Shaftsbury Vacation Packages
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Your Shaftsbury Vacation
Our vacation packages to Shaftsbury give you the power to customize your own adventure. Tailor your getaway to suit your interests and needs and make the most of your time in this fantastic city. Fill up your itinerary with visits to Sugar Shack, Lake Shaftsbury State Park and Park McCullough House, some of the attractions you shouldn't miss during your trip to Shaftsbury. Check out Expedia's extensive range of travel options and begin planning your ideal vacation to Shaftsbury today.
Top Shaftsbury Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Vacation Village in the Berkshires
Price was CA $1,129, price is now CA $981 per person
CA $981
per person
Jul 14 - Jul 17
found 2 hours ago
Roundtrip non-stop flight included
St. John's (YYT) to Albany (ALB)
8.8/10 Excellent! (2,369 reviews)
So clean and spacious, had everything you need for a nice getaway
Reviewed on May 31, 2026
The Wiltwyck
Price was CA $2,274, price is now CA $1,685 per person
CA $1,685
per person
Aug 13 - Aug 19
found 17 hours ago
Roundtrip flight included
Montreal (YUL) to Albany (ALB)
9.4/10 Exceptional! (192 reviews)
Great location! Staff is friendly and helpful. Perfect if you are looking for an older house that’s been converted into quaint suites.
Reviewed on May 31, 2026
Berkshires Untold
Price was CA $1,323, price is now CA $1,149 per person
CA $1,149
per person
Jul 14 - Jul 17
found 2 hours ago
Roundtrip non-stop flight included
St. John's (YYT) to Albany (ALB)
9/10 Wonderful! (961 reviews)
I loved the funky vibe of this place. It was also very cozy.
Reviewed on Jun 2, 2026
Shaftsbury Hotel Deals
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Shaftsbury VT
10/10 Exceptional! (239 reviews)
"We had an excellent trip to the barn! Extremely clean and great communication from the owner. The location ended up being perfect, secluded property but close to restaurants, coffee shops and hiking."
Reviewed on May 16, 2026
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is CA $225 per night from Jun 8 to Jun 9
CA $225
CA $252 total
Jun 8 - Jun 9
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Check in was simple and quick. Staff was courteous and helpful. The room was clean and spacious. We had a pleasant stay and checkout was simple."
Reviewed on Jun 1, 2026
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Fully refundable
The price is CA $230 per night from Jun 14 to Jun 15
CA $230
CA $311 total
Jun 14 - Jun 15
includes taxes & fees
9.4/10 Exceptional! (848 reviews)
"dirty room and overcapacity. No breakfast"
Reviewed on Jun 2, 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.
Stay near popular Shaftsbury attractions
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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.
