Family-Friendly rentals near Old Mill District

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Top-rated family-friendly rentals near Old Mill District

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

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Top guest favorite
An inviting hot tub is positioned alongside a sauna grotto, both nestled within a natural setting. The hot tub features clear water with soft illumination, while the sauna's wooden exterior is accentuated by warm light. Surrounding trees and rocks enhance the tranquil atmosphere.
Bungalow in Bend
5.0 out of 5 average rating, 172 reviews

River Run Bend Bungalow & Romantic Spa Grotto

Relaxing, private spa & sauna grotto is ready for your romantic Bend getaway! This quiet, wooded, centrally located standalone bungalow is steps from the Deschutes River trail and within easy walking distance of Mill Dist. and Hayden Amphitheater. It boasts a comfy king bed w/premium down bedding & pillows, dedicated free parking (+ extra cars or small RVs), outdoor dining and patio area, washer/dryer, and a kitchen fully stocked with everything you need for fun and relaxation for all seasons!

Top guest favorite
The bedroom features a spacious bed with white linens, complemented by two bedside tables with lamps. A green bench sits at the foot of the bed, while a landscape painting hangs above the headboard. Soft curtains frame a window, allowing natural light to fill the space.
Guesthouse in Bend
4.97 out of 5 average rating, 195 reviews

NEW Tranquil Retreat On Canal

Charming, clean, comfortable, fully renovated guest house on 3 acres, nestled by a canal. A quiet escape near Pine Nursery Park, just 5 miles from downtown and less than 20 minutes from the airport. Enjoy beautiful natural light, vaulted ceilings, large bathtub, and balcony with outdoor seating and a beautiful view. Fully stocked kitchen, washer & dryer, heat & AC, blackout shades, board games, books, amenities for kids, smart TV, and a Blu-ray player for rentals from The Last Blockbuster.

Top guest favorite
Cottage in Bend
4.93 out of 5 average rating, 151 reviews

Old Mill Charmer with Hot Tub

The Mill House cottage is one of three historic cottages on this property. It is located in the heart of Bend between the historic downtown and desirable Old Mill district. There is no better location than this one, just steps from Columbia river park and walking distance from the amphitheater, 10 Barrel Brewery, Good Life Brewery, Jackson's Corner and Active Culture. We offer complimentary bikes making it easy for you to zip downtown for your morning coffee or evening happy hour.

Top guest favorite
A historic two-story building is showcased in a monochrome setting. It features a large entrance with broad steps flanked by neatly trimmed hedges. The exterior has a simplistic design, with a gabled roof and multiple windows, contributing to its classic architectural style.
Home in Old Bend
5.0 out of 5 average rating, 100 reviews

The Church In Bend

The Alliance Tabernacle Church, built in 1923, is reported to be the first house of worship west of the Mississippi to be built entirely by volunteers from the congregation. By the 1970s the building had fallen into disrepair. Beginning in October 2014 the current owners began the process of restoring the building to it's original condition under the supervision of the Historic Landmark Commission. This special place is close to everything, making it easy to plan your visit.

Top guest favorite
A spacious living room features a light-colored sectional sofa positioned around a glass coffee table. Large windows invite natural light, revealing a view of the outdoors. A stone fireplace provides a warm focal point, complemented by a cozy armchair and decorative elements throughout.
Home in Bend
4.99 out of 5 average rating, 218 reviews

Airy Bend Oasis - Two Ensuites

Cheers to your stay at Bent Pine Oasis, located in the picturesque west side of Bend! This home provides the ideal location for any outdoor enthusiast: Mt Bachelor's slopes are just a 20 minute drive & the Deschutes River Trail is mere steps from the front door- your avenue to biking, running and exploring Bend. Looking for a more relaxing day? You can make the 5 minute drive into the Old Mill District to enjoy food trucks, a river float, or fresh hops at a local brewery.

Guest favorite
The exterior of Tokyo Starfish displays a welcoming façade with dark wood siding and vibrant red accents. Potted plants line the entrance, and a white flag featuring a green cross signals cannabis offerings. A bicycle leans against the building, adding to the inviting atmosphere.
Home in Old Bend
4.96 out of 5 average rating, 254 reviews

Westside "Bud-And- Breakfast"

The first and only "Bud-And-Breakfast" in Bend, Or, located in the heart of Bend's Westside. Situated above Tokyo Starfish, the unparalleled cannabis dispensary in Central Oregon, this fantastic 2-bedroom apartment isn't just in a great location, but is also cannabis friendly. Just head downstairs to Tokyo Starfish with your complimentary gift card and experience the freshest selection of flower, edibles, drinks and other top cannabis products the dispensary has on hand.

