Vacation rentals in Upper Highland

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Top-rated vacation rentals in Upper Highland

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Guest favorite

Tiny home in Sandy

4.98 out of 5 average rating, 203 reviews

The Woodlands Hideout

The Woodlands Hideout is a small intentional retreat space, recently featured in Dwell. Designed and created with so much love, and with the hope that guests could immerse in the beauty of the natural world, but still offer some cozy and more essential comforts. You will love the large windows, the wood stove, and the calming aesthetic. Although the footprint of the space is small, we designed the experience to be outward focussed, so feels very expansive with the towering pine trees in view.

Apr 3 – 10

G$38,382 GYD per night

Guest favorite

Guest suite in Molalla

4.97 out of 5 average rating, 129 reviews

Old Oak Acres Relaxing Country Getaway

Old Oak Acres is 5 acres of rustic lodge feel w/ all the creature comforts, a beautiful view, & plenty of parking for your towable boat or trailer. Be our guest! Relax around our fire pit, cozy up on our inviting patio & enjoy the view. Fun to be had year-round. Paintball, hiking, boating, kayaking, wine tasting, skydiving, golf, antiques, shopping, snowshoeing, skiing & the fantastic annual Molalla Buckaroo in July! We are a short drive from Mt. Hood, Molalla River Corridor, Portland, & Salem

Aug 2 – 9

G$19,336 GYD per night

Guest favorite

Farm stay in Hillsboro

5.0 out of 5 average rating, 360 reviews

Oakwood Gardens Studio •Alpaca Farm• Wine Country

Experience an immersive farm adventure on 70-acres in the quaint community of Scholls, while being close to quality markets, great restaurants and exceptional vineyards. The Willamette Valley is recognized as one of the best Pinot Noir producing regions in the world. Enjoy hand-feeding alpacas and exploring paths in enchanting gardens and natural wetlands. Located six miles from Hillsboro and 14 miles from Portland. Offering seven unique and private accommodations. Please read all information.

Oct 7 – 14

G$25,288 GYD per night

Guest favorite

Tiny home in Sandy

4.96 out of 5 average rating, 1047 reviews

Mt Hood View Tiny House

Sandy's first and only Tiny House! Although this home is located just a mile from Hwy 26 within Sandy's city limits, it's located on a private 23 acres, so you'll feel completely secluded. This makes it the perfect place to stay while visiting the Mt. Hood area. The tiny house was built to capture the amazing view of Mt. Hood. The home was designed around a moving window wall system that completely opens to the outdoors allowing for one of the best views of Mt. Hood. We hope you enjoy!!!

Oct 5 – 12

G$38,214 GYD per night

Guest favorite

Guesthouse in Beavercreek

5.0 out of 5 average rating, 139 reviews

Muse Cabin in old growth forest w/cedar hot tub

Enjoy our beautifully remodeled cabin that is heated exclusively by the wood stove, on the edge of an old growth cedar forest on our 11 acre farm/vineyard. Relax on the deck built into the trees, and sleep in the cozy loft with ladder, as you soak in the nature around you. The cabin has a mini kitchen for cooking. The cute out house is just across the path, and is seasonally shared with other hip campers. We have a hot/cold shower at the hot tub. The cedar hot tub is next to the garden.

Mar 29 – Apr 5

G$24,491 GYD per night

Guest favorite

Place to stay in Woodburn

4.91 out of 5 average rating, 164 reviews

A-Frame Cabin: Picturesque view and cozy interior

Minutes from the Tulip Festival, a peaceful and cozy A-Frame, nestled in the trees overlooking a rippling creek. The stairs to the loft lead to a room where there is a comfortable queen-size bed and television. The downstairs area has a fully-stocked kitchen, dining area and living area with lots of windows to enjoy the view. There is also patio with a table and chairs and propane grill where you can sit and enjoy the view of the pasture and water, with beautiful trees scattered about.

Feb 24 – Mar 3

G$21,630 GYD per night

Guest favorite

Vacation home in Oregon City

4.93 out of 5 average rating, 460 reviews

Sunday Quiet, awesome Hood view, hot tub!

Welcome to our country home a mile to the Clackamas River, with panoramic view of Mt Hood from deck and hot tub. Advertised rate is for a private studio (queen bed) with its own entrance in the lower level of our two story home. You enter along a garden path onto private deck. Extra bedroom (king bed) is available only to guests staying in the studio for an additional $25/night per guest. (for all nights of the stay.) 14 mins to I-205, a mile to restaurants, 30 mins to airport (PDX).

Dec 8 – 15

G$17,377 GYD per night

Guest favorite

Tiny home in Damascus

4.92 out of 5 average rating, 637 reviews

Quaint Tiny House In The Trees. Damascus, Oregon.

Tiny House In The Trees (must leave message upon booking & 2 hour notice before arriving). A 150 ft. walk down a steep driveway takes you to a unique private little studio with everything an adventurous spirit needs. You must be in physically good shape to handle this location. We have friendly dogs you may see outside. 30 min. to Portland, One hour or less to the mountain, 40 min to waterfalls in the Columbia Gorge. Located in Damascus Oregon. Pool open in the summer season only.

Nov 22 – 29

G$12,345 GYD per night

Guest favorite

Apartment in Hubbard

4.96 out of 5 average rating, 140 reviews

Peace and Quiet on a Farm in the Country

Enjoy the peace and quiet of the country in a 2 bedroom apartment on a working berry farm. The apartment is located in a separate building away from the main house so there is lots of privacy as well. You can even pick your own marionberries and blueberries when in season. There are also a number of u-pick farms and farm stands in the area. When the restrictions for COVID-19 are lifted, you can be assured that the space will be thoroughly cleaned and disinfected.

Sep 19 – 26

G$19,544 GYD per night

Guest favorite

Guesthouse in Canby

4.95 out of 5 average rating, 180 reviews

Cozy Country Bungalow

*Cozy studio apartment on ten-acre farm. *One queen-size bed *Complete kitchen w/ range, dishwasher, microwave, refrigerator, toaster, and coffeemaker. *Large bathroom, sleeping area with queen bed, living/dining area, and washer and dryer access. *Wireless internet and wall-mounted 40" Smart TV with Netflix. *Relax on your private veranda, or go for a stroll on our 10 acre property. *Enjoy a picnic in the woods. Creek, pond, bridge, & view to enjoy.

Apr 14 – 21

G$19,827 GYD per night

Guest favorite

Guest suite in Oregon City

4.95 out of 5 average rating, 187 reviews

Farm Charm: 1000sq ft private studio in rural area

With unique vintage decor, this comfortable studio offers modern amenities in a peaceful country setting. The space has a private keypad entrance & 16 stairs (sorry, no elevator) to the guest studio attached to our home. Our friendly golden retriever Ollie will gladly greet you. Groceries & highway access are a mere 3 miles away. Portland is a short easy drive from our quiet country home.

Apr 15 – 22

G$23,800 GYD per night

Guest favorite

Cabin in Estacada

4.98 out of 5 average rating, 274 reviews

Creekside Cozy Cabin

Nestled among tall cedars, you'll find the Creekside Cozy Cabin a perfect place to relax and enjoy its calm surroundings. While there are neighbors on both sides of the cabin, you still get that country feel away from the city. We are 20 miles from PDX Airport and 21 miles from Downtown Portland, but the drive out to the cabin is worth every mile.

Jan 4 – 11

G$29,210 GYD per night