Holiday rentals with outdoor seating near Old Mill District

5 out of 5 average rating, 108 reviews

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

River Run Bend Bungalow & Romantic Spa Grotto

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

An outdoor seating area is arranged under a wooden porch, featuring plush chairs and decorative cushions. A fire pit sits at the center, surrounded by rocks. The green lawn extends to a fenced area with pine trees providing a natural backdrop.

4.97 out of 5 average rating, 137 reviews

<SALE> River Canyon Retreat | Dogs | Old Mill |

Welcome to the River Canyon Retreat! A peaceful, pet friendly, single level home filled with fun and hip upscale décor. Enjoy hiking the Deschutes River Trail and walking or biking to the shops and breweries in the Old Mill District. Miles of Mountain bike trails and the road to Mt. Bachelor and Cascade Lakes are close by. Cozy up to the wood burning stove with a good book or enjoy the forested hillside full of birds, deer and all sorts of nature on the back porch. Welcome to your Retreat!

An inviting entryway is featured, with a green door framed by a porch. A wicker chair sits beside a white planter, adding a touch of greenery. Brick columns complement the wooden deck and ceiling, creating a warm and accessible entrance.

5 out of 5 average rating, 411 reviews

Downtown Craftsman with King Bed and Private Yard

Stay at a rare home in the core of downtown. A beautifully restored 1922 craftsman with plants and warm wood throughout including natural light from vaulted ceilings, charming architecture and paintings by local artist Sheila Dunn. Walk to dozens of restaurants, breweries, coffee and shops. Cross the alley to food trucks and frequent live music or relax in your private walled courtyard. No parties or pets please. Trip insurance recommended if illness, weather or smoke may be an issue.

A bright living area features a light-colored sofa draped with yellow and gray cushions. Two stylish chairs provide additional seating, while a central wooden table holds decorative items. Natural light filters through sheer white curtains, illuminating plants and a patterned rug on the hardwood floor.

4.97 out of 5 average rating, 235 reviews

Villa77: Renovated Stay Near Downtown & Old Mill

Newly renovated and thoughtfully designed, our airy apartment in Bend’s Midtown offers a 5-star experience. Enjoy crisp linens, plush towels, and fresh-ground local coffee brewed just the way you like it. Perfectly located near Downtown, the Old Mill District, and Bend’s best shops and eateries, our apartment is a cozy and stylish retreat. After a day of adventure, unwind in comfort at this charming home base! Owned by locals, this is the perfect launch pad for your Bend adventures!

4.94 out of 5 average rating, 126 reviews

The exterior of the townhome is showcased, featuring a blend of stone and wood materials. A spacious deck with a railing is visible on the upper level, while a pathway leads through well-maintained landscaping and manicured grass, enhancing the inviting look of the residence.

Townhouse in Bend

Salmon Lodge Luxury 3BR Bend OR Old Mill District

The Salmon Lodge is a West Bend luxury 3 BR 3 Bath townhome in the Old Mill District. It has served as a premier vacation rental for the last decade. Under new ownership since 2022, we are excited to honor the legacy of the thoughtfully built Salmon Lodge. We will continue to offer the quintessential Bend experience. Walk or bike everywhere! Close to Old Mill shopping, downtown, Mt Bachelor, Deschutes & concert venue. Mountain view from upstairs deck with attached bar. Sleeps 8 to 9

A modern living room features large windows that provide views of the outdoors. A gray sectional sofa and a bright orange chair are arranged around a light area rug. A wooden coffee table is positioned nearby, and a TV is mounted on the wall. A stove adds a touch of warmth to the space.

4.99 out of 5 average rating, 186 reviews

Modern high-end home, walk downtown

This fantastic modern home is in the sweet spot of Bend...just next door to the Deschutes River, Downtown Bend, parks, restaurants and dining, nightlife, and family-friendly activities. You'll love our home because of the amazing location, the mid-century inspired ambiance, the high ceilings, the people, and the local views. We are the perfect centrally located home for any Bend adventure. Our place is great for couples and solo adventurers. This is not a party house. Sorry no pets.

