Weston Vacation Packages
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Your Weston Vacation
The easiest way to experience this city is with a customized Weston vacation package. Base yourself in the neighborhood of Bromley Mountain, which is good for views, families and nature or choose someplace else — our packages are all about you. A trip to Weston is an excellent opportunity to see the sights. Be sure to visit popular attractions like Viking Nordic Center, Weston Priory and Weston Playhouse. No matter your travel plans or budget, organizing your ultimate tailored Weston vacation is a piece of cake with Expedia.
Top Weston Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
Price was CA $1,380, price is now CA $1,185 per person
CA $1,185
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (847 reviews)
No inflatable mattress offered anymore.
Reviewed on Mar 18, 2026
The Shire Woodstock
Price was CA $1,467, price is now CA $1,244 per person
CA $1,244
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
8.8/10 Excellent! (914 reviews)
Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!
Reviewed on Jan 30, 2026
The Vesper
Price was CA $1,454, price is now CA $1,238 per person
CA $1,238
per person
May 17 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
9.2/10 Wonderful! (57 reviews)
Uniqueness of rooms, breakfast options and walking distance to so many great spots!
Reviewed on Feb 18, 2026
Woodstock Inn & Resort
Price was CA $3,702, price is now CA $3,174 per person
CA $3,174
per person
May 17 - May 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
9.2/10 Wonderful! (567 reviews)
Always an Amazing time when we stay here. Property well maintained, staff is super friendly and the food here is above and beyond. Did I mention I got married here 👍👍
Reviewed on Apr 5, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
Price was CA $1,659, price is now CA $1,469 per person
CA $1,469
per person
May 16 - May 23
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.
Reviewed on Jun 26, 2025
Weston Hotel Deals
COHO Inn & Motor Lodge
287 Vermont Rte 100 Weston VT
9.4/10 Exceptional! (71 reviews)
Perfect ski hotel !
Reviewed on Mar 15, 2026
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is CA $193 per night from Apr 19 to Apr 20
CA $193
CA $213 total
Apr 19 - Apr 20
includes taxes & fees
7.4/10 Good! (1,002 reviews)
was put in a room next to elevator, elevator was rubbing squeeling reported to front desk, they refused to move us, noise kept us up all night long. terrible experience. she said they didn't have any other rooms and refused to move us the hotel was clearly NOT full capacity. Elevator certificate ...
Reviewed on Mar 31, 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
The price is CA $198 per night from Apr 7 to Apr 8
CA $198
CA $226 total
Apr 7 - Apr 8
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Have stayed here many times. Close to town and Okemo. Very convenient.
Reviewed on Mar 30, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
