Holiday rentals in Sherwood

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Top-rated holiday rentals in Sherwood

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Top guest favourite

Home in Sherwood

4.99 out of 5 average rating, 144 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.

Guest favourite

Home in Northeast Portland

4.9 out of 5 average rating, 334 reviews

Huge Home with King Beds in Prime Spot with Views!

Architectural masterpiece on a safe, quiet street just blocks from Williams and Mississippi Ave, home to some of Portland’s best dining, drinking, shopping and more. Spread out across three spacious levels with multiple living areas, a large open kitchen with two eating bars, four king bedrooms and a bunk room (each with its own TV!), and 3.5 bathrooms. Relax and dine alfresco on the beautiful back patio, then watch sunrises and sunsets from the east and west facing roof decks!

Top guest favourite

Shipping container in Oregon City

4.97 out of 5 average rating, 124 reviews

Sustainable Dream Container Getaway with a View

A private green-luxury container home inside a bamboo grove and lavender field overlooking a serene valley. This brand-new, single-level home features picture windows leading out to a quiet deck with sunset views every night. Situated in the heart of the Pacific Northwest between the mountain, lakes and coast - exploration, wine tasting and the best nature spots are just a short drive away. This private home can comfortably host couples or up to 3 people including the couch.

Guest favourite

Cottage in Beaverton

4.93 out of 5 average rating, 105 reviews

Cozy Cooper Mtn Cottage

Uniquely cozy with all the amenities of home but in a cottage up on Cooper Mt. Where you are surrounded by trees , feel the breezes, sunrise and sunset in the same day, and sometimes the wonderful wildlife around us. Birds in the sky , rabbits and sometimes deer, and yes our two friendly goats. Oh yes and the expansive midnight sky with the bright stars twinkling above or the big round moon shining down on you as you sit on the patio in the evening enjoying the night air.

Top guest favourite

Guest house in North Portland

5 out of 5 average rating, 222 reviews

Richmond Cottage in St Johns, Portland

This light, bright cottage is located in the heart of the St Johns neighborhood in Portland. Full of charm it features loads of reclaimed wood with an industrial farmhouse vibe. Complete with a private deck, keyless entry, full kitchen with eat-in island and a sleeping loft with a queen sized bed. It is a close walk to restaurants, coffee shops, bars and shopping. Easy access to downtown Portland, University of Portland, the airport and the rest that Portland has to offer.

Guest favourite

Home in Laurelhurst

4.95 out of 5 average rating, 330 reviews

❤️ CLEAN ★ LUXURY OASIS ★ NEAR DOWNTOWN

☀ 10 Mins to downtown + Airport ☀ Free Private on-site parking ☀ Luxury queen bed • premium bedding ☀ Queen sleeper sofa in living room ☀ Fully stocked cook’s kitchen ☀ Large private patio ☀ Fire Pit + Gas BBQ ☀ Super Fast Wifi • USB charging outlets ☀ 65” 4K Smart TV ☀ Smart Home • Alexa equipped ☀ Nebia Spa shower ☀ Heated floors ☀ Steps from public transit ☀ Safe walkable neighborhood ☀ Bikes to explore Portland ★☆Learn More Below & Experience Portland With Us!★☆

Superhost

Home in Vancouver

4.76 out of 5 average rating, 188 reviews

Style Meets Comfort in Beautiful Design

Discover unparalleled comfort and style in this beautifully designed Vancouver retreat, perfect for families and groups seeking a memorable getaway. This spacious home hosts two living rooms, king-sized beds in every bedroom, and a fully equipped kitchen, this is where comfort meets convenience. Nestled in a peaceful neighborhood with easy access to local attractions, dining, and shopping, making it the ideal home base for your Pacific Northwest exploration.

Top guest favourite

Guest house in Central Northeast Portland

4.99 out of 5 average rating, 471 reviews

LoftHousePDX w/ Sauna & Hot Tub

Debuted during Portland's Accessory Dwelling Tour, “Loft House PDX” is centrally located just off beautiful Alameda Ridge. Business and leisure travelers alike will find a peaceful retreat awaiting them in this tastefully-appointed, open and airy, modern loft house with all the accoutrements one might wish for—including a Finlandia Sauna, and STIL hot tub to enjoy after a long day of work or play, and a custom gas firepit for evening lounging...

Top guest favourite

Guest suite in Sandy

4.97 out of 5 average rating, 240 reviews

The Cedar House at Riverbend Orchard

Escape to nature’s beauty at this serene retreat on 23 wooded acres overlooking the Sandy River. Sip coffee on the heated wraparound deck, curl up by the stone fireplace, or soak in the hot tub under the stars. Hike the private trails, discover the pond, and unwind in the sauna. Thoughtfully designed for relaxation, with cozy nooks, books, and breathtaking views. Well-trained dogs welcome! No cats or other pets due to severe owner allergy.

Superhost

Flat in Portland

4.82 out of 5 average rating, 122 reviews

La Petite- BRAND NEW!

ELEGANT URBAN OASIS IN PORTLAND'S DIVISION NEIGHBORHOOD. Step into an enclave of opulence and comfort in our newly designed Accessory Dwelling Unit (ADU). This private haven, sculpted with attention to every detail, stands as a testament to luxury and comfort, offering you Portland's finest in an intimate, and sleek setting. You'll cherish our ADU's tranquil ambiance and our foodie forward neighborhood.

Guest favourite

Home in Carlton

4.94 out of 5 average rating, 107 reviews

Lofty Vibes | Vineyard Views

Porch Light Vacation Rentals is proud to present Summers Hill Retreat, a peaceful escape with stunning vineyard views. This charming property features two queen bedrooms, two bathrooms, and a well-equipped kitchen. Outdoor spaces include a covered firepit, hot tub, and large patio, and a game cottage for cards and board games add to the fun. Book your stay now and experience this special retreat!

Guest favourite

Bungalow in Vancouver

4.98 out of 5 average rating, 66 reviews

Designer Bungalow | Walk to Water & Downtown

Location, location, location! Escape to this stylishly decorated 2-bedroom bungalow, just a short stroll from downtown Vancouver and the vibrant Waterfront District. Enjoy upscale dining, boutique shopping, and wine tasting rooms within walking distance. After a day of exploring, relax by the fireplace in the beautifully designed mid-century modern living space.