Charlestown Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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!
Top Charlestown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Grand Summit Resort, A Vail Resorts Property
Price was CA $1,767, price is now CA $1,484 per person
CA $1,484
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Springfield (VSF)
8.6/10 Excellent! (268 reviews)
Rooms were very clean, great coffee in the room. The resort(the actual area in general )is in “mud month”. Very few restaurants and stores were open. Not the fault of the resort. Refrigerator needed to be requested. The views were spectacular and the lobby was beautiful
Reviewed on May 2, 2026
Stone Hearth Inn and Eatery
Price was CA $2,221, price is now CA $1,812 per person
CA $1,812
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Springfield (VSF)
9.2/10 Wonderful! (118 reviews)
Fantastic breakfast in this quaint inn. Right in the road so very easy to find. Wonderful meal in the attached restaurant. Friendly staff. Easy parking.
Reviewed on Mar 29, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was CA $2,017, price is now CA $1,649 per person
CA $1,649
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Springfield (VSF)
8.6/10 Excellent! (852 reviews)
No inflatable mattress offered anymore.
Reviewed on Mar 18, 2026
Winterplace at Okemo, A Vail Resorts Property
Clock Tower Base Area
Price was CA $2,140, price is now CA $1,776 per person
CA $1,776
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty
Reviewed on Dec 1, 2025
Windham Hill Inn
Price was CA $2,132, price is now CA $1,792 per person
CA $1,792
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Springfield (VSF)
8.4/10 Very Good! (40 reviews)
The Inn is situated near the top of a mountain and surrounded by other hilltops. There are trails that help you to reconnect with nature. Our room was lovely and comfortable. There is a attention to detail in the decor of this establishment which is both delightful and humorous.
Reviewed on Jul 11, 2025
Charlestown Hotel Deals
Best Western Plus Keene Hotel
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $211 per night from May 17 to May 18
CA $211
CA $229 total
May 17 - May 18
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
Clean rooms, the full breakfast was a great addition! Friendly staff, clean pool!!!
Reviewed on May 14, 2026
Days Inn by Wyndham Keene NH
3 Ash Brook Road Keene NH
Fully refundableReserve now, pay when you stay
The price is CA $147 per night from May 27 to May 28
CA $147
CA $159 total
May 27 - May 28
includes taxes & fees
7/10 Good! (1,000 reviews)
The water was hot but the hotle is very very old. Everything needs an upgrade.
Reviewed on May 9, 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
The price is CA $185 per night from May 27 to May 28
CA $185
CA $211 total
May 27 - May 28
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Very clean. Well equipped kitchen. Helpful staff.
Reviewed on May 12, 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.
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.
