First Street Rapids Park Rentals
From $294 per night (USD)VRBO
Bluebird Day - The Annex Experience a Luxury 30 Day Stay in Bend, OR
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Annex! Originally built in 1927 by local builder John Peterson, the structure began as the historic “Del ...
From $294 per night (USD)VRBO
From $445 per night (USD)Expedia
3 Bedroom house 2 blocks from down town Bend
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Office is a retro modern Bend bungalow packed with personality. Velvet bedrooms, cocktail lounge vibes, shag rugs, a ...
From $445 per night (USD)Expedia
From $293 per night (USD)VRBO
Bluebird Day - Desert Zen in Bend with 2 queens, fenced yard, fireplace, Walk Everywhere!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Desert Zen! The location of the Desert Zen cannot be beat! Located on Bend's popular Westside, just 4 blocks ...
From $293 per night (USD)VRBO
From $337 per night (USD)Expedia
New! Charming Bend Cottage | 5 Min Walk to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
St. Helens Cottage is a sunny downtown Bend retreat just steps from Drake Park, the Deschutes River, and the heart of ev ...
From $337 per night (USD)Expedia
From $329 per night (USD)VRBO
New! Luxury Westside Home | Prime Walkable Location
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Perfectly positioned in the heart of Bend's beloved west side, this spacious 2,300 sq. ft. four-bedroom retreat puts som ...
From $329 per night (USD)VRBO
From $160 per night (USD)Expedia
New Listing! Downtown Bend Studio | Walk Everywhere
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Location, location, location. The Broadway Cottage sits directly across the street from the beloved Jackson's Corner, ju ...
From $160 per night (USD)Expedia
From $291 per night (USD)VRBO
New Listing! Restored Bungalow | Walk to Downtown Bend
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This restored historic Newport Bungalow is a sun-drenched 1,250 sq. ft. retreat in the heart of downtown Bend. Reclaimed ...
From $291 per night (USD)VRBO
From $371 per night (USD)Expedia
New Listing! Westside Gem | Hot Tub | Walk Downtown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Perfectly positioned on Bend's west side just steps from downtown, this spacious, sun-filled four-bedroom home is the id ...
From $371 per night (USD)Expedia
From $202 per night (USD)VRBO
New! Downtown Bungalow | Walk to River, Dining & Breweries
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked near from Drake Park and the Deschutes River in the heart of downtown Bend, the St. Helens Bungalow is an adorabl ...
From $202 per night (USD)VRBO
From $168 per night (USD)Expedia
New Listing! Cozy Historic Studio | Walk to Downtown Bend
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked beneath the Georgia Cottage in one of Bend's most charming historic neighborhoods, this 400 sq. ft. studio is a c ...
From $168 per night (USD)Expedia
From $359 per night (USD)VRBO
New! NW Bend Home | Private Hot Tub | Walk to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Walk to everything Bend has to offer from this 4-bedroom, 2.5-bathroom vacation home in the quiet River West neighborhoo ...
From $359 per night (USD)VRBO
From $108 per night (USD)Expedia
New! Historic Bend Cottage | Walk to Breweries & Drake Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Step into a piece of Bend history at the Hawthorne House — a beautifully renovated 1930s cottage with a modern twist, tu ...
From $108 per night (USD)Expedia
From $197 per night (USD)VRBO
New Listing! Historic Cottage | Heart of Downtown Bend
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Georgia Cottage is a beautifully restored historic Mill house that puts you right in the heart of it all. Walk to downto ...
From $197 per night (USD)VRBO
From $257 per night (USD)Expedia
Meet Me on Milwaukee | Hot Tub, EV Charger & Walkable Bend Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Meet Me on Milwaukee is a beautifully furnished 2-bedroom, 2.5-bath home located in one of Bend's most desirable Westsid ...
From $257 per night (USD)Expedia
From $587 per night (USD)VRBO
Awbrey Perch ~ Sauna, Hot Tub/Cold Plunge, Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Awbrey Perch is a newly renovated hillside retreat perched in the trees of Awbrey Butte with forested east-facing views ...
From $587 per night (USD)VRBO
- From $251 per night (USD)
Expedia
NW Nest 30 Day Minimum
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to your ideal vacation retreat in sunny Central Oregon located on the picturesque west side of Bend ...
