Rupert Vacations from $873
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest Rupert vacation packages
Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
$873
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
8.6/10 Excellent! (878 reviews)
Pool was nice with dry and steam sonna. Restaraunt and bar was good not a big food selection but food was good quality. Lift base was very near the facility with a lot of trails nearby
Reviewed on Aug 9, 2026
Mountain Green Resort
$3,117
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
4/10 (2 reviews)
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 2026
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
$1,150
per person
Sep 28 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
9/10 Wonderful! (64 reviews)
Beautiful place! In the middle of no where but everything you need is only 10 mins away
Reviewed on Aug 12, 2026
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.
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.
Rupert Hotel Deals
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Fully refundable
$257 nightly
$283 total
Sep 7 - Sep 8
Total with taxes and fees
9.4/10 Exceptional! (860 reviews)
"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."
Reviewed on Aug 3, 2026
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
$198 nightly
$217 total
Aug 24 - Aug 25
Total with taxes and fees
7.4/10 Good! (657 reviews)
"Good place to stay, but not great."
Reviewed on Aug 4, 2026
The Palmer House Resort, an Ascend Collection Hotel
5383 Main St Manchester Center VT
Fully refundable
$116 nightly
$128 total
Sep 2 - Sep 3
Total with taxes and fees
8.2/10 Very Good! (989 reviews)
"Property is very run down. Our room was filthy. Bedding stained, toilet seat stained and floor was extremely dirty. My kids were very much looking forward to the fishing pond advertised as an amenity. Unfortunately the dock was sinking, a rowboat was full of water and beer cans, and the pond was ..."
Reviewed on Aug 9, 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.
Find the Best Rupert Vacation Packages
Rupert Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rutland Southern Vermont Regional Airport (RUT) |
Population | 700 |
Top Sights | Emerald Lake State Park, Dorset Playhouse and Lye Brook Falls |
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Frequently asked questions
How much does a Rupert vacation package cost?
You'll find cheap prices from $873 on Expedia for your Rupert getaway. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Rupert costs.
What are the cheapest months to go to Rupert?
April, May and October are great times to look for cheap Rupert vacation packages. Opting to travel in quieter periods means you can generally find lower prices on flights and hotels.
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 prefer to discover lesser-known spots or go on day tours, 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 select some filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Rupert package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Rupert escape underway.
Is it cheaper to book a Rupert vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Rupert vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Rupert?
If you're considering a spur-of-the-moment Rupert vacation, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Rupert vacation packages?
Your Rupert trip is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to give you that extra flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no hidden costs or late payment fees to worry about.
Explore a world of travel with Expedia
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- Mount Snow
- Visit East Dorset
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- Dana L. Thompson Memorial Park
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- Stratton Golf School
- Emerald Lake State Park
- Norman Rockwell Exhibition
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.