Rollingstone Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Rollingstone

Express Suites Riverport Inn & Suites

Express Suites Riverport Inn & Suites

3 out of 5
900 Bruski Dr, Winona, MN
Fully refundableReserve now, pay when you stay
The price is S$172 per night from 21 Jul to 22 Jul
S$172
21 Jul - 22 Jul
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"Property was convenient and there was a bar connecting. Pool and hot tub were warm!"

Reviewed on 10 Jul, 2025

Express Suites Riverport Inn & Suites
Super 8 by Wyndham Winona MN

Super 8 by Wyndham Winona MN

2 out of 5
1025 Sugar Loaf Rd, Winona, MN
Fully refundableReserve now, pay when you stay
The price is S$103 per night from 31 Jul to 1 Aug
S$103
31 Jul - 1 Aug
includes taxes & fees
7.4/10 Good! (1,008 reviews)
"Clean. Would have a bigger room to lounge in"

Reviewed on 15 Jul, 2025

Super 8 by Wyndham Winona MN
The Plaza Hotel & Suites Winona

The Plaza Hotel & Suites Winona

3 out of 5
1025 Highway 61 E, Winona, MN
Fully refundableReserve now, pay when you stay
The price is S$208 per night from 28 Jul to 29 Jul
S$208
28 Jul - 29 Jul
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Loved the adorable giant pool statue-decorations-toys in the kiddie/ wading pool area!! Our own kids are older, but I am SURE younger ones would be thrilled by this! A baby whale with a water-spout fountain? How delightful! (Okay - I DID climb on the giant dragon sofa/ decoration in the adjoining ..."

Reviewed on 15 Jul, 2025

The Plaza Hotel & Suites Winona
See all 159 properties in Rollingstone
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.

Frequently asked questions

How much does a Rollingstone holiday package cost?
You can snap up a holiday package to this destination on Expedia. However, how much your holiday 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?
If you're looking to book a cheap Rollingstone holiday package, consider travelling in January, February and November. You'll typically find better prices on airfares and hotels during these months --- perfect for a budget-friendly break.
How many days is enough for Rollingstone?
Typically, a handful of days is enough to go to the major attractions during your Rollingstone holiday. However, if you want to have some time to kick back or go on day tours, consider extending your itinerary.
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 personalise 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 holiday as a package?
An Expedia holiday package could score you significant savings when compared to arranging flights and hotels individually. Better still, you can customise 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 holiday 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.
How to plan a trip to Rollingstone?

  1. Pick your travel dates: The things you'd like to do in Rollingstone and your preferred season can help you decide when to go.
  2. Set a budget: Consider costs such as flights, transportation and food when working out how much to save for your trip to Rollingstone. Then, pick a property that works with your budget, whether that's a wallet-friendly stay or a lavish retreat.
  3. Set the duration of your trip: Start by compiling a list of the activities and sights you'd like to get to in Rollingstone. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Rollingstone holiday package that brings all your bookings together.