Sherwood holiday rentals

We found 1,970 holiday rentals — enter your dates for availability
Discover a selection of 10 homes and other holiday rentals in Sherwood that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you expect for your stay, which might include a fireplace and a washer and dryer. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Sherwood

Showing deals for:25 Dec - 1 Jan

Interior
Exterior
Interior
Private kitchen
Exceptional
(29 reviews)

Huge Luxury Home with huge Deck near Powell Butte Park

Portland

7% off
AU$9,309
for 7 nights, 1 home
AU$1,330 per night
includes taxes & fees
Huge Luxury Home with huge Deck near Powell Butte Park
Living area
Outdoor dining
Interior
Private kitchen
Exceptional
(116 reviews)

Intimate Wine Experience with a "home" feel

Carlton

12% off
AU$5,506
for 7 nights, 1 home
AU$787 per night
includes taxes & fees
Intimate Wine Experience with a "home" feel
Interior
Terrace/patio
Property grounds
Property grounds
Wonderful
(65 reviews)

Stafford River House

West Linn

8% off
AU$3,551
for 7 nights, 1 home
AU$507 per night
includes taxes & fees
Stafford River House
Interior
Outdoor dining
Private kitchen
Interior
Exceptional
(34 reviews)

Room for Everyone! 7BR, 6.5BA Wine Country Retreat near Downtown

McMinnville

16% off
AU$13,101
for 7 nights, 1 home
AU$1,872 per night
includes taxes & fees
Room for Everyone! 7BR, 6.5BA Wine Country Retreat near Downtown
Formal living room with floor to ceiling curtains for privacy.
Exterior detail
36" Kitchen Aid french door fridge H20 & ice, windows to hot tub.
Tiled entry with original wood trim.
Excellent
(9 reviews)

Gorgeous private home! Central Air 4 beds, hot tub, patio, designer furnishings

Portland

7% off
AU$5,782
for 7 nights, 1 home
AU$826 per night
includes taxes & fees
Gorgeous private home! Central Air 4 beds, hot tub, patio, designer furnishings
Living area
Living area
Private kitchen
Interior
Exceptional
(22 reviews)

Stunning Ranch Home in Walkable Gorgeous Happy Valley Neighborhood

Happy Valley

8% off
AU$3,672
for 7 nights, 1 home
AU$525 per night
includes taxes & fees
Stunning Ranch Home in Walkable Gorgeous Happy Valley Neighborhood
1911 Wine Country Farmhouse Kitchen | Island Table
1911 Wine Country Farmhouse | 2-Blocks to McMinnville's Historic Downtown & Third Street | Steps to Chef-Driven Dining & Wine Tasting
Living Room Open to Dining Room | SmartTV & Wifi
Living Room | SmartTV | Wifi | Living Open to Dining
Exceptional
(232 reviews)

1911 Wine Country Farmhouse • Dog Friendly • 2 BKs to Wine & Chef-Driven Dining

McMinnville

9% off
AU$4,674
for 7 nights, 1 home
AU$668 per night
includes taxes & fees
1911 Wine Country Farmhouse • Dog Friendly • 2 BKs to Wine & Chef-Driven Dining
Dining
Living area
Room
Private kitchen
Exceptional
(6 reviews)

2 King Suites • Mountain Views • Near Rose Garden

Portland

7% off
AU$5,582
for 7 nights, 1 home
AU$797 per night
includes taxes & fees
2 King Suites • Mountain Views • Near Rose Garden
Terrace/patio
Living area
Living area
Exterior detail
Exceptional
(39 reviews)

The Carlton Pinot House - Modern Vacation Home in the Heart of Willamette Valley

Carlton

8% off
AU$3,079
for 7 nights, 1 home
AU$440 per night
includes taxes & fees
The Carlton Pinot House - Modern Vacation Home in the Heart of Willamette Valley
Exterior
Living area
Interior
Interior
Exceptional
(7 reviews)

Remodeled cozy farmhouse on a 100 acre hazelnut orchard!

