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Rutland County Vacations & Trips from $877
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Top destinations in Rutland County
Killington
Rutland
Brandon
Castleton
Bomoseen
Poultney
Chittenden
Fair Haven
Mount Holly
The Latest Rutland County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- My Place Hotel-Randolph VT
Sep 24 - Sep 30My Place Hotel-Randolph VT + Flight
Randolph Center6 nights2.0 star property9.4/10 - Exceptional (506 reviews)Roundtrip • Houston (HOU) - Lebanon (LEB)IAH - BTV • 1 stop BTV - IAH • 1 stop$1,051$877found 1 day agoper traveler - The Shire Woodstock
Sep 8 - Sep 14The Shire Woodstock + Flight
Woodstock6 nights3.0 star property8.8/10 - Excellent (969 reviews)"It would be great to have a coffee maker in the room"Reviewed July 31, 2026Roundtrip • Chicago (CHI) - Springfield (VSF)ORD - RUT • 1 stop RUT - ORD • 1 stop$2,019$1,558found 1 day agoper traveler - Winterplace at Okemo, A Vail Resorts Property
Sep 8 - Sep 14Winterplace at Okemo, A Vail Resorts Property + Flight
Clock Tower Base Area6 nights4.0 star property8.8/10 - Excellent (27 reviews)"Enjoyable and beautiful place. Ann"Reviewed July 20, 2026Roundtrip • Chicago (CHI) - Springfield (VSF)ORD - RUT • 1 stop RUT - RFD • 2 stops$1,497$1,254found 1 day agoper traveler - Jackson Gore Village, A Vail Resorts Property
Sep 8 - Sep 14Jackson Gore Village, A Vail Resorts Property + Flight
Jackson Gore Base Area6 nights3.0 star property8.6/10 - Excellent (876 reviews)"Staff, room, and amenities were awesome. Would stay here again in a heartbeat. A few hot tubs to chose from for adults and pool for kids."Reviewed July 26, 2026Roundtrip • Chicago (CHI) - Springfield (VSF)ORD - RUT • 1 stop RUT - RFD • 2 stops$1,160$972found 1 day agoper traveler - The Mountain Inn at Killington
Sep 8 - Sep 14The Mountain Inn at Killington + Flight
Killington6 nights2.5 star property9.2/10 - Wonderful (1,000 reviews)"The carpet was filthy. Looked like it hadn't been vacuumed in weeks. The bedding was dirty - a brown spot and it was off putting."Reviewed July 31, 2026Roundtrip • Chicago (CHI) - Rutland (RUT)ORD - RUT • 1 stop RUT - RFD • 2 stops$1,296$1,087found 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, (1,001 reviews)
8.2/10
Very Good
(1,001 reviews)
$125 nightly
The price is $138
$138 total
Aug 9 - Aug 10
Total with taxes and fees
9.0 out of 10, Wonderful, (1,001 reviews)
9.0/10
Wonderful
(1,001 reviews)
"The room was beautiful!! And… it was the BEST hotel breakfast we have had in a very long time!!"
$151 nightly
The price is $166
$166 total
Aug 9 - Aug 10
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, (1,001 reviews)
8.8/10
Excellent
(1,001 reviews)
"Staff was very nice and went extra miles with finding activities I was interested in doing."
$152 nightly
The price is $167
$167 total
Aug 9 - Aug 10
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, (4 reviews)
10/10
Exceptional
(4 reviews)
"We had an absolutely lovely stay at Bentley House! The owners were so welcoming and we felt right at home in their whimsical Victorian wonderland :)
Oh! And breakfast was delicious!"
$126 nightly
The price is $138
$138 total
Aug 11 - Aug 12
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, (1,001 reviews)
6.8/10
(1,001 reviews)
"."
$124 nightly
The price is $137
$137 total
Aug 25 - Aug 26
Total with taxes and fees
8.8 out of 10, Excellent, (1,000 reviews)
8.8/10
Excellent
(1,000 reviews)
"Absence de personnel au desk lors de notre départ à 7h le matin. Restaurant ouvert seulement les vendredis et samedis."
$121 nightly
The price is $133
$133 total
Aug 3 - Aug 4
Total with taxes and fees
8.8 out of 10, Excellent, (1,004 reviews)
8.8/10
Excellent
(1,004 reviews)
"This is my number one choice when I need to stay in Killington. Such a cool place, super helpful staff, fair prices. The air-conditioning in the room was a welcome addition, even though it was a tad bit loud. Absolutely fantastic definitely recommended."
$114 nightly
The price is $125
$125 total
Aug 3 - Aug 4
Total with taxes and fees
9.6 out of 10, Exceptional, (251 reviews)
9.6/10
Exceptional
(251 reviews)
"Can't recommend this place highly enough. Victoria, the manager was super friendly and helpful, taking the time to show us round"
$168 nightly
The price is $185
$185 total
Aug 17 - Aug 18
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.