From $251 per night (USD)Expedia
From $242 per night (USD)VRBO
Wall Street Wander - Steps to Downtown & River
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Wall Street Wander | Downtown Bend Set in one of Bend's most desirable neighborhoods, Wall Street Wander is a stylish d ...
From $242 per night (USD)VRBO
From $145 per night (USD)Expedia
Comfy 3BR Retreat in Beautiful Bend, OR
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Enjoy a relaxing stay in this inviting 3-bedroom home located in one of Central Oregon’s most desirable destinations. Th ...
From $145 per night (USD)Expedia
From $722 per night (USD)VRBO
Charming home blocks from river, downtown and Mt Bachelor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover the beauty of Bend from this gorgeous 3-bedroom house. Guests will find a king bed and two queen beds, plus a c ...
From $722 per night (USD)VRBO
From $566 per night (USD)Expedia
Fireplace & Hot Tub Nights | Walk to Downtown Bend
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Private hot tub and firepit under twinkle lights set the mood at Magnolia House, a lovingly restored 1925 West ...
From $566 per night (USD)Expedia
From $256 per night (USD)VRBO
Bluebird Day - Pine Rosa Retreat, Cozy 2 BR, West side!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Pine Rosa Retreat! You can WALK EVERYWHERE! This little retreat is located right up the street from one of o ...
From $256 per night (USD)VRBO
From $373 per night (USD)Expedia
Historic Bungalow in Walkable Old Bend
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the heart of Old Bend! Our historic one-bedroom bungalow blends vintage charm with modern comforts, perfect ...
From $373 per night (USD)Expedia
From $276 per night (USD)VRBO
The Crosby Hall Shevlin House | Built 1920
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Summary: Stay in a piece of Bend history at The Crosby Hall Shevlin House, a beautifully preserved 1920 Revival-style h ...
From $276 per night (USD)VRBO
From $169 per night (USD)VRBO
The Bend Shed - A modern home in the heart of town
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Bend Shed is a modern urban cabin in the heart of Bend, Oregon. Designed by the architect owner as a family retreat, ...
From $169 per night (USD)VRBO
From $267 per night (USD)VRBO
Great Downtown Location And House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This is a completely remodeled 1920's Bungalow. The house has an old charm with modern touches. The house is surrounde ...
From $267 per night (USD)VRBO
From $229 per night (USD)VRBO
Downtown Bungalow, Gourmet Kitchen 2BR/1.5BA, 3-5 blocks Downtown & Box Factory
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Address is 237 NW Georgia Ave, Bend, OR 97703 Here's the rates in a nutshell, Email for an exact quote. Add 11% tax and ...
From $229 per night (USD)VRBO
From $240 per night (USD)VRBO
First Street Rapids and River Trail
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
One side of a cute and cozy cottage style duplex on the west side of Bend. The host lives on one side and rents the oth ...
From $240 per night (USD)VRBO
From $487 per night (USD)Expedia
Contemporary Chic Cottage │Downtown Historic District │Hot Tub │Gourmet Kitchen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Featuring classic cottage charm with a contemporary modern twist, The Modern Mill Cottage perfectly embodies the spirit ...
From $487 per night (USD)Expedia
From $979 per night (USD)VRBO
Located on Bend's most sought after historic district street, provides the perfe
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The house was built in 1920 and completely renovated in 2007. It's located in the heart of Bend's premiere historic dis ...
From $979 per night (USD)VRBO
From $252 per night (USD)Expedia
The Cascade River Trail Retreat - a short walk to river & downtown! Pets OK!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the desirable River West neighborhood, a short stroll to restaurants, breweries & shopping in Downtown Bend a ...
From $252 per night (USD)Expedia
From $410 per night (USD)VRBO
Historic Downtown │Walk Everywhere │Private Hot Tub │One Block to River
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The River Run radiates warmth and comfort. This delightful craftsman style home beautifully blends old fashion charm wit ...
From $410 per night (USD)VRBO
From $472 per night (USD)Expedia
West Side Bungalow │Cali King Bed │Walk Everywhere │Hot Tub │One Block to River
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Drake West Bungalow is an adorable one bedroom, one bathroom home in the River West Neighborhood near the Galveston ...
From $472 per night (USD)Expedia
From $292 per night (USD)VRBO
River Views + Prime Bend Location
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Book Direct with Central Oregon Vacation Homes. Lovely 3rd-floor Condo with a private balcony overlooking the ...