Saint Paul

8% off
AU$4,855
for 7 nights, 1 home
AU$694 per night
includes taxes & fees
Remodeled cozy farmhouse on a 100 acre hazelnut orchard!
1st-Bedroom (Primary-King) | Attached to 1st-Full Bath En-Suite | Walk-in Closet
Living Room | Open to Dining & Kitchen | Step Out to Patio | Hot Tub | Wifi
Private Hot Tub | Fully Fenced Yard | Gas Grill | Outdoor Seating
Living Room | Open Living Space | SmartTV | Step Out to Hot Tub | Wifi
Exceptional
(26 reviews)

Carlton Townhouse No. 2 • Private Hot Tub • Dog Friendly • 1 BK to Wine-Dining

Carlton

9% off
AU$3,643
for 7 nights, 1 home
AU$520 per night
includes taxes & fees
Carlton Townhouse No. 2 • Private Hot Tub • Dog Friendly • 1 BK to Wine-Dining
Living area
Property grounds
Private kitchen
Property grounds
Exceptional
(16 reviews)

Charming and minimal with private Backyard ADU 1-bedroom, 1-Bath. Tesla Charger

Portland

7% off
AU$1,749
for 7 nights, 1 home
AU$250 per night
includes taxes & fees
Charming and minimal with private Backyard ADU 1-bedroom, 1-Bath. Tesla Charger
Patio | Fully Fenced Yard | Umbrella Seating | Gas Grill | Twinkle Lights | Heat Lamp | Dog Friendly
Kitchen Open to Dining & Living Room
Living Room | Fireplace | Open to Dining & Kitchen | Step Out to Patio | SmartTV | Wifi
Upstairs Leads to 2-Bedrooms, 2 Bathrooms, Office w/ Sleeper Sofa & Laundry
Exceptional
(37 reviews)

Carlton Townhouse No. 6 • Dog Friendly • Fireplace • BBQ • 1 BK to Wine & Dining

Carlton

9% off
AU$2,878
for 7 nights, 1 home
AU$411 per night
includes taxes & fees
Carlton Townhouse No. 6 • Dog Friendly • Fireplace • BBQ • 1 BK to Wine & Dining
Fully stocked Chef's kitchen.
Picture yourself enjoying a glass of wine surrounded by modern chic.
A lovely cozy room to wake up in.
Oversize custom Italian tiled shower.
Exceptional
(169 reviews)

★ CLEAN ★ NEAR DOWNTOWN + PRIVATE PATIO ★ WALKABLE

Portland

7% off
AU$2,581
for 7 nights, 1 apartment
AU$369 per night
includes taxes & fees
★ CLEAN ★ NEAR DOWNTOWN + PRIVATE PATIO ★ WALKABLE
Exterior detail
Exterior detail
Outdoor dining
Garden gnomes abound!
Exceptional
(272 reviews)

Peaceful Garden Cottage, Close to Mt. Tabor Park & Downtown Bus

Portland

6% off
AU$1,637
for 7 nights, 1 cottage
AU$234 per night
includes taxes & fees
Peaceful Garden Cottage, Close to Mt. Tabor Park & Downtown Bus
Garden room private deck looking to Council Crest. Deck seats two.
Our home on a snowy day in winter
Living Room from entry way looking to French doors to deck.
Living room looking at front door
Exceptional
(176 reviews)

Sunny 1400 SQFT Dutch Colonial in Portland Heights - 5 min to downtown, NW 23rd

Portland

7% off
AU$2,005
for 7 nights, 1 home
AU$286 per night
includes taxes & fees
Sunny 1400 SQFT Dutch Colonial in Portland Heights - 5 min to downtown, NW 23rd
Living room
Property grounds
Exterior detail
Living area
Exceptional
(340 reviews)

A garden view hideaway in the Irvington neighborhood

Portland

7% off
AU$1,637
for 7 nights, 1 apartment
AU$234 per night
includes taxes & fees
A garden view hideaway in the Irvington neighborhood
Terrace/patio
Exterior detail
Living area
Room
Exceptional
(8 reviews)

Cozy caravan in Mississippi area of Portland with WiFi, AC

Portland

9% off
AU$1,276
for 7 nights, 1 home
AU$182 per night
includes taxes & fees
Cozy caravan in Mississippi area of Portland with WiFi, AC
Dining
Private kitchen
Living area
Exterior
Exceptional
(10 reviews)

For 2 - Perfect, Cozy Wine Country Escape

Dayton

10% off
AU$1,656
for 7 nights, 1 home
AU$237 per night
includes taxes & fees
For 2 - Perfect, Cozy Wine Country Escape
Property grounds
Dining
Exterior detail
Living area
Exceptional
(17 reviews)

