Cuttingsville Vacation Packages

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Top Cuttingsville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was CA $1,106, price is now CA $987 per person
CA $987
per person
Oct 2 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
9.4/10 Exceptional! (123 reviews)
Very friendly and courteous owner, great location 5 mins away from Mount Snow.

Reviewed on Jul 10, 2026

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was CA $1,402, price is now CA $1,181 per person
CA $1,181
per person
Oct 2 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
10/10 Exceptional! (200 reviews)
Beautiful place, extraordinary, Christina was so kind and accommodating.

Reviewed on Jul 15, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was CA $1,320, price is now CA $1,165 per person
CA $1,165
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Lebanon (LEB)
9/10 Wonderful! (850 reviews)
Nice staff, fun activities

Reviewed on Jul 12, 2026

Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,348, price is now CA $1,198 per person
CA $1,198
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
8.6/10 Excellent! (915 reviews)
The uniqueness of the '30s/40's era vibe brought us back for another visit.It was like stepping back in time. The movie theaters are classic. Sages is the adjoining cocktail lounge complete with cosy,stuffed chairs,40's style decor.Again, we felt like we stepped back in time. The cocktails were quite unusual and thoughtful and we wish we could have tried them all. Tapas and waffles! So yummy. The staff at the hotel were gracious, friendly, helpful.And there was a never-ending supply of plain or cucumber ice water at the front desk. The beds were crisply sheeted and super comfy. Best part? The record player in the room with a whole library of vinyl to choose from.We enjoyed some classical tunes and some Beatles! Though the town itself has seen a bit of degradation since our last visit, with some noticably vacant store fronts, there are still some cool boutiques, art galleries and eateries.And check out the huge co-op grocery store.

Reviewed on Jul 16, 2026

The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was CA $1,419, price is now CA $1,269 per person
CA $1,269
per person
Oct 2 - Oct 5
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Rutland (RUT)
9.2/10 Wonderful! (1,004 reviews)
Good location. Small pool and no chairs around pool

Reviewed on Jul 16, 2026

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Cuttingsville Hotel Deals

Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Aug 2 to Aug 3
CA $218
CA $240 total
Aug 2 - Aug 3
includes taxes & fees
7.4/10 Good! (1,001 reviews)
"The property is absolutely gorgeous. Front desk was great. The room I got had a skylite, which is nice but the sun was right in the pillows of the bed, so in the afternoon, if you wanted to take a rest from your days activities, you couldn’t due to the sun being in the pillows, and no way to block ..."

Reviewed on Jul 15, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is CA $188 per night from Jul 23 to Jul 24
CA $188
CA $217 total
Jul 23 - Jul 24
includes taxes & fees
9.2/10 Wonderful! (1,017 reviews)
"Good location. Small pool and no chairs around pool"

Reviewed on Jul 16, 2026

The Mountain Inn at Killington
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
The price is CA $340 per night from Jul 21 to Jul 22
CA $340
CA $405 total
Jul 21 - Jul 22
includes taxes & fees
9.4/10 Exceptional! (1,010 reviews)
"when we got to the hotel after a long day of travel we found that the bar and restaurant were closed those days of the week so had to buy chips for dinner. we found a cockroach in the room and when we put out the room cleaning notice, nobody came and cleaned. when we had a nice dinner my daughter ..."

Reviewed on Jul 13, 2026

On The River Inn
See all 2,334 properties in Cuttingsville
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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Stay near popular Cuttingsville attractions

Shrewsbury Free Library

After visiting Shrewsbury Free Library, make a plan to see the other sights and activities in Cuttingsville.
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Frequently asked questions

How much does a Cuttingsville vacation package cost?
You'll find cheap prices from CA $987 on Expedia for your Cuttingsville escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Cuttingsville costs.
What are the cheapest months to go to Cuttingsville?
You're likely to find reduced prices and better availability in January, February and March. Browse our cheap Cuttingsville vacation packages and you could get some great off-season deals.
How many days is enough for Cuttingsville?
The ideal duration of your Cuttingsville 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 main sights and discover some hidden spots along the way.
How to find the best Cuttingsville package deals?
Landing a cheap Cuttingsville package deal is a breeze with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add some filters and browse what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Cuttingsville package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Cuttingsville vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still have the freedom to create a tailored Cuttingsville vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Cuttingsville?
If you have your Cuttingsville travel dates finalized, book as soon as you can to bag some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Cuttingsville?

  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to visit Cuttingsville.
  2. Plan your budget wisely: As well as the cost of your accommodations, you'll need to factor in other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Cuttingsville.
  3. Set the duration of your trip: Start by listing all the attractions you'd like to get to in Cuttingsville. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the right Cuttingsville vacation package for you.

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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.