Rupert Vacations from $618

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.
The Vermont Inn

The Vermont Inn

3 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
9.2/10 Wonderful! (403 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul 23, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (772 reviews)
The Air Conditioning unit was waking me up every time it started up. Room 225. That is my only inconvenience. Everything else was wonderful.

Reviewed on Aug 1, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rutland (RUT)
7.2/10 Good! (1,001 reviews)
Views were spectacular

Reviewed on Jul 16, 2025

Inn At Mount Snow

Inn At Mount Snow

2 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Springfield (VSF)
10/10 Exceptional! (7 reviews)
The property was conveniently located near Mt. Sniw.

Reviewed on Jul 26, 2025

The Vesper

The Vesper

3 out of 5
per person
Oct 16 - Oct 19
found 1 hour ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
9.2/10 Wonderful! (24 reviews)
Charming quaint place with artistic decor. Care was taken with the breakfast - delicious, homemade and wonderful presentation. It felt very homey. Prompt response to my texts; excellent communication. Welcoming and friendly. I would definitely stay here again and recommend the Vesper highly.

Reviewed on Jul 17, 2025

Don't see what you're looking for?
See all available trips from Columbus to Rupert
View all trips

Discover the most popular places to visit in Rupert

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.

Merck Forest Farmland Center

Rupert Hotel Deals

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
$230 nightly
The price is $253 total per night from Aug 20 to Aug 21
$253 total
Aug 20 - Aug 21
Total includes taxes and fees
9.2/10 Wonderful! (781 reviews)
"Great location, nice front porch. Nice bar. There is no gym, breakfast, snacks, or gift shop, however, a clothing boutique is available. As a pet-friendly hotel, oftentimes I was interrupted by dogs barking and growling at each other - I felt I was at a kennel. Value for the room rate was ..."

Reviewed on Jul 24, 2025

Kimpton Taconic Hotel by IHG
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
$191 nightly
The price is $211 total per night from Sep 1 to Sep 2
$211 total
Sep 1 - Sep 2
Total includes taxes and fees
7.4/10 Good! (500 reviews)
"Beautiful setting! Comfortable rooms"

Reviewed on Jul 25, 2025

The Equinox Golf Resort & Spa
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St, Manchester Center, VT
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $167 total per night from Aug 10 to Aug 11
$167 total
Aug 10 - Aug 11
Total includes taxes and fees
9.6/10 Exceptional! (1,000 reviews)
"2nd time here and we were extremely satisfied"

Reviewed on Jul 19, 2025

Hampton Inn and Suites Manchester
See all 1,108 properties in Rupert
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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Rupert vacation package cost?
You'll find cheap prices from $618 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.