Holiday rentals in Pine Grove

5 out of 5 average rating, 120 reviews

Tent in The Dalles

Creek-side Glamping Adventure

** no cleaning fees ** Experience year-round glamping at our Oregon retreat! Nestled by a serene creek, our cozy tent area harmonizes comfort with nature. Explore forest trails and a mountain snow-fed creek, relax by the fire pit, and wake up to alpacas, goats, ducks, and chickens amid scenic views. With a rustic barn, outdoor kitchen retreat, private bathroom, tub and invigorating outdoor shower, it's the ultimate escape, just 90 minutes from Portland. Book now for an unforgettable experience!

4.93 out of 5 average rating, 137 reviews

Cabin in Tygh Valley

Beautiful Log Cabin at Rock Creek Reservoir

Welcome to our log cabin! We are a family with 6 kids who really love this cabin and want to share it. Please enjoy yourselves and know that we are not a big corporation but a family. The deer come out in every season, don't be surprised if you see them in the driveway. We have a feeder on the side fence for them. The cabin has comfy beds, extra blankets and pillows, a fully stocked kitchen including cast iron to cook, chilly A/C, a wood stove for winter, & new reclining La-Z-Boy couches.

4.96 out of 5 average rating, 1,158 reviews

Tiny home in Sandy

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!!!

4.98 out of 5 average rating, 283 reviews

Home in Terrebonne

Pointe of Blessing with hot tub and canyon views

Prepare to be blown away by the astounding sunrises , sunsets and awesome moonrises you will enjoy at the Pointe of Blessing. We feel our canyon perch is a gift from God too good to keep to ourselves. Our cozy home sits atop an outcropping of rock which juts out from the canyon rim affording us unobstructed views up and down the length of the Crooked River Canyon. We overlook several holes of the Crooked River Ranch golf course and Smith Rock is visible in the distance to the South.

4.99 out of 5 average rating, 248 reviews

Home in Terrebonne

Stunning! Smith Rock • King Beds • Steam Shower

A wall of glass provides panoramic views of the iconic Smith Rock formation, creating a seamless connection between the indoor and outdoors. A sleek and sophisticated modern home perched on the rimrock and flooded with sunshine. King beds and a luxurious bathroom with steam shower. Includes Smith Rock Pass. *No parties or pets* (including support animals) please - this is a 'pet-free' home for guests with allergies. Trip insurance recommended if illness, weather or smoke may be an issue.

4.91 out of 5 average rating, 173 reviews

Cabin in Culver

Cabin on The Rim

Take it easy at this unique and private getaway. This off the grid studio cabin is located just 10 minutes from Smith Rock and 10 minutes from Lake Billy Chinook. It is positioned on the edge of the Crooked River Gorge with breathtaking views of the canyon. Near the cabin is a trail head to a private hiking trail that takes the adventurer down into the canyon where the scenery is otherworldly. Enjoy a sunset with full cascade Mountain View’s, green pastures, and grazing horses.

4.98 out of 5 average rating, 190 reviews

Cottage in Cook

Cozy Cottage In The Woods

Take it easy at this cozy and tranquil getaway located in the trees to give you a peaceful setting. This tiny cottage has everything you need. It’s located 25 mins away from the unique town of Hood River where there are endless activities. Everything from restaurants, breweries, hiking, kite boarding, Windsurfing, fishing, kayaking and more. It’s the perfect spot to get away from city life, but an easy drive if you want to enjoy what the surrounding towns have to offer!

4.78 out of 5 average rating, 181 reviews

Tiny home in Tygh Valley

A Tiny Home by the Lake & boat dock

Our place at the lake is amazing and relaxing!! This cabin is stocked with all the comforts of home. Along with extra activities...fishing, hunting, hiking, relaxing, ice cream, and much more.. This place is good for a couple or solo adventurers. This adorably decorated cozy cabin has a full-size bed and a twin size bunk. This cabin is about 200 feet from the lake, a short walk to the dock for water fun and beautiful sunsets!! NO DOGS NO PARTIES

4.92 out of 5 average rating, 144 reviews

Cabin in Tygh Valley

log cabin by lake in Pine Hollow Hot tub pizzaoven

Beautiful 1200 square foot log home is located a short walk away to Pine Hollow Lake in scenic Tygh Valley. This quiet community is great for family getaways or romantic weekends away. Enjoy hiking, skiing, fishing and many more outdoor activities in the heart of Mt Hood’s Tygh Valley. Located within driving distance of Timberline lodge, White River Falls and the Deschutes river. This is a family cabin and we do not allow parties!

