Holiday houses in Jennings Lodge

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Top-rated holiday rentals in Jennings Lodge

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Top Guest favourite
An open living area features wooden ceiling beams and large windows that offer views of the surrounding trees. A comfortable sofa sits beside a wooden table. The kitchen area includes modern appliances and white cabinetry, enhancing the space's functionality.
Guesthouse in West Linn
4.96 out of 5 average rating, 163 reviews

Charming one bedroom apartment in the forest.

This unique apartment above a garage/shop , detached from the main house. Tucked away into a urban forest. I call it Our Robin's Nest because you look out on to branches of large fir trees. It is very private , yet Starbucks is right next door. Private entry and off street parking. This space has everything you need full kitchen, washer&dryer, queen size bed and fold out couch , plus a Play and Pack for the Littles. Walkable neighborhood , parks market and restaurants within walking distance.

Top Guest favourite
A studio apartment features a cozy sleeping area with a spacious bed dressed in dark bedding accented by yellow cushions. An orange sofa is positioned in front of a coffee table. A dining table for two is visible, with a kitchenette in the background.
Apartment in West Linn
4.91 out of 5 average rating, 137 reviews

The Sweet Suite

This fully renovated studio apartment is designed with you in mind! The amazingly central location is less than a 2 minute drive to I-205 and walking distance to to B OTH West Linn's Central Village Shopping Center and Downtown Oregon City's Main Street! You will be surrounded by restaurants, shopping, cafes, and groceries, to name a few! All of that plus the thoughtfully designed interior make this sweet little suite the perfect place to rest your head for a night...or a week....or a month!

Top Guest favourite
A serene garden scene captures early morning fog enveloping vibrant fall foliage. Lush greenery is interspersed with colorful autumn leaves, providing a peaceful backdrop. The landscape features a variety of shrubs and trees, adding depth and texture to the tranquil environment.
Guest suite in Milwaukie
4.96 out of 5 average rating, 183 reviews

River Garden Cottage.

Charming cottage apartment on a garden and forest hill. Next to the Willamette River, 30 mins from downtown Portland. Relax, and enjoy the quiet and peaceful surroundings. Fully stocked kitchen. Fast wifi at 50 Mbps. Cozy inside in the wintertime, also with a park-like setting with walking access down the lush backyard to the river where you can enjoy swimming, fishing, kayaking, and bird watching. You can use the shared recreation room with ping pong, pool table, shuffleboard, and weights.

Guest favourite
A serene river view is visible, framed by lush trees and greenery. The clear water reflects the sky, while a gentle wake from a boat creates ripples. A sandy beach area is located in the foreground, alongside a manicured lawn and a fire pit.
Guesthouse in Milwaukie
4.88 out of 5 average rating, 183 reviews

Milwaukie Riverfront Guest House

Incredibly majestic river-front guest house. This is the ultimate romantic getaway and peaceful retreat. Large windows and double french doors look out on the Willamette river from the cottage living room and loft sleeping area. It includes a semi-private rocky beach, and a large manicured lawn with fire pit. Kayaks are available for use, and guests are welcome to bring their own too! The guesthouse has its own drive-way, and is completely separate from the main-house grounds for privacy.

Guest favourite
A charming blue cottage is framed by a welcoming front porch with wooden railings. Lush green plants and purple flowers decorate the landscape. An American flag is displayed on the railing, and a car is parked in the driveway alongside the property.
Bungalow in Gladstone
4.91 out of 5 average rating, 185 reviews

The Wee Humble Cottage

Cozy 1 bed, 1 bath, 100 yr old smoke/vape free cottage is conveniently located in Gladstone, OR; walking distance to local shops & antique mercantile. Within blocks of the confluence the Clackamas & Willamette Rivers. Just 1.5 mi from historic downtown Oregon City Main Street, Willamette Falls, Abernethy Center & End of the Oregon Trail Museum. Also conveniently located near the Trolley Trail Loop, a 19 mile long meandering walking/cycling trail through a series of quiet communities.

Top Guest favourite
A bright, modern room features a Queen Murphy bed with crisp white linens and yellow accent pillows. Two windows allow natural light, with views of a fenced outdoor space, enhancing the airy atmosphere. A small built-in sofa is positioned beside the bed, offering additional seating.
Guest suite in Milwaukie
4.99 out of 5 average rating, 315 reviews

Room In Between

Private and secure entrance to this modern and 5-Star space! Comfortable Queen Murphy bed that converts to a sofa. Fast Wifi and Smart TV w/access to Netflix & Prime Video. Fenced yard with security gate entrance, off of private paved driveway, to lead you to your own private patio & room entrance. Self check-in is at 2pm or later. Check out is 11am. No pets. Smoking allowed on the outside patio only. Flat entrance pathway is well lit from your parking space to your room & patio.

