A grassy field with a wooden fence, surrounded by autumn-colored trees and a hill in the background.

Charlestown Vacations from $793

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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.
  • Jan 15 - Jan 18

    Days Inn by Wyndham Rutland/Killington Area + Flight

    Rutland
    3 nights
    2.5 star property
    7.0/10 - Good (1,004 reviews)
    "Spacious updated rooms. LOVE the vinyl vs. carpeted floors in the rooms, much cleaner. Breakfast needs more healthy options... low fat or fat free yogurts/milk, lower sugar options, eggs. Overall, a great overnight stay."
    Reviewed November 7, 2026
    Roundtrip • West Palm Beach (DJT) - Rutland (RUT)
    DJT - RUT • 2 stops RUT - DJT • 1 stop
    $927
    $793
    per traveler
    found 3 hours ago
    Days Inn by Wyndham Rutland/Killington Area
  • Jan 15 - Jan 18

    The Suites at Killington Center + Flight

    Killington
    3 nights
    3.5 star property
    Roundtrip • West Palm Beach (DJT) - Rutland (RUT)
    DJT - RUT • 2 stops RUT - DJT • 1 stop
    $2,662
    $1,861
    per traveler
    found 3 hours ago
    The Suites at Killington Center
  • Jan 15 - Jan 18

    Mountain Green Resort + Flight

    Killington
    3 nights
    4.0 star property
    4.0/10 - (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 January 28, 2026
    Roundtrip • West Palm Beach (DJT) - Rutland (RUT)
    DJT - RUT • 2 stops RUT - DJT • 1 stop
    $2,568
    $1,941
    per traveler
    found 3 hours ago
    Mountain Green Resort
  • Dec 30 - Jan 3

    The Shire Woodstock + Flight

    Woodstock
    4 nights
    3.0 star property
    8.8/10 - Excellent (1,002 reviews)
    Roundtrip • Washington (DCA) - Springfield (VSF)
    DCA - RUT • 1 stop RUT - DCA • 1 stop
    $1,498
    $1,249
    per traveler
    found 1 day ago
    The Shire Woodstock
  • Dec 30 - Jan 5

    Latchis Hotel + Flight

    Brattleboro
    6 nights
    2.5 star property
    8.6/10 - Excellent (1,001 reviews)
    Roundtrip • San Juan (SJU) - Springfield (VSF)
    SJU - ALB • 1 stop ALB - SJU • 2 stops
    $1,000
    $848
    per traveler
    found 1 day ago
    Latchis Hotel

Where to stay near Charlestown

Charlestown, New Hampshire, offers a perfect weekend getaway with its charming downtown area and scenic outdoor adventures. Explore the historic vibes of the city center and enjoy the natural beauty along Hill Rd. Whether you seek relaxation or adventure, Charlestown has something for every traveler.

Springfield

Discover Springfield, a welcoming destination perfectly suited for travelers seeking outdoor adventures and cultural experiences. With attractions like the historic Baltimore Covered Bridge and the enriching Springfield Art and Historical Society Museum, there’s plenty to explore. Outdoor enthusiasts will appreciate the nearby mountains and national state park, ideal for year-round activities. Located about 5 miles by car from Charlestown, Springfield is a smart choice for your vacation, offering a blend of history and adventure just a short drive away.

Rockingham

Experience the charm of Rockingham, a fantastic hub for travelers seeking a weekend getaway with family or an outdoor adventure. This village offers easy access to attractions like the Bellows Falls Fish Ladder, Connecticut River State Park, and the Bellows Falls Historical Society Museum, ensuring a delightful mix of nature and history. Located about 5 miles from Charlestown, Rockingham makes for a smart booking choice for a refreshing escape into Vermont's natural beauty.

Langdon

If you are a family or outdoor enthusiast, look no further than Langdon, New Hampshire, a charming village known for its inviting ski fields and beautiful mountain views. This destination offers a delightful blend of adventure and relaxation, with attractions like the Shedd-Porter Memorial Library and the Alstead Historical Society to explore. Located about 5 miles from Charlestown, Langdon presents an ideal base for your vacation, making it a smart choice for those seeking budget-friendly accommodations amid nature's beauty.

Chester

Ideally situated for outdoor enthusiasts and families, Chester offers a captivating blend of adventure and relaxation. With access to stunning lakes and mountains, visitors can enjoy skiing at nearby resorts or explore the natural beauty of the national state park. Attractions like Bonnie's Bundles Dolls, the Vermont Museum of Mining and Minerals, and the Grafton Historical Society enrich your stay. Located about 13 miles by car from Charlestown, Chester is a smart choice for your next getaway.

Bellows Falls

Travelers seeking a blend of family-friendly adventures and nature will find Bellows Falls to be the ideal base for their vacation, featuring engaging activities like skiing and exploring nearby parks. With attractions such as the Bellows Falls Fish Ladder and Hetty Green Park, visitors can immerse themselves in the area's rich natural beauty. Located about 7 miles from Charlestown, Bellows Falls offers easy access to outdoor experiences and cozy accommodations, making it a smart choice for a memorable getaway.

Discover the most popular places to visit in Charlestown

Charlestown Hotel Deals

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.

Frequently Asked Questions

How much does a Charlestown vacation package cost?

You'll find cheap prices from $793 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.

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