Randolph Vacations from $589

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The Latest Randolph vacation packages

Price found within the past 48 hours. Click for updated prices.
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
Price was $703, price is now $589 per person
$589
per person
Jul 9 - Jul 13
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
No reviews
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $784, price is now $662 per person
$662
per person
Jul 9 - Jul 13
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
9.2/10 Wonderful! (1,006 reviews)
Great location, eat and drink on site. Relaxed atmosphere.

Reviewed on May 17, 2026

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $801, price is now $679 per person
$679
per person
Jul 9 - Jul 13
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
8.8/10 Excellent! (1,005 reviews)
Another great stay. The hot pool is rad. It is super mega to have the bar and restaurant on-site! Staff are always friendly and helpful.

Reviewed on Apr 27, 2026

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
Price was $851, price is now $731 per person
$731
per person
Jul 9 - Jul 13
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
9.4/10 Exceptional! (1,189 reviews)
Convenient location, easy check in experience, clean room , helpful staff and free breakfast. We would definitely stay there again.

Reviewed on May 22, 2026

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
Price was $790, price is now $686 per person
$686
per person
Jul 9 - Jul 13
found 18 hours ago
Roundtrip flight included
Orlando (MCO) to Rutland (RUT)
8.8/10 Excellent! (1,002 reviews)
Hotel is not near any resturants and it had no on-premisis restaurant for breakfast.

Reviewed on May 17, 2026

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Discover the most popular places to visit in Randolph

Playhouse Movie Theatre

You can enjoy a show at Playhouse Movie Theatre on your trip to Randolph. While you're in the area, wander around the parks.

Playhouse Movie Theatre

Montague Golf Club

Enjoy a round of golf in Randolph at Montague Golf Club. While you're in the area, wander around the parks.

Montague Golf Club

Whale Dance Sculpture

Learn about the local history of Randolph when you take a trip to Whale Dance Sculpture. While you're in the area, wander around the parks.

Whale Dance Sculpture

Randolph Hotel Deals

Secluded retreat in the trees

Secluded retreat in the trees

Roxbury VT
$216 nightly
The price is $242 total per night from May 25 to May 26
$242 total
May 25 - May 26
Total with taxes and fees
10/10 Exceptional! (43 reviews)
"Lovely location with babbling brook next to the home. Everything was well stocked with nice amenities. Memory foam mattress was the most comfortable I slept on. Well maintained dirt road for about a mile or so to get there. All & all, excellent place to stay."

Reviewed on May 4, 2026

Secluded retreat in the trees
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $143 total per night from May 25 to May 26
$143 total
May 25 - May 26
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
"Place is beautiful well kept rooms are clean nice sized. My only “complaint” was hot tub area which is fabulous opens at 10am, and we were leaving that day at 9. But that was a very minor inconvenience I will be back next year for sure!"

Reviewed on May 15, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night from May 25 to May 26
$395 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (580 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."

Reviewed on May 22, 2026

Woodstock Inn & Resort
See all 2,080 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 $589 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.