Cuttingsville Vacations from $926
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The Latest Cuttingsville vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
$926
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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
Mountain Green Resort
$2,124
per person
Dec 27 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
4/10 (2 reviews)
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 2026
The Landgrove
$1,454
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Rutland (RUT)
8.6/10 Excellent! (7 reviews)
Beautiful room especially with our dog. Outside entrance was a plus! Comfortable bed and chairs. Excellent staff. Every detail was well thought out . We will come again!
Reviewed on Sep 20, 2026
The Shire Woodstock
$1,710
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Springfield (VSF)
8.8/10 Excellent! (994 reviews)
The location of this hotel is perfect. Lovely surroundings too. Plenty of free parking onsite and a coffee station on every floor. Rooms are spotlessly clean and the bed is just so comfortable.
Reviewed on Sep 30, 2026
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View all tripsStay near popular Cuttingsville attractions
Shrewsbury Free Library
After visiting Shrewsbury Free Library, make a plan to see the other sights and activities in Cuttingsville.
Cuttingsville Hotel Deals
The Mountain Inn at Killington
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
$156 nightly
$172 total
Oct 19 - Oct 20
Total with taxes and fees
9.2/10 Wonderful! (1,012 reviews)
"Nice staffs Pretty good breakfast Nice parking and free. Beautiful view Towels might need to be updated."
Reviewed on Oct 3, 2026
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
$139 nightly
$152 total
Nov 2 - Nov 3
Total with taxes and fees
Jackson Gore Village, A Vail Resorts Property
111 Jackson Gore Road Ludlow VT
Fully refundableReserve now, pay when you stay
$193 nightly
$213 total
Oct 28 - Oct 29
Total with taxes and fees
8.6/10 Excellent! (909 reviews)
"My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff ..."
Reviewed on Oct 2, 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.
Find the Best Cuttingsville Vacation Packages
Cuttingsville Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Rutland Southern Vermont Regional Airport (RUT) |
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Frequently asked questions
How much does a Cuttingsville vacation package cost?
You'll find cheap prices from $926 on Expedia for your Cuttingsville getaway. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Cuttingsville costs.
What are the cheapest months to go to Cuttingsville?
If you'd like to snag a cheap Cuttingsville vacation package, consider visiting in April, May and October. You're likely to find lower prices on flights and accommodations during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Cuttingsville?
The ideal duration of your Cuttingsville vacation depends on what you'd like to do. Generally, a few days to a week will give you time to tick off all the major attractions and explore some hidden treasures along the way.
How to find the best Cuttingsville package deals?
Start your search for a Cuttingsville package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Cuttingsville package deal right away, simply play around with your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Cuttingsville escape off to a flying start.
Is it cheaper to book a Cuttingsville vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and hotels separately. Better still, you can tailor your Cuttingsville escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Cuttingsville?
If you're considering a spontaneous Cuttingsville adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find sensational deals on your hotels and flights by booking ahead.
Does Expedia offer Book Now, Pay Later Cuttingsville vacation packages?
Jet off on your perfect escape to Cuttingsville with help from our Book Now, Pay Later vacations. There's no need to save like crazy or wait for the next payday — we've joined forces with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to stay on budget and snag great deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
