Charlestown Vacations from $1,010

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Your Charlestown Vacation

When a city break is calling your name, answer it with a vacation package to Charlestown. With all your travel arrangements taken care of before you go, all you need to do here is concentrate on enjoying yourself. When it's time to head out and explore, be sure to put Vermont Country Store and The Fort at No.4 Open Air Museum on the itinerary for your trip to Charlestown. Stop dreaming and start doing. Check out the broad range of options on Expedia today and put your Charlestown vacation plans into action!

The Latest Charlestown vacation packages

Price found within the past 48 hours. Click for updated prices.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,127, price is now $1,010 per person
$1,010
per person
Feb 9 - Feb 12
found 6 hours ago
Roundtrip flight included
Columbia (CAE) to Rutland (RUT)
7.4/10 Good! (1,003 reviews)
Amenities are great!

Reviewed on Dec 29, 2025

Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,718, price is now $1,318 per person
$1,318
per person
Feb 9 - Feb 12
found 6 hours ago
Roundtrip flight included
Columbia (CAE) to Rutland (RUT)
No reviews
Clean room, elevator broken and not enough bathroom towels.

Reviewed on Dec 28, 2025

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,532, price is now $1,250 per person
$1,250
per person
Feb 9 - Feb 12
found 6 hours ago
Roundtrip flight included
Columbia (CAE) to Rutland (RUT)
No reviews
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,224, price is now $1,080 per person
$1,080
per person
Feb 9 - Feb 12
found 6 hours ago
Roundtrip flight included
Columbia (CAE) to Rutland (RUT)
9.2/10 Wonderful! (941 reviews)
JP and the staff at the Inn were great. Breakfast was really nice to have as so many places no longer even offer breakfast. Great stay

Reviewed on Jan 1, 2026

Mt Green 1-d09 in Killington

Mt Green 1-d09 in Killington

2 out of 5
Price was $1,904, price is now $1,689 per person
$1,689
per person
Feb 9 - Feb 12
found 6 hours ago
Roundtrip flight included
Columbia (CAE) to Rutland (RUT)
No reviews
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Discover the most popular places to visit in Charlestown

Hang gliding with Morningside Flight Park! AMAZING! For $175, you will be strapped into a tandem hang-glider and towed up for a 10-minute flight over the Connecticut River Valley. Your instructor will do all the work if you'd rather, OR they will let you try controlling the aircraft while you're drifting through the air!

Morningside Flight Park

Walk around the campus at Morningside Flight Park during your stay in Charlestown. Discover the area's mountain views and seek out the ski slopes.

Morningside Flight Park

The Fort at No.4 Open Air Museum

You can spend an afternoon exploring the galleries in The Fort at No.4 Open Air Museum during your trip to Charlestown. Wander the riverfront or discover the area's stargazing spots.

The Fort at No.4 Open Air Museum

Charlestown Hotel Deals

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$138 nightly
The price is $150 total per night from Feb 3 to Feb 4
$150 total
Feb 3 - Feb 4
Total with taxes and fees
8.8/10 Excellent! (942 reviews)
Nice hotel! Very friendly staff and great value compared to other accommodations.

Reviewed on Jan 4, 2026

Pointe at Castle Hill Resort
Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
1403 New Hampshire Rte 103 Newbury NH
$136 nightly
The price is $148 total per night from Jan 11 to Jan 12
$148 total
Jan 11 - Jan 12
Total with taxes and fees
8.6/10 Excellent! (71 reviews)
The property and location were great! Having a restaurant in walking distance in a remote location was wonderful. We brought an issue to customer service and they handled swiftly. We will be back again!

Reviewed on Jan 6, 2026

Hideaway Inn Mt.Sunapee
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
485 Hotel Road Brownsville VT
$159 nightly
The price is $173 total per night from Jan 8 to Jan 9
$173 total
Jan 8 - Jan 9
Total with taxes and fees
8.8/10 Excellent! (781 reviews)
Amenities great

Reviewed on Jan 4, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
See all 1,483 properties in Charlestown
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 Charlestown Vacation Packages

Charlestown Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
1,150
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Arrowhead Recreation Area, Maple Lanes and Claremont Opera House

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Frequently asked questions

How much does a Charlestown vacation package cost?
You'll find cheap prices from $1,010 on Expedia for your Charlestown break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Charlestown costs.
What are the cheapest months to go to Charlestown?
If you're looking to score a cheap Charlestown vacation package, consider traveling in February, March and November. You're likely to find lower prices on hotels and flights during these months — perfect for travelers wishing to save money.
How many days is enough for Charlestown?
With a well-organized travel plan, you can easily hit the most popular Charlestown sights in a few days. But if you want to venture off the beaten track or go on day trips, consider booking your Charlestown vacation for longer.
How to find the best Charlestown package deals?
Landing a cheap Charlestown package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add a few filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Charlestown package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Charlestown vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still have the freedom to create a customized Charlestown vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Charlestown?
If you're planning a spontaneous Charlestown trip, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Charlestown?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the activities available will also help you decide when to visit Charlestown.
  2. Budget wisely: Besides the cost of your hotel, you'll need to factor in other expenses too. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that may crop up during your trip to Charlestown.
  3. Use our trip planning tool to discover Charlestown: Research every part of your trip to Charlestown with this handy planner. Invite your family and friends to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Decide your trip length: Consider how long you'd like to spend exploring Charlestown. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Charlestown vacation package.
  6. Add on experiences and excursions: Have a look at our travel guide to find some incredible things to do in Charlestown. Book tickets or make reservations as soon as you can to save time and avoid the hassle of looking for activities when you arrive.

Does Expedia offer Book Now, Pay Later Charlestown vacation packages?
If you're anything like us, you love traveling but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Charlestown vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great 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.