From $292 per night (USD)VRBO
From $464 per night (USD)Expedia
Downtown Bend Vacation Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Light and bright downtown cottage with a landscaped, fenced private yard and hot tub. Walk to breweries, restaurants, co ...
From $464 per night (USD)Expedia
From $424 per night (USD)VRBO
***NEW*** Charming home located in Downtown Bend!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This quaint bungalow was originally constructed in the 1920’s and now features current amenities for you to enjoy while ...
From $424 per night (USD)VRBO
From $440 per night (USD)VRBO
Mid Century Luxury Home; Westside; Walk Everywhere
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located in the heart of Bend and walking distance to downtown, Newport Ave shopping and restaurants and quick warm up ri ...
From $440 per night (USD)VRBO
From $223 per night (USD)VRBO
Bend Bungalow - a Walk in the Park to Downtown and River!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Use the Bend Bungalow as your home base as you explore and taste all Bend has to offer. We welcome you. Looking for a s ...
From $223 per night (USD)VRBO
From $367 per night (USD)VRBO
Westlake Cottage - Great Weekly & Monthly Rates - walk Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our highly walkable neighborhood. Enjoy the hospitality of one of Bend's family-owned, micro businesses on a ...
From $367 per night (USD)VRBO
From $227 per night (USD)VRBO
Cozy Modern Apartment Close To Town; Walk Everywhere
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the heart of Bend and walking distance to downtown, Newport Ave shopping and restaurants and short warm up ri ...
From $227 per night (USD)VRBO
From $287 per night (USD)Expedia
A private zen-like home, panoramic views, super chill!Total relaxation for you.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Parking on the first floor with large sauna and shower. 2nd floor is the main living and entertaining floor with kitche ...
From $287 per night (USD)Expedia
From $384 per night (USD)VRBO
Historic Downtown Location │Heart of Bend │Walk Everywhere │Hot Tub │High Demand
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
NOTE: Intermittent area construction August 4-8, 2025 with discounted rates! This amazing little downtown cottage provi ...
From $384 per night (USD)VRBO
From $88 per night (USD)VRBO
Close to everything! Recently updated. Walk Downtown, stroll River trail.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
You'll love this comfortable 2nd floor condo unit in the heart of it all. It's stone's throw from the Deschutes River, P ...
From $88 per night (USD)VRBO
From $1164 per night (USD)VRBO
Location! Historical District Downtown - Walk everywhere, new 4 Bedroom, 3 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This is a recently remodeled 4 bedroom, 3 bath house in the historical district of Bend. Rare - original structure burn ...
From $1164 per night (USD)VRBO
From $686 per night (USD)Expedia
WALK EVERYWHERE! 4 BEDROOMS +BONUS RM & QUAINT BACKYARD
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This Historic Home has over 2,100 square feet. The newly updated finishes seamlessly blend the historic character and co ...
From $686 per night (USD)Expedia
From $253 per night (USD)VRBO
Stay In The Heart Of Bend, Walk Everywhere!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our vacation home. The Chalet is two-levels, with a king bed in the master upstairs, and two twin beds in th ...
From $253 per night (USD)VRBO
From $413 per night (USD)Expedia
*NEW* Downtown Modern Nostalgia, completely updated and convenient
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Century-old mill home that was completely renovated to modern standards while keeping its' nostalgic charm. Location! ...
From $413 per night (USD)Expedia
From $134 per night (USD)VRBO
1st Floor Studio, stunning view of Deschutes River
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: This ground-floor studio on the edge of downtown comfortably sleeps two and has an incredible view of the Desc ...
From $134 per night (USD)VRBO
From $251 per night (USD)Expedia
Riverside Cottage - Just Steps from the Deschutes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Here at “Otter Sight”, you will be a few steps away from the water and feel completely immersed in nature with ...
From $251 per night (USD)Expedia
From $134 per night (USD)VRBO
1st Floor Updated Studio, incredible river access
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: ‘Riverside Runs Through It’ is a gorgeous, updated studio, perfect for a 2-person getaway. You will have every ...
From $134 per night (USD)VRBO
From $130 per night (USD)Expedia
Riverfront Studio in Downtown Bend
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: This ground-floor, riverfront studio is on the edge of downtown Bend with eight-foot sliding glass doors openi ...
