Rupert Vacations from $503
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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.
The Latest Rupert vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
$503
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Rutland (RUT)
9/10 Wonderful! (865 reviews)
The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus.
Reviewed on Aug 22, 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
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
$257 nightly
$283 total
Sep 7 - Sep 8
Total with taxes and fees
9.4/10 Exceptional! (863 reviews)
"Very nice hotel off main road in and out of Manchester. Great outdoor porches to sit and relax. Free beverage coupons at social hour with free popcorn and pretzels. Staff friendly. Rooms very nice, spacious and beds very comfortable. Room temps were great. Free coffee in lobby area, free easy parking. ..."
Reviewed on Aug 26, 2026
The Equinox Golf Resort & Spa
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
$219 nightly
$241 total
Sep 7 - Sep 8
Total with taxes and fees
7.4/10 Good! (660 reviews)
"The bed sunk into the middle and had no support and the shower didn’t drain so you had to shower in standing water Overall rooms were tired and needed updating Poor lighting in bathroom vanity area."
Reviewed on Aug 23, 2026
The Palmer House Resort, an Ascend Collection Hotel
5383 Main St Manchester Center VT
Fully refundable
$116 nightly
$128 total
Sep 16 - Sep 17
Total with taxes and fees
8.2/10 Very Good! (997 reviews)
"👍"
Reviewed on Aug 25, 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 $503 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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- Ludlow Hotels
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- Mount Equinox
- Stratton Vacations
- Visit Arlington
- Tamarack Ski Lift
- Villager Ski Lift
- Pond Hill Ranch and Pro Rodeo
- Sugar Shack
- Manchester Designer Outlets
- American Express Ski Lift
- Stratton Mountain Resort
- Saint James Cemetery
- Merck Forest Farmland Center
- Bromley Mountain Ski Resort
- Visit Manchester
- Hildene
- Visit Dorset
- Equinox Preservation Trust
- Visit Manchester Center
- Visit Pawlet
- Manchester Vacations
- Shaftsbury Historical Society Museum
- Ursa Express Ski Lift
- Winhall River
- Killington Resort
- Stratton Mountain Summit Gondola
- Taylor Farm
- Visit Rupert
- Green Mountain National Forest
- Mount Snow
- Visit East Dorset
- Battenkill River
- Arlington Green Covered Bridge
- Dana L. Thompson Memorial Park
- Dorset Vacations
- 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.
