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Vacation rentals in Sherwood

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Top-rated vacation rentals in Sherwood

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The living area features a comfortable sofa and two armchairs arranged around a coffee table, with artwork displayed on the walls. Natural light enters through a window, and a dining table for four is positioned nearby, creating an inviting environment.

Home in Sherwood

4.87 out of 5 average rating, 142 reviews

Sherwood Inn - in Charming old town Sherwood

LOCATION! We have it!! Charming 4 bed/1.5 bath house in Old Town Sherwood, the Gateway to Oregon's Wine Country and all that the Dundee Hills/and Yamhill Carlton has to offer. Our remodeled house is walking distance to local restaurants, bars, wine bars, bakeries,antiques and a super cute coffee/whiskey house with a fire pit next door. The Library as well as several parks are close by. Plan your vacation or business trip with us in Sherwood and the enjoy what surrounding areas have to offer!

Top guest favorite

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

4.99 out of 5 average rating, 251 reviews

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.

Top guest favorite

A charming sign reading 'Willow Creek Cottage' is mounted on a yellow wooden wall. Lush greenery surrounds the entrance, adding a touch of nature to the welcoming facade.

Guesthouse in Wilsonville

4.95 out of 5 average rating, 545 reviews

Willow Creek Cottage

Enjoy country living in our charming and unique 1890s guest house. Situated on 12 acres in horse country. Great location - 20 minutes to Portland, 25 minutes to Oregon Wine Country, 90 minutes to the coast and five minutes from I-5 and Wilsonville. Bedroom with comfy pillow top queen bed. Breakfast nook with refrigerator, microwave and Keurig coffee maker. Direct TV and WiFi. **Please be assured that we continue to take all steps necessary to sanitize and air the cottage before your visit.

Top guest favorite

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

4.97 out of 5 average rating, 118 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.

Top guest favorite

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

4.88 out of 5 average rating, 193 reviews

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.

Top guest favorite

A cozy cabin with wooden exterior is set on a well-maintained grassy area, surrounded by a wooden fence. A concrete path leads to a welcoming porch with seating. A shed is visible nearby, adding to the charm of this peaceful outdoor space.

Guesthouse in Sherwood

4.99 out of 5 average rating, 167 reviews

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 (out of order), smart TV and second queen pull-out. The full bath features walk-in rain shower and full vanity.

Top guest favorite

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

4.98 out of 5 average rating, 301 reviews

Sherwood Hollow- Senior discount (60+) $88/night

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.

Top guest favorite

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

4.99 out of 5 average rating, 160 reviews

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.

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

4.85 out of 5 average rating, 138 reviews

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.

Top guest favorite

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

4.87 out of 5 average rating, 351 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.

Top guest favorite

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

4.96 out of 5 average rating, 140 reviews

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.

Top guest favorite

Two mini-Highlander cows are seen grazing in a grassy field, surrounded by a wooden fence and lush green bushes. A bright blue sky with fluffy white clouds creates a serene backdrop, enhancing the peaceful rural atmosphere.

Barn in Sherwood

4.97 out of 5 average rating, 183 reviews

Rustic Barn | Country Getaway

Nestled atop Parrett Mountain is our countryside barn ready for you to enjoy! Conveniently located to many vineyards, and a picturesque drive to close by cities. This space offers a fully stocked kitchen and plush bedding (1 Queen/ 1 Double). Come and slow down with our rural pace of life, unique accommodations and say hi to the mini cows. Check out our photos to imagine yourself in this peaceful paradise.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Cabins

Kick off your hiking boots at these rustic lodgings

Hotels

Stylish accommodations with great services and amenities

Popular amenities for Sherwood vacation rentals

Laptop-friendly workspace

Air conditioning

Other great vacation rentals in Sherwood

Top guest favorite

A cozy bedroom features a spacious bed with a patterned blanket. Light wood cabinetry provides storage options, while a nightstand complements the overall decor. The room is softly lit, creating a comfortable atmosphere for relaxation.

Guest suite in Tigard

4.95 out of 5 average rating, 111 reviews

Comfy Guest Suite on Bull Mountain

Top guest favorite

A cozy living area features a sectional grey sofa with soft throws draped over it. A flat-screen TV is mounted on a wooden wall. Natural light enters through a yellow door, illuminating the open space, which includes a round dining table set with clear glasses.

Apartment in Tualatin

4.96 out of 5 average rating, 281 reviews

Elk Place - Heart of Wine Country. Bdrm & Lvg Rm

An outdoor picnic table is positioned on a bed of natural mulch, surrounded by towering trees. The tiny house, featuring a red and white exterior, is visible in the background, complemented by a small fenced area and a grill.

Tiny home in Sherwood

4.91 out of 5 average rating, 203 reviews

Charming Fall Winery Getaway ~ Comfy and Cozy

Top guest favorite

An aerial view captures a sprawling estate surrounded by lush greenery and mature trees. The main house stands prominently among manicured lawns, while additional outbuildings are visible nearby. A winding driveway leads to the entrance, enhancing the serene country atmosphere.

Home in Wilsonville

4.98 out of 5 average rating, 221 reviews

Beautiful Dog Friendly Cottage on a 10 Acre Estate

Top guest favorite

A charming two-story cottage features light yellow siding and is adorned with lush greenery. An inviting entrance is framed by a trellis, leading into the home. Nearby, the landscaped garden showcases a mix of plants and flowers, contributing to a serene outdoor environment.

Cottage in Newberg

4.97 out of 5 average rating, 175 reviews

Oxberg Lake Retreat, lake & farm view in wine ctry

Top guest favorite

A bright master suite features a spacious bed dressed in white linens. Natural light filters through large windows, illuminating the room. Wall sconces provide gentle lighting, while decorative items are displayed on the walls, adding character to the space.

5 out of 5 average rating, 140 reviews

Mama J's

Top guest favorite

A spacious studio is depicted, featuring a comfortable sofa and a day bed placed near a large window. A king-size bed is positioned thoughtfully in the room. The floor is adorned with a decorative area rug, and dark curtains frame the windows, allowing natural light to filter through.

Guesthouse in Beaverton

4.99 out of 5 average rating, 326 reviews

Park Cottage

Top guest favorite

A golfer stands on a green tee-off area, facing a serene landscape filled with tall trees and lush grass. A small bucket of ice is positioned nearby, amidst the tranquil surroundings of a picturesque outdoor space.

Guesthouse in Newberg

5 out of 5 average rating, 468 reviews

Wine Country Spa House - Hot Tub/Sauna/Pool

Quick stats about vacation rentals in Sherwood

Total rentals
30 properties
Nightly prices starting at
€ 26 before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Sherwood?
Yes! Work meets play with ease at over 20 vacation rentals in Sherwood featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Sherwood?
Four-legged friends are welcome in Sherwood. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there family-friendly house rentals in Sherwood?
Sherwood has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Sherwood?
Experience the best of Sherwood with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Sherwood have wifi?
Absolutely! We offer over 10 house rentals with wifi in Sherwood. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Sherwood have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Sherwood. Enjoy a tailored experience with all the comforts you desire.

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