Charlestown Vacations from $902

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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.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,121, price is now $902 per person
$902
per person
Jan 11 - Jan 14
found 8 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
10/10 Exceptional! (250 reviews)

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $3,369, price is now $2,632 per person
$2,632
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
No reviews

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Price was $3,788, price is now $3,061 per person
$3,061
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
9/10 Wonderful! (70 reviews)
It is a wonderful place to stay at any time for coming foliage or ski. The location is excellent, quiet and very clean inside. We felt like at home, We will stay again when we visit woodstook area next time.

Reviewed on Oct 15, 2026

Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $3,669, price is now $2,993 per person
$2,993
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
4/10 (2 reviews)
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.

Reviewed on Jan 28, 2026

The Landgrove

The Landgrove

3.5 out of 5
Price was $1,348, price is now $1,125 per person
$1,125
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Grand Rapids (GRR) to Rutland (RUT)
9.4/10 Exceptional! (13 reviews)
The Inn is in a beautiful setting. The staff were very friendly and helpful. My room was spacious and a comfortable arm chair and good lamp provided a cozy place for R&R. The spacious common area & well kept grounds would be a very pleasant place to spend time with family and friends. I was advised in advance that the restaurant was not serving dinner, but the staff provided a list of eateries in the local area. I had a very good meal at the New American Grill. The breakfast menu at the hotel was refreshing and the food was VERY good. I thoroughly enjoyed my stay and would highly recommend the inn especially to those who enjoy the atmosphere of well kept historical structures.

Reviewed on Oct 29, 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

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
111 Jackson Gore Road Ludlow VT
Fully refundableReserve now, pay when you stay
$204 nightly
The price is $224 total per night from Nov 18 to Nov 19
$224 total
Nov 18 - Nov 19
Total with taxes and fees
Jackson Gore Village, A Vail Resorts Property
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
$103 nightly
The price is $112 total per night from Nov 15 to Nov 16
$112 total
Nov 15 - Nov 16
Total with taxes and fees
Days Inn by Wyndham Keene NH
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
$139 nightly
The price is $150 total per night from Nov 12 to Nov 13
$150 total
Nov 12 - Nov 13
Total with taxes and fees
Hideaway Inn Mt.Sunapee
See all 1,506 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 $902 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

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