From $130 per night (USD)Expedia
From $134 per night (USD)VRBO
Pet Friendly Studio on the Deschutes With Balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: This ground-floor studio overlooks the Deschutes River on the outskirts of downtown Bend and has a private pat ...
From $134 per night (USD)VRBO
From $200 per night (USD)Expedia
Downtown Corner Studio With 270-Degree River View
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: This ground floor, corner studio sleeps 2 and provides a 270-degree view of the Deschutes River and is a short ...
From $200 per night (USD)Expedia
From $134 per night (USD)VRBO
Downtown Studio on the River
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: License to Grill is a beautifully remodeled ground-floor studio that sleeps up to four guests! It has incredib ...
From $134 per night (USD)VRBO
From $213 per night (USD)Expedia
Riverview Pet Friendly Condo in Downtown Bend
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: “High Desert Hideout” has unobstructed views of the Deschutes River through the 8-foot sliding glass doors and ...
From $213 per night (USD)Expedia
From $710 per night (USD)VRBO
Relax and Recharge! 4 Comfortable Units! Near Cascade Village Shopping Center!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
A delightful Oregon city packed with natural sights and craft breweries. This listing is for 4 separate rooms within a ...
From $710 per night (USD)VRBO
From $130 per night (USD)Expedia
Ground-floor Bend Condo near Pioneer Park
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: “Change Your Altitude” is a ground floor condo that sleeps four in two separate rooms. You will NOT find a be ...
From $130 per night (USD)Expedia
From $350 per night (USD)VRBO
Get Ready for Adventure! 2 Family-friendly Units. Close to Pine Nursery Park!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
A delightful Oregon city packed with natural sights and craft breweries. This listing is for 2 separate rooms within a ...
From $350 per night (USD)VRBO
From $350 per night (USD)VRBO
Comfort and Convenience! 2 Relaxing Units! Close to Bend Municipal Airport!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
A delightful Oregon city packed with natural sights and craft breweries. This listing is for 2 separate rooms within a ...
From $350 per night (USD)VRBO
From $355 per night (USD)VRBO
Your Home Away From Home 2 Comfortable Units! Enjoy Swimming Pool Access!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
A delightful Oregon city packed with natural sights and craft breweries. This listing is for 2 separate rooms within a ...
From $355 per night (USD)VRBO
From $288 per night (USD)Expedia
Bluebird Day - Desert Moon, Cozy 2BR in Bend's River West, Walkable to restaurants!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Desert Moon! This adorable cottage was originally built in the 1920's during Bend's mill town heyday. This is ...
From $288 per night (USD)Expedia
From $147 per night (USD)VRBO
Updated Condo with Deschutes River View
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: This stunning condo was recently redone and sits on the top floor, giving you the best views of the Deschutes ...
From $147 per night (USD)VRBO
From $252 per night (USD)Expedia
Blue Spruce Guesthouse - Walkable to river trail and downtown Bend
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
New to VRBO but more than 350 super positive reviews on another platform. The Blue Spruce is a charming, private second ...
From $252 per night (USD)Expedia
From $100 per night (USD)VRBO
Historic Drake Cottage 30 Day Rental. Across from Drake Park, Mirror Pond, downtown Bend. Furnished.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
*NEWLY RENOVATED* Welcome to Drake Cottage 309 – an adorable, lovingly restored gem nestled in a historic 1930 fourplex ...
From $100 per night (USD)VRBO
From $148 per night (USD)Expedia
Ground Floor Riverside Cottage with Patio!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: This beautiful riverside ground floor corner cottage can sleep up to four people, has two full bathrooms and a ...
From $148 per night (USD)Expedia
From $148 per night (USD)VRBO
Pet Friendly Riverside Studio in Downtown Bend
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: This small but comfortable ground floor studio cottage has everything you need for a Bend adventure! This cott ...
From $148 per night (USD)VRBO
From $242 per night (USD)Expedia
Walk to Downtown & River Bend! Fireplace, quiet
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Relax on the private balconies overlooking the park. After your coffee take a 2 minute walk down to the Deschutes river ...
From $242 per night (USD)Expedia
From $174 per night (USD)VRBO
Riverfront Cottage - Steam Room & Pet Friendly!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Welcome to "Hot Dam". Up to three guests can stay here, on the queen bed and a twin size sleeper sofa (in the ...