A comfortable living area features a dark gray sofa positioned in front of a stone fireplace. A simple coffee table sits on a patterned area rug, and a dining table is visible in the background. The space is complemented by a lofted sleeping area with a ladder for access.

4.93 out of 5 average rating, 343 reviews

The Hub—Apartment @ Downtown & Historic Dist

Located on the edge of Old Bend Historic District and next to the popular downtown area, the newly constructed apartment is the perfect hub to explore Bend. Easily walk downtown or to the Old Mill district, drive just 30 minutes to Mt. Bachelor for a ski day, or bike along the river trail. The modern space features an open layout with a gas fireplace, full kitchen, kids sleeper loft, and many other amenities. It's attached to a commercial building but has a private entrance.

4.99 out of 5 average rating, 440 reviews

A charming red exterior is complemented by natural stone accents, surrounded by lush greenery. A spacious wooden deck invites relaxation, while a driveway provides access to a garage. Tall trees add privacy to the welcoming entrance of the home.

Guest suite in Bend

Old Mill Studio - easy to Mt Bach, river, dining

Your own private studio behind our home is in the quiet, quaint neighborhood on the bluff above the Old Mill District and Deschutes River. Short walk to restaurants, coffee, breweries and concerts. Close to the river for floating, SUP, River Trail. Easy access to Mt Bachelor, Cascade Lakes, and mountain fun. Private entrance and sliding doors out to a private patio for your morning coffee or end-of-day beverage. A fire pit is available to top off a cozy evening (see notes.)

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.

4.97 out of 5 average rating, 178 reviews

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

Welcome to the perfect basecamp for your Central Oregon adventures! The snow is coming!! Book today for your winter adventure in Bend to enjoy this convenient, comfortable, and centrally located 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!!

A single-story house with a welcoming porch is framed by a gravel driveway. Lush greenery surrounds the entrance, complemented by blooming pink flowers. The cloudy sky adds depth to the scene, while large windows provide ample natural light. The structure features a simple, rustic design.

4.96 out of 5 average rating, 164 reviews

Bend 3BR Home Near River Trail | Dog-Friendly

Welcome to your peaceful Bend getaway—a spacious 3-bedroom, 2-bath home near the Deschutes River Trail. Perfect for families and couples, this comfortable retreat features high-speed WiFi, a fully equipped kitchen, washer and dryer, and a bright, open living space designed for relaxation. Located minutes from downtown Bend and the Old Mill District, you’ll have easy access to shopping, dining, breweries, and outdoor adventures like hiking, biking, and paddle boarding.

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.

4.97 out of 5 average rating, 186 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.

4.93 out of 5 average rating, 289 reviews

An inviting entrance is framed by lush greenery and a well-maintained garden. The entryway features a set of steps leading to a light-colored door, welcoming guests into the stylish townhouse. Soft natural light filters through the surrounding trees.

Townhouse in Bend

Aspen @ The DUPE - blocks from Old Mill District -

This beautiful and updated townhouse is located just blocks away from the Old Mill District. You can walk or ride down to the Hayden Homes Amphitheater, shopping, dining and of course the Deschutes River. The 2 bedroom 2 bath house itself is surrounded by trees and is very private. You will love the full tile shower in the master bathroom and the light and bright kitchen with updated appliances. This place is a perfect mix of comfort and location.

Popular amenities for rentals with outdoor seating near Old Mill District

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

A comfortable living area features a green sectional sofa and a gray accent chair. A large coffee table sits in the center, with a light-colored rug beneath. Exposed wooden beams adorn the ceiling, while a staircase leads to an upper level. A television is mounted on the wall.

4.93 out of 5 average rating, 190 reviews

Drake Park Cottage in the Heart of Bend

The Craftsman home features a welcoming front porch with two chairs positioned on either side. A traditional American flag adds a festive touch, while lush greenery surrounds the entrance. The exterior showcases a blend of wood tones and architectural details characteristic of the Craftsman style.