Top Guest favourite
A sunlit sunroom features large windows overlooking greenery, creating a bright space. A dark cushioned seating area is positioned against the window, complemented by a rectangular table. A patterned rug adds texture to the warm wood floor, enhancing the room's inviting atmosphere.
Guest suite in Westmoreland
4.97 out of 5 average rating, 568 reviews

A sunny separate studio w/skylights

Your own modern large studio on 2nd floor with separate entrance, full kitchen, sunroom, skylights, 14-foot ceiling, balcony, desk, full bathroom, washer/dryer, dishwasher, gas stove, lots of windows. All this in a vibrant neighborhood, short walking distance to multiple coffee shops, restaurants, a single-screen movie theater, the light rail station, an open-late grocery store, a small park with a salmon run. One mile to Reed College, where Steve Jobs took a calligraphy class.

Top Guest favourite
The exterior of a garden studio is illuminated by string lights, creating a warm ambiance at night. An inviting patio features two wooden chairs and floral greenery, while blooming white flowers add a touch of natural beauty to the space.
Guest suite in Milwaukie
4.99 out of 5 average rating, 454 reviews

Light Filled Garden Studio

Our wonderfully bright garden studio is perfect for a short stay or for visitors looking to explore Portland for an extended visit. It has a full, well-stocked kitchen, ideal for those looking to stay in and cook, but it’s also just a 20 minute drive from downtown, for those looking to explore the wonderful restaurant scene Portland offers. Keyless entry and private entrance through the side yard gate provide renters with complete autonomy during their visit.

Top Guest favourite
A modern kitchenette features sleek white cabinetry and a granite countertop with bar seating. Stainless steel appliances, including a microwave and coffee maker, are visible. Soft lighting from pendant lights and a lamp creates a warm ambiance. A decorative bowl rests on the counter.
Guest suite in West Linn
5 out of 5 average rating, 255 reviews

Arbor Suite Apt - Washer/Dryer, Desk, Free Parking

There is a private entrance to this 725 sq ft. bright, CLEAN, and SANITIZED guest apartment within a home, in a well established neighborhood on the border of West Linn and Lake Oswego. Spacious, beautifully furnished one bedroom with an office/den (includes fiber optic internet & monitor ) in a quiet and desirable suburb of Portland that offers a lush treed garden with a gas fire pit and patio. YouTube TV available. Close to Mary's Woods!

Top Guest favourite
A welcoming entrance features a vibrant red door bordered by large planters filled with green plants. Flanking the sides are bamboo and ferns, creating a calming atmosphere. The pathway leads to the entrance, showcasing a serene, nature-inspired setting.
Guesthouse in West Linn
4.94 out of 5 average rating, 459 reviews

Sunlit Oasis

This private, renovated art studio has skylights and quiet views of nature. As an interior designer, I loved creating a space that is as much an experience as a night away from home...and only 10 miles from downtown Portland! Please be advised that beginning Dec19, 2025, construction has begun on three homes behind our cottage. Work can begin at 7:00AM-4:00PM Mon-Fri. There could be noise during those hours, it's out of our control.

Top Guest favourite
An open living area is highlighted by a cozy sofa with patterned cushions and a spacious bed dressed in soft linens. A wooden dining table with chairs is set near a window, enhancing the light, airy feel of the space. An inviting side cabinet adds functionality.
Apartment in Milwaukie
4.97 out of 5 average rating, 204 reviews

Milwaukie Retreat in the Woods

Your private apartment is located on a wood filled lot with a private outdoor area, shade and even deer on occasion. We are 12 miles from the airport, near freeways with easy access to downtown, and to make your way to the coast or the Columbia Gorge, Mt Hood and the Willamette Valley for wine tasting. We have added extra cleaning procedures to help fight against Covid 19.

Guest favourite
A vibrant tiny home with a red exterior and blue trim is framed by a cluster of blooming pink flowers in the foreground. The welcoming entrance is highlighted by warm lighting, complementing the colorful garden that surrounds the property.
Tiny home in McLoughlin
4.95 out of 5 average rating, 165 reviews

Tiny Sequoia House

Feel refreshed when you stay in this rustic gem. With a full heated outdoor yet private shower, lofted queen bed and fold-out couch, walking distance to tons of restaurants and shops, 15 - 25 minutes into Portland proper depending on where you're going and very close to the wilderness and hiking.

Popular amenities for Jennings Lodge holiday rentals