From $174 per night (USD)VRBO
From $215 per night (USD)Expedia
Ground Floor River Front Studio Cottage
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Unit 251 here at Bend Riverside Rentals is a riverfront studio that is a perfect getaway spot for one or two t ...
From $215 per night (USD)Expedia
From $526 per night (USD)VRBO
Spacious ranch style home snuggled in the West Hills neighborhood of Bend
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This spacious ranch style home snuggled in the West Hills neighborhood of Bend, could be your next vacation destination, ...
From $526 per night (USD)VRBO
From $125 per night (USD)VRBO
Great Relaxing Overnight Stay! Pet-friendly Unit! Close to Pine Nursery Park!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
A delightful Oregon city packed with natural sights and craft breweries. This listing is for a room within a hotel. ✦ ...
From $125 per night (USD)VRBO
From $125 per night (USD)VRBO
Better Choice For Your Vacation! Spacious Unit. Near Dowtown!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
A delightful Oregon city packed with natural sights and craft breweries. This listing is for a room within a hotel. ✦ ...
From $125 per night (USD)VRBO
From $167 per night (USD)VRBO
Better Choice For Your Vacation! Accessible Unit! Near Pine Nursery Park!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
A delightful Oregon city packed with natural sights and craft breweries. This listing is for a room within a hotel. ✦ ...
From $167 per night (USD)VRBO
From $438 per night (USD)VRBO
Heart of Bend-Walkable, Ping Pong, Billards
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stay close to everything at this centrally-located place, on a quiet street, right in the heart of all Bend has to offer ...
From $438 per night (USD)VRBO
From $496 per night (USD)VRBO
Sweet Historic Craftsman on Bend’s West Side has Modern Amenities, Fenced Yard!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Aspen Bungalow - Meredith Lodging You’ll love the quaint, Craftsman vibe of this distinctive home in Bend’s historic we ...
From $496 per night (USD)VRBO
From $688 per night (USD)VRBO
Downtown Villa with Private Spa
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Welcome to your own private spa escape—where historic charm meets modern comfort. Perfect for families, groups, and remo ...
From $688 per night (USD)VRBO
From $298 per night (USD)Expedia
Bluebird Day - Pilot Butte Pad: Spacious 3BR home in Bend, ideal for family getaways.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Pilot Butte Pad An adorable Midtown home built in 1952. This three bedroom two bath home has been fully remo ...
From $298 per night (USD)Expedia
From $262 per night (USD)VRBO
Bend Home Near Orchard Park Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: This Bend home sits one block from Orchard Park and minutes from downtown, Old Mill District, and Mt Bachelor. ...
From $262 per night (USD)VRBO
From $236 per night (USD)Expedia
Bluebird Day - Westside Retreat, Discover luxury at a spacious 4-bedroom home in Bend, OR.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Westside Retreat! Perfect location. Perfect 30 day furnished rental! Come and stay for 30 days and experienc ...
From $236 per night (USD)Expedia
From $452 per night (USD)VRBO
The Hastings House - Walker's Paradise W/Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
NEW VRBO LISTING | PLEASE VISIT SITE BELOW FOR CURRENT REVIEWS: https://www.airbnb.com/hosting/listings/editor/140731156 ...
From $452 per night (USD)VRBO
From $355 per night (USD)Expedia
Modern bungalow charm! Steps to downtown & the surf wave, salt water hot tub!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
DOWNTOWN LOCATION This is where all the best neighborhoods meet...downtown, Old Mill, Westside...this is the location yo ...
From $355 per night (USD)Expedia
From $236 per night (USD)VRBO
Middle Sister - Sweet Bungalow, Queen bed, Parking, Walkable downtown Bend
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Middle Sister Bungalow! The Middle Sister Bungalow is the middle unit of three attached but completely indepe ...
From $236 per night (USD)VRBO
From $251 per night (USD)Expedia
Sweet South Sister - Bungalow charm, King bed, Parking, So Walkable
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to South Sister Bungalow! The South Sister Bungalow is one of three attached but completely independent homes in ...
From $251 per night (USD)Expedia
From $263 per night (USD)VRBO
North Sister - Bungalow Charm, Fireplace, Queen bed, Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to North Sister Bungalow! The North Sister Bungalow is the largest of the three attached but completely independ ...
