Charlestown Vacations from $432

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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.
Super 8 by Wyndham Ticonderoga

Super 8 by Wyndham Ticonderoga

2.5 out of 5
Price was $506, price is now $432 per person
$432
per person
Oct 11 - Oct 16
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
8/10 Very Good! (1,007 reviews)
Price and location were right for getting around Fort Ticonderoga. Limited Continental breakfast was available, but opted to dine other places.

Reviewed on Aug 29, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $966, price is now $756 per person
$756
per person
Oct 25 - Oct 28
found 17 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Springfield (VSF)
8.8/10 Excellent! (811 reviews)
This is a perfect family oriented spot for visiting downtown Woodstock. We stayed in one of their family suites. It was spacious and comfortable without being ostentatious. Loved the details in the outdoor space--well tended plants and flowers, as well as, fire pits and Adirondack chairs to hang out by the river.

Reviewed on Aug 18, 2025

Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was $1,102, price is now $889 per person
$889
per person
Oct 8 - Oct 10
found 6 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Springfield (VSF)
9.6/10 Exceptional! (62 reviews)
Very authentic and comfortable.

Reviewed on Aug 22, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,204, price is now $1,028 per person
$1,028
per person
Oct 17 - Oct 20
just found
Roundtrip non-stop flight included
Baltimore (BWI) to Rutland (RUT)
8.6/10 Excellent! (1,006 reviews)
The Inn is located in the Green Mountains at Killington so at night you can open the windows and breathe the mountain air.

Reviewed on Aug 26, 2025

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $952, price is now $835 per person
$835
per person
Oct 17 - Oct 20
just found
Roundtrip non-stop flight included
Baltimore (BWI) to Lebanon (LEB)
9.4/10 Exceptional! (257 reviews)
This hotel is pretty new. The beds were comfortable, the room and the hotel was clean. The laundry room was convenient and was not overly expensive.

Reviewed on Aug 23, 2025

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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

Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $136 total per night from Sep 7 to Sep 8
$136 total
Sep 7 - Sep 8
Total with taxes and fees
Keene Elm City Hotel, Ascend Hotel Collection
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road, Keene, NH
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $121 total per night from Sep 2 to Sep 3
$121 total
Sep 2 - Sep 3
Total with taxes and fees
Days Inn by Wyndham Keene NH
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
Fully refundableReserve now, pay when you stay
$134 nightly
The price is $146 total per night from Sep 7 to Sep 8
$146 total
Sep 7 - Sep 8
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
See all 1,447 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.

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Frequently asked questions

How much does a Charlestown vacation package cost?
You'll find cheap prices from $432 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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