Photo by Holly Warren Norman
Open Photo by Holly Warren Norman
Rutland County Vacations & Trips from $839
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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.
- Golden Stage Inn B&B
Oct 15 - Oct 20Golden Stage Inn B&B + Flight
Cavendish5 nights3.5 star property10/10 - Exceptional (45 reviews)"Julie and Mike were the nicest most amazing hosts! The breakfast was fantastic, the atmosphere was perfect for rest and relaxation. Our room was clean and cool and cozy, the bathroom was nice and the bath products were great, and sold on sight. We had such a nice time! We will definitely be back!"Reviewed July 6, 2026Roundtrip • Minneapolis (MSP) - Rutland (RUT)MSP - BOS • 1 stop BOS - MSP • 1 stop$1,053$839found 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$2,024$1,563found 1 day agoper traveler - Lincoln Inn & Gallery
Oct 15 - Oct 20Lincoln Inn & Gallery + Flight
Woodstock5 nights3.0 star property8.8/10 - Excellent (83 reviews)"Building is of historical interest, clean, comfortable, simple rooms, friendly staff."Reviewed July 31, 2026Roundtrip • Minneapolis (MSP) - Springfield (VSF)MSP - BOS • 1 stop BOS - MSP • 1 stop$1,637$1,358found 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 - ORD • 1 stop$1,508$1,265found 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 (1,001 reviews)"Food delish for dinners . Breakfast boring. Pool nice"Reviewed August 2, 2026Roundtrip • Chicago (CHI) - Rutland (RUT)ORD - RUT • 1 stop RUT - ORD • 1 stop$1,307$1,098found 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, (1,003 reviews)
8.2/10
Very Good
(1,003 reviews)
"Quiet room decent size...would have liked a second chair"
$115 nightly
The price is $126
$126 total
Aug 30 - Aug 31
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
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!"
$130 nightly
The price is $142
$142 total
Aug 4 - Aug 5
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
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 front desk clerk, and older woman, was repeatedly rude and condescending"
$124 nightly
The price is $137
$137 total
Aug 19 - Aug 20
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."
$109 nightly
The price is $120
$120 total
Aug 4 - Aug 5
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 4 - Aug 5
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, (1,001 reviews)
9.2/10
Wonderful
(1,001 reviews)
"We stayed here as the hotel for the event we were attending was booked. Paid same price and got breakfast, was a plus!"
$177 nightly
The price is $195
$195 total
Aug 4 - Aug 5
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.