Vacation Rentals

Stay Local

Location: Bend, Oregon

Property Type: Cottage

from $109 /nt
3
1
6

Stay Local is a cozy and newly remodeled 1920’s house with vintage touches mixed with new decor. This 100 yr old home is small but so very charming. Every part of this home is designed to maximize use and function. We think you will sleep deeply in these comfortable beds. Try your luck and skill at the hand coffee grinder + pour over coffee maker. Too much work? Palate coffee…...

Welcome to Stay Local! You'll love this modern cabin and modern charms! Embrace your amazing location in the heart of downtown Bend. Walk in any direction and you’ll find lots to do in downtown Bend and the Old Mill.

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Stay Local

Stay Local is a cozy and newly remodeled 1920’s house with vintage touches mixed with new decor. This 100 yr old home is small but so very charming. Every part of this home is designed to maximize use and function. We think you will sleep deeply in these comfortable beds. Try your luck and skill at the hand coffee grinder + pour over coffee maker. Too much work? Palate coffee…

Bedrooms 3
Bathrooms 1
# of Guests 6
Pet Friendly? Yes

Cinder Cone Cottage

Location: Bend, Oregon

Property Type: Cottage

from $109 /nt
2
1
6

Welcome to the westside of Bend and the Cinder Cone Cottage. You want the best location in Bend for your getaway and you'll find it here. This newly renovated cottage is in one of the best neighborhoods in Bend! Walk 1 block to shops and restaurants on Galveston (10 Barrel, The Victorian Cafe, Ida's Cupcakes, the Food Cart Pod and much more). So convenient to the very popular west side…...

Cinder Cone is the perfect spot on the popular westside of Bend. Exposed wooden beams, vaulted ceilings with skylights, just 1-2 blocks from Galveston Ave restaurants, shops, cafes! Enjoy your own private hot tub and yard.

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Cinder Cone Cottage

Welcome to the westside of Bend and the Cinder Cone Cottage. You want the best location in Bend for your getaway and you'll find it here. This newly renovated cottage is in one of the best neighborhoods in Bend! Walk 1 block to shops and restaurants on Galveston (10 Barrel, The Victorian Cafe, Ida's Cupcakes, the Food Cart Pod and much more). So convenient to the very popular west side…

Bedrooms 2
Bathrooms 1
# of Guests 6
Pet Friendly? Yes

Branch & Thistle

Location: Bend, Oregon

Property Type: House

from $129 /nt
3
2
6

Welcome to your rustic modern Bend abode! The branch & thistle is everything you need for your authentic Bend stay! With rustic modern decor, it's the perfect getaway for friends and family. BBQ in the summer, kick back by the fireplace in the winter and enjoy the outdoor hot tub year round! DOWNTOWN LOCATION Branch & Thistle is located right between the 3 most popular neighborhoods in Bend - Newport…...

Rustic modern cabin home in the heart of westside Bend! So cozy! Gas fireplace, outdoor hot tub, wifi internet, HDTV, BBQ, outside dining. Walk a block to Galveston for some of Bend's favorite breweries, food carts and shops! Amazing location!

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Branch & Thistle

Welcome to your rustic modern Bend abode! The branch & thistle is everything you need for your authentic Bend stay! With rustic modern decor, it's the perfect getaway for friends and family. BBQ in the summer, kick back by the fireplace in the winter and enjoy the outdoor hot tub year round! DOWNTOWN LOCATION Branch & Thistle is located right between the 3 most popular neighborhoods in Bend - Newport…

Bedrooms 3
Bathrooms 2
# of Guests 6
Pet Friendly? No

RiverBend Bungalow | Waterfront Home

Location: Bend, Oregon

Property Type: Cottage

from $199 /nt
2
2
6

The RiverBend Bungalow is a sweet riverfront hide-away on the super popular westside of Bend. Enjoy your riverfront perch from the outdoor deck, hot tub or from the living room where you can watch the stand up paddle boarders and floaters drift by OR join them! Choose the RiverBend Bungalow for your next Bend getaway. Experience all that Bend and Central Oregon have to offer and enjoy this quality crafted…...

Riverfront home with modern amenities in the heart of westside Bend! Outdoor hot tub, free internet, HDTV, gas outdoor BBQ, riverfront dining. Walk a block to Galveston Ave for some of Bend's best restaurants, cafes and shops! Welcome to Bend!

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RiverBend Bungalow | Waterfront Home

The RiverBend Bungalow is a sweet riverfront hide-away on the super popular westside of Bend. Enjoy your riverfront perch from the outdoor deck, hot tub or from the living room where you can watch the stand up paddle boarders and floaters drift by OR join them! Choose the RiverBend Bungalow for your next Bend getaway. Experience all that Bend and Central Oregon have to offer and enjoy this quality crafted…

Bedrooms 2
Bathrooms 2
# of Guests 6
Pet Friendly? Yes

Columbia Spring

Location: Bend, Oregon

Property Type: House

from $222 /nt
2
1
6

Welcome to Columbia Spring in the heart of westside Bend! This sweet home is high on modern style while staying true to its vintage roots. This charming home has 2 bedrooms (king, queen) with one full bathroom. This is a spacious 2 bedroom home and there are numerous sitting areas for relaxing, playing games or getting some work done. Don't miss the backyard fire pit, hot tub, sauna AND outdoor…...

