Keswick Vacations from $776

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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
Price was $909, price is now $776 per person
$776
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
9.2/10 Wonderful! (331 reviews)
Free street parking was very convenient.

Reviewed on May 9, 2026

Dinsmore Boutique Inn

Dinsmore Boutique Inn

4 out of 5
Venable
Price was $1,193, price is now $1,020 per person
$1,020
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
9.6/10 Exceptional! (374 reviews)
I am not typically a bed and breakfast person, but the reviews and location tempted me into booking. I am so glad I did. From checking in with the host, to the quaint and well kept room, to the fabulous location and of course the incredible breakfast - everything was wonderful. Do not hesitate to book here, you absolutely will love it.

Reviewed on May 10, 2026

Oakhurst Inn at the University

Oakhurst Inn at the University

4 out of 5
Jefferson Park Avenue
Price was $1,011, price is now $872 per person
$872
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
9.2/10 Wonderful! (559 reviews)
Clean room. Comfortable beds.

Reviewed on May 8, 2026

Virginia Guesthouse Hotel

Virginia Guesthouse Hotel

2 out of 5
Lewis Mountain
Price was $1,060, price is now $922 per person
$922
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
9/10 Wonderful! (12 reviews)
This hotel is fantastic! Gorgeous design, super friendly staff, perfect location, and great connection to the uva community. The rooms were well appointed with super soft robes and towels. The staff went above and beyond to greet us. We also ate at the main restaurant Poplar and the food, decor and service was perfect! I’m excited to continue to visit this fantastic addition to the uva community!

Reviewed on May 6, 2026

Kimpton The Forum Hotel by IHG

Kimpton The Forum Hotel by IHG

4 out of 5
UVA
Price was $1,251, price is now $1,097 per person
$1,097
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Charlottesville (CHO)
9.6/10 Exceptional! (462 reviews)
The room and hotel was great... I thought the $8 bottled water in the room was a bit excessive, I would recommend bringing your own water into the hotel.

Reviewed on Apr 22, 2026

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Discover the most popular places to visit in Keswick

Keswick Vineyards and Winery

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 acclaimed theater scene 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

Chains, Coffins, & Curses: Charlottesville Ghost Tours

Chains, Coffins, & Curses: Charlottesville Ghost Tours

$26
per adult
Chains, Coffins, & Curses: Charlottesville Ghost Tours
Private Wine Tours

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
See all activities in Keswick

Keswick Hotel Deals

Keswick Hall

Keswick Hall

5 out of 5
701 Club Drive Keswick VA
$843 nightly
The price is $964 total per night from May 26 to May 27
$964 total
May 26 - May 27
Total with taxes and fees
9.4/10 Exceptional! (68 reviews)
The hotel and grounds are beautiful! We were only there for 1 night so not able to take advantage of all the amenities. The Front Desk clerk was new and did not provide all information about the property. The instructions on how to get to our room were incorrect. We decided to have a drink in the ...

Reviewed on Apr 16, 2026

Keswick Hall
English Inn of Charlottesville

English Inn of Charlottesville

3 out of 5
2000 Morton Drive Charlottesville VA
$105 nightly
The price is $120 total per night from May 27 to May 28
$120 total
May 27 - May 28
Total with taxes and fees
9.2/10 Wonderful! (2,823 reviews)
This was my first time staying at this hotel and will definitely be my last! The staff were cold and unpleasant! It was like pulling teeth getting them to provide information about my stay. The room was right next to the elevator and the large window was broken and didn’t align very well which made ...

Reviewed on May 13, 2026

English Inn of Charlottesville
Omni Charlottesville Hotel

Omni Charlottesville Hotel

4 out of 5
212 Ridge McIntire Rd Charlottesville VA
$163 nightly
The price is $187 total per night from Jun 1 to Jun 2
$187 total
Jun 1 - Jun 2
Total with taxes and fees
9.4/10 Exceptional! (1,032 reviews)
Would stay again.

Reviewed on May 13, 2026

Omni Charlottesville Hotel
See all 788 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 $776 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.