Rutland County Vacations & Trips from $1,187
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 Center. Leicester is another favorite city with Rutland County travelers. 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 destinations in Rutland County
Killington
Rutland
Brandon
Chittenden
Poultney
Mount Holly
Castleton
Bomoseen
The Latest Rutland County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
1846 Inn and Tavern
$1,187
per person
Dec 26 - Jan 2
found 17 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
10/10 Exceptional! (1 review)
The Inn also has an adjacent nice food tavern and music this weekend. Friendly host - embodied the helpful spirit of old inns. Helped with allowing a late dinner due to late arrival. Adjusted the heat for us and allowed us to set a bit extra in their library.
Very welcoming. A ++ for hospitality and making us welcome!
Reviewed on Oct 12, 2026
Mountain Green Resort
$3,551
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
4/10 (2 reviews)
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 2026
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
$3,763
per person
Dec 27 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
9.2/10 Wonderful! (68 reviews)
It is a wonderful place to stay at any time for coming foliage or ski. The location is excellent, quiet and very clean inside. We felt like at home, We will stay again when we visit woodstook area next time.
Reviewed on Oct 15, 2026
Find the Best Rutland County Vacation Packages
Rutland County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rutland Southern Vermont Regional Airport (RUT) |
Top Sights | Pond Hill Ranch and Pro Rodeo, Lake Saint Catherine State Park and Otter Creek |
Rutland County Hotel Deals
Comfort Inn Rutland - Killington
19 Allen St Rutland VT
Fully refundable
$118 nightly
$130 total
Oct 25 - Oct 26
Total with taxes and fees
8/10 Very Good! (1,007 reviews)
"Good breakfast very busy area, needs more than one person to keep up with the volume of people eating. This facility is getting ready to start a complete redo, this will make it nice i feel sure."
Reviewed on Oct 20, 2026
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
$141 nightly
$155 total
Nov 3 - Nov 4
Total with taxes and fees
Mountain Meadows Lodge
285 Thundering Brook Road Killington VT
$154 nightly
$169 total
Nov 9 - Nov 10
Total with taxes and fees
9.6/10 Exceptional! (345 reviews)
"Beautiful place that offers lots for guest to do. Room was beautiful with nice view and personal balcony with furniture! Only suggestions are our room was a king suite with lake deck and there was only one mirror to get ready with over the sink. This would be fine but sinks are small with no counter ..."
Reviewed on Oct 21, 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.
Stay near popular Rutland County attractions
Photo by Killington Resort
Killington Resort
9.4/10 (1,216 reviews)
Terrain parks, hiking trails, golf, après-ski entertainment and a range of slopes for all levels of skiers welcome visitors to this resort in the Green Mountains.
Pico Mountain at Killington Ski Resort
9.2/10 (274 reviews)
Hit the slopes in Killington with a visit to Pico Mountain at Killington Ski Resort. Discover the mountain views while you're in the area.
Killington Peak
9.6/10 (731 reviews)
Explore the great outdoors at Killington Peak and enjoy the mountain views during your trip to Killington. You can seek out the ski slopes while in the area.
Paramount Theater
8.6/10 (46 reviews)
You can enjoy a show at Paramount Theater during your stay in Rutland. Discover the area's mountain views, or seek out its ski slopes.
Killington Golf Course
8.4/10 (40 reviews)
Tee off on pretty and challenging fairways surrounded by the lush Green Mountains in one of Vermont’s premier golf courses.
K-1 Express Gondola
9.6/10 (355 reviews)
Enjoy a trip to K-1 Express Gondola and popular activities like skiing in Killington. Discover the mountain views while you're in the area.
Sunrise Village Triple Ski Lift
9.2/10 (25 reviews)
Enjoy a trip to Sunrise Village Triple Ski Lift and popular activities like skiing in Killington. Discover the mountain views in this quaint area.
Explore a world of travel with Expedia
Other vacations you might like
- Top cities in Rutland County
- Vacations and getaways similar to Rutland County
- Best vacation destinations by month
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
