The Wayside: Newly remodeled dog-friendly wine country home in the heart of Dundee

Historic home to gather walking distance to tasting rooms & restaurants

  4 guests
  2 bedrooms
  1 full / 1 half bathrooms
  Allows Pets
  1450 sq. ft.

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Sleeping Arrangement

Upstairs Guestroom 1
1 Queen
Upstairs Guestroom 2
1 Queen


When planning your travels to Dundee wine country, look no further than this comfortable, fully remodeled, centrally located home at the gateway to town. This home is situated on the main road through town, so it makes for an easy walk to the many tasting rooms, restaurants, and events, as well as a quick drive to all of the attractions around the picturesque North Willamette Valley. Sound proof windows were installed so when you are sitting in the living room the night life will not disturb your stay!

Our mission is to offer high-quality hospitality to Willamette Valley tourists while coordinating with the best local partners to maximize guest experiences with our customizable concierge services, and hand-selected amenities. We specialize in luxury, short-term lodging options with the highest standards of cleanliness and attention to detail so that you feel right at home during your vacation.

Use our private wine tour service, Pinot Car Wine Tours, to experience the beauty and unique culture in Oregon’s world-renowned wine country, where every visitor walks away with lifetime memories.  Enjoy the beauty of Oregon Wine Country with our knowledgeable guides and discover all the best our valley has to offer.

This beautifully remodeled and smartly laid-out home has a stunning kitchen with new floors, cabinets, sink, stove, and appliances. There is a large island made from reclaimed wood from the original kitchen. Perfect for making memorable home-cooked meals and warmly crafted dishes. You will find the home well stocked to prepare a full meal or to bring in some tasty local takeout.


Passing through the kitchen, there is a small eat-in area in addition to a formal dining room next to the living room. The furniture in the living room is also newly upholstered. Next to the kitchen, is a small deck located just off the side of the house. A large apple tree stands next to the deck. Use the deck to sit back and enjoy your cup of coffee or linger outside with a glass of wine.  There is also a fully manicured grass yard.

In addition to the kitchen, living room, and dining room, there is also a half bathroom and a new washing machine and dryer on the main level of the house.

Head upstairs from the living room area to the two cozy bedrooms each with queen-sized beds. The bedrooms share a fully remodeled bathroom with a new vanity, lighting, and shower tub combo. Each bed comes with comfortable pillows, linens, and warm blankets. The bathroom is stocked with soft fluffy towels, locally sourced bath soap, shampoo and conditioner, and a hairdryer.

Centrally located in downtown Dundee, The Wayside sits in the heart of Dundee. Stroll down to the main street for a great mix of local eating establishments and downtown tasting rooms such as Dobbes, Methven, and Alit. Or venture just outside the city to nearby wineries such as Duskey Goose, Domaine Roy, Winderlea, and Bergstrom.

Family items (baby gate, high chair, pack 'n play), yoga mats, air mattresses, and outdoor games (bocce ball, croquet) are available to rent upon request.

Bring your pups too - they'll love roaming around as well in the large fully enclosed yard. The home is dog friendly!  

The two storage sheds and garage are off-limits and not available to guests.

*Lifestyle Properties would like to assure you that all homes have been aerated, deep cleaned, and commonly used surfaces have been sanitized prior to your arrival. Our team is committed to following all CDC and WHO guidelines regarding the use of PPE and Cleaning Equipment. You will also have a contactless self-check-in upon arrival.*


The Details
  • Sleeps up to 4
  • 2 queen bedrooms
  • Plush Towels
  • High-Quality Bedding
  • Fully stocked, Gourmet Kitchen
  • Glassware
  • Dining Sets
  • Cookware
  • Dishwashing Soap
  • Dishwashing Detergent
  • Paper Towels
  • Locally-Roasted Ground Coffee and Drip Coffee maker with Filters
  • A Selection of Hot Teas
  • Sugar in the Raw
  • Hand Soap
  • Shampoo, Conditioner & Local Handcrafted Bath Soap
  • TV with streaming services
  • Complimentary WiFi  
  • Air-conditioning
  • Concierge Services 

Floor Plan

Floor Plan for The Wayside: Newly remodeled dog-friendly wine country home in the heart of Dundee