4.93 out of 5 average rating, 218 reviews

Paddle House

A charming outdoor space features a wooden deck with a red sofa set under a pergola, accented by string lights. The blue exterior of the cottage serves as a cheerful backdrop, complemented by a well-maintained green lawn and a fenced yard for privacy.

4.99 out of 5 average rating, 128 reviews

Charming Millhouse w/ hot tub close to everything

The exterior of the two-story cabin features a charming combination of wood and siding. A welcoming porch with seating is visible, framed by manicured landscaping. Above, a private balcony invites relaxation, showcasing the property’s connection to the surrounding natural beauty.

5 out of 5 average rating, 284 reviews

Mountain Bliss: Gateway to Mt. Bachelor and More

The modern exterior of the ADU features wooden accents and large windows, surrounded by lush greenery. A small outdoor seating area with two chairs and a fire pit is visible. The entrance is framed by a wooden fence, providing privacy and inviting atmosphere.

4.99 out of 5 average rating, 209 reviews

Modern retreat in central Bend

The living area features engineered hardwood floors and a cozy leather sofa positioned near a wall-mounted smart HDTV. A rustic wooden coffee table is set with snacks, while the open kitchen showcases modern stainless appliances and quartz countertops. Natural light fills the space through multiple windows.

4.97 out of 5 average rating, 108 reviews

Mt. Bachelor | Fireplace | Chef’s Kitchen

4.95 out of 5 average rating, 252 reviews

Park Place - Walk to Downtown & Old Mill

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.

4.99 out of 5 average rating, 187 reviews

Airy Bend Oasis - Two Ensuites

Apartment rentals with outdoor seating

A modern living area showcases a comfortable dark sofa alongside a bright orange armchair. A wooden coffee table is positioned in front, with a small plant and speaker on top. A dining table with four chairs is visible in the background, and a fireplace adds warmth to the space.

4.93 out of 5 average rating, 104 reviews

Modern Condo~Fireplace~Walk to Old Mill & River

An inviting living area showcases a gray sofa paired with a patterned area rug. A wooden dining table with two chairs occupies one corner. Natural light is offered through two windows, enhancing the warm color scheme of the walls.

4.96 out of 5 average rating, 527 reviews

Riverside loft closest to amphitheater, rapids

A cozy living area is furnished with a leather couch and wooden chairs, accented by a glass coffee table. Natural light fills the space through the large window with blinds, highlighting potted plants and decor on the side table.

4.93 out of 5 average rating, 458 reviews

Private Spacious Studio Apartment

A newly remodeled studio features a king-sized bed with a textured orange coverlet against a wood-paneled accent wall. A cozy seating area is arranged with a leather couch and natural wood coffee table. A flat-screen TV is mounted on the wall, enhancing the living space.

4.9 out of 5 average rating, 73 reviews

Sunriver Studio with Pool & Hot Tub

The exterior of the two-story apartment is framed by tall pine trees, showcasing a robust wooden structure. A private entrance and garage are visible, while a deck extends from the second story, offering an inviting extension of the living space.

4.96 out of 5 average rating, 114 reviews

Spring River Guest Apartment

A cozy living area features a green sofa against a mural of a vibrant forest. Indoor plants are arranged around the space, complemented by natural light filtering through sheer curtains. A round dining table with two chairs sits adjacent to the seating area, enhancing the inviting atmosphere.

4.96 out of 5 average rating, 151 reviews

The Grove at Midtown Manor - King Beds & Hot Tub!

A cozy living area features a blue sofa and a matching armchair, set on a patterned area rug. A round wooden coffee table occupies the center, while natural light streams through a small window. The walls are adorned with artwork and decor, creating a welcoming ambiance.

4.96 out of 5 average rating, 1,032 reviews

Urban Studio Loft-Hot Tub AC 250+Mbps Views

Superhost

A couple is seated on a cozy balcony, wrapped in a blanket, overlooking the tranquil river at sunset. Warm colors fill the sky, reflecting on the water. A fire pit offers warmth and light, enhancing the serene setting, complemented by glasses of wine held in their hands.

