Deals on vacations and trips to Rupert

Save when you book Rupert package deals

Choose two or more items and save on your trip:

Rupert flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,173, price is now $984 per person
$984
per person
Feb 19 - Feb 25
found 2 hours ago
Roundtrip flight included
Greenville (GSP) to Rutland (RUT)
This resort features a restaurant, an indoor pool, and a bar/lounge. There's an outdoor tennis court on site, and a fireplace in the lobby and a picnic area are also provided.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
Price was $3,487, price is now $2,832 per person
$2,832
per person
Feb 19 - Feb 25
found 2 hours ago
Roundtrip flight included
Greenville (GSP) to Springfield (VSF)
Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $2,716, price is now $2,316 per person
$2,316
per person
Feb 19 - Feb 25
found 2 hours ago
Roundtrip flight included
Greenville (GSP) to Rutland (RUT)
An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,327, price is now $1,134 per person
$1,134
per person
Feb 19 - Feb 25
found 2 hours ago
Roundtrip flight included
Greenville (GSP) to Springfield (VSF)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $2,444, price is now $2,116 per person
$2,116
per person
Feb 19 - Feb 25
found 2 hours ago
Roundtrip flight included
Greenville (GSP) to Rutland (RUT)
An outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. Concierge services, barbecue grills, and a virtual front desk are also on offer.

Top Rupert hotels deals

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Free Cancellation
$221 nightly
The price is $243 total per night
$243 total
Jan 25 - Jan 26
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A Manchester VT
Free Cancellation
Reserve now, pay when you stay
$249 nightly
The price is $273 total per night
$273 total
Jan 26 - Jan 27
Total with taxes and fees
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3 out of 5
5 Village Lodge Road Stratton VT
$202 nightly
The price is $222 total per night
$222 total
Jan 26 - Jan 27
Total with taxes and fees
This smoke-free resort's 10 restaurants, 2 bars/lounges, and hot tub are some of the featured amenities. There's a free ski shuttle, and ski passes and ski storage are available on site. Families will appreciate the arcade/game room, kid-friendly dining, and supervised childcare.
The Manchester View

The Manchester View

2.5 out of 5
77 High Meadow Way & VT-7A Manchester Center VT
Free Cancellation
Reserve now, pay when you stay
$104 nightly
The price is $115 total per night
$115 total
Jan 26 - Jan 27
Total with taxes and fees
A seasonal outdoor pool is featured at this hotel, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and luggage storage are also on offer.
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
Free Cancellation
$105 nightly
The price is $115 total per night
$115 total
Jan 27 - Jan 28
Total with taxes and fees
This smoke-free hotel features a golf course, 2 outdoor tennis courts, and a restaurant. Enjoy the indoor pool and free perks like continental breakfast and free self parking. You'll appreciate the seasonal outdoor pool, bar/lounge, and free newspapers.
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St Manchester Center VT
Free Cancellation
Reserve now, pay when you stay
$130 nightly
The price is $143 total per night
$143 total
Feb 1 - Feb 2
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
Don't see what you're looking for?
See all available properties in Rupert
View all properties
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.

Popular places to visit

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

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.

R. K. Kittay Public Library

Frequently asked questions

How much are vacation packages to Rupert?
Adventure calls in Rupert, with Travelocity vacation packages starting as low as $984. Providing both hotels and flights, these incredible deals are a simple way to see every corner of the globe.
How long should my Rupert vacation be?
There's no hard and fast rule when it comes to how long you should spend in Rupert, but most people stay around 3 nights. Got some leeway with your travel dates? Extend your vacation by a few extra nights. Then you'll have sufficient time to check out the nearby areas too.
Where can I get the best vacation package deals for Rupert?
No matter how you like to travel, Travelocity can help you snap up an unbeatable Rupert package deal. The only thing you have to do is pick and choose between our 400 airlines and 1,000,000 properties worldwide.
Why should I purchase my Rupert vacation bundle via Travelocity?
Fantastic savings, an abundance of exciting destinations and 24/7 customer service you can rely on — that's why. And with our Price Match Guarantee, you can rest easy knowing that you'll always get the best possible deal with Travelocity.
Can I save on my Rupert car rental if I bundle it with my hotel or flight?
You most certainly can — combine your car, hotel and flight into a Rupert vacation package and you'll save a handsome sum. With so much to see and do in Rupert, that set of wheels will make exploring a joy. Once you've settled into the driver's seat, put the stereo on and head toward Harvard Square, an unmissable attraction approximately 120 mi from Rupert.
Which airport is best for Rupert?
Albany Intl. Airport (ALB) is one of the most popular airports in Rupert. It's located 45 mi southwest of the buzzing city center. Other options available to you are Lebanon Municipal Airport (LEB) (50 mi away from central Rupert) and Rutland Southern Vermont Regional Airport (RUT) (25 mi away from central Rupert).
What is there to do in Rupert?
Merck Forest Farmland Center is just one of the outstanding sights that make Rupert such a tourist hot spot. But allow some extra time to discover the city's lesser-known attractions too. This is sometimes where the best memories are made.
Where should I stay when visiting Rupert?
The Family Farmhouse Retreat is the first choice of many visitors. Book now to avoid missing out.

Photos of local treasures

Browse Rupert vacation photos for more inspiration

Explore More Ways to Travel with Travelocity