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* Rates are subject to change without notice. Pricing excludes taxes, additional options or fees.
Vacation Rental Standard Pricing Sun Mon Tue Wed Thu Fri Sat     Min Nights
Standard Rate $400 $400 $400 $400 $400 $400 $400     2


Write a Review
Hailey, US
Reviewed: Jul 7, 2024
Property Manager
During our stay, your team was incredibly responsive and attentive to our needs. We appreciated the great communication and assistance!
A lot of attention to detail made for a pleasant stay.
Reviewed: Jun 25, 2024
Property Manager
Reviewed: Jun 8, 2024
Property Manager
Great communication and information
Beautiful house with everything you need. Walking distance to wineries and food. Had a wonderful time! Thank you!
Reviewed: May 27, 2024
We absolutely loved staying here! It is a great location within easy walking distance to some great food and wine. We appreciated all of the perks provided for our pets, and we loved enjoying a complimentary bottle of wine upon arrival! Plus, Miss Hannah's Popcorn? Stop it, already! We will definitely be back!
Reviewed: May 25, 2024
Great house right in the middle of the Willamette wine country. Highly recommend.
Reviewed: May 12, 2024
Great house in the heart of Oregon wine country. Had everything we needed and great outdoor space to relax after a day exploring.
Medford, US
Reviewed: May 10, 2024
Property Manager
The Lifestyle team is friendly and very knowledgeable. The sister company, Pinot Wine Tours is a must for anyone who wants to be driven around by a friendly (& knowledgeable driver) for wine tasting. We will be using this company for all our future trips to the Willamette Valley.
The Wayside is the perfect spot for any family to stay at! We were greeted with a bottle of wine, a bag of delicious Caravan coffee, and a personalized note welcoming us to the home.The charming restyled farmhouse combines the charm of an old home with modern amenities. The water pressure was fantastic, the kitchen is large and easy to maneuver around, and the yard large enough to enjoy the outdoors. The home was close to everything we wanted to visit, and a prime location.
Firestone , US
Reviewed: Aug 22, 2023
Property Manager
Everyone was friendly and helpful.
Had a great stay at the Wayside and will be staying there again.
Reviewed: Aug 10, 2023
We were in Oregon wine country for a balloon ride. The location was perfect for our adventure as well as access to great restaurants and bountiful local produce. The Wayside had everything needed to make our stay comfortable and feel like home.
Reviewed: Jul 17, 2023
Property Manager
Reviewed: Jun 27, 2023
Our stay at this newly renovated country home was incredibly comfortable, and the space was thoughtfully designed for social gatherings. Checking in was a breeze, and although there is a secure gate, we could conveniently park right outside. The kitchen was a delight, equipped with everything we needed to cook an extensive meal and host a dinner party for our friends after a day of wine tasting. We were pleasantly surprised that despite being near a busy road, we never noticed any noise and slept soundly, thanks to such comfortable beds and fantastic blackout curtains. One of the highlights was the cleverly designed extended bathroom, and the water pressure was simply awesome. We highly recommend this house as a perfect central stay for anyone visiting the beautiful Willamette Valley.
Reviewed: Jun 27, 2023
Beautiful home and amazing yard for dogs, kids, and adults. Dundee is a lovely little community. I really enjoyed my stay and hope I get to visit again in the future.
Reviewed: Jun 21, 2023
Great stay for the night. Came into town for a football camp at George Fox and it was the perfect location. Will definitely be back when we come up for wine tasting.
Reviewed: May 12, 2023
Lovely home, great location! Will be back!
Reviewed: May 2, 2023
Thanks to the team we where able to get a great price we are already having a roughy time we appreciate the efforts and the support plus how the greeted us it was perfect and made us feel at ease
Reviewed: Apr 18, 2023
Awesome location and walkable. Everything was super clean and we had everything we needed.


  • Standard Check-in is at 4:00 PM
  • Standard Check-out is at 11:00 AM. 
    • Please inquire to request early check in or late check out.
  • At the time of booking, we require a deposit of 50% of the reservation total. The remaining balance is due 30 days prior to arrival.
  • Cancellation Period: 30 days prior to arrival.If you cancel before the 30 days, the total cost will be refunded to you (with the exception of the reservation fee). If the reservation is canceled within that time period, it is non-refundable.

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