Charlestown Vacations from $570
Book a Hotel + Flight or Car together to unlock savings
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.
Lake Bomoseen Lodge
$570
per person
Sep 29 - Oct 2
found 16 hours ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
9.4/10 Exceptional! (972 reviews)
The view was gorgeous and the rental home was perfect for few adults along with few kids. Would visit again! The lodge tap room was a delight each night and the boating rental and free boat access was enjoyed by all. We loved the access to sit in Adirondack chairs along the lake any time of day or night
Reviewed on Aug 29, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
$672
per person
Sep 30 - Oct 4
found 18 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9/10 Wonderful! (865 reviews)
The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus.
Reviewed on Aug 22, 2026
The Mountain Inn at Killington
$708
per person
Sep 30 - Oct 4
found 18 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Rutland (RUT)
9.2/10 Wonderful! (1,020 reviews)
We loved this hotel. We were here in the summer, so we enjoyed the outdoor seating and the outdoor heated pool, plus very close distance to Killington Adventure Center (could have walked but we chose to drive). The game room was great for our teenagers, with a full pool table and board games. The staff was extremely friendly and knowledgable of the area, and gave suggestions for nearby restauarants and hikes. The upstairs has a large indoor lounge area to relax outside your hotel room with friends, which I can see being awesome after a day of skiing.
Reviewed on Aug 29, 2026
Don't see what you're looking for?
See all available trips from Columbus to Charlestown
View all tripsStay near popular Charlestown attractions
Connecticut River State Park
This forested sanctuary offers a moderately challenging 2.5-mile trail with rewarding woodland views. Tackle the initial steep ascent in the morning hours when the trail is quieter and cooler.
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.
The Fort at No.4 Open Air Museum
Step back in time at this reconstructed colonial frontier village, where costumed interpreters bring 1746 to life. Witness authentic demonstrations of 18th-century crafts and daily life.
Charlestown Town Hall
Charlestown Town Hall serves as the administrative heart of this New Hampshire community, hosting municipal offices and public meetings. Visitors can engage with local governance during business hours.
Spaulding Wildlife Management Area
This 3,000-acre nature reserve showcases diverse wetlands, forests, and fields teeming with wildlife. Explore trails for exceptional birdwatching, or find a quiet spot near Spaulding Pond for fishing and photography.
Hubbard Hill State Forest
This peaceful 757-acre forest offers a moderate 3.9-mile trail through diverse terrain and quiet woodlands. Hikers can enjoy the serene natural setting while exploring paths that connect to local routes.
Silsby Free Public Library
This historic Romanesque library has served Charlestown since 1894, housing over 20,000 books and media items. Browse the extensive collection or attend community events like Baby Goat Therapy in this architectural gem.
Swan Commons
Swan Commons offers a tranquil green space in the heart of Charlestown for picnics and leisurely strolls. Bring a blanket and enjoy this peaceful local gathering spot near the Town Hall and Post Office.
Charlestown Hotel Deals
Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$128 nightly
$139 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"Has everything necessary for a two night stay."
Reviewed on Aug 28, 2026
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$149 nightly
$162 total
Aug 31 - Sep 1
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
"Mattress was hard and some door locks for key cards didn't work."
Reviewed on Aug 26, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
485 Hotel Road Brownsville VT
Fully refundable
$154 nightly
$168 total
Aug 31 - Sep 1
Total with taxes and fees
9/10 Wonderful! (868 reviews)
"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."
Reviewed on Aug 22, 2026
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 |
More vacations you might like
Frequently asked questions
How much does a Charlestown vacation package cost?
You'll find cheap prices from $570 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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
- New Hampshire Hotels
- Lebanon Hotels
- Wyndham Hotels in Charlestown
- Claremont Hotels
- Concord Hotels
- Langdon Hotels
- Rv Parks in Claremont
- Cottages in Claremont
- Hanover Hotels
- Cottages in Unity
- Inns in Alstead
- Hotels with a Pool in Claremont
- Cabin Rentals in New Hampshire
- Hotels near North Country Smokehouse
- Hotels near Morningside Flight Park
- Hotels with Free Breakfast in Claremont
- Resorts in Claremont
- South Acworth Hotels
- Apartments in Claremont
- Vacation Homes in Alstead
- Historic Hotels in Claremont
- Motels in Acworth
- Cabin Rentals in Langdon
- Best Western Hotels in Charlestown
- Keene Hotels
- Unity Hotels
- Guest Houses in Alstead
- 5 Star Hotels in Charlestown
- Motels in Claremont
- Charlestown Hotels
- Hotels near Arrowhead Recreation Area
- Acworth Hotels
- Motels in Charlestown
- Newport Hotels
- Farmstay in Langdon
- Best Western Hotels in Claremont
- Alstead Hotels
- Cabin Rentals in Charlestown
- Walpole Hotels
- Family Hotels in Claremont
- Manchester Hotels
- Cabin Rentals in Claremont
- Hotels near The Fort at No.4 Open Air Museum
- Walpole Vacations
- New London Barn Playhouse
- Visit Acworth
- Chesterfield Vacations
- Visit Alstead
- Alumni Field
- Newport Vacations
- John Hay National Wildlife Refuge
- New Hampshire Vacations
- Colby-Sawyer College
- Horatio Colony Museum
- Cornish-Windsor Covered Bridge
- Keene State College
- Blow-Me-Down Bridge
- Visit Charlestown
- Visit Keene
- The Fells
- Franklin Pierce Homestead
- Claremont Vacations
- Pillsbury State Park
- Historic Main Street
- Visit Claremont
- Arrowhead Recreation Area
- Madame Sherri Forest
- Granite Gorge
- Brentwood Golf Course
- Bayberry Barn Christmas Shop
- Spofford Lake
- Thorne-Sagendorph Art Gallery
- Morningside Flight Park
- Visit Walpole
- Cheshire Children's Museum
- Maple Lanes
- Spofford Vacations
- Keene Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.