Tiller Vacations from $799

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The Latest Tiller vacation packages

Price found within the past 48 hours. Click for updated prices.
Green Springs Inn

Green Springs Inn

2 out of 5
Price was $920, price is now $799 per person
$799
per person
Aug 15 - Aug 22
found 14 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Medford (MFR)
9.2/10 Wonderful! (130 reviews)
Very clean and cozy.

Reviewed on Jul 4, 2026

A Cowslip's Belle Inn

A Cowslip's Belle Inn

3 out of 5
Price was $1,405, price is now $1,107 per person
$1,107
per person
Aug 15 - Aug 22
found 24 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Medford (MFR)
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 on Jun 25, 2026

Callahan's Mountain Lodge

Callahan's Mountain Lodge

3 out of 5
Price was $1,495, price is now $1,208 per person
$1,208
per person
Aug 15 - Aug 22
found 14 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Medford (MFR)
8.8/10 Excellent! (1,151 reviews)
Callahan is a quaint resort in the woods. Staff is very friendly and accommodating. Great porch overlooking the woods.

Reviewed on Jul 5, 2026

The Peerless Hotel by WanderLodges

The Peerless Hotel by WanderLodges

2 out of 5
Historic Railroad District
Price was $1,600, price is now $1,332 per person
$1,332
per person
Aug 15 - Aug 22
found 24 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Medford (MFR)
9.6/10 Exceptional! (109 reviews)
We loved our stay at The Peerless. The room was beautiful and comfortable and the hotel’s lobby, back room, and patio are lovely for hanging out in. The in-room coffee needs filters and a suggestion of amount for those of us who are coffee making impaired. We would stay here again!

Reviewed on Jun 27, 2026

Riverside Inn

Riverside Inn

2.5 out of 5
Price was $1,158, price is now $994 per person
$994
per person
Aug 15 - Aug 22
found 7 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Medford (MFR)
9.6/10 Exceptional! (2,084 reviews)
..

Reviewed on Jul 6, 2026

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Tiller Hotel Deals

Travelodge by Wyndham Canyonville

Travelodge by Wyndham Canyonville

2 out of 5
554 SW Pine St Canyonville OR
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $102 total per night from Jul 20 to Jul 21
$102 total
Jul 20 - Jul 21
Total with taxes and fees
7.4/10 Good! (568 reviews)
"Older hotel, but easy shuttle to casino, staff was very nice. Easy check-in."

Reviewed on Jun 25, 2026

Travelodge by Wyndham Canyonville
Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Azalea OR
$305 nightly
The price is $310 total per night from Jul 12 to Jul 13
$310 total
Jul 12 - Jul 13
Total with taxes and fees
9.4/10 Exceptional! (23 reviews)
"Everything was good."

Reviewed on Jun 14, 2026

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Charming, Private Cottage near I-5 and Golf Course.

Charming, Private Cottage near I-5 and Golf Course.

Myrtle Creek OR
$200 nightly
The price is $200 total per night from Jul 19 to Jul 20
$200 total
Jul 19 - Jul 20
Total with taxes and fees
10/10 Exceptional! (46 reviews)
"Quiet, beautiful and dog friendly."

Reviewed on Jun 16, 2026

Charming, Private Cottage near I-5 and Golf Course.
See all 12 properties in Tiller
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 Tiller Vacation Packages

Tiller Essential Information

Language
English
Currency
U.S dollars

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Frequently asked questions

How much does a Tiller vacation package cost?
You'll find cheap prices from $799 on Expedia for your Tiller getaway. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Tiller costs.
What are the cheapest months to go to Tiller?
December, January and February are great times to search for cheap Tiller vacation packages. Choosing to travel in less busy months means you can generally find reduced prices on accommodations and flights.
How many days is enough for Tiller?
The ideal length for your Tiller vacation depends on what you'd like to see and do. Generally, a few days to a week will give you time to hit all the main sights and explore some hidden gems along the way.
How to find the best Tiller package deals?
Start your search for a Tiller package deal by entering your destination and preferred trip dates under our "Packages" tab. Then apply a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Tiller package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Tiller getaway off to a flying start.
Is it cheaper to book a Tiller vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking stays and flights separately. Better still, you can personalize your Tiller getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Tiller?
Enjoy fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Tiller escape.
Does Expedia offer Book Now, Pay Later Tiller vacation packages?
Jet off on your dream trip to Tiller with our Book Now, Pay Later vacations. No need to scrimp and save or wait until payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to budget for your trip and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.