Charming 1-bedroom apt; cleaned with non-toxic, plant based cleaning products

Milwaukie

9% off
AU$1,545
for 7 nights, 1 apartment
AU$221 per night
includes taxes & fees
Charming 1-bedroom apt; cleaned with non-toxic, plant based cleaning products
Living area
Room for 8 at the dining room table
Terrace/patio
Private kitchen
Exceptional
(8 reviews)

Flower Farm with Vineyard Views

Dayton

12% off
AU$3,016
for 7 nights, 1 home
AU$431 per night
includes taxes & fees
Flower Farm with Vineyard Views
Welcome to the Irvington Guesthouse!
Living area
clean and fully stocked professional kitchen
nice details, fun lighting.
Exceptional
(47 reviews)

Cottage in Historic Irvington neighborhood near Convention Center and shops!

Portland

7% off
AU$1,655
for 7 nights, 1 room
AU$236 per night
includes taxes & fees
Cottage in Historic Irvington neighborhood near Convention Center and shops!
Exterior
Exterior
Interior
Property grounds
Exceptional
(91 reviews)

Charming, Private, Detached Studio!

Portland

7% off
AU$914
for 7 nights, 1 apartment
AU$131 per night
includes taxes & fees
Charming, Private, Detached Studio!
Outdoor dining
Living area
Private kitchen
Exterior
Exceptional
(59 reviews)

Cozy Modern Farmhouse, King bed, great yard, pets!

Milwaukie

17% off
AU$3,806
for 7 nights, 1 home
AU$544 per night
includes taxes & fees
Cozy Modern Farmhouse, King bed, great yard, pets!

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The lush setting of Sherwood is ready to explore

The forests and wildlife create a pretty picture of Sherwood. Renowned for its cycling, bird watching and restaurants, this city welcomes all visitors. Oregon Convention Center and Moda Center are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Sherwood

Are you hoping to discover things to do during your stay? Venture out of your cosy holiday rental and experience everything that makes Sherwood a one-of-a-kind holiday spot. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Chehalem Winery (4.8 mi / 7.7 km)
  • Wilsonville Family Fun Center and Bullwinkle's Restaurant (4.8 mi / 7.8 km)
  • Charbonneau Golf Course (6.1 mi / 9.9 km)
  • Cooper Mountain Vineyards (6.9 mi / 11 km)
  • Langdon Farms Golf Club (6.9 mi / 11.1 km)
  • Oswego Hills Vineyard and Winery (8.4 mi / 13.5 km)

Exploring the natural landscape of Sherwood

Whether you're an active traveller or just want to appreciate the scenery, Sherwood is a great place to get outside. These are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • Wilsonville Memorial Park (5.6 mi / 9.1 km)
  • Tualatin Hills Nature Park (9.9 mi / 15.9 km)
  • Gabriel Park (9.9 mi / 16 km)
  • Pendleton Park (10.1 mi / 16.2 km)
  • Willamette Falls (10.7 mi / 17.3 km)
  • Sellwood Riverfront Park (11.5 mi / 18.5 km)

Travelling to and around Sherwood

The nearest airport is in Portland International Airport (PDX), located 20.1 mi (32.4 km) from the city centre. If you're unable to find a flight that fits your schedule, you can also fly into Salem, OR (SLE-McNary Field), which is 32.1 mi (51.7 km) away.