4.89 out of 5 average rating, 383 reviews

Cabin in Maupin

Deschutes River front w/hot tub, Fire Table & AC

The cabin is just steps away from the Deschutes River. The cabin has all the creature comforts of a home. The kitchen has everything needed for preparing a gourmet meal and entertaining. The living room is cozy has a large smart TV and DVD play. There are books, games and DVDs for your entertainment. This is a wonderful place to work from home. A n extra monitor is provided and a printer scanner is available as well.

Place to stay in Estacada

4.99 out of 5 average rating, 260 reviews

"Worth 10 stars" Lucky Dawg Hideaway

Our LUCKY DAWG Hideaway is a well-equipped unique comfortable space with a queen bed, small kitchen, laundry area and bathroom. The cozy outdoor patio adds to your living area. Estacada is centrally located (abt an hour drive) to both downtown Portland and Mt Hood for all-year skiing and world-class hiking...Plus, we're about a 2.5 hour drive to either the beach or the high desert of central Oregon...

4.99 out of 5 average rating, 582 reviews

Cabin in Rhododendron

Klaus Haus-A cozy, modern retreat

This remodeled cabin is a beauty! It is architecturally unique with interesting lines, floor to ceiling windows, an open concept main floor, wood burning stove and a king sized bed in the loft. This is a great home base for exploring all that Mt. Hood has to offer and a beautiful space to relax in afterwards! We do have a deck but unfortunately it is under construction and currently unavailable.

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Other great holiday rentals in Pine Grove

4.91 out of 5 average rating, 33 reviews

Gorgeous Log Cabin At The Lake!

JoeRating, 5 stars1 month ago

Place was very clean lots of wildlife, deer geese Host was very quick to get back to us

5 out of 5 average rating, 40 reviews

Cabin in Brightwood

Barlow Haus

JenniferRating, 5 stars1 day ago

We had an absolutely wonderful stay at this cabin. From the moment we arrived, we were blown away by how thoughtfully decorated and cozy everything was. The interior has that perfect blend of rustic charm and modern comfort, with beautiful touches in every corner that made it feel warm and inviting. The area surrounding the cabin is incredibly peaceful and serene. It felt like our own private retreat—tucked away enough to enjoy total privacy, but still close enough to explore nearby sights if we wanted. Mornings were especially magical with the sounds of nature and the fresh, crisp air. It was the perfect place to unwind and disconnect. If you're looking for a quiet, beautifully decorated cabin in a stunning, private location, this is it. We can't wait to come back! The best for last is we accidentally left something behind and the host’s were so kind to ship it out to us !

4.89 out of 5 average rating, 53 reviews

Cabin in Lyle

Klickitat Canyon Cabin

KatherineRating, 5 stars1 week ago

My husband and I absolutely adored Klickitat Cabin. Before we even arrived Beda was excellent about communicating, and when we stepped inside we wanted to move in immediately (and wished we'd booked a few extra days there). The interior design is pitch perfect, from the colors of the pillows and linens and rugs to the art on the walls, but it's one of those places that's also as cozy and comfortable as it is stylish and chic (which I find to be rare). The kitchen had everything we needed; they more than provided for our little mini schnauzer with a bed and blankets and bowls; the views out the windows are beautiful; the beds were superbly comfortable, and the sound of the bugs was the perfect white noise. We had a great hike on Catherine Creek, too! Would absolutely recommend.

4.94 out of 5 average rating, 35 reviews

Cabin in Rhododendron

Glacier View Chalet

EmilyRating, 5 stars2 weeks ago

This place is stunning-- just as beautiful as the pictures and descriptions, with an incredible view of Mt. Hood from the living room. Thoughtfully designed, beautiful art, comfy furniture, with all the amenities you need for a peaceful getaway. The hot tub was a particular hit-- very clean, well-maintained, with an easy-to-remove cover. Just what our crew needed after our nearby day hike!

4.83 out of 5 average rating, 29 reviews

Luxury Lakefront Home!

JulieRating, 5 stars2 weeks ago

We loved the place, and Scott and Carrie were super easy to communicate with! They met our every need, and made our vacation weekend wonderful!

5 out of 5 average rating, 85 reviews

Cabin in Sandy

Arched Cabin with sauna on the Sandy River

ZoeRating, 5 stars5 days ago

This is such a special spot! So grateful we found it and we will definitely be back! So many thoughtful touches and attention to detail throughout the house, and an incredible location right on the river with views of Mt. Hood. Highly recommend!

4.92 out of 5 average rating, 90 reviews

Lake Front Home on Pine Hollow

MattRating, 5 stars6 months ago

This was our second time booking Jamie’s house. When our plans changed, Jamie was super flexible to accommodate our 2 day early arrival/ extension. House is comfortable and the kitchen is fully stocked. Checkout is a breeze with clear instructions. We will be back.