
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.


The Shire Woodstock
per person
Oct 17 - Oct 22
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (791 reviews)
The Air Conditioning unit was waking me up every time it started up. Room 225. That is my only inconvenience. Everything else was wonderful.
Reviewed on Aug. 1, 2025


Jackson Gore Village
Jackson Gore Base Area
per person
Oct 17 - Oct 22
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (738 reviews)
The property itself was nice. The restaurant was good, a little overpriced for quality but still pretty good. The bed wasnt the most comfortable but also ok. Our room didnt have a mini fridge, which made it hard to buy and store the delicious cheeses you cam purchase at all the neighboring cheese factories and dairy farms. There was enough things to do in the area for a few summer days. The pool was large and clean. They also had a bunch of hot tubs, which was nice.
Reviewed on Aug. 4, 2025

Mountain Lodge at Okemo
Clock Tower Base Area
per person
Oct 17 - Oct 22
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8/10 Very Good! (207 reviews)
Loved the location for this ski in ski out. Nice to look out the balcony and be right in the middle of the action. The sofa bed was uncomfortable with springs popping up all over. The back door didn't lock and the window handle was broken . There was a light bulb that was out and not all the outlets worked. The tv situation was a nightmare with one tv all snowy and the other one whose remote was missing the select button and could not choose a channel. The location was great but would not choose this room again .
Reviewed on Feb. 19, 2025
Rupert Hotel Deals

The Equinox Golf Resort & Spa
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is CA $189 per night from Aug 13 to Aug 14
CA $189
CA $283 total
Aug 13 - Aug 14
includes taxes & fees
7.2/10 Good! (504 reviews)
"Beautiful setting! Comfortable rooms"
Reviewed on Jul. 25, 2025

Kimpton Taconic Hotel by IHG
3835 Main St., Manchester, VT
The price is CA $269 per night from Aug 20 to Aug 21
CA $269
CA $348 total
Aug 20 - Aug 21
includes taxes & fees
9.2/10 Wonderful! (782 reviews)
"Great location, nice front porch. Nice bar. There is no gym, breakfast, snacks, or gift shop, however, a clothing boutique is available. As a pet-friendly hotel, oftentimes I was interrupted by dogs barking and growling at each other - I felt I was at a kennel. Value for the room rate was ..."
Reviewed on Jul. 24, 2025

Hampton Inn and Suites Manchester
4519 Main St, Manchester Center, VT
The price is CA $210 per night from Sep 1 to Sep 2
CA $210
CA $231 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
"We really enjoyed our stay at this property. It's nicely kept.. and EV charging is included in stay. Great breakfast, too."
Reviewed on Aug. 4, 2025
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.