Rupert Vacations from $696

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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 Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $859, price is now $696 per person
$696
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to Springfield (VSF)
7.6/10 Good! (1,002 reviews)
Easy check in and good parking

Reviewed on Jan 9, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,019, price is now $839 per person
$839
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!

Reviewed on Jan 30, 2026

Beechwood Home in Mendon

Beechwood Home in Mendon

2 out of 5
Save 100% on your flight
Price was $3,417, price is now $2,837 per person
$2,837
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Rutland (RUT)
No reviews
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,537, price is now $1,285 per person
$1,285
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Rutland (RUT)
No reviews
Mt Green 3-f04 in Killington

Mt Green 3-f04 in Killington

2 out of 5
Price was $1,850, price is now $1,564 per person
$1,564
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Rutland (RUT)
No reviews
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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
$180 nightly
The price is $198 total per night from Feb 23 to Feb 24
$198 total
Feb 23 - Feb 24
Total with taxes and fees
7.4/10 Good! (595 reviews)
Room was great. The hallways, lobby and bar area were very cold (understand very cold out but they need to do something about this, you shouldnt have to wear a coat inside). Staff just seemed focused on doing what they need to do...just a simple good morning with eye contact.

Reviewed on Feb 2, 2026

The Equinox Golf Resort & Spa
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
$122 nightly
The price is $134 total per night from Feb 22 to Feb 23
$134 total
Feb 22 - Feb 23
Total with taxes and fees
8.4/10 Very Good! (890 reviews)
The people were great! The room was quite large and comfortable. It was relatively quiet! Very clean! Nice stay! Again thanks o the staff for making it a nice stay.

Reviewed on Feb 8, 2026

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

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$206 nightly
The price is $227 total per night from Mar 15 to Mar 16
$227 total
Mar 15 - Mar 16
Total with taxes and fees
9.4/10 Exceptional! (831 reviews)
Best atmosphere and family stay ever. Kids friendly.

Reviewed on Feb 8, 2026

Kimpton Taconic Hotel by IHG
See all 1,179 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 $696 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.