Cuttingsville Vacations

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Find the Best Cuttingsville Vacation Packages

Cuttingsville Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is ₩565,884 per night from Sep 1 to Sep 2
₩565,884
₩683,351 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (532 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul 30, 2025

Woodstock Inn & Resort
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 ₩173,086 per night from Aug 25 to Aug 26
₩173,086
₩199,928 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (874 reviews)
We’ll be back.
"Beautiful area, outside of facility looks dated, but that’s not realistic to change. Inside has had a nice update. The staff is very friendly and helpful. We had an inconsiderate and noisy person upstairs over us, just a matter of who is there. We would surely stay here again."

Reviewed on Aug 23, 2025

The Mountain Inn at Killington
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Fully refundableReserve now, pay when you stay
The price is ₩207,896 per night from Aug 28 to Aug 29
₩207,896
₩242,411 total
Aug 28 - Aug 29
includes taxes & fees
8.6/10 Excellent! (807 reviews)
"Forth time at The Shire, everything was wonderful!!"

Reviewed on Aug 21, 2025

The Shire Woodstock
See all 2,310 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.

Frequently asked questions

How much does a Cuttingsville vacation package cost?
You'll find cheap prices 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're hoping to snag a cheap Cuttingsville vacation package, consider planning a trip in January, February and March. You'll usually find better rates on flights and accommodations during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Cuttingsville?
The ideal duration for your Cuttingsville vacation depends on what you'd like to do. Generally, a few days to a week will give you time to hit all the major attractions and explore some hidden gems 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.
How to plan a trip to Cuttingsville?

  1. Choose the best time to travel: Your schedule, preferred season and the type of weather you like can all influence your decision on when to go to Cuttingsville.
  2. Work out your budget: Ensure you have enough money to pay for everything from dining out and transportation to activities and airfares. Your accommodations will likely be the largest expense during your trip to Cuttingsville.
  3. Decide how long to go away for: Now that you know more about Cuttingsville, you can figure out the perfect length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your airfare and accommodations: Once you've nailed down your travel dates and duration, book the perfect Cuttingsville vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.