Rupert Holidays
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Top Flight + Hotel Deals in Rupert
Price found within the past 48 hours. Click for updated prices.
Greenbrier Inn
€659
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Rutland (RUT)
9.4/10 Exceptional! (686 reviews)
Nice place. Rooms are large, and there is ample space in the common areas. Breakfast was simple but sufficient. My room had a small balcony.
Reviewed on 3 Aug 2026
The Mountain Inn at Killington
€658
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Rutland (RUT)
9.2/10 Wonderful! (1,020 reviews)
We loved this hotel. We were here in the summer, so we enjoyed the outdoor seating and the outdoor heated pool, plus very close distance to Killington Adventure Center (could have walked but we chose to drive). The game room was great for our teenagers, with a full pool table and board games. The staff was extremely friendly and knowledgable of the area, and gave suggestions for nearby restauarants and hikes. The upstairs has a large indoor lounge area to relax outside your hotel room with friends, which I can see being awesome after a day of skiing.
Reviewed on 29 Aug 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
€762
per person
10 Oct - 12 Oct
found 1 day ago
Return direct flight included
New York (NYC) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.
Reviewed on 26 Jun 2025
Top hotels in Rupert
The Equinox Golf Resort And Spa
3567 Main Street Manchester VT
Fully refundableReserve now, pay when you stay
€216
7 Sept - 8 Sept
includes taxes & fees
7.4/10 Good! (661 reviews)
"First time stay here since we used to own a house in the area. Found the Inn comfortable and the amenities are amazing."
Reviewed on 29 Aug 2026
Hampton Inn and Suites Manchester
4519 Main St Manchester Center VT
Fully refundableReserve now, pay when you stay
€147
8 Sept - 9 Sept
includes taxes & fees
9.6/10 Exceptional! (1,005 reviews)
"Very good breakfast, clean and spacious room, friendly staff."
Reviewed on 27 Aug 2026
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Fully refundable
€244
9 Sept - 10 Sept
includes taxes & fees
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 holiday package cost?
You'll find cheap prices from €608 on Expedia for your Rupert getaway. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Rupert costs.
What are the cheapest months to go to Rupert?
If you're hoping to snag a cheap Rupert holiday package, consider visiting in January, February and March. You'll typically find lower rates on flights and hotels during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Rupert?
With a well-organised itinerary, you can easily hit the most popular Rupert attractions in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Rupert holiday 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 holiday as a package?
Expedia holiday 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 customised Rupert holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Rupert?
If you're considering a spur-of-the-moment Rupert holiday, 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.
How to plan a trip to Rupert?
- Pick your travel dates: What you'd like to do in Rupert and your favourite season can help you decide when to get away.
- Set your budget: Consider expenses like flights, food and transportation when calculating how much to set aside for your trip to Rupert. Then, select a property that fits your budget, whether that's a wallet-friendly stay or a lavish retreat.
- Work out your trip length: Consider how much time you want to spend discovering Rupert. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customised Rupert holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
