Holiday rentals in Sheridan

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Top-rated holiday rentals in Sheridan

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Top guest favourite

A view from a balcony showcases a lush garden with well-maintained paths and diverse greenery. A gentle slope leads to a picturesque landscape, featuring trees and shrubs. In the distance, a figure can be seen tending to the garden, adding subtle activity to the serene environment.

Guest house in Amity

5 out of 5 average rating, 246 reviews

Wine Country Garden Retreat

Located in the heart of wine country, dozens of wineries within miles, the nearest across the drive "BraVuro Cellars" featuring Big, Bold Reds. 12 miles to Historical McMinnville. One hour to the Oregon Coast and Portland. Our farm offers 1.5 acres of year round specialty gardens, attracting the rare blue butterfly, Willamette Valley birds including migrating evening grosbeak. Horses, goats chickens and 3 friendly labs Enjoy our other listing at https://www.airbnb.com/h/heartofwinecountryretreat

Top guest favourite

A serene pond reflects a red barn and surrounding evergreen trees at sunset. Tall grasses frame the foreground, enhancing the tranquil scene. The warm hues of the sky contrast with the calm water, contributing to the peaceful ambiance of the setting.

Guest house in Sheridan

4.97 out of 5 average rating, 129 reviews

Chalet Retreat-Pond, Mountains & Barn View

The Chalet is nestled in the Coastal Range Mountains. It includes 2 decks with views of the beautiful pond & barn in front & secluded acreage out back. Waiting for you are winding paths with wooden bridges over a trickling stream. You will enjoy a variety of wildlife following the paths or just sitting on the deck! Relax in the stylish, roomy studio in the heart of wine country. Just 14 miles from Spirit Mountain Casino, 21 miles from McMinnville, 41 miles to Lincoln City and 27 miles to Salem.

Guest favourite

A spacious studio apartment is presented with a comfortable cream-colored couch and a patterned area rug. A queen-sized bed is visible in the background, accompanied by a cozy wood stove. Natural light enters through a window, enhancing the neutral-toned walls.

Loft in Willamina

4.94 out of 5 average rating, 153 reviews

MerryOtt's Owl'sLoft (near Spirit Mountain Casino)

AWAY FROM IT ALL BUT NEAR THE BEST--Oregon Private entrance, breath-taking views, clean, spacious, serene, secluded, rural, 5 acres, studio apt. above garage. Approx. driving minutes to: Oregon coast/Lincoln City(40); Spirit Mnt Casino(10); wineries(15-40); golf(25); fishing(40); WhipUp trailhead: 103 trails for cycles, bikes & hikes(15); McMinnville: Linfield College, 3rd Street restaurants, shops & wine bars(30); Willamina(5); Sheridan(10); Delphian School(15); airports: PDX(90), Salem(45).

Top guest favourite

A spacious living area features a light grey sofa complemented by two armchairs. A large, flat-screen TV is mounted above a decorative fireplace. Natural light streams through sheer curtains, and a dog sits on a rug, contributing to the inviting atmosphere.

Home in Sheridan

4.87 out of 5 average rating, 151 reviews

Cozy 2-bed Spanish Home on the River

The Casita Del Rio has been set up for maximum comfort and enjoyment on your vacation. We have two 4K TVs (one in the living room and one in the front bedroom) and a smaller TV in the back bedroom. There is a small workstation setup for remote work in the living room with both WiFi and ethernet cable access and board games available for your entertainment. A beautiful view over the river and a full kitchen also await you! *Brand New Ductless AC units in both bedrooms & living room!*

Top guest favourite

A handcrafted yurt is nestled among lush greenery, surrounded by tall trees. The structure features a round shape with a white exterior and decorative wooden lattice windows. In the foreground, a stack of firewood is visible, indicating readiness for cozy fires.

Yurt in McMinnville

4.94 out of 5 average rating, 156 reviews

Amico Roma Year Round Yurt and Sauna

Year round all season glamping yurt in wine country. Private hand crafted yurt nestled among wild life and hiking trails. Experience a cozy wood stove, dome with view of stars and an out of this world hot shower with views. Picnic, sit around our outdoor campfire or read a book under a Pendleton blanket in front of the indoor wood stove. All of the kitchen ammenities for cooking. An adventure you won't forget. Sauna with cold shower rinse and private hot shower also on property!

Guest favourite

A yurt is nestled among mature oak trees, surrounded by natural greenery. Wildflowers are in the foreground, contrasting with the earthy tones of the yurt’s exterior. A wooden deck extends from the yurt, providing outdoor seating and a serene view of the tranquil landscape.

