Keswick Vacations from $783
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Your Keswick Vacation
Lock in a Keswick vacation package that includes everything you need and nothing you don't. Great for dining, culture and bars and pubs, consider staying in the neighborhood of North Downtown. Want to explore your new surroundings? Monticello, Jefferson Vineyards and Keswick Vineyards and Winery are just three of the top-rated places to visit during your trip to Keswick. Stop daydreaming and start adventuring. Browse the many options on Expedia today and finally put your Keswick vacation plans into motion!
The Latest Keswick vacation packages
Price found within the past 48 hours. Click for updated prices.
Little Mod Hotel at the University
Venable
$856
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (360 reviews)
Nice redo of an old structure! Decor is cool. Check in was easy . Very close to restaurants and UVA grounds.
Room noise next door was a problem late at night . Front desk did assist with addressing. You can hear through the walls quite easily!
Also the train is so close-it’s super loud !!
Coffee was promised at 6 am, I went to lobby at 8 am and no one was at the desk and no coffee had been brewed.
Reviewed on Aug 19, 2026
Stay near popular Keswick attractions
Keswick Vineyards and Winery
9.4/10 (16 reviews)
Keswick Vineyards crafts award-winning wines with a minimalist approach that lets the grapes' natural flavors shine. Savor estate-grown varietals on their scenic courtyard overlooking the Southwest Mountains.
Castle Hill Cider
10.0/10 (2 reviews)
This Virginia estate crafts award-winning ciders using traditional qvevri vessels buried in the earth. Sample distinctive flavors in the tasting room while enjoying sweeping views of the 600-acre countryside.
What to do in Keswick
Chains, Coffins, & Curses: Charlottesville Ghost Tours
$26
per adult
Private Wine Tours Transportation, starting from 3 people & more
$95
per adult
100% of travellers recommend
Monticello World Heritage Site - Private Tour from Williamsburg
$600
per adult
Keswick Hotel Deals
Keswick Hall
701 Club Drive Keswick VA
$663 nightly
$758 total
Sep 8 - Sep 9
Total with taxes and fees
9.4/10 Exceptional! (71 reviews)
"The gentleman at the front desk who helped me out, (C Note) you know who you are, was fantastic! All the young men who worked the front bell stand are absolutely fantastic as well! Everybody there was just absolutely fantastic and phenomenal!"
Reviewed on Jul 17, 2026
Stonemont Farm Cabin with Hot Tub- in Keswick by Vineyards!
Keswick VA
$367 nightly
$417 total
Sep 3 - Sep 4
Total with taxes and fees
9.8/10 Exceptional! (48 reviews)
"This property was lovely. My wife and I very much enjoyed the peaceful surroundings and the views. The property was well kept and had an upscale feel to it. We enjoyed the peaceful evenings out on the front porch and the hot tub. My only complaint was that the kitchen was not very well stocked with ..."
Reviewed on Aug 8, 2026
Stonemont Farm Cottage with Hot Tub! in Keswick near Vineyards
Keswick VA
$681 nightly
$774 total
Sep 6 - Sep 7
Total with taxes and fees
9.8/10 Exceptional! (36 reviews)
"Idyllic spot perfect if you need a place to relax and enjoy some R&R. The hot tub was clean, the backyard fairy lights were a great touch. Lots of spots to sit outside and enjoy the views."
Reviewed on Aug 4, 2026
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.
Find the Best Keswick Vacation Packages
Keswick Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Charlottesville-Albemarle Airport (CHO) |
Max Temp Winter | 45ºF |
Max Temp Summer | 90ºF |
Top Sights | Trump Winery, The Jefferson Theater and Barboursville Vineyards |
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Frequently asked questions
How much does a Keswick vacation package cost?
You can snap up a vacation package to this destination from $783 on Expedia. However, how much your vacation to Keswick costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Keswick?
November, December and January are great times to look for cheap Keswick vacation packages. Choosing to travel in quieter months means you'll typically find lower prices on flights and hotels.
How many days is enough for Keswick?
The ideal length for your Keswick vacation depends on what you'd like to see. Generally, a few days to a week will give you enough time to go to all the top sights and explore some hidden treasures along the way.
How to find the best Keswick package deals?
Use Expedia's filter tool to find some of the best Keswick package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Keswick package deals in the off-peak season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Keswick vacation as a package?
You can enjoy significant savings on your next Keswick getaway by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Keswick?
If you're planning a spur-of-the-moment Keswick getaway, browse our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Keswick?
- Choose your dates: The things you plan to do in Keswick and your preferred season will help you decide when to get away.
- Set a budget: Consider costs like flights, food and transportation when working out how much to set aside for your trip to Keswick. Then, pick a hotel that fits your budget, whether that's an economical stay or a high-end getaway.
- Organize your Keswick getaway with Expedia's trip planning tool: Look for and book accommodations and activities all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Keswick together.
- Decide how long to go for: Now that you know more about Keswick, you can work out the perfect length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to see.
- Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Keswick vacation package that brings all your bookings together.
- Book activities and experiences in advance: Whether it's entrance to a major attraction or a walking tour, you won't have to worry about missing out on the highlights of Keswick. Find all the incredible things to do in Keswick with our dedicated travel guide.
Does Expedia offer Book Now, Pay Later Keswick vacation packages?
If you're anything like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Keswick trip across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
Explore a world of travel with Expedia
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- Charlottesville Vacations
- Ragged Branch Distillery
- Barracks Road Shopping Center
- Birdwood Golf Course
- Paramount Theater
- John Paul Jones Arena
- Amf Kegler's Lanes
- Arcady Vineyard
- Civil War Museum At The Exchange Hotel
- Historic Court Square
- Culbreth Theatre
- Rotunda
- Downtown Mall
- Visit Keswick
- Sheridan Snyder Tennis Center
- Visit Charlottesville
- New Lyric Theater
- Keswick Vineyards and Winery
- Lake Monticello Vacations
- Michie Tavern
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- King Family Vineyards
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- Jefferson Vineyards
- Trump Winery
- Pippin Hill Farm & Vineyards
- Reynard Florence Vineyard
- University of Virginia Hospital
- University of Virginia
- Monticello
- Carter Mountain Orchard
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
