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.
Latchis Hotel
Price was CA $794, price is now CA $643 per person
CA $643
per person
Jun 19 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (853 reviews)
If you love retro/vintage/history/ quiet and pet friendly this place is wonderful for a short stay and lowkey weekend. So many cool local businesses and delicious food. We went for a show at the stone church- walking distance from hotel! And everything we could have needed was easily accessible. They have a bar downstairs and a movie theatre in the hotel! All rooms have record players and vinyls to play with more available. Big rooms. “Dated” but it’s keeping with the retro style- very clean and neat. Only negatives were the parking lot (really small but we got a spot! There’s plenty of on street parking and a nearby parking garage as well). Staff was so friendly and helpful!
This would be a great “staycation” or mom night away as well. Stop at some of the amazing thrift/vintage/2nd hand stores for books, music, clothes and more. If you’re a crafter, Bobbins’and Skeins and Beadnik are great places to take a look at. I’d definitely come back!
Reviewed on Mar 30, 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
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
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 $200 per night from Apr 13 to Apr 14
CA $200
CA $228 total
Apr 13 - Apr 14
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.
