Keswick Vacations from $460

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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.
Boardwalk Hotel on Lake Anna by Kasa

Boardwalk Hotel on Lake Anna by Kasa

4 out of 5
Price was $514, price is now $460 per person
$460
per person
Apr 19 - Apr 24
found 4 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Charlottesville (CHO)
9.2/10 Wonderful! (55 reviews)
Very clean room and facilities. Quiet and relaxing

Reviewed on Feb 6, 2026

Little Mod Hotel at the University

Little Mod Hotel at the University

3 out of 5
Venable
Save 100% on your flight
Price was $715, price is now $481 per person
$481
per person
Apr 19 - Apr 24
found 4 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Charlottesville (CHO)
9.2/10 Wonderful! (281 reviews)
Room was amazing, loved the records and record player. Very cozy!

Reviewed on Feb 15, 2026

Virginia Guesthouse At University Of Virginia

2 out of 5
Lewis Mountain
Save 100% on your flight
Price was $842, price is now $589 per person
$589
per person
Apr 19 - Apr 24
found 4 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Charlottesville (CHO)
No reviews
Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Save 100% on your flight
Price was $802, price is now $566 per person
$566
per person
Apr 19 - Apr 24
found 4 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Charlottesville (CHO)
9.2/10 Wonderful! (517 reviews)
Beautiful artistic room and friendly service

Reviewed on Feb 14, 2026

Sonesta ES Suites Charlottesville University

Sonesta ES Suites Charlottesville University

3 out of 5
Barracks Road
Price was $540, price is now $511 per person
$511
per person
Apr 19 - Apr 24
found 4 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Charlottesville (CHO)
8.8/10 Excellent! (679 reviews)
Great stay! Nothing to complain about. Enjoyed the larger room. Breakfast was good- staff very friendly. Would stay there again.

Reviewed on Feb 12, 2026

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The Annual Vacation Sale

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Discover the most popular places to visit in Keswick

Keswick Vineyards is one of the wineries located at the Monticello Wine Trail. It’s another great winery located in Charlottesville, VA. I am not a big fan of rose, but their latest rose has a great taste. #trovember #foodie #wine

Keswick Vineyards and Winery

4.5/5(15 reviews)

You can enjoy a tasting or tour at Keswick Vineyards and Winery during your travels to Keswick. Discover the entertainment choices and shops in this walkable area.

Keswick Vineyards and Winery

Castle Hill Cider

5/5(1 review)

You can enjoy a tasting or tour at Castle Hill Cider during your travels to Keswick. Discover the entertainment choices and shops in this walkable area.

Castle Hill Cider

What to do in Keswick

Memorable and exciting Vineyard in Virginia

Private Wine Tours (Minimum 3 & Maximum 6 ) Pickup Maximum 30 Mi

$118
per adult
100% of travellers recommend
Private Wine Tours (Minimum 3 & Maximum 6 ) Pickup Maximum 30 Mi
Monticello's West Lawn, which features the "Nickel View" as seen on the back of an American nickel

Private tour from Williamsburg to Monticello World Heritage Site

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

Keswick Hotel Deals

Keswick Hall

Keswick Hall

5 out of 5
701 Club Drive Keswick VA
$742 nightly
The price is $848 total per night from Mar 11 to Mar 12
$848 total
Mar 11 - Mar 12
Total with taxes and fees
Keswick Hall
Wine Country! Unique 2-bedroom horse farm, close by 5 star dining, 5 wineries

Wine Country! Unique 2-bedroom horse farm, close by 5 star dining, 5 wineries

2 out of 5
Keswick VA
$479 nightly
The price is $548 total per night from Mar 1 to Mar 2
$548 total
Mar 1 - Mar 2
Total with taxes and fees
10/10 Exceptional! (14 reviews)
Great house, lovely horses

Reviewed on Feb 19, 2026

Wine Country! Unique 2-bedroom horse farm, close by 5 star dining, 5 wineries
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive Charlottesville VA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $121 total per night from Feb 28 to Mar 1
$121 total
Feb 28 - Mar 1
Total with taxes and fees
9.2/10 Wonderful! (2,734 reviews)
Everything was great!

Reviewed on Feb 26, 2026

English Inn of Charlottesville
See all 813 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 $460 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.