
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.

Modern retreat in central Bend
Enjoy our new custom-built ADU located a block away from the Deschutes River in a quiet residential neighborhood, just a 10-minute walk from downtown along the River Trail. In this modern, bright, and private space, you'll enjoy the luxuries of hardwood floors, waterfall countertops, a built-in workspace, heated tile bathroom floors, a 55" Smart TV, BBQ and fire pit, and endless hot water—plus off-street parking and EV charger. One king bed, one daybed with a trundle, and one queen sleeper sofa.

<SALE> River Front | Hot Tub | Old Mill | Dogs
Enjoy this Contemporary Luxury Home directly on the Deschutes River. Literally step out your back door and stroll, run or paddle up and down the river. The river trail is a 3 3/4 mile loop and one of the best hikes around. Back at home sit on your deck or in the Hot Tub and listen the the sounds of the river going by and enjoy peaceful solitude. Shop or get a bite to eat at The Old Mill, Box Factory, Food Carts and more which are a peaceful 3/4 mile stroll along the river trail. Enjoy!

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.

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.

Location! Bungalow River & Beach Access
Welcome to our 1918 Bungalow on Riverfront Street. This simple, no frills one bedroom, one bath sleeps two to three. Enjoy a fully equipped kitchen, floor to ceiling river rock gas fireplace, inviting front porch, back deck with propane BBQ, table/ chairs. The Bungalow has a peek of the river, as it is considered the "guest house" to the larger "main house" it shares the lot with. Enjoy low bank river access to launch your kayak. Park the car and experience the best Bend has to offer.

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

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.

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.

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.

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.
Popular amenities for family-friendly rentals near Old Mill District
Family-friendly home rentals with a hot tub

OldMilOasis,Theatre,HotTubSauna,Gym,BrickPizzaOven

Drake Park Cottage in the Heart of Bend

Pool, AC, close to Amphitheater & Old Mill

Lucinder - Modern historic home, views, Downtown

The Blackberry Cottage

Hot Tub~King Bed~Dog Friendly-New Construction

A Stone's Throw | Riverfront Retreat | Waterfront

Contemporary Chic, Walk Downtown, Gourmet Kitchen
Family- and pet-friendly home rentals

Cozy, Pet Friendly, Hot Tub. Garage.

Charming Millhouse w/ hot tub close to everything

Bend 3BR Home Near River Trail | Dog-Friendly

The Oasis Airstream

Sunny Getaway: fenced | Near trails, dining, music

Treetop Escape in NW Bend

Rajneesh Aframe/Hot Tub, 10 min from downtown Bend

Bend Mid-Century Getaway• Near Old Mill & Downtown
Family-friendly home rentals with a pool

Mt Bachelor Village Resort- Room in River Ridge II

River Views at First Street Rapids + Walk Downtown

Romantic Guest House w/Hot Tub, Pool, Tennis Court

Mt. Bachelor Village Condo - Near Town & River

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

Charming Mt. Bachelor Village Condo

Indoor Pool, Game Room, EV Charger, Pets Welcome!

Klubhouse in Sunriver AC/Hot Tub/Heated Pool/BBQ
Family-friendly home rentals with Wifi

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

Franklin Flat - House @ Downtown & Historic Dist

Larkspur Lodge — Cozy, Private Guest Suite

Historic Drake Park Neighborhood .

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

Craftsman Style Retreat in Bend River West

Riverside loft closest to amphitheater, rapids

Great location! Highly rated by guests.
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$14,619 GYD per night before taxes and fees

Verified guest reviews
Over 9,520 verified reviews to help you choose

Pet-friendly vacation rentals
Find 60 rentals that welcome pets

Rentals with dedicated workspaces
70 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!
Destinations to explore
- Rentals with outdoor seating Old Mill District
- Rentals with a fireplace Old Mill District
- House rentals Old Mill District
- Rentals with a patio Old Mill District
- Rentals with a washer and dryer Old Mill District
- Pet-friendly rentals Old Mill District
- Rentals with a fire pit Old Mill District
- Cottage rentals Old Mill District
- Rentals with a hot tub Old Mill District
- Family-friendly rentals Bend
- Family-friendly rentals Deschutes County
- Family-friendly rentals Oregon
- Family-friendly rentals United States





