Rupert Vacations from $1,119
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.
Mountain Green Resort
$1,764
per person
Nov 20 - Nov 27
just found
Roundtrip non-stop flight included
San Juan (SJU) 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
Emrose Luxury Cabins
$1,183
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
8.8/10 Excellent! (124 reviews)
The locks on door require a key inside to lock which could be a fire hazard if a fire started and the lock is a pain to unlock. Bathroom door would not latch closed, cabin had a funny smell.
Reviewed on Sep 27, 2026
The Shire Woodstock
$1,590
per person
Oct 27 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
8.8/10 Excellent! (989 reviews)
We loved everything about this hotel. It was a short walk to get downtown. Rooms were very clean. We loved the different areas for coffee so we didn’t have to walk too far in the morning.
Reviewed on Sep 26, 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.
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.
Rupert Hotel Deals
Aspen At Manchester
5669 Main Street Manchester Center VT
Fully refundableReserve now, pay when you stay
$145 nightly
$160 total
Oct 25 - Oct 26
Total with taxes and fees
8.8/10 Excellent! (694 reviews)
"The grounds and rooms are simple and clean. Location is close shops and restaurants. You are able to access to staff when needed. The only comment I will make is that I wish there was a bench or something like it where the guests have a place their personal item in the bathroom."
Reviewed on Sep 27, 2026
The Manchester View
77 High Meadow Way & VT-7A Manchester Center VT
Fully refundableReserve now, pay when you stay
$122 nightly
$134 total
Oct 26 - Oct 27
Total with taxes and fees
9.4/10 Exceptional! (908 reviews)
"Great value super clean I will be back"
Reviewed on Sep 27, 2026
The Equinox Golf Resort And Spa
3567 Main Street Manchester VT
Fully refundableReserve now, pay when you stay
$214 nightly
$235 total
Oct 25 - Oct 26
Total with taxes and fees
7.4/10 Good! (666 reviews)
"Lovely setting and cozy atmosphere. No coffee maker or mini fridge in room due to electrical system. Pool, hot tub, steam room and sauna were good. Needs to be managed a little better."
Reviewed on Sep 23, 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 $1,119 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.