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.
Lake Bomoseen Lodge
CA $1,128
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
9.4/10 Exceptional! (985 reviews)
We had a great stay here! This was a long weekend girls' trip. There was easy access to the lake, a clean property, and really good food on-site at the restaurant with live music. The sweet potato hummus is a must-try! The pool was refreshing with plenty of activities to choose from: cornhole, volleyball, and pickleball. There's a little ice cream shop open in the afternoon. You can take a ride on the catamaran or the tiki boat for a small fee. Our stay was reasonably priced. The staff was friendly. Just an easy, no-nonsense, enjoyable getaway. We loved it and are thinking about making this a yearly girls' trip! Thank you so much for a great stay!
Reviewed on Sep 17, 2026
Latchis Hotel
CA $1,238
per person
Nov 30 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
8.6/10 Excellent! (989 reviews)
This place is a gem.
I love and like the proximity to the train station, Brattleboro Food Coop, River Art School and Brattleboro Museum and Art Center,
I visited twice: first with my teen son and husband, and the second by myself, and both times were great.
There are signs of the passing of time in this lovely Art Deco structure, and that adds to its beauty,
Super courteous staff
The first time we watched a movie, so if you stay at the hotel, please treat yourself to that or some of their baskets.
I missed eating at their restaurant, so I guess next time.
My husband loved that there was always coffee for him, and my son loved our mini fridge and microwave.
We love the history of this place and how is part of the larger arts and culture scene of Brattleboro
Reviewed on Sep 28, 2026
Sinclair Inn Bed and Breakfast
CA $1,252
per person
Nov 30 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (124 reviews)
Friendly owners and the property was amazing Beautiful garden, even in the fall Breakfast was delicious
Reviewed on Sep 25, 2026
Ready to book your vacation to Rupert?
Rupert Hotel Deals
Aspen At Manchester
5669 Main Street Manchester Center VT
Fully refundableReserve now, pay when you stay
CA $169
CA $201 total
Oct 25 - Oct 26
includes taxes & fees
8.8/10 Excellent! (696 reviews)
"It was ok for a one night stay with very close proximity to Manchester Center."
Reviewed on Sep 28, 2026
The Manchester View
77 High Meadow Way & VT-7A Manchester Center VT
Fully refundableReserve now, pay when you stay
CA $152
CA $167 total
Oct 26 - Oct 27
includes taxes & fees
9.4/10 Exceptional! (909 reviews)
"We really enjoyed our stay at The Manchester View. Our terrace room was spacious and comfortable, and the view was absolutely to die for—definitely one of the highlights of our stay. Check-in and checkout were both very easy, and the included breakfast was a nice touch and a great way to start the ..."
Reviewed on Sep 28, 2026
The Equinox Golf Resort And Spa
3567 Main Street Manchester VT
Fully refundableReserve now, pay when you stay
CA $195
CA $292 total
Oct 27 - Oct 28
includes taxes & fees
7.4/10 Good! (667 reviews)
"The Inn"
Reviewed on Sep 27, 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.
Stay near popular Rupert attractions
Merck Forest Farmland Center
Enjoy the mountain views and explore Merck Forest Farmland Center, a lovely green space in Rupert. Discover the spas in this quaint area, or seek out its hiking trails.
Haystack Mountain
Commune with nature and explore the great outdoors at Haystack Mountain during your travels in Rupert. Wander the parks or discover the area's countryside.
R. K. Kittay Public Library
After visiting R. K. Kittay Public Library, make a plan to see the other sights and activities in Rupert. Wander the parks or discover the area's countryside.
Frequently asked questions
How much does a Rupert vacation package cost?
You'll find cheap prices from CA $1,128 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?
- 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.
- 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.
- 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.
- 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.
