Rupert Vacation Packages
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Your Rupert Vacation
Our Rupert vacation packages offer endless opportunities to indulge in new sights, sounds and experiences. And with all of the travel arrangements taken care of, you can chill out and enjoy your city adventure without a care in the world. If seeing the sights is a priority during your trip to Rupert, make sure you check out well-known attractions like Dorset Playhouse and Merck Forest Farmland Center. A few quick clicks is all it takes to create a customized Rupert vacation on Expedia.
Top Rupert Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn
Price was CA $1,085, price is now CA $1,001 per person
CA $1,001
per person
Jun 24 - Jun 28
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.4/10 Exceptional! (118 reviews)
Way overpriced . I’ve stayed in other hotels in the area that included breakfast with hot tubs that are 50% less than this place. The place to put your shoes in the room had mud all over it. Maybe clean it before your next guest.
Reviewed on Mar 2, 2026
Stone Hearth Inn and Eatery
Price was CA $1,567, price is now CA $1,343 per person
CA $1,343
per person
Jun 24 - Jun 28
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) 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
Golden Stage Inn B&B
Price was CA $1,760, price is now CA $1,571 per person
CA $1,571
per person
Jun 24 - Jun 28
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
10/10 Exceptional! (44 reviews)
We stayed for the weekend and went skiing at Okemo. It was a 10 min drive away. The staff was very accommodating, welcoming and friendly. The food provided was delicious. We will definitely be back!
Reviewed on Mar 8, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was CA $1,370, price is now CA $1,256 per person
CA $1,256
per person
Jun 24 - Jun 28
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (852 reviews)
I’ve stayed here with my two daughters multiple times and it’s always incredible.
Reviewed on May 17, 2026
Solitude Village at Okemo by Vail Resorts
Clock Tower Base Area
Price was CA $1,499, price is now CA $1,393 per person
CA $1,393
per person
Jun 24 - Jun 28
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
7.8/10 Good! (35 reviews)
Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know
Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also.
Reviewed on Oct 8, 2025
Rupert Hotel Deals
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Fully refundable
The price is CA $228 per night from Jun 1 to Jun 2
CA $228
CA $304 total
Jun 1 - Jun 2
includes taxes & fees
9.4/10 Exceptional! (841 reviews)
"We always love this property!!"
Reviewed on May 4, 2026
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
The price is CA $181 per night from Jun 3 to Jun 4
CA $181
CA $276 total
Jun 3 - Jun 4
includes taxes & fees
7.4/10 Good! (621 reviews)
"Clean rooms. Lovely atmosphere. Staff was great food in the bar was great. Great location"
Reviewed on May 18, 2026
The Palmer House Resort, an Ascend Collection Hotel
5383 Main St Manchester Center VT
Fully refundable
The price is CA $168 per night from May 28 to May 29
CA $168
CA $208 total
May 28 - May 29
includes taxes & fees
8.4/10 Very Good! (936 reviews)
"Comfy room and bed. Very clean. Pillows were too fat. There were roof shingles on the deck and the deck wood needs some sanding. The buildings where the suites are located needs serious roof work. Grounds are beautiful and well maintained. Staff was awesome!"
Reviewed on May 18, 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.
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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.
