Randolph Vacations from $1,003

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The Latest Randolph vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,431, price is now $1,003 per person
$1,003
per person
Dec 28 - Jan 2
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Rutland (RUT)
9/10 Wonderful! (890 reviews)

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Save 100% on your flight
Price was $3,540, price is now $2,529 per person
$2,529
per person
Dec 28 - Jan 2
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Rutland (RUT)
No reviews

Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $4,223, price is now $3,071 per person
$3,071
per person
Dec 28 - Jan 2
found 14 hours ago
Roundtrip flight included
Chicago (CHI) 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

The Landgrove

3.5 out of 5
Price was $1,361, price is now $1,036 per person
$1,036
per person
Dec 28 - Jan 2
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Rutland (RUT)
9.4/10 Exceptional! (13 reviews)
It was certainly a remote property and if you want to get away from it all then this is the place!

Reviewed on Oct 21, 2026

The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,774, price is now $1,420 per person
$1,420
per person
Dec 28 - Jan 2
found 14 hours ago
Roundtrip flight included
Chicago (CHI) to Rutland (RUT)
9.2/10 Wonderful! (433 reviews)
Our room was large and comfortable, with a large, well-supplied bathroom. The fellow at the front desk was friendly and helpful. It feels like a very nice rural country inn. There isn't a lot else there, as there aren't 24-hour onsite staff or a fitness room or many other lobby amenities. I wouldn't hesitate to come back.

Reviewed on Oct 15, 2026

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Stay near popular Randolph attractions

Allis State Park

Vermont's second oldest state park offers a historic fire tower with breathtaking 360-degree views of the Green Mountains. Hike the serene Bear Hill Nature Trail and bring binoculars for spotting distant White Mountains.
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Randolph Hotel Deals

Secluded retreat in the trees

Secluded retreat in the trees

Roxbury VT
$220 nightly
The price is $246 total per night from Nov 2 to Nov 3
$246 total
Nov 2 - Nov 3
Total with taxes and fees
10/10 Exceptional! (52 reviews)
"Super cute! Wish there was a TV there, but it was a nice stay."

Reviewed on Oct 26, 2026

Secluded retreat in the trees
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
$156 nightly
The price is $172 total per night from Oct 28 to Oct 29
$172 total
Oct 28 - Oct 29
Total with taxes and fees
The Mountain Inn at Killington
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$409 nightly
The price is $450 total per night from Nov 16 to Nov 17
$450 total
Nov 16 - Nov 17
Total with taxes and fees
9.4/10 Exceptional! (624 reviews)
"Amazing venue for our wedding!"

Reviewed on Oct 25, 2026

Woodstock Inn & Resort
See all 2,098 properties in Randolph
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 Randolph Vacation Packages

Randolph Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
1,950
Max Temp Winter
25ºF
Max Temp Summer
70ºF

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Frequently asked questions

How much does a Randolph vacation package cost?
You'll find cheap prices from $1,003 on Expedia for your Randolph getaway. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Randolph costs.
What are the cheapest months to go to Randolph?
August, October and December are great times to look for cheap Randolph vacation packages. Opting to travel in less busy months means you'll typically find reduced prices on hotels and flights.
How many days is enough for Randolph?
Generally, a handful of days is enough to see the main attractions during your Randolph vacation. However, if you prefer to have more time to unwind or take day trips, think about extending your trip.
How to find the best Randolph package deals?
Landing a cheap Randolph package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add some filters and see what's available. You can customize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Randolph package deals. Want a simple trick to get the biggest 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 Randolph vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Randolph vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Randolph?
If you have your Randolph vacation dates locked in, book as early as you can to score some unbeatable deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are perfect for impromptu escapes.
Does Expedia offer Book Now, Pay Later Randolph vacation packages?
Your Randolph break should be a relaxing escape from your busy life, not a reason for money-related stress. So to give you extra flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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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.