Vacation rentals in Milwaukie

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Top-rated vacation rentals in Milwaukie

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
A detached guest house is highlighted, featuring a blue exterior with large windows and a front door. A small patio area with a wooden table is visible, surrounded by lush greenery and decorative plants. A wooden fence provides additional privacy.
Home in Milwaukie
4.95 out of 5 average rating, 110 reviews

Secluded Studio

This a fully private and detached guest house is quiet and relaxing. Walk down your very own pathway to a completely private, safe and secure patio with a quaint garden, a small yard and outdoor seating. With tall ceilings and a large nice bright kitchen, this place is very comfortable. Blackout curtains. Close to many desirables: Max Orange Line Commuter Train, Reed College, Woodstock, Sellwood, & East Moreland & Milwaukie Providence Hospital. Ride, walk or run along the Springwater Corridor.

Superhost
Guest suite in Milwaukie
4.79 out of 5 average rating, 374 reviews

Clean & Cozy "Private" Studio Suite

Private studio suite (500 sq ft). The unit is on the lower half of this 2 level duplex (host lives upstairs), private entry is on the ground level, self check-in, off street parking. There is a kitchenette, private bathroom with a stand-up shower, washer & dryer, queen bed, high speed internet, expanded cable, Netflix/Amazon Prime. Also, there is a lovely private patio for your enjoyment with a fire table. The space is warm and inviting, very safe location, great neighborhood and dog friendly.

Top guest favorite
The kitchen features a retro blue fridge and dark cabinetry, providing a blend of modern and vintage aesthetics. Natural light enters through a window above the sink, illuminating the space. Indoor plants are placed around the room, enhancing the overall atmosphere.
Guesthouse in Milwaukie
4.94 out of 5 average rating, 172 reviews

Spacious Studio near Historic Milwaukie/Sellwood

No cleaning fees! Unique retro inspired LARGE studio Private entrance, driveway parking. One Full sized bed and a comfy twin sized cot (set up upon request). Bright sunny space with skylights and beautiful details. Uncluttered, quiet and clean. Full sized fridge and plenty of kitchen amenities. Large dining room table and sitting space. Located in peaceful neighborhood, close to Historic Downtown Milwaukie, 15 min to downtown Portland, minutes away from SE Portland attractions!

Top guest favorite
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, 188 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.

Top guest favorite
A cozy kitchen is highlighted by warm wood cabinetry and a decorative countertop. A binder titled 'Crossroads Country Cottage' is prominently displayed, accompanied by a flower vase filled with vibrant blooms. Colorful stained glass pieces allow natural light to filter in, adding charm to the space.
Home in Milwaukie
4.97 out of 5 average rating, 177 reviews

Crossroads Country Cottage

Conveniently located at the crossroads of HWY 224 and SE Lake Road, our home, cottage and garden are the last remnants of a time gone by and what was once a large family farm. When you walk through the private gate leading to the cottage, you might feel you have stepped through a portal into another time. Everything about the cottage is secluded, peaceful and private. We are pleased to have many return visitors. The garden features a waterfall, chairs and table, BBQ and fresh herbs.

Top guest favorite
A vibrant area features a comfortable gray couch paired with a glass coffee table. A colorful rug with bold patterns adds warmth to the space, while a potted plant and wall art enhance the cheerful atmosphere.
Apartment in Milwaukie
4.94 out of 5 average rating, 341 reviews

Peaceful Oasis in Portland Neighboring Milwaukie

Our names are Danusia and Ron. Welcome to our world. We have done the best with our resources to create a welcoming oasis . Portland is a great place to live and we're glad to invite you. We are offering a light, sunny second story apartment. Portland is known for its eclectic food carts, brew pubs, music venues, theatres,restaurants and its special brand of quirkiness. Upon your arrival,you will not have to travel far, we are 20 minutes from the airport,15 from downtown.

