Randolph Vacations from $785

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The Latest Randolph vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $942, price is now $785 per person
$785
per person
Dec 24 - Dec 28
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
7/10 Good! (1,003 reviews)

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Save 100% on your flight
Price was $2,468, price is now $1,747 per person
$1,747
per person
Dec 24 - Dec 28
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
No reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,200, price is now $864 per person
$864
per person
Dec 24 - Dec 28
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
9/10 Wonderful! (890 reviews)
This is our third visit. Always a great pleasure to stay here. -PM

Reviewed on Oct 31, 2026

Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $2,721, price is now $2,146 per person
$2,146
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
Save 100% on your flight
Price was $2,818, price is now $2,361 per person
$2,361
per person
Dec 24 - Dec 28
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Rutland (RUT)
9/10 Wonderful! (70 reviews)
It is a wonderful place to stay at any time for coming foliage or ski. The location is excellent, quiet and very clean inside. We felt like at home, We will stay again when we visit woodstook area next time.

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
$207 nightly
The price is $232 total per night from Nov 5 to Nov 6
$232 total
Nov 5 - Nov 6
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 Nov 3 to Nov 4
$172 total
Nov 3 - Nov 4
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
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
Total with taxes and fees
9.4/10 Exceptional! (628 reviews)
"Absolutely beautiful hotel and property, which is a destination just in and of itself. Very comfortable, great dining options, gorgeous spa, and very walkable, if you decide to wander; Woodstock is a town right out of a Hallmark movie, after all."

Reviewed on Oct 28, 2026

Woodstock Inn & Resort
See all 2,105 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 $785 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.