
Tiller Vacations from $474
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Tiller vacation packages
Price found within the past 48 hours. Click for updated prices.

Wine Country Inn
Price was $589, price is now $474 per person
$474
per person
Jul 9 - Jul 12
just found
Roundtrip non-stop flight included
Burbank (BUR) to Medford (MFR)
9.4/10 Exceptional! (1,005 reviews)
Absolutely lovely and quiet place to stay in Jacksonville. The property is an upscale charming motel/hotel property, tucked away in cute corner on the main road, 238, heading out of town. Lots of trees in the lot. My double bed room was spacious, with a high ceiling, calming decor and comfortable beds. Very clean room.
I especially appreciated the large refrigerator that also had a small freezer for ice packs. (Good for road trippers.)
The Inn is a short half mile walk to the Main street in “downtown” Jacksonville (half that to the Pony Espresso, Rays grocery and the Back Porch).
The walk is flat, with a good sidewalk the entire way and VERY safe at night. It’s across the street from a senior living complex.
I suggest a flashlight as some sections are a little dark at night.
Note that the upstairs rooms require carrying your items up a set of outdoor stairs.
The rooms right next to the road may have some road noise in the morning, but not much. (This is Jacksonville after all.)
I’ve stayed in downtown several times before and would stay here again.
It’s perfect if you’re going to a concert at the Britt, providing your OK with the walk back, which would probably be about a mile total from the pavilion.
Reviewed on May 11, 2026

Callahan's Mountain Lodge
Price was $758, price is now $611 per person
$611
per person
Jul 9 - Jul 12
just found
Roundtrip non-stop flight included
Burbank (BUR) to Medford (MFR)
8.8/10 Excellent! (1,167 reviews)
Beautiful place. Not in the greatest of shape, but a nice change from the bustle of Ashland. Gorgeous views, lovely patio off the room, excellent dinner.
Reviewed on May 9, 2026

Hummingbird Estate Wine & Suites
Price was $838, price is now $677 per person
$677
per person
Jul 9 - Jul 12
just found
Roundtrip non-stop flight included
Burbank (BUR) to Medford (MFR)
9.6/10 Exceptional! (157 reviews)
Charming vintage winery with great history and lovely rooms. The Syrah suite was clean and comfortable. The sunrise in the morning was spectacular. The tasting room is directly below the suite and can be loud but closes around 7 during the week. I don’t think I would stay here during an event unless I was participating in the event. So check the calendar first if noise is an issue for you. The grounds are wonderful and there are many spots to sit and enjoy. At night the terrace is lovely with the fires going. We played a bit of pickleball as well. Highly recommend with the caveat of checking for events first if noise is an issue for you.
Reviewed on Feb 28, 2026

Lithia Springs Resort
Price was $827, price is now $691 per person
$691
per person
Jul 9 - Jul 12
just found
Roundtrip non-stop flight included
Burbank (BUR) to Medford (MFR)
9.4/10 Exceptional! (1,003 reviews)
The property is beautiful. Having a mineral springs tub in the room is fantastic!! Breakfast was delicious!
Reviewed on May 11, 2026

Grandview of Ashland
Price was $1,837, price is now $1,540 per person
$1,540
per person
Jul 9 - Jul 12
just found
Roundtrip non-stop flight included
Burbank (BUR) to Medford (MFR)
10/10 Exceptional! (7 reviews)
The residence was fantastic in every way. Me and my family enjoyed all the amenities and seeing the wildlife around the house outside. This place is a magical place! Thank you again! We will be back in the near future.
Reviewed on Apr 20, 2026
Tiller Hotel Deals

Travelodge by Wyndham Canyonville
554 SW Pine St Canyonville OR
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $79 total per night from May 25 to May 26
$79 total
May 25 - May 26
Total with taxes and fees
7.4/10 Good! (539 reviews)
The hotel back is 20 ft from a freeway off ramp. It was clean, staff was friendly but the whole thing looked like it was put together from garage sale items. The breakfast was literally coffee, 8 yogurts, 3 bagels, 1 cream cheese packet, 6 apples, 3 kinds of cereal. Literally that was it. It wasn’t ...
Reviewed on May 10, 2026

Water front Cabin Retreat
✨️ A Vacation Wonderland ✨️
Azalea OR
$329 nightly
The price is $334 total per night from May 13 to May 14
$334 total
May 13 - May 14
Total with taxes and fees
9.4/10 Exceptional! (22 reviews)
The space was very welcoming and comfortable! The pantry and other amenities were very thoughtful.Would definitely recommend
Reviewed on Jan 26, 2026

Charming, Private Cottage near I-5 and Golf Course.
Myrtle Creek OR
$173 nightly
The price is $173 total per night from May 13 to May 14
$173 total
May 13 - May 14
Total with taxes and fees
10/10 Exceptional! (45 reviews)
My visit was very nice and the home owners were very friendly and helpful. I will definitely keep this home in mind for future visits
Reviewed on Apr 21, 2026
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 |
More vacations you might like
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















