
9.6 out of 10, Exceptional, (54)
"Everything is wonderful and comfortable!"
United States
Yasmine
The price is NZ$271
includes taxes & fees
4 Jan - 5 Jan 2026
Postcard Cabins Shenandoah, Outdoor Collection by Marriott Bonvoy
10.0 out of 10, Exceptional, (43)
"Nice piece of property for our dogs to run around. Clean and had we had a great experience. "
United States
amy c.
The price is NZ$266
includes taxes & fees
16 Dec - 17 Dec
Newly renovated entire guest suite in Orange County.
9.0 out of 10, Wonderful, (17)
"We had a wonderful stay at the White"
United States
Elizabeth
The price is NZ$338
includes taxes & fees
29 Dec - 30 Dec
Pond View (Second bedroom at extra cost)
10.0 out of 10, Exceptional, (29)
"Stew was a great surprise, pleasant and very hospitable "
United States
Jeff H.
The price is NZ$346
includes taxes & fees
16 Dec - 17 Dec
Moonfire Farm Shenandoah region cozy getaway
10.0 out of 10, Exceptional, (42)
"Love staying here. It’s always a great place to stay "
United States
Jamie D.
The price is NZ$464
includes taxes & fees
16 Dec - 17 Dec
Bluebird Cottage A: Across from Lake Monticello, Near Charlottesville, 1 Dog Ok
9.8 out of 10, Exceptional, (137)
"Beautiful setting and very peaceful. We enjoyed the friendly horse, too. Next time we are in the area, we will certainly plan on staying here again."
United States
William H.
The price is NZ$342
includes taxes & fees
16 Dec - 17 Dec
Servants' Cottage on 600 Acre Working Horse/Cattle Estate
9.0 out of 10, Wonderful, (10)
"We attended a special dinner at Barboursville and this was a convenient place to stay. "
United States
Brett H.
The price is NZ$314
includes taxes & fees
23 Dec - 24 Dec
Lovers Lane FarmStay on a working family farm. Horses, cows, sheep, bees & more
9.0 out of 10, Wonderful, (128)
"Great Place, well located close to Charlottsville. "
United States
James H.
The price is NZ$361
includes taxes & fees
16 Dec - 17 Dec
Pine Grove Cottage - Visit Monticello, Charlottesville & Many Local Wineries
10.0 out of 10, Exceptional, (11)
"Great location that was peaceful and made us feel right at home! Highly recommend to anyone in the area. Also loved the proximity to walking/running trails. "
United States
Rachel T.
The price is NZ$418
includes taxes & fees
28 Dec - 29 Dec
Charming Historic Carriage House Studio Apartment
9.8 out of 10, Exceptional, (7)
"Nice and quiet like I wanted. Overall great place "
United States
Tyrone S.
The price is NZ$263
includes taxes & fees
28 Dec - 29 Dec
P · Suite Pea at White Lotus Eco Spa Retreat
2.0 star property
10.0 out of 10, Exceptional, (18)
"The house was clean, fully stocked kitchen, comfortable beds, nice big full bathroom, and convenient location!"
United States
Margaret W.
The price is NZ$565
includes taxes & fees
16 Dec - 17 Dec
Rosé All Day: Wine Country Getaway! Walk to Dining
10.0 out of 10, Exceptional, (47)
"A perfect place to stay! Very clean and quiet!"
United States
Joanne
The price is NZ$389
includes taxes & fees
16 Dec - 17 Dec
Private Guest Suite by Wineries/Orchards/Cville
10.0 out of 10, Exceptional, (40)
"It was a lovely place to stay and the hosts were so kind. "
United States
Cooper C.
The price is NZ$322
includes taxes & fees
16 Dec - 17 Dec
Hometract Cottage, Historic Property, UVA/Charlottesville/Ivy

Cabin in Stanardsville

Log Cabin on the River
9.8 out of 10, Exceptional, (43)
"Great place to get away for peace and quiet"
United States
Winslow
The price is NZ$306
includes taxes & fees
16 Dec - 17 Dec
Log Cabin on the River

Cottage in Charlottesville

Charming Eastham Guesthouse
2.0 star property
9.6 out of 10, Exceptional, (4)
"Lovely spot near Charlottesville, great for families or small groups. Guesthouse was clean and has a nice kitchen. "
United States
Nicholas K.
The price is NZ$382
includes taxes & fees
16 Dec - 17 Dec
Charming Eastham Guesthouse
9.8 out of 10, Exceptional, (8)
"Wonderful home, great location. "
United States
Jeanna S.
The price is NZ$556
includes taxes & fees
15 Jan - 16 Jan 2026
Charming 3-Bed Cottage on Main Street in Historic Gordonsville

Apartment in Fry's Spring

Affordable Suites Charlottesville
2.0 star property
8.0 out of 10, Very good, (80)
"Simple, clean comfortable suite. Full kitchen with frig, stove and microwave. Convenient to UVA campus and football stadium. "
United States
Anonymous traveller
Affordable Suites Charlottesville
9.8 out of 10, Exceptional, (84)
"Fifth year at Wolftrap Farm. Booked again for 2025.Thanks!"
United States
J C.
The price is NZ$532
includes taxes & fees
16 Dec - 17 Dec
'Pond House' on Huge Horse Farm; Great for Young Families: Escape the City.
10.0 out of 10, Exceptional, (27)
"Studio 5 was just as described. Everything we needed and immaculately clean. It is convenient to Charlottesville and minutes from Monticello. Our children live nearby so we will surely return. "
United States
Kate B.
The price is NZ$230
includes taxes & fees
29 Dec - 30 Dec
Unit 5 - Cozy Lower Level Studio Suite
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 Keswick Hotel Reviews

Find out more about Keswick

Everything you need to know about Keswick holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Keswick holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Keswick holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Keswick holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Keswick. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Keswick holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Keswick holiday rentals we have selected for you start as low as NZ$271 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Keswick rentals

At Expedia, we put the best Keswick holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Keswick rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Keswick holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Keswick. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Keswick?

Yes, there are holiday rentals close to the most popular sights in Keswick, or you can select a more secluded option if you're looking for a relaxing stay. Keswick is known for its wineries and restaurants.

What are some of the best holiday rentals that Keswick has to offer?

Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious: This holiday home rental outside of Keswick is located in a rural location, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Keswick?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Keswick stay.

What can I see and do in Keswick?

Explore the area and family-friendly sights such as Charlottesville Ice Park, or get out into nature at a spot like Carter Mountain Orchard. Other places in town to visit include Keswick Vineyards and Winery and Castle Hill Cider.

What are holiday rentals like in Keswick?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Keswick. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.