Tiller Vacations from $821

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The Latest Tiller vacation packages

Price found within the past 48 hours. Click for updated prices.
Wine Country Inn

Wine Country Inn

3 out of 5
Price was $1,012, price is now $821 per person
$821
per person
Nov 22 - Nov 29
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Medford (MFR)
9.4/10 Exceptional! (1,004 reviews)
We enjoyed the room and Jacksonville very much

Reviewed on Sep 26, 2025

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was $1,483, price is now $1,207 per person
$1,207
per person
Nov 22 - Nov 29
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Medford (MFR)
9.2/10 Wonderful! (571 reviews)
Location was very convenient to walking everywhere. Breakfast was fresh and delicious.

Reviewed on Oct 12, 2025

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
Price was $1,412, price is now $1,154 per person
$1,154
per person
Nov 22 - Nov 29
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Medford (MFR)
9.2/10 Wonderful! (1,001 reviews)
It would be so charming to sit in the hotel lobby and have a cocktail by the beautiful fireplace except the fireplace hasn’t been used in years and there’s no bar

Reviewed on Oct 9, 2025

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $1,212, price is now $1,012 per person
$1,012
per person
Nov 22 - Nov 29
found 19 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Medford (MFR)
9.6/10 Exceptional! (991 reviews)
Small town. No dining choices. You have to drive to Ashland which is great.

Reviewed on Oct 13, 2025

Paschal Winery

Paschal Winery

4.5 out of 5
Price was $1,153, price is now $974 per person
$974
per person
Nov 22 - Nov 29
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Medford (MFR)
9.6/10 Exceptional! (11 reviews)
It is a beautiful property. We stayed in the little trailer, glamp cottage and it was so cute. Also enjoyed the private hot tub provided. We did some wine tasting, a flight of white and a flight of reds and enjoyed their fabulous cork and fork dinner. The location is beautiful. My travelling companion said if she didn’t know better she would think she was in Switzerland.

Reviewed on May 3, 2025

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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
$69 nightly
The price is $70 total per night from Oct 19 to Oct 20
$70 total
Oct 19 - Oct 20
Total with taxes and fees
7.4/10 Good! (444 reviews)
"didn't have breakfast"

Reviewed on Oct 12, 2025

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

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️

Azalea
$231 nightly
The price is $234 total per night from Oct 14 to Oct 15
$234 total
Oct 14 - Oct 15
Total with taxes and fees
9.4/10 Exceptional! (16 reviews)
"Super cozy, way bigger then expected great place for a couple getaway or to bring your family or to even bring a couple of couples up friends! Very quiet loved the fact that there was everything you needed honestly all you need to bring are your clothes! Definitely renting again soon!!! Thank you! ..."

Reviewed on Oct 11, 2025

Water front Cabin Retreat ✨️ A Vacation Wonderland ✨️
Airstream in Azalea Forest creek side, lake front

Airstream in Azalea Forest creek side, lake front

Azalea
$272 nightly
The price is $276 total per night from Oct 14 to Oct 15
$276 total
Oct 14 - Oct 15
Total with taxes and fees
2/10 (1 review)
Terrible!
"We went here after talking to the host about needing a place where there would be no fireworks for our very scared dog. He said he would discuss it with the only people that were within a mile of the property and ask them to not do fireworks. They did fireworks and they were only 50 yards from us!! ..."

Reviewed on Jul 6, 2025

Airstream in Azalea Forest creek side, lake front
See all 13 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.

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 $821 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.