Redwood Vacations from $628

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The Latest Redwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Aug 23 - Aug 27

    My Place Hotel-Medford OR + Flight

    Medford
    4 nights
    3.0 star property
    9.2/10 - Wonderful (1,574 reviews)
    Roundtrip Chicago (ORD) - Medford (MFR)
    ORD - MFR1 stop MFR - ORD1 stop
    $729
    $628
    per traveler
    found 1 day ago
    My Place Hotel-Medford OR
  • Sep 3 - Sep 7

    Winchester Inn + Flight

    Historic Downtown District
    4 nights
    3.5 star property
    9.6/10 - Exceptional (280 reviews)
    "Good location. Good breakfast"
    Reviewed July 14, 2026
    Roundtrip Chicago (ORD) - Medford (MFR)
    ORD - MFR1 stop MFR - ORD2 stops
    $1,813
    $1,365
    per traveler
    found 1 day ago
    Winchester Inn
  • Aug 23 - Aug 27

    A Cowslip's Belle Inn + Flight

    Ashland
    4 nights
    3.0 star property
    9.6/10 - Exceptional (46 reviews)
    "We stayed in the upper appartment. The place is beautiful, comfortable, quite, and clean. The kitchen is well equipped. The balcony overlooks a beautiful garden patio. The location is a short walking distance to Ashlands' center with its theaters, coffee shops and restaurants. Steve, our host, was welcoming, bery communicative and accessible. Our stay was perfect."
    Reviewed June 25, 2026
    Roundtrip Chicago (ORD) - Medford (MFR)
    ORD - MFR1 stop MFR - ORD1 stop
    $987
    $815
    per traveler
    found 1 day ago
    A Cowslip's Belle Inn
  • Sep 3 - Sep 7

    The Peerless Hotel by WanderLodges + Flight

    Historic Railroad District
    4 nights
    2.0 star property
    9.6/10 - Exceptional (109 reviews)
    "Beautiful rooms, walkable, comfortable rooms, really enjoyed. Great for couples"
    Reviewed May 30, 2026
    Roundtrip Chicago (ORD) - Medford (MFR)
    ORD - MFR1 stop MFR - ORD2 stops
    $1,092
    $914
    per traveler
    found 1 day ago
    The Peerless Hotel by WanderLodges
  • Aug 23 - Aug 27

    Meadowsweet Farm by WanderLodges + Flight

    Medford
    4 nights
    3.0 star property
    Roundtrip Chicago (ORD) - Medford (MFR)
    ORD - MFR1 stop MFR - ORD1 stop
    $1,813
    $1,588
    per traveler
    found 1 day ago
    Meadowsweet Farm by WanderLodges

What to do in Redwood

Redwood Hotel Deals

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 Redwood vacation package cost?

You can grab a vacation package to this top destination from $628 on Expedia. But how much your vacation to Redwood costs will depend on factors like your hotel choice, length of stay and season.

What are the cheapest months to go to Redwood?

February, October and December are the best times to look for cheap Redwood vacation packages. Traveling in less busy periods means you'll typically find lower prices on flights and hotels.

How many days is enough for Redwood?

The ideal length of your Redwood vacation depends on what you'd like to do. Generally, a few days to a week will give you plenty of time to go to all the major attractions and discover some hidden gems along the way.

How to find the best Redwood package deals?

Use Expedia's handy filters to help you find some tempting Redwood package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Redwood package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.

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

You can enjoy significant savings on your Redwood retreat by booking a personalized vacation package. Click on the "Package" heading, then select your travel dates and destination to browse the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Redwood?

Land fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Redwood getaway.

How to plan a trip to Redwood?

  1. Choose your dates: The things you plan to do in Redwood and your preferred season can help you decide when to travel.
  2. Set your budget: Factor in expenses such as flights, meals and transportation when working out how much to set aside for your trip to Redwood. Then, pick a hotel that fits your budget, whether that's an economical option or a high-end retreat.
  3. Organize your Redwood getaway with our trip planning tool: Look for and book accommodations and experiences all in one place. You can also collaborate with your group to plan an unforgettable trip to Redwood together.
  4. Decide your trip length: Think about how much time you'd like to spend exploring Redwood. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  5. Bundle your accommodations and airfare: After you've settled on your travel dates and duration, lock in the right Redwood vacation package for you.
  6. Book experiences or activities ahead of time: Whether it's entrance to a big attraction or a day trip, you won't have to worry about missing out on the best Redwood has to offer. Find all the incredible things to do in Redwood with our dedicated travel guide.

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

If you're like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the total cost of your Redwood trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.