Keswick Vacations from $1,068

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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.
Mayhurst Inn

Mayhurst Inn

3.5 out of 5
Save 100% on your flight
Price was $1,472, price is now $1,068 per person
$1,068
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Charlottesville (CHO)
9.2/10 Wonderful! (293 reviews)
This was one of the best stays we have ever had. A truly phenomenal place.

Reviewed on Jun 9, 2026

The Estate at Meander

The Estate at Meander

4 out of 5
Price was $1,274, price is now $1,095 per person
$1,095
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Charlottesville (CHO)
9.2/10 Wonderful! (168 reviews)
We had a lovely stay!

Reviewed on Jul 11, 2026

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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.
See properties

What to do in Keswick

Memorable and exciting Vineyard in Virginia

Private Wine Tours Transportation, staring from 3 people & more

$95
per adult
100% of travellers recommend
Private Wine Tours Transportation, staring from 3 people & more
Monticello's West Lawn, which features the "Nickel View" as seen on the back of an American nickel

Monticello World Heritage Site - Private Tour from Williamsburg

$600
per adult
Monticello World Heritage Site - Private Tour from Williamsburg
See all activities in Keswick

Keswick Hotel Deals

Keswick Hall

Keswick Hall

5 out of 5
701 Club Drive Keswick VA
$652 nightly
The price is $745 total per night from Jul 28 to Jul 29
$745 total
Jul 28 - Jul 29
Total with taxes and fees
9.4/10 Exceptional! (70 reviews)
"This was my first time staying at Keswick Hall, and it was to meet with business associates. The staff was a delight to work with, and they made sure all of our needs, as well as our expectations, were met."

Reviewed on Jul 13, 2026

Keswick Hall
Stonemont Farm Cottage with Hot Tub! in Keswick near Vineyards

Stonemont Farm Cottage with Hot Tub! in Keswick near Vineyards

Keswick VA
Get rates
Stonemont Farm Cottage with Hot Tub! in Keswick near Vineyards
Stonemont Farm Cabin with Hot Tub- in Keswick by Vineyards!

Stonemont Farm Cabin with Hot Tub- in Keswick by Vineyards!

Keswick VA
$351 nightly
The price is $399 total per night from Jul 16 to Jul 17
$399 total
Jul 16 - Jul 17
Total with taxes and fees
10/10 Exceptional! (45 reviews)
"The cabin was clean, cozy, and beautifully decorated. We loved the property overall and it was the perfect place to relax and recharge. Great location for visiting local wineries."

Reviewed on Jul 10, 2026

Stonemont Farm Cabin with Hot Tub- in Keswick by Vineyards!
See all 851 properties in Keswick
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 $1,068 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?

  1. Choose your dates: The things you plan to do in Keswick and your preferred season will help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.