Charlestown Vacations from $513

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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.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $592, price is now $513 per person
$513
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
9.4/10 Exceptional! (125 reviews)
Good price, really quite, clean, person on site very friendly helpful with places we can go & things to do I recommend the place

Reviewed on Jul 25, 2026

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $902, price is now $703 per person
$703
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
10/10 Exceptional! (207 reviews)
A charming and unexpected stop! Beautiful property, very comfortable, outdoor games to play and sheep to watch. Everyone was really kind and helpful.

Reviewed on Jul 25, 2026

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $681, price is now $549 per person
$549
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
8.6/10 Excellent! (928 reviews)

The Landgrove

The Landgrove

3.5 out of 5
Price was $694, price is now $585 per person
$585
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Rutland (RUT)
10/10 Exceptional! (1 review)
Very cool place to stay to get a true feeling of Vermont. Must stay!

Reviewed on Jul 25, 2026

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $831, price is now $702 per person
$702
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9.2/10 Wonderful! (1,013 reviews)
Location is excellent

Reviewed on Jul 26, 2026

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Stay near popular Charlestown attractions

Morningside Flight Park

Soar above the Connecticut River Valley with tandem hang gliding and paragliding at Morningside Flight Park. Also enjoy zip-lining and outdoor laser tag at this premier New England adventure destination.
See properties

Charlestown Hotel Deals

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $140 total per night from Jul 27 to Jul 28
$140 total
Jul 27 - Jul 28
Total with taxes and fees
Keene Elm City Hotel, an Ascend Collection Hotel
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
$139 nightly
The price is $151 total per night from Jul 27 to Jul 28
$151 total
Jul 27 - Jul 28
Total with taxes and fees
Best Western Plus Keene Hotel
Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
1403 New Hampshire Rte 103 Newbury NH
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $173 total per night from Aug 18 to Aug 19
$173 total
Aug 18 - Aug 19
Total with taxes and fees
8.6/10 Excellent! (226 reviews)
"Nice room. Could have used some water cups in the bathroom and maybe some sort of table or small desk to go with the chairs that were there."

Reviewed on Jul 22, 2026

Hideaway Inn Mt.Sunapee
See all 1,461 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 $513 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.