The Best Vacation Rentals in Bend’s Old Mill District: Your Complete Local Guide
If you’ve been searching for a vacation rental in Bend that puts you within walking distance of the Deschutes River Trail, restaurants, shopping, live music, and breweries without compromising on the quality of the home itself, Millpointe Modern and Millwood Modern are exactly what you’ve been looking for.
The properties sit side by side at The Eight at the Old Mill, a collection of luxury townhomes in the heart of one of Bend’s most walkable neighborhoods. Book one for a mid-sized group or book both together for up to 20 guests. Either way, you’ll be in one of the best locations in Bend with a home you won’t want to leave.
This guide covers everything you need to know about the properties, the neighborhood, and how to spend 36 hours in the Old Mill District while you’re here.
Why the Old Mill District is one of Bend’s Best Vacation Rental Locations
The Old Mill District sits along the Deschutes River on Bend’s south side, and it’s walkable in every direction. During your visit you’ll find shopping, dining, a movie theater, the Deschutes River Trail, and Hayden Homes Amphitheater for summer and fall concerts.
From Millpointe Modern and Millwood Modern, here’s what you can reach on foot:
Old Mill District — 5-minute walk for shopping, dining, and riverside strolling. You’ll find well-known shops like REI, lululemon, Madewell, Anthropologie, and local favorites like Dudley’s Bookshop, Vanilla Clothing Co., and The Stacks Art Studios.
Deschutes River Trail — 5-minute walk to one of the most beautiful urban trail systems in the Pacific Northwest. Don’t miss watching the surfers at the Whitewater Park, a quintessential Bend landmark.
Box Factory — 8-minute walk for restaurants, wine bars, coffee, and smoothies.
Hayden Homes Amphitheater — 10-minute walk for summer and fall concerts in one of the best outdoor music venues on the west coast.
Downtown Bend — 15-minute walk for coffee shops, boutiques, galleries, cocktail bars, and farm-to-table dining.
Drake Park — 20-minute walk along the river to one of Bend’s most iconic parks.
Park the car when you arrive and don’t think about it again until checkout!
Millpointe Modern
Millpointe Modern is a newly built, pet-friendly luxury townhome with four bedrooms, 3.5 bathrooms, and beds for up to 12 guests across three thoughtfully designed floors.This high-end vacation rental features amenities you won't find at any other Bend vacation home: a private 6-person sauna, temperature-controlled cold plunge, fully-equipped home gym, rooftop firepit, and more.
This property combines two sophisticated spaces: a 3-bedroom main home with soaring ceilings and custom finishes, plus a lock-off studio apartment with private entrance. Rent the entire property for large family gatherings and special celebrations, or book either unit separately for ultimate flexibility.
→ View the full Millpointe Modern listing and check availability
Millwood Modern
Millwood Modern sits right next door with the same exceptional address and equally refined design. Four bedrooms, 3.5 bathrooms, sleeps up to 10. Light wood and natural stone finishes, high-end appliances, Cascade Mountain views from the dining area and balconies, a 3rd floor gas firepit, and a self-contained lock-off suite always included plus parking for up to 4 vehicles.
→ View the full Millwood Modern listing and check availability
Book Both Properties for Groups Up to 20
Here’s what makes Millpointe Modern and Millwood Modern unique in the Bend vacation rental landscape: you can book them together.
The Homes at a Glance:
8 bedrooms · 6.5 bathrooms · Sleeps 20
6-person sauna + cold plunge
Fully equipped home gym
4 cruiser bikes + 2 inflatable paddleboards
6 dedicated off-street parking spots
Two fully equipped chef’s kitchens
Multiple balconies with Cascade Mountain views
Gas firepits on both properties
Perfect for:
Family reunions and multigenerational trips
Bachelor and bachelorette groups
Corporate retreats and team offsites
Milestone celebrations and group getaways
Anyone who wants the whole crew together without sacrificing luxury or location
→ Learn More About Booking Both Properties
How to Spend 36 Hours in the Old Mill District
This is our favorite local itinerary for guests staying at Millpointe Modern or Millwood Modern, built around the best restaurants, trails, and experiences within walking distance of your front door.