From $263 per night (USD)VRBO
From $288 per night (USD)Expedia
Mill Modern - Beautiful Historic Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Mill Modern. Completely rebuilt in 2023, this completely refreshed, historic, bungalow is located in Bend’s b ...
From $288 per night (USD)Expedia
From $271 per night (USD)VRBO
Bluebird Day - Lakewood Cottage in Bend with 2 beds, perfect for 4 guests.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Lakewood Cottage! Come and stay in this adorable rustic modern cottage! Lakewood in located downtown in the ...
From $271 per night (USD)VRBO
From $118 per night (USD)Expedia
Cozy 2nd Story Condo Overlooking Pioneer Park
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Located in the most perfect spot for exploring all of what Bend has to offer, up to two travelers can stay her ...
From $118 per night (USD)Expedia
From $302 per night (USD)VRBO
Bluebird Day - Aspen Getaway, a cozy 1-bedroom retreat in Bend, OR.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Aspen Getaway! This charming historic 1 bedroom 1 bath home is 100 years old! It has many modern amenities w ...
From $302 per night (USD)VRBO
From $681 per night (USD)Expedia
Walkable Downtown Spa Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Step into the newly renovated Greeley Lodge, a historic gem masterfully transformed in 2024. Located just one block from ...
From $681 per night (USD)Expedia
From $292 per night (USD)VRBO
Charming downtown Bend Cottage.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Walk downtown Bend in minutes. Three blocks to Box Factory and Market of Choice, 15 minute walk to Harden Homes Amphithe ...
From $292 per night (USD)VRBO
From $122 per night (USD)Expedia
Park Side Getaway! Walk to Downtown & Trails
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: Unit 130/131 in the Pioneer Park condos is a true gem! Located just 10 minutes from downtown Bend and a short ...
From $122 per night (USD)Expedia
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Charming 2-bedroom house, king bed, walk to downtown, fully equipped kitchen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your Bend basecamp! Our beautifully designed home offers an open floor plan, a spacious primary bedroom with ...
Click For PricingVRBO
From $129 per night (USD)VRBO
Monthly Pet-Friendly Midtown House, fast WiFi, A/C
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Our 3 bedroom home-away-from-home is perfect for digital nomads and traveling professionals looking to blend work and ad ...
From $129 per night (USD)VRBO
From $246 per night (USD)VRBO
Modern cottage charm & walk to Downtown Bend
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Cascade Cottage! Modern and charming, this sweet Old Mill era home is fully furnished for your Bend adventure ...
From $246 per night (USD)VRBO
From $299 per night (USD)Expedia
Bluebird Day - Huckleberry Cottage in Bend, OR, perfect for a romantic getaway.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Huckleberry Cottage! Come to Central Oregon and visit our one bedroom Huckleberry Cottage, located in a quie ...
From $299 per night (USD)Expedia
From $226 per night (USD)VRBO
Bluebird Day - Twin Mills Bungalow in Bend, OR, featuring 2 cozy bedrooms.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Twin Mills Bungalow! Located right in the heart of Bend, this two bedroom duplex is nestled between the Old ...
From $226 per night (USD)VRBO
From $275 per night (USD)Expedia
Bluebird Day - Sierra Nook, one-bedroom retreat in Bend, ideal for couples and pet-friendly.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Sierra Nook! This modern getaway on the Westside of Bend is a one bedroom duplex within walking distance to ...
From $275 per night (USD)Expedia
From $284 per night (USD)VRBO
Riverfront Luxury In Downtown Bend. Pool/Hot Tub.
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Summary: Planning a family reunion and need separate yet connected spaces? These two units offer private living areas w ...
From $284 per night (USD)VRBO
From $388 per night (USD)Expedia
Newly renovated and 3 minute walk to the center of downtown!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your downtown Bend retreat. Sunshine Daydream is IN Downtown Bend. This sweet and completely redone 1941 cott ...
From $388 per night (USD)Expedia
From $188 per night (USD)VRBO
Luxury in Bend, OR | Guestroom + Nature Experience
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience the ultimate getaway in Central Oregon's stunning scenery with unparalleled beauty, picturesque views of the ...
From $188 per night (USD)VRBO
From $172 per night (USD)Expedia
Shaffer's Flat - Stay and play IN downtown Bend!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
****30+ night stays only**** Enjoy a stylish experience at this centrally-located place. The building was built in the ...
From $172 per night (USD)Expedia