
Family-Friendly rentals near Old Mill District
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals near Old Mill District
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!

BEST location in Bend! *HOT TUB*
Welcome to Columbia House! Just steps away to Downtown Bend, Drake Park, Galveston Corridor (10 Barrel, Sunriver Brewing, Boss Rambler, The Lot Food Trucks, Westside Tavern, Victorian Cafe and more!), Old Mill (shops and eateries), Hayden Homes Amphitheater - leave your car at home! This updated and spacious home accommodates up to 6 guests and is kid and pet-friendly. We pride ourselves on having meticulously clean vacation homes and top-notch local management to make your stay exceptional.

Best for Old Mill:River Trail, Views & Town
Enjoy an unbeatable location within walking distance of the Hayden Homes Amphitheater, Old Mill and the scenic Deschutes River Trail. Experience all the best of Bend right outside your door! Whether you’re here for a concert, outdoor adventure, or a relaxing weekend, you’ll be close to everything that makes Bend special—riverfront trails, restaurants, breweries, nightlife, cycling, kayaking, paddleboarding, and hiking. Mt. Bachelor is just a short drive away—approx. 25 minutes.

The Heart Of Bend. Brownstone Apartment.
LOCATION CAN'T BE BEAT Meticulously Clean Modern Space Private apartment STEPS AWAY FROM THE DESCHUTES RIVER AND A 5 MINUTE WALK TO THE SUMMER SHOWS AT THE AMPHITHEATER A PERFECT BASE FOR WINTER AT MT. BACHELOR NO-CONTACT EASY CHECK-IN OLD MILL LOCATION IN THE MOST DESIRED NEIGHBORHOOD IN BEND Perfect setting in the heart of Bend between downtown & The Old Mill District Walk to fine dining, boutiques, galleries, theaters, coffee and the Deschutes River Trail steps away

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.

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! **

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.

Central Modern Guesthouse with EV Charger
We built this home out of a passion for creating welcoming spaces. Years ago, we renovated a motel on the coast - an experience that sparked our love of hospitality and shapes how we host today. We live around the corner with our kids, a golden retriever, and a few cats. Mike’s a local realtor, and Betsy manages business ops for the local fire department. We love books, music, and helping you discover the best of Bend - trails, eats, and community.

Contemporary Chic, Walk Downtown, Gourmet Kitchen
Featuring classic cottage charm with a contemporary modern twist, The Modern Mill Cottage embodies the spirit of Bend. This charming two bedroom, one bathroom vacation home is ideal for those Bend explorers who wish to be in the heart of it all. This house is located on a vibrant and eclectic street, situated just two blocks from downtown Bend. You are just a short stroll to all the superb dining, infamous breweries, art galleries, and festivals.

Old Mill ~ Deschutes River
Desert Sun is the perfect place to enjoy all that Bend has to offer. You'll have the Deschutes River right around the corner where you can access floating, fishing, kayaking, SUP or walk/running the 3.5 mile River Trail Loop. The Old Mill District and Les Schwab Amphitheater are a short walk along the river. This home's location makes for a perfect retreat with convenience of being close to Downtown, Mt Bachelor and Cascade Lakes.

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.

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
Family-friendly home rentals with a hot tub

Five minutes from old mill with hot tub.

Pool, AC, close to Amphitheater & Old Mill

Charming Millhouse w/ hot tub close to everything

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

A Stone's Throw | Cecil Sly

Modern Home Close to OLD MILL | HOT TUB! | 6 Bikes

The Church In Bend

Game Room | Hot Tub | Easy 2 Bachelor | Old Mill
Family- and pet-friendly home rentals

Cozy 3-BR house w/ EV charger & trailer parking

Sunny Getaway: fenced | Near trails, dining, music

Bend 3BR Home Near River Trail | Dog-Friendly

Kid & Dog Friendly Bungalow In The Heart Of Bend

Alpenglow Vista

Westside "Bud-And- Breakfast"

Pet-Friendly Flat with Private Yard
Spacious Pet-Friendly Home • Fire Pit • Fenced Yd
Family-friendly home rentals with a pool

Serenity Retreat | Pool, Spa, Trails & Mt Bachelor

Charming Mt. Bachelor Village Condo

Riverfront Condo, Walk to Downtown Bend

Hot Tub +Bikes +8SHARC Passes +PingPong +Fireplace

Luxury in the Forest

A Little Peace of Paradise, A/C, & 8 SHARC Passes

Modern Cabin Oasis Near Village

Updated Game Room! Hot Tub, SHARC (8), 2,800sq/ft
Family-friendly home rentals with Wifi

Near Old Mill - No Pets - Top 5% - Nordic Sauna

Craftsman Style Retreat in Bend River West

Larkspur Lodge — Cozy, Private Guest Suite

Modern retreat in central Bend

Old Mill Studio - walk to concerts, river, dining

Historic Drake Park Neighborhood .

Salmon Lodge Luxury 3BR Bend OR Old Mill District

Airy Bend Oasis - Two Ensuites
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$12,551 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!