Day 1
4PM — Check In
Arrive, get settled, and enjoy the views from the balcony.
6PM — Stoller Wine Bar
Start the evening with drinks and snacks at Stoller Wine Bar in the Box Factory, one of Oregon’s most celebrated wineries with a Bend outpost. Sit on the patio on a sunny day or enjoy the cozy atmosphere inside.
7:30PM — The Podski
Walk across the street for dinner at The Podski, which includes some of the most beloved food trucks in Bend. Don’t leave without trying Americana and Toasty, two of our personal favorites!
Or try takeout from Miyagi Ramen
If you’d rather enjoy a night in, Miyagi Ramen is less than ½ a mile from Millpointe + Millwood Modern and perfect to grab for takeout. This is an especially great option for our gluten free + Celiac friends!
Day 2
7AM — Coffee at the Vacation Rental
Enjoy a slow start to the day with a warm mug of complimentary coffee by the firepit.
8AM — Sisters Coffee + Mill A Loop
Second cup and pastries at Sisters Coffee in the Old Mill, then follow the Mill A Loop, an easy 1.1-mile trail along the Deschutes River past the Whitewater Park and Hayden Homes Amphitheater. This is one of the most scenic short walks in the city.
10AM — Old Mill District Shopping
We love the mix of national retailers like Madewell, lululemon, and Anthropologie alongside local favorites like Dudley’s Bookshop, Vanilla Clothing Co., and The Stacks Art Studios.
12:30PM — Lunch
Two great options within easy reach: Pho 88 Bend for a warm + comforting meal, or Pastini for a patio seat with river views. Don’t skip the garlic bread!
2PM — Tumalo Creek Kayak and Canoe
Get on the water with a rental from Tumalo Creek Kayak and Canoe, open year-round for canoe, kayak, and SUP rentals. This is one of the best ways to experience Bend from a completely different perspective.
5PM — Crosscut Warming Hut
Craft beer, wine, and food trucks with indoor + outdoor seating. We love popping in here before a concert or for a bite to eat after a day of exploring.
7PM — Va Piano Vineyards
Wind down on the patio at Va Piano Vineyards with Deschutes River views and an amazing staff.
8PM — Ladybird
Dinner at Ladybird to close out the day with prohibition-style cocktails, wood-fired pizzas, pastas, meat and seafood. The food + ambiance are top notch! We recommend grabbing a reservation in advance.
Day 3
7:30AM — M’s Bakery
Start the morning at M’s Bakery in the heart of the Old Mill for coffee and the best baked goods in Bend. Get the cinnamon roll, the kouign amann (butter cake in French — trust us), and the ham and cheese croissant. Don’t forget to grab a sourdough loaf for the road!
8AM — South Canyon Reach Trail
One last walk along the Deschutes via the South Canyon Reach, a 3-mile stretch of river views on a blend of paved, gravel, and natural surface trail. We think this is the best way to close out your trip.
11AM — Check Out
Load the car, head home, and start looking at dates for next time. Bend has a way of doing that!
Where to Book
Millpointe Modern and Millwood Modern are both professionally managed by Sojourn Homes, a boutique vacation rental company based right here in Bend with over 15 years of local hosting experience. Our team is available 24/7 throughout your stay and we love helping our guests make the most of their time in Central Oregon.
Book direct at sojournhomes.com for the lowest available rate with no third-party service fees and direct access to our local team from the moment you book.
Have questions about which property or combination is right for your group? Send us a message and we’ll help you figure out the perfect setup.
→ Browse Millpointe Modern
→ Browse Millwood Modern
→ Book Both Properties
See you in the Old Mill. 🌲