Top guest favorite
An open-space studio features high ceilings with wooden beams, enhancing the airy feel. A queen-sized bed is set against the wall with soft linens. A small kitchenette and dining area are visible, with a full bathroom enclosed in glass. Natural light brightens the interior.
Guesthouse in Woodstock
4.96 out of 5 average rating, 503 reviews

SE Portland Guest Cottage

The guest cottage offers self check-in. It is located in a quiet neighborhood in SE Portland. High ceilings make this studio airy and bright. We think of it as a perfect hotel room without the hotel. The small galley kitchen has everything you need to cook a gourmet meal including filtered water. There is a full bathroom with tub and shower. The cottage stands on its own making it perfect for coming and going as you please. City of Portland Permit #24 013532

Guest favorite
A bright living area features a red sectional sofa adorned with decorative throw pillows. Two pieces of abstract wall art add color, while a wooden side table sits beside the sofa. Light enters through a window, enhancing the space's warmth.
Vacation home in Portland
4.86 out of 5 average rating, 184 reviews

Lovely 1-bed vacation home w/ off street parking.

Welcome to the artists nook - where characters and wayfinders come to relax. A stylish, freshly remodeled 1bed, 1bath, in a quiet, serene neighborhood. 1 Private off street park space. Private Back porch with bbq. Every room has heat keeping it nice and toasty on those cold, winter nights and AC for July's sultry, sticky evenings. Kitchen comes fully equipped. Large bathroom, and don't forget to use the huge washer and dryer to get your laundry in check.

Superhost
The cabin, nestled among towering cedar trees, features a rustic exterior with warm lighting from the windows. A serene creek flows nearby, with smooth stones and mossy patches lining the water's edge. A wooden bridge connects to the surrounding natural landscape.
Cabin in Milwaukie
4.89 out of 5 average rating, 749 reviews

Rustic Creekside Cabin

This tranquil hideaway feels like you're in the middle of the forest, but is just minutes from Portland. Relax next to the burbling creek surrounded by towering cedar trees. The MAX Orange line and downtown Milwaukie are only five minutes away. Built in 1928, the cabin has one bedroom and bathroom, living room, full kitchen and central heat. The bedroom has one queen bed and an en suite bathroom. There is a pull-out queen futon in the living room.

Top guest favorite
A comfortably appointed studio features a queen bed with decorative pillows and a soft blanket. A seating area includes a modern chair beside a sleek storage unit, with a coffee setup and a mini refrigerator. Natural light filters through sheer curtains, enhancing a relaxed atmosphere.
Guest suite in Milwaukie
4.96 out of 5 average rating, 282 reviews

Cozy, Private Studio

This beautifully remodeled studio with private bathroom, entrance and off-street parking is nestled in a quiet, relaxed neighborhood in Milwaukie- a neighborhood south of Portland. Extremely comfortable queen bed will provide you with an excellent nights sleep. Great atmosphere for those traveling for business or vacation. Located 5 minutes from I-205 and a 10-minute drive to downtown Portland.

Top guest favorite
The exterior showcases a red house featuring a bright yellow door. Two colorful chairs are placed beside a small table adorned with potted flowers. Lush greenery surrounds the area, with a stone walkway leading up to the entrance.
Home in Milwaukie
4.97 out of 5 average rating, 285 reviews

Lovely Art Filled Home 15 min to Downtown

This comfortable and newly remodeled home sits on a quiet residential street in the Ardenwald neighborhood a few blocks from the Portland border in Milwaukie. It's thoughtfully decorated throughout with local original artwork that's been curated by us, also artists! The trendy Sellwood and Woodstock neighborhoods are a little over a mile away filled with locally owned shops, bars, and restaurants.

Top guest favorite
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, 212 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.

Popular amenities for Milwaukie vacation rentals

When is the best time to visit Milwaukie?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$21,757 GYDG$21,966 GYDG$20,920 GYDG$19,874 GYDG$20,711 GYDG$21,338 GYDG$22,175 GYDG$21,966 GYDG$20,920 GYDG$21,757 GYDG$21,966 GYDG$22,594 GYD
Avg. temp5°C7°C9°C12°C15°C18°C21°C21°C19°C13°C8°C5°C

Frequently Asked Questions

  • What are the best places to stay in Milwaukie?

    Stays in downtown Milwaukie or in residential neighborhoods near parks are frequently suggested. Many accommodations have easy access to the river, green spaces, and a walkable local dining scene.

  • What are the best things to do in Milwaukie with kids?

    Families can explore riverside parks, playgrounds, and community gardens in Milwaukie. Seasonal farmers markets, public art walks, and family-focused events frequently draw visitors of all ages.