Frequently asked questions

What is the best area to stay in Sherwood when booking a holiday rental?
When considering the best area to stay in Sherwood, Oregon, for a holiday rental, the downtown district is an excellent choice. This charming neighbourhood offers a vibrant setting with a variety of shops, cafes, and restaurants, making it a delightful place to explore. One of the top attractions in the area is the Sherwood Historical Museum, which provides insight into the local heritage and culture. Additionally, the nearby Sherwood Forest Park offers beautiful green spaces, great for leisurely walks or picnics.Another appealing option is the surrounding residential areas, which often feature a mix of quaint homes and modern properties. These neighbourhoods are typically quieter and provide a more suburban feel, while still being conveniently located near essential amenities. The proximity to the Tualatin River National Wildlife Refuge is a significant draw for nature enthusiasts, offering opportunities for birdwatching and hiking.
What is the most popular type of holiday rental accomodation in Sherwood?
In Sherwood, holiday houses are the most popular type of holiday rental, with around 27 available throughout the area. These properties are typically spacious and family-friendly, featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for gatherings. Additionally, there are approximately 12 cottages that provide a quaint and charming feel, often set in scenic surroundings. For those seeking a rustic experience, several cabins can be found, which usually offer cozy interiors and outdoor spaces for relaxation. There are also several apartments and mobile homes available, suiting different types of travellers.
Are there any family house rentals in Sherwood?
In Sherwood, Oregon, there are several family-friendly house rentals available, making it a great destination for those travelling with children. The town features a variety of properties, many of which boast spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces for kids to enjoy.Visitors can explore nearby attractions such as the scenic Tualatin River National Wildlife Refuge, which offers opportunities for hiking and wildlife viewing, or the charming local parks that are great for picnics and playtime. Additionally, the area is close to the vibrant city of Portland, providing easy access to its myriad of cultural and culinary experiences.
Are there pet-friendly house rentals in Sherwood?
In Sherwood, there are several pet-friendly house rentals available, offering a comfortable stay for you and your furry companions. Many of these properties come equipped with modern amenities such as fully stocked kitchens, spacious living areas, and private outdoor spaces where pets can roam freely.The rentals often feature features like fenced yards, ensuring a safe environment for your pets, and some even provide access to nearby walking trails and parks. The charming downtown area of Sherwood has pet-friendly cafes and shops, making it easy to enjoy the local scene with your four-legged friends.
Are there any remote work holiday rentals in Sherwood?
In Sherwood, Oregon, there are ample options for remote work holiday rentals, with around 45 properties available to choose from. This charming town offers a conducive environment for working remotely, featuring amenities tailored for productivity. Many rentals come equipped with high-speed internet, dedicated workspaces, and comfortable furnishings that allow for a seamless work-life balance.Sherwood itself is known for its picturesque surroundings, including easy access to parks and nature trails, providing great opportunities for relaxation during breaks. The nearby Tualatin River National Wildlife Refuge offers scenic walking paths and wildlife viewing, enhancing your remote work experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Sherwood?
In Sherwood, popular holiday rental amenities include well-equipped kitchens, allowing guests to prepare their own meals, as well as decks or patios for enjoying the outdoors. Many rentals also provide coffee and tea makers for a convenient caffeine fix, onsite parking for added convenience, and fireplaces that create a warm and inviting atmosphere.
When is the best time to visit Sherwood for a holiday rental?
The best time to visit Sherwood for a holiday rental is during the vibrant summer months of June to August, with July being particularly popular. This peak season attracts travellers who are eager to explore the local wineries, enjoy outdoor activities, and soak up the sun in the beautiful parks. The warm temperatures, typically ranging from 15 to 30 degrees Celsius, create a friendly space for both relaxation and adventure.During this period, visitors can indulge in Sherwood's renowned wine country, where vineyard tours and tastings are a delightful way to experience the region's rich agricultural heritage. Additionally, outdoor enthusiasts can take advantage of the pleasant weather for hiking, biking, and leisurely strolls in the picturesque surroundings.For those looking for a more budget-friendly option, consider planning your visit in December. While this month falls into the low season, it offers a unique charm with festive decorations and a quieter pace, allowing for a more intimate experience of the town's attractions.
What are the top attractions in Sherwood?
In Sherwood, visitors can enjoy a range of attractions that highlight the charm of this small town. The historic downtown area offers a selection of quaint shops and eateries, great for a leisurely stroll. Nearby, the Sherwood Centre for the Arts hosts various cultural events and performances, making it a cultural hub for locals and visitors alike.For nature enthusiasts, the Tualatin River National Wildlife Refuge is a must-visit, providing scenic walking trails and opportunities for birdwatching. The adjacent parks, such as Woodhaven Park and Sherwood Nature Park, offer ample space for outdoor activities, picnics, and play areas for children.Additionally, the annual Sherwood Robin Hood Festival celebrates the town's history and community spirit, drawing visitors with its lively option and family-friendly activities.
Are all fees included in the Sherwood holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Sherwood holiday homes with parking?
Stayz offers a wide selection of holiday homes in Sherwood with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Sherwood holiday homes?
You can find great discounts on holiday homes in Sherwood on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Sherwood holiday home booking on Stayz?
To find Sherwood holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Sherwood?
A long-stay holiday home in Sherwood is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Sherwood holiday home?
Book your Sherwood holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Sherwood?
Prices for holiday homes in Sherwood vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Sherwood to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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