Holiday rentals in Chehalem

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Top-rated holiday rentals in Chehalem

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

A tranquil outdoor space features two wooden chairs and a round table, positioned to enjoy a breathtaking sunset. The sky is adorned with vibrant purple and orange clouds, casting a serene light over the landscape below.

Home in Newberg

Parrett Mtn Estate · Hot Tub, Sauna & Valley Views

8 private acres atop Parrett Mountain — sweeping Pinot Noir vineyard & valley views, Tempur-Pedic suites & heated stone floors. The only estate in Willamette Valley with an Oregon Red Cedar sauna, cold plunge, starlit hot tub & Universal EV Charging. Two full chef's kitchens, Egyptian cotton linens, Dyson air purifiers & hair tools, 4 bedrooms, sleeps 12. Optional add-ons available: private chef, Sommelier wine tasting & concierge services. 5 min to Newberg · 30 min to Portland · 40 min to PDX.

LocationValueAccess

4.96 out of 5 average rating, 271 reviews

Top guest favourite

A vibrant outdoor space features a patio set with black metal chairs and a table, overlooking a lush garden. Colorful autumn foliage surrounds the area, with greens, oranges, and reds, while a double rainbow arcs gracefully over the scene, enhancing the landscape.

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.

FamilyValueView

4.99 out of 5 average rating, 294 reviews

Top guest favourite

The living area features a comfortable reclining couch paired with a woven chair and an upholstered armchair. A bookshelf filled with books and decorative items enhances the space. Wall art and unique decor items are displayed throughout, contributing to a cozy and inviting atmosphere.

Guest suite in Sherwood

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.

LocationValueSolo travel

4.98 out of 5 average rating, 149 reviews

Top guest favourite

A picturesque vineyard landscape features rows of young grapevines leading up to a charming two-story house. The property is adorned with lush greenery and trees, set against a cloudy sky that hints at a tranquil atmosphere.

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.

ValueLocationKitchen

4.89 out of 5 average rating, 212 reviews

Top guest favourite

A spacious deck features a table set with gourmet snacks, a bottle of wine, and glasses, surrounded by comfortable seating. The lush vineyards and cherry blossoms are visible in the distance, under a clear blue sky, offering a serene outdoor setting.

Home in Newberg

Vineyard and Mountain View Wine Country Retreat

Our property is available to adults looking for some peaceful time. Conveniently located, our home will be a retreat to come back to after a day of exploring gastronomy and wineries in nearby towns. Numerous vineyards are in the immediate vicinity. On clear days enjoy views from our large deck of Mt Hood, St Helens, Rainier, and local vinery. We take great pride in maintaining a quality environment to share with others. Carefully read Additional Rules to decide if our home fits your needs.

ValueLocationBiking

4.94 out of 5 average rating, 142 reviews

Top guest favourite

The living room features a comfortable large sofa and an armchair, arranged around a coffee table on a patterned area rug. A flat-screen TV is mounted above a brick fireplace, and natural light filters through the window, complemented by light-colored curtains.

Guest suite in Sherwood

Sherwood Hollow- Senior discount (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.

FamilyValueKitchen

4.98 out of 5 average rating, 337 reviews

Top guest favourite

A charming craftsman home is framed by a white picket fence, with a welcoming front porch and a pergola overhead. The exterior features dark blue siding, three front-facing windows, and lush greenery surrounding the entrance.

Home in Sherwood

Old Town Retreat - Best place in Old Town Sherwood

At the gateway to wine country, our peaceful Old Town 1916 craftsman home brings historical charm with many amenities right in the heart of Old Town Sherwood. Sleeps 9 with 6 new beds, 2.5 remodeled baths and an open kitchen with gas range, everything you need for a few or many. Owner occupies the basement and rear separated dwelling on property. However, both the basement and rear dwelling are completely locked off and have entirely separate entrances. The best place in town.

FamilyLocationBathroom

4.99 out of 5 average rating, 189 reviews

Superhost

A light-filled living area features a comfortable gray sofa with accent pillows, situated adjacent to a wooden coffee table. A large mirror reflects the space, and a dining area with blue chairs is visible in the background, enhancing the welcoming ambiance.

Townhouse in Sherwood

Cozy 2 bed, 1 bath, private backyard in Sherwood

Whether you are visiting family, on a getaway, going wine tasting, or want to be close to Portland but not in it....you will feel right at home staying in our 2 bedroom, 1 bath duplex! (This is half of the duplex- all one level- LEFT SIDE). You can enjoy the private fenced back yard, fenced front yard, and 1 car garage. It is located close to wine country, lots of parks (including dog parks), VERY close to local restaurants, shopping, family game center (Langers), and highway 99W.

ValueLocationHeating

4.81 out of 5 average rating, 166 reviews

Guest favourite

A spacious outdoor deck features a white Adirondack chair overlooking a vast landscape. The view encompasses rolling hills and a horizon that fades into the distance under a clear sky. Hues of autumn are visible in the trees and ground, adding color to the scenery.

Home in Newberg

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

LocationFamilyWifi

4.94 out of 5 average rating, 236 reviews

Guest favourite

A light blue teapot with delicate floral designs is positioned in the foreground. Behind it, several clear glass wine glasses are arranged, reflecting soft light from a nearby lamp that casts a warm glow across the surface.

Guest suite in Sherwood

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.

LocationValueBack garden

4.88 out of 5 average rating, 388 reviews

Top guest favourite

A modern living area features a light grey sectional sofa and a round coffee table placed on a textured area rug. Natural light enters through large windows, illuminating the space. A wall-mounted TV and a cozy armchair complement the inviting atmosphere, with a fireplace enhancing the comfort.

Home in Newberg

Villa Fontana: Modern, Wine-Country Comfort

Welcome! Enjoy a fresh, clean, retreat while you sip your way through Oregon's Wine Country. A modern home nestled amid local historic landmarks, you will be 6 blocks from the downtown Newberg strip and within a 5 mile radius of the closest wineries, making this home the perfect choice for accessibility. Enjoy complimentary Prosecco to toast your arrival and plan to cook meals that pair with your local wine purchases using our high-end appliances!

FamilyLocationSleep quality

4.98 out of 5 average rating, 224 reviews

Top guest favourite

An inviting entrance showcases a fountain surrounded by lush greenery and stone pathways. The front door, framed by ornate pillars, opens to a well-lit interior. Soft lighting enhances the welcoming atmosphere, with a seasonal wreath adorning the door.

Home in Sherwood

Chateau Chardonnay:Tuscan home in NW wine country

Equipped with two HEPA air filtration systems that work continuously to filter and sanitize the air, this home is a clean and safe space to relax and enjoy nature! The house sits on 4 acres in the picturesque Oregon wine country. The back deck looks out over a lush back yard that cascades down to a lazy creek. Gaze out the large kitchen window to the paver patio, vibrant lawn and rimmed with beautiful mature landscaping, koi pond and fountain.

LocationValueHospitality

4.95 out of 5 average rating, 170 reviews