Holiday rentals in Chehalem

4.97 out of 5 average rating, 159 reviews

Cottage in Newberg

Oxberg Lake Retreat, lake & farm view in wine ctry

A storybook oasis with lake/farm views. Enjoy your morning coffee or evening wine while listening to the sheep and chickens. One loft bedroom, one full bath with large living room/kitchen. Hosts live in attached home, but you have full privacy. * 5 min to George Fox University * 2 min to The Allison Inn & Spa * 50+ wineries within 10 min drive *Walk to Farm Craft brews at Wolves and People on Benjamin *Enjoy canoeing, feeding the sheep, or reading a book by the fire pit. roll-away bed available

5 out of 5 average rating, 100 reviews

Home in Tigard

Mama J's

I've created what I think is a relaxing stay. You will sleep on a memory foam mattress with cotton linens. Additionally, there is a 55 inch smart TV with free Netflix and Apple TV, along with a selection of books and games. The patio and gazebo are also available and are the smoking areas. This master suite in my house has a private entrance and yard. There are no shared spaces and there is a lock on both sides of the sound-baffled door to the main house to value your privacy as well as mine.

4.99 out of 5 average rating, 230 reviews

Guest suite in Hillsboro

Willamette Valley Wine Country Hub

Located in the heart of the Willamette Valley wine country the 1100 SqFt private unit provides a unique opportunity to experience the north west. We are at the center of a hub with equal access to Hillsboro, Sherwood, Newberg and Beaverton for all of the night life and restaurants while being within a few miles of 100+ wineries. We also offer a wood fired pizza making experience (see below for details). All of this while experiencing rural Oregon. We are on 6 acres with only a few neighbors.

4.88 out of 5 average rating, 593 reviews

Loft in Newberg

Vintage 2 Bedroom Loft | Above Boutique | GFU

Enjoy your wine country getaway from our charming 100 year old Victorian. Located in the heart of Downtown Newberg, you are walking distance to multiple tasting rooms, restaurants (The Painted Lady is right across the street!) and George Fox University is just a short stroll away. Our unique property is home to popular gift boutique, Pulp & Circumstance (downstairs) and has 2 beautiful attic rooms for rent (upstairs). This gem is the perfect place for a visit to Newberg and the OR wine country.

4.96 out of 5 average rating, 244 reviews

Luxury Wine Country Estate

Welcome to Luxury Wine Country Estate, an oasis where luxurious refinement meets the epitome of wine country indulgence. Revel in unmatched hositality, thoughtfully designed to include Tempur-Pedic suites, therapeutic hot tub, rejuvenating sauna, invigorating cold plunge, and the most stunning valley and vineyard views. Every touch is meticulously crafted, from heated stone floors and Dyson innovations to dual gourmet kitchens, Yeti picnic essentials, EV charging capabilities, and so much more.

4.97 out of 5 average rating, 107 reviews

Bacchus Fields - Oregon Wine Country Studio

Bacchus Fields is a private, quiet, studio in the gateway of Oregon’s wine country, with views of Mt. Hood and beautiful scenery. The studio has a queen bed, full kitchen, private bathroom and entrance. We offer self-check in, dedicated parking with complementary Level 2 EV charging, a private outdoor patio with seating, a gas grill and fire pit. The studio is nicely situated for short and long-term stays, visits to wine country, the coast, mountains, Portland, and surrounding communities.

4.89 out of 5 average rating, 183 reviews

Farm stay in Sherwood

Ariniello Vineyard - Private 2 Bedroom Suite

Perfect location for wine tasting and touring the beautiful Pacific NW. A unique opportunity to stay on a newly planted small vineyard in your own private suite. Enjoy your very own 1st floor living quarters. The property is also located on a small farm. You will enjoy your own entry with two private bedrooms (1 king and 1 queen), living room and private bathroom. Basic kitchen set up -NO oven. The space can easily sleep 4 (6 includes an air mattress). No smoking allowed in the suite.

4.98 out of 5 average rating, 285 reviews

Sherwood Hollow- Senior discount at request - 60+

Welcome to Sherwood Hollow! This completely refurbished retreat is a large 1200 square foot downstairs suite in our 1960's home. This spacious area has a large living room, eat-in kitchen, and spacious bedroom. The unit is private and completely closed off from the upstairs. Our home is located just a short walk from Old Town Sherwood and beautiful Stella Olsen park. This unit is near the bottom of a hill, a bit of a climb coming up from Old Town, and the driveway is on an incline.

4.96 out of 5 average rating, 185 reviews

Spectacular Valley View in Wine Country

Relax and enjoy the best of what Oregon Wine country has to offer in our newly renovated country home. With a stunning view overlooking the Willamette Valley, you are close to over 300 wineries and tasting rooms, local craft beer, and a great social atmosphere in our small town. Enjoy soaking in the hot tub or having dinner outside under the gazebo. Have your pets outside, worry free with a large fenced back yard. A pellet grill is on the deck as well for outside cooking.

