
Charlestown Holidays
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Top Flight + Hotel Deals in Charlestown
Price found within the past 48 hours. Click for updated prices.

Greenbrier Inn
€653
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Rutland (RUT)
9.4/10 Exceptional! (686 reviews)
Nice place. Rooms are large, and there is ample space in the common areas. Breakfast was simple but sufficient. My room had a small balcony.
Reviewed on 3 Aug 2026



Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
€757
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.
Reviewed on 26 Jun 2025

Pointe at Castle Hill Resort
€692
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Rutland (RUT)
8.8/10 Excellent! (1,002 reviews)
I’m genuinely at a loss as to how this place has such high reviews. I would not stay here again or recommend it. I’ll give it two positives: it was clean (pretty much the only reason I gave it any stars) and it was cheap (reflective of the quality).
There are two properties, the Castle and the Pointe. I stayed at the Pointe, which is perhaps an entirely different experience. The room was essentially a rebranded 1992 Holiday Inn, complete with a strong smell of stale cigarettes and mildew.
By far, the biggest issue for me was the air conditioning. It was August, the room was stifling, and the AC barely blew warm air. A technician reset the condenser, which temporarily fixed it, but I later learned this is an ongoing issue. Around 1 a.m., I woke up sweating. The overnight employee reset it again and brought me a fan upon request. By 4 a.m., I was sweating again and the thermostat showed the room was 12 degrees warmer than the temp it was set at.
Other issues included: broken handicap door access, broken ice machine, broken refrigerator that spoiled my coffee creamer, a questionable toilet, a horribly sunken mattress, and no microwave. You have to give your food to them to take in the back, which is so unsanitary. I also found most staff rude, and I witnessed other guests commenting on this as well. Some advice, perhaps don't speak negatively about guests within earshot...
I have much more detail but limited characters. Suffice it to say though, I would not stay here again.
Reviewed on 1 Sept 2026
Top hotels in Charlestown

Keene Elm City Hotel, an Ascend Collection Hotel
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
€132
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Room was clean and staff was excellent. Breakfast was good and plentiful."
Reviewed on 30 Aug 2026

Jackson Gore Village, A Vail Resorts Property
111 Jackson Gore Road Ludlow VT
Fully refundableReserve now, pay when you stay
€173
30 Sept - 1 Oct
includes taxes & fees
8.6/10 Excellent! (889 reviews)
"The best place"
Reviewed on 31 Aug 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
485 Hotel Road Brownsville VT
Fully refundable
€145
3 Sept - 4 Sept
includes taxes & fees
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.
Stay 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.
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.
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.
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.
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.
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.
What to do in Charlestown

Colonial Flintlock Musket Experience
€111
per adult
100% of travellers recommend
Frequently asked questions
How much does a Charlestown holiday package cost?
You'll find cheap prices from €653 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?
- 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.
- 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.
- 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.
- Combine your airfare and accommodation: Once you've nailed down your trip dates and duration, book the perfect Charlestown holiday package for you.
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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.
