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.
Deerfield Valley Inn
CA $1,414
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.4/10 Exceptional! (132 reviews)
We returned to this place on a quick 2-day/last minute get away. Owner is new from last time. Nice people; helpful and made a very good breakfast. Only issue we really had was the plumbing. Our room had some kind of venting issue with the sink/toilet/shower. Toilet bubbled and would go down at times; sink would go slow/stop at times; shower also stopped up and went down very slow. Told the owner about it and hopefully they can get it fixed. But overall, pleasant stay.
Reviewed on Aug 17, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
CA $1,521
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop 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
Mountain Lodge at Okemo, A Vail Resorts Property
Clock Tower Base Area
CA $1,473
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8/10 Very good! (225 reviews)
Staff was very helpful, the property is very clean, the room was clean with lots of space. The kitchen had a full size refrigerator and microwave. I was very happy overall
Reviewed on Jul 19, 2026
Ready to book your vacation to Weston?
Weston Hotel Deals
The Weston
630 Main St Weston VT
CA $761
CA $830 total
Sep 4 - Sep 5
includes taxes & fees
10/10 Exceptional! (11 reviews)
"I cannot say enough wonderful things about our stay at The Weston. From the moment we arrived, it was clear this was a truly special place. The property is absolutely beautiful, with a timeless Vermont charm that feels both luxurious and welcoming. Every space is thoughtfully designed, impeccably ..."
Reviewed on Aug 2, 2026
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
CA $155
CA $179 total
Sep 6 - Sep 7
includes taxes & fees
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
CA $220
CA $242 total
Sep 7 - Sep 8
includes taxes & fees
7.4/10 Good! (1,001 reviews)
"A great place to stay when you’re visiting Killington!"
Reviewed on Sep 1, 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.
Stay near popular Weston attractions
Weston Playhouse
7.8/10 (14 reviews)
You can make plans for a show at Weston Playhouse during your stay in Weston. Discover the mountain views in this romantic area, or enjoy its ski slopes.
Weston Priory
9.0/10 (2 reviews)
You can find out about the history of Weston when you stop by Weston Priory. Discover the mountain views in this romantic area, or enjoy its ski slopes.
Mill Museum
You can spend time exploring the galleries in Mill Museum during your travels in Weston. Discover the mountain views in this romantic area, or enjoy its ski slopes.
Frequently asked questions
How much does a Weston vacation package cost?
You'll find cheap prices from CA $1,414 on Expedia for your Weston break. However, a range of factors like the season, choice of hotel and length of stay will determine how much your vacation to Weston costs.
What are the cheapest months to go to Weston?
The off-season is the best time to head to Weston if you're trying to save. Another tip for scoring cheap Weston vacation packages? Try to avoid public holidays and any major events.
How many days is enough for Weston?
The ideal length for your Weston vacation depends on what you'd like to do and see. Generally, a few days to a week will give you time to go to all the major attractions and explore some hidden spots along the way.
How to find the best Weston package deals?
Landing a cheap Weston package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to view the most economical Weston package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Weston vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still get the flexibility to create a customized Weston vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Weston?
If you have your Weston travel dates confirmed, book as soon as you can to bag some awesome deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for travelling on a whim.
How to plan a trip to Weston?
- Choose the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Weston.
- Plan your budget wisely: Besides the price of your stay, you'll need to consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Weston.
- Decide your trip length: Consider how long you want to spend exploring Weston. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Weston vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