Yurt in Salem

4.94 out of 5 average rating, 654 reviews

Wine Country Retreat at "The Yurt at Shady Oaks"

Unique luxury in the heart of Oregon Wine Country! Spacious, beautifully decorated yurt located in a grove of mature Oak trees on 5.5 acres in the Eola Amity Hills AVA, minutes away from many award winning wineries! Near the Willamette River and Basket Slough National Wildlife Refuge. Yurt has private, large living area, a fully equipped kitchen, private bedroom and bathroom with tiled shower. Minutes from downtown Salem, 1 hour to the Oregon Coast! NO CONTACT CHECK IN!

Guest favourite

An outdoor area features a stone fountain with a turquoise finish, surrounded by a variety of potted plants. Lush greenery forms a backdrop, with a wooden trellis providing structure and additional plants adding color and texture to the serene space.

Guest house in Willamina

4.82 out of 5 average rating, 338 reviews

Riverside Cottage on River, by Wineries & Casino

This beautiful riverside cottage sits on a 14 acre estate, in a lush garden setting. Just 2.4 miles from Spirit Mountain Casino, in the heart of wine country, 2 miles from Willamina town, 26 miles from Lincoln City, 14 miles from McMinnville, and 22 miles to Salem. Enjoy this meandering riverfront property, complete with multiple gardens. A shared hot tub is available for ultimate relaxation. Navarra Gardens is a pure delight!

Guest favourite

The spacious main area features large windows that allow natural light to fill the room, highlighting the soft gray sectional sofa and a plush area rug. A stylish spiral staircase leads to the loft bedroom, while a dining table is set in the corner.

Guest house in Salem

4.97 out of 5 average rating, 575 reviews

Charming 1 bedroom loft/barn apt with hot tub

Take it easy at this unique and tranquil getaway! Nestled in the heart of the Willamette Valley, this peaceful loft is perfect for the couple looking to relax and recharge. Enjoy our local farmers markets, or a baseball game at Volcanoes Stadium. Tour our local restaurants and wineries or see what’s happening this summer with our local music scene. Visit our many hikes and trails or float our rivers and lakes - and on and on!

Guest favourite

The charming round house, surrounded by lush greenery, features large windows and a spacious deck. Vibrant flowers and ferns adorn the garden, contributing to the serene setting. Tall trees provide shade, framing a glimpse of the expansive landscape beyond.

Dome in Amity

4.97 out of 5 average rating, 281 reviews

Round House Retreat in the Woods

This peaceful round house offers a retreat from city life. Located on over 20 acres, this property offers complete silence, relaxation, and breathtaking views of the beautiful Willamette Valley below. The design offers an open floor plan as well as the unique experience of living in the round! The house is just a few minutes from numerous wineries and restaurants in Amity and McMinnville.

Guest favourite

A cabin is nestled beside a 40-acre vineyard, with rows of green grapevines leading towards the forested backdrop. The scene is illuminated by soft sunlight, highlighting the cabin's rustic design and the natural setting of trees and open fields.

Cabin in Gaston

4.95 out of 5 average rating, 630 reviews

Great Cabin- Heart Of Wine Country!

Overlooking a 40 acre vineyard, this beautiful cabin is the epitome of Pacific Northwest craftsmanship. Come enjoy views of the Willamette Valley, it's sprawling vineyards, and most importantly sit back and relax! Looking for an event venue? Contact us for great options for your next event - we offer both indoor and outdoor space - plus you can stay on site!

Top guest favourite

A charming gazebo is surrounded by lush greenery, featuring a wooden deck and steps leading to a pair of spacious outdoor seating areas. A circular fire pit made of stone is centered on the deck, providing a cozy gathering place.

Cabin in Dallas

4.95 out of 5 average rating, 253 reviews

Oregon Treehouse Getaway!

The perfect cozy treehouse oasis! Wake up surrounded by greenery next to a cozy fire overlooking a peaceful pond. From the fireplace outside on the balcony to the beautiful octagon windows bringing in all natural light! You will be able to un-plug and truly wake up feeling like you’re in paradise. Come, relax, unplug, and reset!

Top guest favourite

The exterior of a large, white farmhouse is showcased against a blue sky dotted with clouds. Lush greenery surrounds the building, with flowering bushes and a front porch inviting to guests. The sloped roof features traditional shingles in warm tones.

Farm stay in McMinnville

4.96 out of 5 average rating, 103 reviews

Top Floor Flat on Historic Farm, Wine Country!

The Copper Clover Ranch is Conveniently located just 8 miles outside of McMinnville Oregon, directly off Salmon River Hwy, in the heart of wine country. The Bellevue Country Store, and Bernards Farm Stand are just up the road. Private entrance, with patio facing the Coastal range, and Bernard Farms in the distance.