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Rollingstone Vacations from $388

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The Latest Rollingstone Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Coffee service
    Sep 24 - Sep 28

    Aspen Select + Flight

    Kutzky Park
    4 nights
    3.5 star property
    8.4/10 - Very Good (1,000 reviews)
    "good"
    Reviewed July 20, 2026
    Roundtrip • Dallas (DFW) - Rochester (RST)
    DFW - MSP • Nonstop MSP - DFW • Nonstop
    $496
    $388
    per traveler
    found 1 day ago
    Aspen Select
  • Indoor pool, pool umbrellas, sun loungers
    Sep 21 - Sep 25

    The Towers At Kahler Grand Hotel + Flight

    Downtown Rochester
    4 nights
    4.0 star property
    9.6/10 - Exceptional (115 reviews)
    "Everyone was very helpful throughout our stay. Our Tower Suite was wonderful and amenities were great."
    Reviewed June 29, 2026
    Roundtrip • Dallas (DFW) - Rochester (RST)
    DFW - RST • 1 stop RST - DFW • 1 stop
    $1,558
    $1,287
    per traveler
    found 0 hours ago
    The Towers At Kahler Grand Hotel
  • Lobby
    Sep 21 - Sep 25

    The Berkman + Flight

    Folwell
    4 nights
    3.0 star property
    9.6/10 - Exceptional (421 reviews)
    "Wonderful property with a few caveats. The amenities are great, and the location is ideal for St Mary’s. The apartment is large and parking safe and easy. That said, the bed is very hard and pillows aren’t great. The vents also hit directly on your face in the bed, so that was hard to get used to. I would stay again but only if I brought my own pillows and blankets"
    Reviewed July 2, 2026
    Roundtrip • Dallas (DFW) - Rochester (RST)
    DFW - RST • 1 stop RST - DFW • 1 stop
    $961
    $828
    per traveler
    found 0 hours ago
    The Berkman
  • Indoor pool
    Sep 24 - Sep 28

    Kahler Grand Hotel + Flight

    Downtown Rochester
    4 nights
    3.0 star property
    8.4/10 - Very Good (2,222 reviews)
    "Parking was a problem at the hotel because of construction going on both in the streets and in the public parking lot. If you left the parking lot during the day to eat or for business when you came back you risk the lot being full till 5:00 pm which happened to me. I had to wait until 5:00 or valet my car which cost even more."
    Reviewed July 22, 2026
    Roundtrip • Dallas (DFW) - Rochester (RST)
    DFW - MSP • Nonstop MSP - DFW • Nonstop
    $531
    $465
    per traveler
    found 1 day ago
    Kahler Grand Hotel
  • Terrace/patio
    Aug 24 - Aug 28

    Homewood Suites by Hilton Rochester Mayo Clinic Area / Saint Marys + Flight

    Kutzky Park
    4 nights
    3.0 star property
    9.2/10 - Wonderful (523 reviews)
    Roundtrip • Dallas (DFW) - Rochester (RST)
    DFW - RST • 1 stop RST - DFW • 1 stop
    $788
    $693
    per traveler
    found 1 day ago
    Homewood Suites by Hilton Rochester Mayo Clinic Area / Saint Marys

Rollingstone Hotel Deals

In-room safe, desk, blackout drapes, iron/ironing board

Days Inn by Wyndham Winona

Days Inn by Wyndham Winona
2.0 star property
6.9 mi from Rollingstone
7.8 out of 10, Good, (1,000 reviews)
"Roach in bathroom last morning. Other than that it was good."
$68 nightly
The price is $76
Jul 26 - Jul 27
Total with taxes and fees
Days Inn by Wyndham Winona
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.
See all properties in Rollingstone

Frequently Asked Questions

How much does a Rollingstone vacation package cost?

You can snap up a vacation package to this destination from $388 on Expedia. However, how much your vacation to Rollingstone costs will depend on factors like the length of stay, hotel choice and season.

What are the cheapest months to go to Rollingstone?

January, February and June are great times to search for cheap Rollingstone vacation packages. Choosing to travel in quieter months means you can usually find lower prices on flights and accommodations.

How many days is enough for Rollingstone?

The ideal duration for your Rollingstone vacation depends on what you'd like to see. Typically, a few days to a week will give you time to go to all the major attractions and explore some hidden spots along the way.

How to find the best Rollingstone package deals?

Landing a cheap Rollingstone package deal is easy with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Rollingstone 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 typically lower.

Is it cheaper to book a Rollingstone vacation as a package?

An Expedia vacation package could score you significant savings when compared to arranging flights and hotels individually. Better still, you can customize your Rollingstone getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.

When to book a vacation package to Rollingstone?

If you're planning a spontaneous Rollingstone adventure, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land sensational deals on your flights and hotels by booking well in advance.

Does Expedia offer Book Now, Pay Later Rollingstone vacation packages?

Your Rollingstone getaway is meant to be an escape from your daily routine, not a source of money worries. So to give you a bit more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.