Ascutney Vacations from $636

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Your Ascutney Vacation

Unforgettable adventures await when you lock in a vacation package to Ascutney. Whether you're a foodie, art buff or just a traveler who loves to discover new places, there's something for everyone in this awesome city. Mount Ascutney, Mt Ascutney State Park and American Precision Museum are just some of the many attractions you'll want to see during your trip to Ascutney. Expedia is here to help you escape your routine. Tailor your vacation to Ascutney to suit your style of travel, whatever that may look like.

The Latest Ascutney vacation packages

Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $792, price is now $636 per person
$636
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
It is an accommodation with the most beautiful view. It is very convenient because there is a shop in front of the accommodation.

Reviewed on Jan 17, 2026

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,251, price is now $1,052 per person
$1,052
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
9.2/10 Wonderful! (549 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 2025

Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Clock Tower Base Area
Price was $1,641, price is now $1,389 per person
$1,389
per person
Mar 19 - Mar 22
found 13 hours ago
Roundtrip non-stop flight included
Miami (MIA) 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

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,039, price is now $889 per person
$889
per person
Mar 19 - Mar 22
found 13 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Clean, staff was great.

Reviewed on Dec 23, 2025

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $1,090, price is now $962 per person
$962
per person
Apr 7 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
9.2/10 Wonderful! (106 reviews)
So great all around!

Reviewed on Jan 4, 2026

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Discover the most popular places to visit in Ascutney

American Precision Museum

You can spend time exploring the galleries in American Precision Museum in Windsor. Wander the riverfront in this quaint area.

American Precision Museum

Brownsville Trail

You can take time to visit Brownsville Trail during your travels to Windsor. Discover the mountain views in this family-friendly area, or seek out the ski slopes.

Brownsville Trail

Paradise Park

4/5(4 reviews)

Explore the great outdoors at Paradise Park, a lovely green space in Windsor. Wander the riverfront in this quaint area.

Paradise Park

Ascutney Hotel Deals

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$165 nightly
The price is $180 total per night from Feb 1 to Feb 2
$180 total
Feb 1 - Feb 2
Total with taxes and fees
8.8/10 Excellent! (956 reviews)
Everything/everyone was superb!!!

Reviewed on Jan 17, 2026

Pointe at Castle Hill Resort
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$429 nightly
The price is $472 total per night from Jan 21 to Jan 22
$472 total
Jan 21 - Jan 22
Total with taxes and fees
9.2/10 Wonderful! (560 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 2025

Woodstock Inn & Resort
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $132 total per night from Jan 21 to Jan 22
$132 total
Jan 21 - Jan 22
Total with taxes and fees
9.4/10 Exceptional! (1,075 reviews)
Clean, quiet, good breakfast. Check in was easy and staff was friendly.

Reviewed on Jan 15, 2026

Align Inn Vermont
See all 1,480 properties in Ascutney
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 Ascutney Vacation Packages

Ascutney Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
540
Max Temp Winter
25ºF
Max Temp Summer
75ºF
Top Sights
Harpoon Brewery, American Precision Museum and Old Constitution House

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Frequently asked questions

How much does an Ascutney vacation package cost?
Offering great value package deals from $636 on Expedia, you'll be pleasantly surprised at how much a vacation to Ascutney costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Ascutney?
October, November and December are great times to look for cheap Ascutney vacation packages. Opting to travel in less busy periods means you can typically find lower prices on flights and hotels.
How many days is enough for Ascutney?
Typically, a handful of days is enough to go to the major sights during your Ascutney vacation. However, if you prefer to have time to chill out or take day tours, think about extending your itinerary.
How to find the best Ascutney package deals?
Begin your search for an Ascutney package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Ascutney package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Ascutney adventure underway.
Is it cheaper to book an Ascutney 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 get a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Ascutney vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Ascutney?
Secure fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Ascutney break.
Does Expedia offer Book Now, Pay Later Ascutney vacation packages?
Secure your perfect escape to Ascutney with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or hold off until payday — we've teamed up with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stick to your budget and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.