Charlestown Vacation Packages
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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!
Top Charlestown Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hideaway Inn Mt. Snow
Price was CA $1,076, price is now CA $999 per person
CA $999
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Springfield (VSF)
8.8/10 Excellent! (69 reviews)
I loved staying here and can’t wait to do so again. The room was clean, cozy and comfortable. Loved the automated check in with clear directions. The entire place was decked out with awesome ambience and decor. I just wish the hot tub was working. It’s so close to Mount Snow too!
Reviewed on Mar 18, 2026
Latchis Hotel
Price was CA $1,289, price is now CA $1,120 per person
CA $1,120
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Springfield (VSF)
8.6/10 Excellent! (853 reviews)
The hotel is charming. The location is great. The building is funky, given it's age and need for repair. The staff are friendly, helpful, and knowledgeable. The theater located in the same building is a one of a kind attraction. It was a plus for us that the hotel is owned and run by a nonprofit.
Reviewed on Mar 22, 2026
The Shire Woodstock
Price was CA $1,451, price is now CA $1,283 per person
CA $1,283
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Springfield (VSF)
8.8/10 Excellent! (914 reviews)
Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!
Reviewed on Jan 30, 2026
Chalet 239
Price was CA $1,210, price is now CA $1,101 per person
CA $1,101
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Springfield (VSF)
9.4/10 Exceptional! (113 reviews)
Parking was right in front of the building. The place was very clean all over. Breakfast was included, they served pastries, bagels, yogurt, etc. Super easy check in process. The Chalet is only about a 5 minute drive from mount snow! So grateful to the staff who texted me to let me know we had left something behind and the room when they went to clean it!
Reviewed on Mar 19, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was CA $1,210, price is now CA $1,124 per person
CA $1,124
per person
May 22 - May 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Springfield (VSF)
8.6/10 Excellent! (847 reviews)
No inflatable mattress offered anymore.
Reviewed on Mar 18, 2026
Charlestown Hotel Deals
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
The price is CA $192 per night from Apr 7 to Apr 8
CA $192
CA $219 total
Apr 7 - Apr 8
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
There's a cute little town nearby with a great coffee shop.
Reviewed on Mar 26, 2026
Hideaway Inn Mt.Sunapee
1403 New Hampshire Rte 103 Newbury NH
Fully refundableReserve now, pay when you stay
The price is CA $188 per night from Mar 30 to Mar 31
CA $188
CA $204 total
Mar 30 - Mar 31
includes taxes & fees
8.8/10 Excellent! (149 reviews)
Well maintained, nicely decorated and ticked all of our boxes. I highly recommend staying here.
Reviewed on Mar 27, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
485 Hotel Road Brownsville VT
Fully refundable
The price is CA $179 per night from Mar 29 to Mar 30
CA $179
CA $217 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (818 reviews)
It was great to have so many amenities on site. It felt like a home away from home.
Reviewed on Mar 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.
What to do in Charlestown
Colonial Flintlock Musket Experience
CA $177
per adult
100% of travellers recommend
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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.
