Rupert Vacations from $931

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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.
Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,217, price is now $931 per person
$931
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
10/10 Exceptional! (198 reviews)
This was a hidden gem. It was so clean and quiet. Definitely a place for peace and quiet. Rooms were super clean and the attention to detail was amazing. Will definitely be back.

Reviewed on Jun 22, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,552, price is now $1,272 per person
$1,272
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.8/10 Excellent! (935 reviews)
Walkable to downtown Woodstock. Loved our room with balcony over looking the river.

Reviewed on Jun 27, 2026

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $1,513, price is now $1,304 per person
$1,304
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $1,266, price is now $1,098 per person
$1,098
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.6/10 Excellent! (858 reviews)
Jackson Gore resort far exceeded expectations. Friendly staff, flawless grounds, and plenty of summer activities. Short drives to other beautiful Vermont towns, and much more.

Reviewed on Jun 23, 2026

Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts

4 out of 5
Clock Tower Base Area
Price was $1,369, price is now $1,201 per person
$1,201
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
7.8/10 Good! (35 reviews)
Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also.

Reviewed on Oct 8, 2025

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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.
See properties

Rupert Hotel Deals

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$247 nightly
The price is $272 total per night from Jun 29 to Jun 30
$272 total
Jun 29 - Jun 30
Total with taxes and fees
9.4/10 Exceptional! (852 reviews)
"The lobby and rooms were well maintained and clean. Daytime hotel staff was professional and friendly. Nighttime staff, although may have been doing his job, was curt when inquired about the bar (closed) and fire pit access (“if it’s on. Otherwise, I don’t have the key for it.” A bunch of us sat ..."

Reviewed on Jun 26, 2026

Kimpton Taconic Hotel by IHG
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
5383 Main St Manchester Center VT
Fully refundable
$133 nightly
The price is $146 total per night from Jul 19 to Jul 20
$146 total
Jul 19 - Jul 20
Total with taxes and fees
8.2/10 Very Good! (949 reviews)
"I did not like the fact to have to drive to the pool because it was raining. The gym very outdated. No water in the outside hot tub. Breakfast did not look good so we skipped it. The pond dock was falling apart, the boat was half sunk with cans littered in it. The pond itself needs upkeep. Ice machine ..."

Reviewed on Jun 26, 2026

The Palmer House Resort, an Ascend Collection Hotel
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
$130 nightly
The price is $143 total per night from Jul 5 to Jul 6
$143 total
Jul 5 - Jul 6
Total with taxes and fees
9.6/10 Exceptional! (1,001 reviews)
"Great outside space! Breakfast was outstanding! Staff was very helpful and property was very clean!"

Reviewed on Jun 25, 2026

Hampton Inn and Suites Manchester
See all 1,210 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.

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 $931 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.