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Open Photo by Holly Warren Norman
Rutland County Vacations & Trips from $473
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Top destinations in Rutland County
Killington
Rutland
Brandon
Castleton
Bomoseen
Poultney
Chittenden
Fair Haven
Wells
The Latest Rutland County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Deerfield Valley Inn
Oct 8 - Oct 11Deerfield Valley Inn + Flight
West Dover3 nights2.0 star property9.4/10 - Exceptional (126 reviews)"Very clean"Reviewed July 20, 2026Roundtrip • New York (NYC) - Springfield (VSF)LGA - ALB • Nonstop ALB - LGA • Nonstop$577$473found 1 day agoper traveler - Stone Hearth Inn and Eatery
Oct 8 - Oct 11Stone Hearth Inn and Eatery + Flight
Chester3 nights3.0 star property9.2/10 - Wonderful (120 reviews)"We truly enjoyed the Stone Hearth Inn. We stayed after an event about a half hour away. The Inn was cozy, decorated tastefully with cozy white coaches and antiques and wide plank flooring. The room was air conditioned , the bed was comfy and had everything we needed in the bathroom. We enjoyed speaking with the owner at breakfast and hearing her story. Just a few minutes from town and a great place. We enjoyed the breakfast but, unfortunately , weren’t staying long enough to try lunch or..."Reviewed June 22, 2026Roundtrip • New York (NYC) - Springfield (VSF)LGA - ALB • Nonstop ALB - LGA • Nonstop$807$624found 1 day agoper traveler - Days Inn by Wyndham Rutland/Killington Area
Oct 8 - Oct 11Days Inn by Wyndham Rutland/Killington Area + Flight
Rutland3 nights2.5 star property6.8/10 - (1,004 reviews)"The staff was incredibly kind and welcoming!! It’s an old place but the renovations they are working on make the rooms so comfortable. The bed was extraordinary!! The gentleman at the front was so kind and accommodating!!"Reviewed July 21, 2026Roundtrip • New York (NYC) - Rutland (RUT)LGA - ALB • Nonstop ALB - LGA • Nonstop$696$571found 1 day agoper traveler - The Shire Woodstock
Sep 7 - Sep 11The Shire Woodstock + Flight
Woodstock4 nights3.0 star property8.8/10 - Excellent (967 reviews)"There for one night. Stayed in the river house. Room was good. Very quiet. The fire pits and sitting area along the river was fantastic. Sat out there at night after dinner and for coffee the next morning."Reviewed July 18, 2026Roundtrip • New York (NYC) - Springfield (VSF)JFK - LEB • 1 stop LEB - JFK • 1 stop$1,034$853found 15 hours agoper traveler - Chalet 239
Oct 8 - Oct 11Chalet 239 + Flight
West Dover3 nights2.0 star property9.4/10 - Exceptional (134 reviews)"Only stayed one night- clean and convenient! Looked like new or recently renovated! Nice bathroom! No frills -basic cold breakfast items and Keurig coffee makers available. Easy check in and checkout. Max was there for check-in. Touch-less, paperless checkout."Reviewed July 22, 2026Roundtrip • New York (NYC) - Springfield (VSF)LGA - ALB • Nonstop ALB - LGA • Nonstop$644$532found 1 day agoper traveler
Discover the most popular places to visit in Rutland County
Rutland County Hotel Deals
Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington2.5 star property
0.9 mi from Rutland County
8.2 out of 10, Very Good, (1,006 reviews)
8.2/10
Very Good
(1,006 reviews)
"hallway smelled and room smelled of smoke"
$116 nightly
The price is $128
$128 total
Jul 29 - Jul 30
Total with taxes and fees
Bentley House Bed and Breakfast
Bentley House Bed and Breakfast2.0 star property
14.5 mi from Rutland County
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)
"Great place, friendly owners. I will be coming back."
$148 nightly
The price is $161
$161 total
Jul 27 - Jul 28
Total with taxes and fees
9.0 out of 10, Wonderful, (1,000 reviews)
9.0/10
Wonderful
(1,000 reviews)
"."
$147 nightly
The price is $162
$162 total
Jul 30 - Jul 31
Total with taxes and fees
8.8 out of 10, Excellent, (1,000 reviews)
8.8/10
Excellent
(1,000 reviews)
$109 nightly
The price is $120
$120 total
Jul 26 - Jul 27
Total with taxes and fees
Days Inn by Wyndham Rutland/Killington Area
Days Inn by Wyndham Rutland/Killington Area2.5 star property
1.7 mi from Rutland County
6.8 out of 10, (1,004 reviews)
6.8/10
(1,004 reviews)
"The staff was incredibly kind and welcoming!! It’s an old place but the renovations they are working on make the rooms so comfortable. The bed was extraordinary!! The gentleman at the front was so kind and accommodating!!"
$107 nightly
The price is $118
$118 total
Jul 26 - Jul 27
Total with taxes and fees
The Mountain Inn at Killington
The Mountain Inn at Killington2.5 star property
9.3 mi from Rutland County
9.2 out of 10, Wonderful, (1,005 reviews)
9.2/10
Wonderful
(1,005 reviews)
$139 nightly
The price is $153
$153 total
Jul 26 - Jul 27
Total with taxes and fees
9.8 out of 10, Exceptional, (400 reviews)
9.8/10
Exceptional
(400 reviews)
$141 nightly
The price is $155
$155 total
Jul 28 - Jul 29
Total with taxes and fees
Best Western Inn & Suites Rutland-Killington
Best Western Inn & Suites Rutland-Killington2.5 star property
2.9 mi from Rutland County
8.8 out of 10, Excellent, (1,000 reviews)
8.8/10
Excellent
(1,000 reviews)
"Staff was very nice and went extra miles with finding activities I was interested in doing."
$179 nightly
The price is $197
$197 total
Jul 29 - Jul 30
Total with taxes and fees
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.