Charlestown Holidays

Photo by The Curious Zephyr

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Charlestown

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 S$199 per night from 24 Aug to 25 Aug
S$199
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (1,007 reviews)
"Great service and the room was great! No noise at all and quite possibly the best breakfast in a hotel I’ve ever seen!"

Reviewed on 28 Jul, 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 S$175 per night from 10 Aug to 11 Aug
S$175
10 Aug - 11 Aug
includes taxes & fees
8.2/10 Very Good! (863 reviews)
"Dillon, your front desk associate was amazing. Easy to work with and extremely accommodating. A real asset to the hotel."

Reviewed on 26 Jul, 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 S$185 per night from 28 Aug to 29 Aug
S$185
28 Aug - 29 Aug
includes taxes & fees
8.8/10 Excellent! (722 reviews)
"Great place great scenery amazing staff"

Reviewed on 25 Jul, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
See all 1,467 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.

What to do in Charlestown

Colonial Flintlock Musket Experience

Colonial Flintlock Musket Experience

S$165
per adult
100% of travellers recommend
Colonial Flintlock Musket Experience
See all activities in Charlestown

Frequently asked questions

How much does a Charlestown holiday package cost?
You'll find cheap prices 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 holiday to Charlestown costs.
What are the cheapest months to go to Charlestown?
If you'd like to snag a cheap Charlestown holiday package, consider visiting in January, February and March. You'll usually find better prices on airfares and hotels during these months — ideal for budget-conscious travellers.
How many days is enough for Charlestown?
The ideal duration for your Charlestown holiday depends on what you'd like to do. Usually, 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 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," "Traveller 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 holiday as a package?
Expedia holiday 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 customised Charlestown holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday 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. Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Charlestown.
  2. Work out your budget: Ensure you have enough money to pay for everything from meals and transportation to experiences and flights. Your accommodation will probably be the largest expense during your trip to Charlestown.
  3. Decide your trip length: Think about how much time you want to spend exploring Charlestown. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your airfare and accommodation: Once you've nailed down your trip dates and duration, book the perfect Charlestown holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.