Rutland County Vacation Packages
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Your Rutland County Vacation
Make planning your next big adventure easy with a Rutland County vacation package. Whether it's the cuisine, nature or something else entirely that lures you to this destination, our packages will help you experience the best of it. Your trip to Rutland County wouldn't be complete without exploring some of its most well-known cities, starting with Rutland. Some of the most popular attractions here include Killington Peak and Killington Adventure Centre. Leicester is another favourite city with Rutland County travellers. Visitors to this exciting destination love Lake Dunmore and Robert Frost Wayside Trail. Whether you're planning to travel for a week or a month, Expedia are here to help you tailor-make your next Rutland County vacation.
Top vacation destinations in Rutland County
Killington
Brandon
Top Rutland County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Price was CA $1,389, price is now CA $1,049 per person
CA $1,049
per person
Aug 18 - Aug 25
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to Lebanon (LEB)
9/10 Wonderful! (850 reviews)
Need blackout curtains (very bright before 6am)
Overall nice and spacious room
Air conditiones at times smells musty - needs to be cleaned?
Bummer about pool being closed and ac not -working on lower level amenities (heat wave)
Very pleasant staff- daily check ins via text appreciated
Reviewed on Jul 1, 2026
The Shire Woodstock
Price was CA $2,961, price is now CA $2,067 per person
CA $2,067
per person
Aug 18 - Aug 25
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to Springfield (VSF)
8.8/10 Excellent! (954 reviews)
Absolutely beautiful setting! The room was better than expected-- spacious, clean and gorgeously decorated. The location was also great-- everything was walkable. Highly recommend.
Reviewed on Jul 5, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was CA $1,442, price is now CA $1,063 per person
CA $1,063
per person
Aug 18 - Aug 25
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to Springfield (VSF)
8.6/10 Excellent! (862 reviews)
Staff was super friendly at check-in. Room was very clean and quiet. The location was fantastic as we stayed on 4th of july weekend so fireworks were right down the road. Close to quite a few great things about the area. We had breakfast at the Tavern both mornings and it was quite good and not nearly as expensive as you might expect it to be in this type of resort.
Reviewed on Jul 7, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
Price was CA $2,017, price is now CA $1,506 per person
CA $1,506
per person
Aug 18 - Aug 25
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.
Reviewed on Jun 26, 2025
Winterplace at Okemo, A Vail Resorts Property
Clock Tower Base Area
Price was CA $1,860, price is now CA $1,396 per person
CA $1,396
per person
Aug 18 - Aug 25
found 16 hours ago
Roundtrip flight included
Montreal (YUL) 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
Rutland County Hotel Deals
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Jul 16 to Jul 17
CA $207
CA $228 total
Jul 16 - Jul 17
includes taxes & fees
7.4/10 Good! (1,000 reviews)
"We liked our room because it had double balconies!"
Reviewed on Jul 6, 2026
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is CA $190 per night from Jul 19 to Jul 20
CA $190
CA $219 total
Jul 19 - Jul 20
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Such a great place! Very accommodating with dogs. Beds very comfortable! Great views!"
Reviewed on Jul 7, 2026
Comfort Inn Rutland - Killington
19 Allen St Rutland VT
Fully refundable
The price is CA $167 per night from Jul 19 to Jul 20
CA $167
CA $184 total
Jul 19 - Jul 20
includes taxes & fees
8.2/10 Very good! (1,007 reviews)
"Staff was very friendly. The room was very clean and the breakfast was very nice overall always a very pleasant stay"
Reviewed on Jul 9, 2026
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.
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
