Charlestown Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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!

Ready to book your vacation to Charlestown?

 

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Charlestown Hotel Deals

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St, Keene, NH
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Jul 21 to Jul 22
CA $184
CA $200 total
Jul 21 - Jul 22
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"Great price, clean room, very comfortable King bed. Large TV, A/C worked perfect. Quiet. Nice love seat couch and coffee table made for convenient use plus the desk/chair for laptop use. Plenty of outlets for chargers and plug in devices like a laptop. Close to some very nice restaurants for dinner ..."

Reviewed on Jul. 14, 2025

Best Western Plus Keene Hotel
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
The price is CA $153 per night from Jul 27 to Jul 28
CA $153
CA $166 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very Good! (858 reviews)
"Newly renovated- new inside"

Reviewed on Jul. 18, 2025

Keene Elm City Hotel, Ascend Hotel Collection
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
The price is CA $173 per night from Aug 6 to Aug 7
CA $173
CA $208 total
Aug 6 - Aug 7
includes taxes & fees
8.8/10 Excellent! (719 reviews)
"Peace and tranquility. Excellent staff. Very clean."

Reviewed on Jul. 11, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
See all 1,472 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

What to do in Charlestown

Vermont Wayfinders Sampler Guided Tour

Vermont Wayfinders Sampler Guided Tour

CA $478
per traveller
Vermont Wayfinders Sampler Guided Tour
See all activities in Charlestown

Frequently asked questions

How much does a Charlestown vacation package cost?
You'll find cheap prices on Expedia for your Charlestown escape. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Charlestown costs.
What are the cheapest months to go to Charlestown?
If you'd like to snag a cheap Charlestown vacation package, consider visiting in January, February and March. You'll typically find lower prices on accommodations and flights during these months — ideal for travellers wishing to save money.
How many days is enough for Charlestown?
The ideal length for your Charlestown vacation depends on what you'd like to see. Generally, a few days to a week will give you enough time to check out all the major sights and discover some hidden gems along the way.
How to find the best Charlestown package deals?
Start your search for a Charlestown package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Charlestown package deal right away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Charlestown getaway off to a flying start.
Is it cheaper to book a Charlestown vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking accommodations and flights separately. Better still, you can tailor your Charlestown trip to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Charlestown?
If you've got your Charlestown travel dates finalized, book as soon as you can to grab some unbeatable deals. With Expedia, you can typically reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for setting off on a whim.
How to plan a trip to Charlestown?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Charlestown.
  2. Plan your budget wisely: On top of the price of your accommodations, you'll need to factor in other expenses. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that may arise during your trip to Charlestown.
  3. Determine how many days away: Start by compiling a list of the activities and sights you want to get to in Charlestown. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, book the ideal Charlestown vacation package for you.

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