4.91 out of 5 average rating, 43 reviews

Relax by the Rapids Riverfront Gem Downtown Bend

Apartment rentals with outdoor seating

4.84 out of 5 average rating, 147 reviews

Walk to downtown Bend or stroll river trail condo!

4.98 out of 5 average rating, 122 reviews

Pool, AC, close to Amphitheater & Old Mill

The living area features a comfortable gray sofa with decorative cushions and a glass coffee table. A light-colored chair complements the space, while a dining set for four is positioned nearby. The kitchen, visible in the background, includes wooden cabinetry and modern appliances.

4.94 out of 5 average rating, 117 reviews

Adventure Awaits! Walk to downtown and river!

Superhost

A spacious living area features a grey sectional sofa with a tufted design, accented by a decorative pouf. Natural light filters in through sliding glass doors, leading to a private patio with views of surrounding trees and the outdoors. A round mirror adds depth to the space.

4.83 out of 5 average rating, 105 reviews

Updated Condo with Deschutes River View

A private balcony offers a comfortable seating arrangement with a cushioned sofa and a wooden coffee table. Scenic river views are visible, framed by trees and basking in sunlight. The railings provide safety while enhancing the outdoor space's inviting atmosphere.

4.91 out of 5 average rating, 158 reviews

Riverfront Condo 2 Blocks to Downtown Bend

4.9 out of 5 average rating, 144 reviews

The living area features high vaulted ceilings with wooden beams and large windows allowing natural light to fill the space. A stone fireplace is the focal point, surrounded by comfortable leather seating and a centerpiece table. Colorful accents offer a pop of vibrancy to the neutral decor.

Apartment in Sunriver

Short walk to SR Village and SHARC, includes bikes

4.93 out of 5 average rating, 156 reviews

Apartment in Sunriver

Room With a View Condo, Sharc passes included.

4.9 out of 5 average rating, 431 reviews

Quiet Escape: Fireplace, 5min to Downtown & River

Other holiday rentals with outdoor seating

4.94 out of 5 average rating, 416 reviews

A comfortable living area features a spacious sofa and two armchairs, with a wooden dining table visible. Large windows allow natural light to fill the space, showcasing views of greenery. A television is mounted on the wall, and a colorful artwork adds a touch of style.

Guest house in Bend

Suburban Forest guest house with garage

4.98 out of 5 average rating, 133 reviews

A charming exterior view of the rustic cabin showcases a covered porch with comfortable seating. Surrounding landscaping features a variety of plants and rocks, complemented by a small fire pit area. The home's muted color palette blends harmoniously with the natural setting.

Cottage in Bend

River Camp House

4.89 out of 5 average rating, 492 reviews

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 Bend

Mill Cabin at Deschutes Dunes River/ beach access

4.97 out of 5 average rating, 302 reviews

A spacious living room is featured with a gas fireplace and a large-screen TV, complemented by a pull-out sofa. Large windows allow natural light to fill the room, while bar seating is available at the open kitchen, creating an inviting atmosphere for relaxation or gatherings.

Guest house in Bend

Midtown gem I Cozy Fire I Full kitchen I Park View

The exterior of the home features a welcoming front porch with two black Adirondack chairs and a small table. A path leads to the front door, bordered by low-maintenance landscaping and a natural stone feature. Large windows provide views of the surrounding area.

4.99 out of 5 average rating, 308 reviews

Your gateway to Mt Bachelor & all that Bend offers

4.9 out of 5 average rating, 386 reviews

A spacious sleeping area features a large bed adorned with a patterned comforter and decorative pillows. Dark curtains frame a window that allows natural light to fill the room. Two nightstands with lamps are positioned on either side of the bed.

Guest suite in Bend

Cozy Studio! Walk to NW Crossing and Shevlin Park

4.93 out of 5 average rating, 289 reviews

A cozy bedroom features a log bed with decorative pillows, complemented by a ceiling fan. Natural light filters through a large window, illuminating warm wooden flooring. An accent lamp and a small plant are placed beside the bed, adding subtle elements of design.

Guest suite in Bend

Cozy Queen, Private Bathroom and Entryway