4.99 out of 5 average rating, 147 reviews

Guest house in Sherwood

Cozy Willamette Valley Cabin With Modern Comforts

A cozy retreat on the brink of Oregon's wine country, walking distance to local restaurants and shops. Enjoy being less than 30 minutes from Portland International Airport and some of the most acclaimed wineries in Oregon's Willamette Valley. This luxurious cabin features a full sized kitchen, washer/dryer, bedroom with queen bed and separate office/dressing room, gas fireplace, smart TV and second queen pull-out. The full bath features walk-in rain shower and full vanity.

4.86 out of 5 average rating, 325 reviews

Cozy Wine Country Suite

A cozy suite with private, separate entrance and garden, located a short walk to Sherwood’s charming downtown. Quick access to coffee shops, restaurants, and a local brewery. Close to many of the valley’s best tasting rooms and vineyards. Relax with a glass of Pinot Noir and watch the sunset on your private deck, or take a short drive to Portland and explore the city. Sherwood is centrally located and the perfect distance for a day trip to the coast or the mountains.

Superhost

Tiny home in Sherwood

4.92 out of 5 average rating, 193 reviews

My Tiny Wine Wagon · · Sip & Stay - Charming Tiny

🍷 When our fun-loving guests aren’t exploring local wineries or waterfalls, they’re unwinding—lounging at the picnic table, strolling with their pup 🐶, or cozying up with a book 📖 from our unique library. This bright, stylish retreat has it all: two comfy beds 🛏️, a fresh-air shower 🚿, ample counter space for work or dining, a fully stocked kitchen 🍽️, a large BBQ 🔥, and a pet care kit. Craving downtime in the fresh air? You’ve found it!

Holiday rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Chehalem holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Chehalem

4.95 out of 5 average rating, 93 reviews

Guest suite in Tigard

Comfy Guest Suite on Bull Mountain

GustavoRating, 5 stars5 days ago

Kelcie’s guest house was comfortable and clean. The area was nice and check in/check out instructions weee easy to follow. Kelcie was also responsive via the Airbnb app to answer any questions! We enjoyed our stay.

4.97 out of 5 average rating, 88 reviews

Tiny home in Beaverton

Beaverton Vintage Tiny Home

SamuelRating, 5 stars2 weeks ago

Such a cozy getaway! We wanted a place near the city, but something more unique than a hotel. This was perfect! Just the right amount of space. The house was supplied with everything we could have needed. If we didn’t have something or needed a refill, the hosts were happy to help! We recommend walking the neighborhood near by or going up the road to the hiking/bike trail for great views!

4.98 out of 5 average rating, 87 reviews

Carly's Comfort Inn

AnnaRating, 5 stars2 weeks ago

This is such a lovely and comfortable spot. Wonderful, walkable neighborhood and close to the charming town of Sherwood. Such a comfortable space and bed with patio view of Mt Hood! We loved our stay.

5 out of 5 average rating, 15 reviews

Cozy Haven |Fire Pit |EV Charger |Central A/C

SeijaRating, 5 stars2 weeks ago

Perfect host, spacious and comfortable home, kid friendly!! Would highly recommend 💯 My extended family and I greatly enjoyed our vacation here! We loved the space, indoors and outside, everything was very comfortable. Kristen was friendly and responsive, with clear information at booking and check-in. I was amazed at the thoughtful supplies for young kids! A cute bedroom with toys and a bunk bed, pack and play, black out shades, and even child utensils and dishes! High quality supplies provided in the bathrooms and kitchen made this experience above and beyond. We'd definitely stay here again!

5 out of 5 average rating, 27 reviews

Guest suite in Aurora

Mt Hood View near Champoeg Park!

AlexandraRating, 5 stars2 weeks ago

We had a fantastic stay. The space was even better than I expected from the listing - very clean, nice furnishings, great shower, and a stunning deck. The bed could’ve been bigger for the space, but I found it to be very comfortable. Communication was clear and quick, and I appreciated that Raquel proactively shared a list of local recommendations. If looking for a place to stay in wine country again, I will absolutely seek out this property. It was a wonderful spot!

5 out of 5 average rating, 57 reviews

Oaks Hideaway~ Countryside Privacy, Patio & Cake

CindyRating, 5 stars3 days ago

What a wonderful stay! We appreciated everything about the home. The location was beautiful, peaceful, and perfectly located. Detail was given to everything from homemade soaps from a local shop, blackout blinds in the bedroom, Black Rifle Coffee and more. We were so at peace and comfortable. We will definitely be staying here again.

Superhost

Flat in Newberg

4.79 out of 5 average rating, 14 reviews

Wine Country with a Nature View

JeannetteRating, 5 stars1 month ago

Enjoyed my stay. The property was clean, comfortable and provided all the necessaries - she even had a basket of "often forgottens" for guests which was really nice. 10/10 - would stay again.