Keswick Vacations from $495

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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

Little Mod Hotel at the University

3 out of 5
Venable
Save 100% on your flight
Price was $783, price is now $495 per person
$495
per person
Oct 2 - Oct 5
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (350 reviews)
Very cute small hotel that is reasonably priced! The rooms were bigger than we expected, and it was great having access to the pool at their sister location on the UVA campus. Would stay here again if I were in Charlottesville.

Reviewed on Jul 6, 2026

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Save 100% on your flight
Price was $874, price is now $516 per person
$516
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (579 reviews)
Excellent staff, friendly and very helpful.

Reviewed on Jul 8, 2026

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Save 100% on your flight
Price was $796, price is now $561 per person
$561
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Charlottesville (CHO)
9.6/10 Exceptional! (404 reviews)
Wow, the architecture, history, the amenities (especially the guest lounge), and breakfast were all outstanding! We will be back.

Reviewed on Jun 26, 2026

English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
The Meadows
Save 100% on your flight
Price was $852, price is now $619 per person
$619
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
9.2/10 Wonderful! (2,918 reviews)
Breakfast was well attended. Front desk staff were pleasant. Room was large (superior king). Bathroom door needs to be fixed so it closes properly. Nice afternoon tea offered in the afternoon with cookies.

Reviewed on Jul 9, 2026

Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

3 out of 5
Lewis Mountain
Save 100% on your flight
Price was $1,149, price is now $885 per person
$885
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Charlottesville (CHO)
9.6/10 Exceptional! (44 reviews)
Exceptional hotel and wonderful stay!

Reviewed on Jul 8, 2026

Don't see what you're looking for?
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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

Chains, Coffins, & Curses: Charlottesville Ghost Tours

Chains, Coffins, & Curses: Charlottesville Ghost Tours

$32
per adult
Chains, Coffins, & Curses: Charlottesville Ghost Tours
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
$936 nightly
The price is $1,070 total per night from Jul 12 to Jul 13
$1,070 total
Jul 12 - Jul 13
Total with taxes and fees
9.4/10 Exceptional! (69 reviews)
"Awesome stay great golf course marigolds a touch over rated"

Reviewed on May 17, 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
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $103 total per night from Jul 23 to Jul 24
$103 total
Jul 23 - Jul 24
Total with taxes and fees
9.2/10 Wonderful! (2,931 reviews)
"Breakfast was well attended. Front desk staff were pleasant. Room was large (superior king). Bathroom door needs to be fixed so it closes properly. Nice afternoon tea offered in the afternoon with cookies."

Reviewed on Jul 9, 2026

English Inn of Charlottesville
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 $495 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.