The Woods Vacation Packages
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Top Holiday Package Deals in The Woods
Price found within the past 48 hours. Click for updated prices.
The Landgrove
CA $1,297
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
8.6/10 Excellent! (7 reviews)
We arrived late, there was someone there to greet us. I had left a personal item, they were kind enough to call and mail it to us.
Reviewed on Oct 3, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
CA $964
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Syracuse (SYR) to Rutland (RUT)
9/10 Wonderful! (884 reviews)
The mattress sunk in the middle so bad that we were crushed together and my wife couldn’t even sleep in the bed. I’m still upset with the fact they didn’t mention there was no elevator in our unit. 24 steps up for two 70 year old people is not something I would recommend to anyone.
Reviewed on Sep 29, 2026
Bentley House Bed and Breakfast
CA $1,223
per person
Nov 6 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
10/10 Exceptional! (27 reviews)
The hosts of this bed & breakfast couldn’t have been more welcoming and friendly! The room (and the whole house) are quaint and old-timey charming. We were comfortable and happy there. What a lovely place to stay!
Reviewed on Oct 5, 2026
Where to stay in The Woods
Find the best The Woods areas and neighborhoods for the activities you enjoy most. Learn more about The Woods
Base Area
1 out of top 10 points of interest in this area
If you're spending some time in Base Area, Killington Adventure Center and Snowshed Double Ski Lift are top sights worth seeing.
Telemark Village
While Telemark Village isn't home to many top sights, Gifford Woods State Park and Green Mountain National Golf Course are some notable places to visit nearby.
North Sherburne
While North Sherburne isn't home to many top sights, Green Mountain National Golf Course and Gifford Woods State Park are some notable places to visit nearby.
The Woods Hotel Deals
Comfort Inn Rutland - Killington
19 Allen St Rutland VT
Fully refundable
CA $174
CA $191 total
Oct 28 - Oct 29
includes taxes & fees
8/10 Very good! (1,009 reviews)
"Great hotel. Clean. Breakfast was good. Great location."
Reviewed on Oct 4, 2026
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
CA $191
CA $221 total
Oct 19 - Oct 20
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"This place is right in the middle of the mountains. Beautiful."
Reviewed on Oct 5, 2026
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
CA $626
CA $751 total
Nov 2 - Nov 3
includes taxes & 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.