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.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was CA $902, price is now CA $865 per person
CA $865
per person
Sep 28 - Sep 29
found 3 hours ago
Roundtrip flight included
Edmonton (YEG) to Springfield (VSF)
8.8/10 Excellent! (499 reviews)
It was a beautiful location...so quiet and peaceful The rooms to sit and enjoy were wonderful

Reviewed on Aug. 9, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $1,066, price is now CA $984 per person
CA $984
per person
Sep 28 - Sep 29
found 3 hours ago
Roundtrip flight included
Edmonton (YEG) to Springfield (VSF)
8.8/10 Excellent! (806 reviews)
This is a perfect family oriented spot for visiting downtown Woodstock. We stayed in one of their family suites. It was spacious and comfortable without being ostentatious. Loved the details in the outdoor space--well tended plants and flowers, as well as, fire pits and Adirondack chairs to hang out by the river.

Reviewed on Aug. 18, 2025

Four Columns Inn

Four Columns Inn

3 out of 5
Price was CA $1,002, price is now CA $943 per person
CA $943
per person
Sep 28 - Sep 29
found 3 hours ago
Roundtrip flight included
Edmonton (YEG) to Rutland (RUT)
8.8/10 Excellent! (3 reviews)
The Engel House

The Engel House

3 out of 5
Price was CA $928, price is now CA $901 per person
CA $901
per person
Sep 28 - Sep 29
found 3 hours ago
Roundtrip flight included
Edmonton (YEG) to Rutland (RUT)
9.4/10 Exceptional! (13 reviews)
A very quaint property. The room was comfortable and clean.

Reviewed on May 27, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was CA $925, price is now CA $900 per person
CA $900
per person
Sep 28 - Sep 29
found 3 hours ago
Roundtrip flight included
Edmonton (YEG) to Rutland (RUT)
8.6/10 Excellent! (1,006 reviews)
Every person here was extremely polite and welcoming.They were a very welcoming group.Room was clean. It is disappointing the breakfast area and the bar are closed in the summer.I understand why the bar is closed, since less people stay in the summer, but they could provide a little more then coffee, even just donuts.

Reviewed on Aug. 22, 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 $188 per night from Sep 1 to Sep 2
CA $188
CA $282 total
Sep 1 - Sep 2
includes taxes & fees
7.2/10 Good! (514 reviews)
"Classic colonial inn. Beautiful property in a nice area with good amenities. Golf course is nice. Scenic and challenging design."

Reviewed on Aug. 20, 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
Fully refundable
The price is CA $248 per night from Sep 1 to Sep 2
CA $248
CA $326 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (792 reviews)
"Restaurant could be better"

Reviewed on Aug. 19, 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
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Sep 1 to Sep 2
CA $212
CA $233 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (1,004 reviews)
"Great hotel"

Reviewed on Aug. 19, 2025

Hampton Inn and Suites Manchester
See all 1,107 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.
All Inclusive Vacations
All Inclusive Vacations
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Frequently asked questions

How much does a Rupert vacation package cost?
You'll find cheap prices from CA $865 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.