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.

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Rupert Hotel Deals

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Dorset
10/10 Exceptional! (165 reviews)
Beautiful creek
"Overall a good stay and accurate listing! The kitchen is the best stocked kitchen I've had at a VRBO stay, with various stainless steel pots and pans, oil and vinegar and basic spices, and cooking utensils. The creek, hot tub, and outdoor furnishings were well designed and maintained. The living ..."

Reviewed on Apr. 18, 2025

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Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
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 $146 per night from May 7 to May 8
CA $146
CA $234 total
includes taxes & fees
May 7 - May 8
7.2/10 Good! (470 reviews)
"We a been coming to the Equinox multiple times a year for over 20 years but had not been here in over a year because the last time I was there it was not a pleasant experience. I am happy to say things are back to being very enjoyable again and we will be back soon!"

Reviewed on Apr. 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
Fully refundable
The price is CA $186 per night from May 7 to May 8
CA $186
CA $253 total
includes taxes & fees
May 7 - May 8
9.2/10 Wonderful! (762 reviews)
"Amazng stay"

Reviewed on Apr. 14, 2025

Kimpton Taconic Hotel by IHG
See all 1,099 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

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Rupert vacation package cost?
You’ll find cheap prices 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.