The Best Winery Hotels in Bend, OR from $153 in 2025

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Top Bend Winery Hotels

"Great stay in Bend!"

$137 nightly

Nov 9 - Nov 10

Total with taxes and fees

Outdoor pool, open 10:00 AM to 8:00 PM, cabanas (surcharge)

"Pronghorn is a very nice place to stay. Very convenient to the golf courses. "

$161 nightly

Nov 13 - Nov 14

Total with taxes and fees

"Great stay"

$183 nightly

Oct 21 - Oct 22

Total with taxes and fees

"The Drake Club was great! Really nice little cottage that is well decorated and includes a great kitchen and bathroom. The location is excellent as you are a short walk/bike ride to everything Bend has to offer. The Drake Club is a great little spot in Bend and I would highly recommend it to anyone considering a stay in Bend!"

$180 nightly

Oct 19 - Oct 20

Total with taxes and fees

"Very nice accomodations, plenty of room for our party of 6.Walking distance to pool and rec center. Would definately book this property again."

$319 nightly

Oct 20 - Oct 21

Total with taxes and fees

"Very nice property, great location, comfortable beds, well stocked. We enjoyed our stay here. Thank you."

$301 nightly

Oct 19 - Oct 20

Total with taxes and fees

"The house was well appointed and clean. Beds were comfortable and location within Eagle Crest was great. The host was a great communicator and we had everything we needed and our questions were answered promptly. We will definitely rent this house again. "

$319 nightly

Oct 20 - Oct 21

Total with taxes and fees

"Would stay here again. The hot tub was great. Many games for the kids to play. Lots of space and parking was better than some others I have stayed at. "

$269 nightly

Oct 19 - Oct 20

Total with taxes and fees

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Top Bend Hotel Reviews

Cascade Lodge

10/10 Excellent

"Excellent room; friendly staff. Very well maintained. We will definitely stay here again when passing through Bend. Highly recommend. Room was immaculate and huge—plenty of floor space, and giant, recently renovated bathroom. Comfy bed."