  • What are some of the best things to do in Milwaukie?

    Explore public art downtown, walk along riverside trails, and visit local farmers markets or craft breweries. Community events and green spaces invite visitors to connect with local culture and nature.

  • How is the weather in Milwaukie?

    Milwaukie has cool, wet winters averaging 36–47°F (2–9°C), and mild to warm summers with afternoons up to 82°F (28°C) and lighter rainfall. Layered clothing and a rain jacket are suggested, especially in the rainier months.

  • When is the best time to visit Milwaukie?

    Late spring through early autumn is often recommended in Milwaukie, when days are milder and rainfall is lighter. July and August have warm afternoons around 82°F (28°C), which are popular for outdoor events and activities.

  • What are the best places to visit in Milwaukie?

    Explore downtown Milwaukie for shops, eateries, and public art, or visit local parks along the river for open green spaces. Farmers markets and community gardens are often recommended for a glimpse into local life.

  • What are some hiking trails in Milwaukie?

    Milwaukie has riverside paths and greenway trails, often recommended for casual walks and family outings. Nature areas nearby invite exploration through shaded forests and local wildlife habitats.

  • What are some family activities we can do in Milwaukie?

    Visit riverside parks for play and picnics, attend community festivals, or stroll through the farmers market together. Family-friendly attractions and public art spaces are popular with visitors traveling with children.

  • What are some of the best day trip ideas from Milwaukie?

    Day trip ideas include exploring Portland’s cultural neighborhoods, hiking in local forests, or visiting regional wineries and farm stands. Many travelers enjoy experiencing gardens, wildlife centers, or scenic walks just outside the city.

  • Are there any pet friendly accommodations available in Milwaukie?

    Milwaukie has a variety of pet-friendly vacation rentals, so you can bring your companion along. Many hosts in residential neighborhoods are open to pets—be sure to check each listing’s policies before booking.

  • What are some local tips for visiting Milwaukie?

    Bring comfortable shoes to explore parks and neighborhoods, and consider a reusable bag for farmer’s market finds. Locals appreciate early mornings for quieter walks, and rain gear is useful outside summer months.

  • What is Milwaukie known for?

    Milwaukie is known for its riverside parks, community-driven farmers markets, and its legacy in agriculture. The city is also recognized for a vibrant downtown, hosting locally owned shops and public art installations.

  • What are the best hidden gems to explore in Milwaukie?

    Look for community gardens, smaller parks tucked in neighborhoods, and independent shops for unique finds. Locally curated art spaces and historic buildings around downtown often surprise visitors seeking quieter spots.

  • What are the best foods to try in Milwaukie?

    Milwaukie’s food scene celebrates Pacific Northwest flavors, including locally roasted coffee, fresh produce, and artisanal baked goods. Many visitors enjoy seasonal farmers markets, craft breweries, and independent restaurants serving contemporary American dishes.

  • What should I bring for a trip to Milwaukie?

    Pack layered clothing, a light rain jacket, and comfortable shoes for outdoor walks. A reusable bag is handy for farmers market purchases, and if visiting in summer, include sunscreen and a hat.

  • What is the nightlife in Milwaukie like?

    Milwaukie has casual bars, craft breweries, and live music venues, especially around downtown. Evening events and community gatherings bring a relaxed, social atmosphere, often centered on local food and drinks.

  • What are the most popular events or festivals in Milwaukie?

    Milwaukie has community farmers markets throughout the warmer months, along with arts and music festivals in late spring and summer. Seasonal celebrations and street fairs are often highlights for visitors and locals.

  • Are there family friendly vacation rentals in Milwaukie?

    Milwaukie has many family-friendly vacation rentals, often located in quiet neighborhoods or near parks. Parents can filter for amenities such as kitchens, multiple bedrooms, and outdoor spaces to suit their family’s needs.

Quick stats about vacation rentals in Milwaukie

  • Total vacation rentals

    Explore 120 vacation rentals in Milwaukie

  • Nightly prices starting at

    Milwaukie vacation rentals start at G$6,276 GYD per night before taxes and fees

  • Verified guest reviews

    Over 9,090 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Milwaukie vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Milwaukie rentals

  • 4.9 Average rating

    Milwaukie stays are highly rated by guests—averaging 4.9 out of 5!

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