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.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
per person
Oct 17 - Oct 22
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
8.6/10 Excellent! (1,000 reviews)
Great little place. Very friendly and clean.

Reviewed on Jul. 31, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
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

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
per person
Oct 17 - Oct 22
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
7.4/10 Good! (1,000 reviews)
Views were spectacular

Reviewed on Jul. 16, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
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

Mountain Lodge at Okemo

3 out of 5
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

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Rupert Hotel Deals

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
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

The Equinox Golf Resort & Spa
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
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

Kimpton Taconic Hotel by IHG
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
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

Hampton Inn and Suites Manchester
See all 1,110 properties in Rupert
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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Frequently asked questions

How much does a Rupert vacation package cost?
You'll find cheap prices from CA $1,239 on Expedia for your Rupert getaway. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Rupert costs.
What are the cheapest months to go to Rupert?
January, February and March are the best times to search for cheap Rupert vacation packages. Travelling in quieter months means you can usually find lower prices on hotels and flights.
How many days is enough for Rupert?
With a well-planned itinerary, you can easily hit the most popular Rupert attractions in a handful of days. But if you want to explore off the beaten track or go on day trips, think about booking your Rupert vacation for longer.
How to find the best Rupert package deals?
Start your search for a Rupert package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Rupert package deal right away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Rupert getaway off to a flying start.
Is it cheaper to book a Rupert vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and stays individually. Better still, you can personalize your Rupert trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Rupert?
Score fantastic discounts by booking your flights early with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Rupert getaway.
How to plan a trip to Rupert?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to go to Rupert.
  2. Set a budget: Consider costs such as food, flights and transportation when working out how much to save for your trip to Rupert. Then, pick a property that suits your budget, whether that's an economical option or a lavish getaway.
  3. Decide how long to go away for: Now that you're more familiar with Rupert, you can work out the right length of your vacation. Put together a rough itinerary and allocate enough time to cover everything you want to do.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a Rupert vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.