Charlestown Vacation Packages

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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!

Top Charlestown Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was CA $902, price is now CA $865 per person
CA $865
per person
Sep 28 - Sep 29
found 1 hour ago
Roundtrip flight included
Edmonton (YEG) to Springfield (VSF)
8.8/10 Excellent! (499 reviews)
It was a beautiful location...so quiet and peaceful The rooms to sit and enjoy were wonderful

Reviewed on Aug. 9, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $1,066, price is now CA $984 per person
CA $984
per person
Sep 28 - Sep 29
found 1 hour ago
Roundtrip flight included
Edmonton (YEG) to Springfield (VSF)
8.8/10 Excellent! (806 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

Four Columns Inn

Four Columns Inn

3 out of 5
Price was CA $1,002, price is now CA $943 per person
CA $943
per person
Sep 28 - Sep 29
found 1 hour ago
Roundtrip flight included
Edmonton (YEG) to Rutland (RUT)
8.8/10 Excellent! (3 reviews)
The Engel House

The Engel House

3 out of 5
Price was CA $928, price is now CA $901 per person
CA $901
per person
Sep 28 - Sep 29
found 1 hour ago
Roundtrip flight included
Edmonton (YEG) to Rutland (RUT)
9.4/10 Exceptional! (13 reviews)
A very quaint property. The room was comfortable and clean.

Reviewed on May 27, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was CA $925, price is now CA $900 per person
CA $900
per person
Sep 28 - Sep 29
found 1 hour ago
Roundtrip flight included
Edmonton (YEG) to Rutland (RUT)
8.6/10 Excellent! (1,006 reviews)
Every person here was extremely polite and welcoming.They were a very welcoming group.Room was clean. It is disappointing the breakfast area and the bar are closed in the summer.I understand why the bar is closed, since less people stay in the summer, but they could provide a little more then coffee, even just donuts.

Reviewed on Aug. 22, 2025

Ready to book your vacation to Charlestown?

 

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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
The price is CA $174 per night from Aug 31 to Sep 1
CA $174
CA $189 total
Aug 31 - Sep 1
includes taxes & fees
8.4/10 Very Good! (881 reviews)
"Had a great time at this location"

Reviewed on Aug. 19, 2025

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
The price is CA $155 per night from Sep 1 to Sep 2
CA $155
CA $168 total
Sep 1 - Sep 2
includes taxes & fees
7/10 Good! (1,002 reviews)
"Would stay again"

Reviewed on Aug. 16, 2025

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
The price is CA $157 per night from Sep 1 to Sep 2
CA $157
CA $190 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (731 reviews)
Great option
"Traving for business this was a nice departure from business hotels. Staff was great and room was a 1 bedroom apartment with full kitchen."

Reviewed on Aug. 17, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
See all 1,451 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
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What to do in Charlestown

Vermont Wayfinders Sampler Guided Tour

Vermont Wayfinders Sampler Guided Tour

CA $617
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 from CA $865 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.