Top guest favorite
Townhouse in Bend
4.95 out of 5 average rating, 332 reviews

Drake @ The DUPE - blocks from Old Mill District -

Drake: Located blocks from the Old Mill District, this beautifully updated 2-bed, 2-bath townhouse blends privacy with an unbeatable location. Walk or bike to the Old Mill, Deschutes River, dining, and the Hayden Homes Amphitheater. Tucked in a serene, tree-lined setting, the private home features a bright kitchen with updated appliances, a primary suite with a walk-in tile shower, and a separate porch with a BBQ grill. The perfect mix of modern comfort and convenience.

Top guest favorite
A modern three-story apartment building features a striking combination of wood and contemporary architectural elements. Large windows provide ample natural light, while a wide staircase leads to the entrance. Trees are visible in the background, contributing to a serene outdoor setting.
Loft in Bend
4.94 out of 5 average rating, 459 reviews

Cozy River Front "NEST" | Old Mill | Dog | Bikes

Enjoy this Luxury 2nd level apartment directly on the Deschutes River. Easy trail access is steps away where you can run/hike the 3 1/2 mile loop or paddle up and down the river. Back at home sit on your deck and listen to the sounds of the river going by. The Old Mill, Box Factory, Food Carts and more are a peaceful 3/4 mile stroll along the river trail ....yet you are a world away in your "Nest" within the Ponderosa Pines along the river. ** Enjoy! **

Top guest favorite
A spacious living area is highlighted by a modern entertainment center and a comfortable seating arrangement, including a large ottoman. Light-colored walls complement the wooden floors, while natural light filters through windows, enhancing the room's inviting appearance.
Home in Bend
4.98 out of 5 average rating, 203 reviews

Old Mill Charm

Great Location in Old Mill District – Walk to Summer Concerts! ♥ Fenced Backyard ♥ Pet Friendly Nestled in the heart of Bend, Old Mill Charm offers the perfect blend of comfort and convenience. Thoughtfully designed with many amenities to ensure a seamless stay, this charming rental is ideal for relaxing or exploring all that Bend has to offer. There is a tenant in the apartment above the detached garage who does not use the driveway ensuring your privacy.

Guest favorite
An exterior view of a single-story home is shown, surrounded by landscaped gardens with rocks and greenery. A cozy patio area features blue and white striped lounge chairs, an umbrella, and string lights overhead, creating a welcoming outdoor space.
Home in Bend
4.97 out of 5 average rating, 204 reviews

Close, Cute & Clean! *Hot Tub* Bend Adventure Base

Welcome to your Central Oregon adventure base! Book now to enjoy the convenience and comfort of this centrally located Bend home!! Quick access to all of the activities and events that make this area so special! Conveniently located for walking and biking to the Old Mill, Deschutes River, concerts, parks, restaurants, breweries, and grocery stores. Come settle in for exploration and recreation!!

Top guest favorite
Guest suite in Bend
4.84 out of 5 average rating, 406 reviews

Haven’s Nest | Walk to Old Mill / Deschutes River

Welcome to Haven’s Nest, a peaceful Bend getaway perfectly located near the Deschutes River trails and an easy walk to the Old Mill District. Start your mornings with coffee and fresh mountain air, then stroll to the river, bike scenic trails, or enjoy local shops and dining just minutes away. Thoughtfully designed for comfort, privacy, and relaxation—this is your ideal home base for exploring Bend.

Top guest favorite
A wooden deck provides seating with two Adirondack chairs facing the tranquil river. Potted flowers add a touch of color to the space, while lush greenery lines the riverbank. Kayakers can be seen leisurely paddling on the water under a bright blue sky.
Cabin in Old Bend
4.9 out of 5 average rating, 539 reviews

Mill Cabin at Deschutes Dunes River/ beach access

This Mill Cabin is located in one of the most central, westside Bend neighborhoods along the Deschutes River. The modest, no frills two bedroom 1918 cabin was home to some of Bend’s earliest mill workers. It features a rustic theme and most of the basic stuff you'll need for a great stay. The main highlight is LOCATION, the fabulous yard and direct river access.

Popular amenities for family-friendly rentals near Old Mill District

Quick stats about family-friendly rentals near Old Mill District

  • Total vacation rentals

    Explore 120 vacation rentals in Old Mill District

  • Nightly prices starting at

    Old Mill District vacation rentals start at G$12,543 GYD per night before taxes and fees

  • Verified guest reviews

    Over 10,180 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Old Mill District vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Old Mill District rentals

  • 4.9 Average rating

    Old Mill District stays are highly rated by guests—averaging 4.9 out of 5!