Rupert Vacations from $437
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
The Alpine Lodge
$437
per person
Oct 8 - Oct 11
found 5 hours ago
Roundtrip flight included
Miami (MIA) to Glens Falls (GFL)
9/10 Wonderful! (695 reviews)
Always a great stay. The location is convenient, the rooms are quite nice and unique, and the staff is wonderful. We always stay here when we're passing through. Highly recommend.
Reviewed on Sep 4, 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
The Equinox Golf Resort And Spa
3567 Main Street Manchester VT
Fully refundableReserve now, pay when you stay
$236 nightly
$260 total
Sep 9 - Sep 10
Total with taxes and fees
Hampton Inn and Suites Manchester
4519 Main St Manchester Center VT
$155 nightly
$170 total
Sep 21 - Sep 22
Total with taxes and fees
9.6/10 Exceptional! (1,003 reviews)
"Na"
Reviewed on Sep 7, 2026
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
$287 nightly
$316 total
Sep 9 - Sep 10
Total with taxes and fees
9.4/10 Exceptional! (868 reviews)
"Nice town!"
Reviewed on Sep 7, 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 |
More vacations you might like
Frequently asked questions
How much does a Rupert vacation package cost?
You'll find cheap prices from $437 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
- Pawlet Hotels
- Cottages in Dorset
- Hotels near Okemo Mountain Resort
- Woodstock Hotels
- Guest Houses in Dorset
- B&B in West Rupert
- Vacation Homes in Dorset
- Condo Rentals in Pawlet
- Rv Parks in West Pawlet
- 4 Star Hotels in Dorset
- B&B in West Pawlet
- Manchester Hotels
- Hotels near Southern Vermont Arts Center
- Hotels near Bromley Mountain Ski Resort
- Manchester Center Hotels
- Dorset Hotels
- Relais & Chateaux Hotels in Dorset
- Hotels near Merck Forest Farmland Center
- 5 Star Hotels in Manchester
- 5 Star Hotels in Pawlet
- Motels in Rupert
- B&B in Pawlet
- Inns in Dorset
- Cabin Rentals in Rupert
- Rupert Hotels
- Cabin Rentals in Manchester
- B&B in Manchester
- West Pawlet Hotels
- Pet-Friendly Hotels in Dorset
- East Dorset Hotels
- B&B in Dorset
- Hotels with an Indoor Pool in Manchester
- Hotels near Mount Snow
- Rutland Hotels
- Cheap Hotels in Manchester
- Pet-Friendly Hotels in Manchester
- Motels in Dorset
- Bennington Hotels
- Killington Hotels
- Intrawest Corporation Hotels in Sandgate
- Resorts & Hotels with Spas in Manchester
- Lodges in Sandgate
- Stratton Hotels
- Vacation Homes in Pawlet
- Hotels near Golf Club at Equinox
- Hotels near Green Mountain National Forest
- Hotels with an Outdoor Pool in Manchester
- Ludlow Hotels
- Apartments in West Pawlet
- 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.
