Rupert Vacations from $681

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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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $864, price is now $681 per person
$681
per person
Feb 26 - Mar 1
found 20 hours ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
Clean and spacious room. Check-in was quick and staff were kind and helpful.

Reviewed on Dec 24, 2025

Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $1,673, price is now $1,147 per person
$1,147
per person
Jan 25 - Jan 30
found 10 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Rutland (RUT)
No reviews
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
Price was $2,599, price is now $1,917 per person
$1,917
per person
Feb 8 - Feb 14
found 6 hours ago
Roundtrip flight included
Knoxville (TYS) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Clean, staff was great.

Reviewed on Dec 23, 2025

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,383, price is now $1,043 per person
$1,043
per person
Jan 25 - Jan 30
found 10 hours ago
Roundtrip non-stop flight included
Raleigh (RDU) to Rutland (RUT)
No reviews
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,715, price is now $1,358 per person
$1,358
per person
Feb 8 - Feb 14
found 6 hours ago
Roundtrip flight included
Knoxville (TYS) to Rutland (RUT)
9.2/10 Wonderful! (941 reviews)
Great inn!!! Close to everything and specially the mountain

Reviewed on Dec 17, 2025

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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

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
$223 nightly
The price is $245 total per night from Jan 12 to Jan 13
$245 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
7.4/10 Good! (577 reviews)
Nicely decorated for Christmas. Helpful and attentive staff, Lack of heat in some of the public areas like near the library was an issue, but they tried by keeping the fireplace going. As a helpful hint- the fireplace area in the library was drafty and cold. You can go a long way toward fixing this ...

Reviewed on Dec 7, 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
$130 nightly
The price is $143 total per night from Jan 4 to Jan 5
$143 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.6/10 Exceptional! (1,003 reviews)
Room was spotless. Staff was friendly.

Reviewed on Dec 15, 2025

Hampton Inn and Suites Manchester
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$190 nightly
The price is $209 total per night from Jan 26 to Jan 27
$209 total
Jan 26 - Jan 27, 2026
Total with taxes and fees
9.2/10 Wonderful! (821 reviews)
10/10 Perfect Stay. So accommodating and kind staff.

Reviewed on Dec 22, 2025

Kimpton Taconic Hotel by IHG
See all 1,147 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 $681 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.