Randolph Vacations from $604

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 $673, price is now $604 per person
$604
per person
Aug 18 - Aug 22
found 20 hours ago
Roundtrip flight included
Chicago (CHI) to Rutland (RUT)
6.6/10 (1,003 reviews)
Easy access off route 7. Easy walk to Dennys.

Reviewed on Jul 3, 2026

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
Price was $1,002, price is now $790 per person
$790
per person
Sep 26 - Oct 2
found 22 hours ago
Roundtrip flight included
Chicago (ORD) to Rutland (RUT)
9.4/10 Exceptional! (476 reviews)
This place is wonderful. Super clean. Bathroom shower/tub was so shiny. Beds clean and comfortable. Loved the full fridge with the built-in ice maker. We really enjoyed that. It was nice to have a stovetop too and the toaster. The sink even had a garbage disposal. They have frozen dinners for sale if you forget to bring your own and they sell ice cream as the fridge has the freezer. We will definitely stay there again. Best place and very reasonably priced too. My only issue was the super big/thick pillows. Luckily I did bring my own. Over all it is a really terrific place to stay. Staff was friendly and helpful. Very, very clean. I highly recommend this place.

Reviewed on Jul 4, 2026

Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $844, price is now $709 per person
$709
per person
Aug 18 - Aug 22
found 20 hours ago
Roundtrip flight included
Chicago (CHI) to Rutland (RUT)
9.4/10 Exceptional! (944 reviews)
Perfect stay for my toddler and older guests - accessible and pleasant staff. Great view and fun activities! Only wish there were to-go boxes for the breakfast - it gets a little hard to bring cereal and milk down the hill to the lodge. The floors could be cleaned a little more carefully - there was some dust and dirt - especially near the beds. Other than that - it was one of the most positive experiences my family has had when traveling. Highly recommend!

Reviewed on Jul 6, 2026

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $737, price is now $635 per person
$635
per person
Aug 18 - Aug 22
found 20 hours ago
Roundtrip flight included
Chicago (CHI) to Rutland (RUT)
9/10 Wonderful! (849 reviews)
Need blackout curtains (very bright before 6am) Overall nice and spacious room Air conditiones at times smells musty - needs to be cleaned? Bummer about pool being closed and ac not -working on lower level amenities (heat wave) Very pleasant staff- daily check ins via text appreciated

Reviewed on Jul 1, 2026

Harvest Barn Inn

Harvest Barn Inn

3 out of 5
Price was $727, price is now $650 per person
$650
per person
Aug 18 - Aug 22
found 20 hours ago
Roundtrip flight included
Chicago (CHI) to Rutland (RUT)
9.8/10 Exceptional! (268 reviews)
Easy check in. Had a wonderful stay. Very clean and comfortable. Very friendly and accommodating. Breakfast was 3-course.. .amazing! Beautiful view overlooking the Connecticut River.

Reviewed on Jun 29, 2026

Don't see what you're looking for?
See all available trips from Columbus to Randolph
View all trips

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.
See properties

Randolph Hotel Deals

Secluded retreat in the trees

Secluded retreat in the trees

Roxbury VT
$218 nightly
The price is $244 total per night from Jul 7 to Jul 8
$244 total
Jul 7 - Jul 8
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
$139 nightly
The price is $152 total per night from Jul 19 to Jul 20
$152 total
Jul 19 - Jul 20
Total with taxes and fees
7.4/10 Good! (1,005 reviews)
"We had a great stay. The staff was nice and the property was awesome. The beds were super comfy and the rooms were clean.Close to everything."

Reviewed on Jul 5, 2026

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

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$489 nightly
The price is $538 total per night from Jul 7 to Jul 8
$538 total
Jul 7 - Jul 8
Total with taxes and fees
9.4/10 Exceptional! (589 reviews)
"Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town. The grounds and amenities were immaculate and authentic to the area. A memorable stay."

Reviewed on Jun 25, 2026

Woodstock Inn & Resort
See all 2,057 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Randolph vacation package cost?
You'll find cheap prices from $604 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.

Explore a world of travel with Expedia

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