Cozy modern cottage at the intersection of all things westside. Steps to all the best shops and restaurants on Galveston and Newport Ave. Mirror Pond is only 2 blocks away. You'll love the backyard fire pit, hot tub, sauna AND outdoor shower

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Columbia Spring

Welcome to Columbia Spring in the heart of westside Bend! This sweet home is high on modern style while staying true to its vintage roots. This charming home has 2 bedrooms (king, queen) with one full bathroom. This is a spacious 2 bedroom home and there are numerous sitting areas for relaxing, playing games or getting some work done. Don't miss the backyard fire pit, hot tub, sauna AND outdoor…

Bedrooms 2
Bathrooms 1
# of Guests 6
Pet Friendly? No

Hillside Loft

Location: Bend, Oregon

Property Type: Studio

from $69 /nt
1
1
2

This light, bright, cheerful and modern studio just a couple blocks above all the great shops on Newport Ave. Walk to Newport Market, Backporch Coffee, Spork and more in under 10 minutes. 10 Barrel, The Lot & Sun River Brewing are just a few minutes walk further. Enjoy your very own quiet balcony and tree top views from this lofted retreat. Vaulted ceilings, gas fireplace for chilly nights, A/C for…...

Treetop views from this wonderful lofty, private duplex home. This studio is above the garage and shares only a bathroom wall with the adjacent home. Light, bright and with it's own balcony, you'll love making this your home away from home in Bend!

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Hillside Loft

This light, bright, cheerful and modern studio just a couple blocks above all the great shops on Newport Ave. Walk to Newport Market, Backporch Coffee, Spork and more in under 10 minutes. 10 Barrel, The Lot & Sun River Brewing are just a few minutes walk further. Enjoy your very own quiet balcony and tree top views from this lofted retreat. Vaulted ceilings, gas fireplace for chilly nights, A/C for…

Bedrooms 1
Bathrooms 1
# of Guests 2
Pet Friendly? No

Federal

Location: Bend, Oregon

Property Type: House

from $99 /nt
3
1
6

Welcome to The Federal House! This classic Westside Bend home is fully furnished for your Bend getaway for summer or winter activities! Located between downtown and the very popular Galveston and Newport Avenues. This is one of the best locations in Bend and a prime location to explore all Bend has to offer! DOWNTOWN LOCATION Just two blocks from 10 Barrel Brewing and Sunriver Brewing, and only a 15-minute stroll…...

Warm and cozy getaway in the heart of Bend's westside...So walkable to downtown, and all the shops on Newport and Galveston Avenues. You'll love your basecamp home, tucked into one of the best neighborhoods in Bend!

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Federal

Welcome to The Federal House! This classic Westside Bend home is fully furnished for your Bend getaway for summer or winter activities! Located between downtown and the very popular Galveston and Newport Avenues. This is one of the best locations in Bend and a prime location to explore all Bend has to offer! DOWNTOWN LOCATION Just two blocks from 10 Barrel Brewing and Sunriver Brewing, and only a 15-minute stroll…

Bedrooms 3
Bathrooms 1
# of Guests 6
Pet Friendly? Yes

Strawbale Basecamp

Location: Bend, Oregon

Property Type: House

from $100 /nt
2
1
4

Here is your chance to experience an amazing straw bale home in one of Bend's best locations! This eco friendly, lofted home is the perfect perch for either work or play in Bend. Located on a quiet street just a block from Drake Park you can walk to coffee every morning, walk to your river float every afternoon and truly experience the relaxing routine of downtown Bend living. On the…...

Spacious and stylish straw bale home in Bend's historic district. Just steps from Mirror Pond float location in Drake Park! You can't get any closer to the center of Bend...A great location for your month or more in Bend!

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Strawbale Basecamp

Here is your chance to experience an amazing straw bale home in one of Bend's best locations! This eco friendly, lofted home is the perfect perch for either work or play in Bend. Located on a quiet street just a block from Drake Park you can walk to coffee every morning, walk to your river float every afternoon and truly experience the relaxing routine of downtown Bend living. On the…

Bedrooms 2
Bathrooms 1
# of Guests 4
Pet Friendly? Yes

Heart of Bend

Location: Bend, Oregon

Property Type: Bungalow

from $109 /nt
3
1
6

Enjoy playing around Bend (hiking, Ale Trail, SUPs, mountain biking, skiing, shopping, l) and retreat back to Bend's premier River West neighborhood for a peaceful night sleep. Heart of Bend is kid & pet friendly. Fully stocked kitchen. Modern feel. And a fenced in private patio for relaxing. Heart of Bend is a charming 3 bed, 1 bath home located on Bend’s popular West Side right in the heart of…...

Come stay in one of Bend's original Craftsmen style Mill homes built in 1932 and renovated in 2022 with AC. Located 3 blocks from the river/Drake Park & a 5 min walk to Downtown. Experience what life is like in Bend!

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Heart of Bend

Enjoy playing around Bend (hiking, Ale Trail, SUPs, mountain biking, skiing, shopping, l) and retreat back to Bend's premier River West neighborhood for a peaceful night sleep. Heart of Bend is kid & pet friendly. Fully stocked kitchen. Modern feel. And a fenced in private patio for relaxing. Heart of Bend is a charming 3 bed, 1 bath home located on Bend’s popular West Side right in the heart of…

Bedrooms 3
Bathrooms 1
# of Guests 6
Pet Friendly? Yes

Aspen House

Location: Bend, Oregon

Property Type: Cottage

from $99 /nt
2
1
4

The Aspen House cozy home is a great place to relax and enjoy all that Bend has to offer. A classic Bend millworker’s house at its roots, it's been modernizing while keeping the Old Bend feel. Look for creative reuse and recycled materials and enjoy energy efficient systems to keep you just the perfect temperature. This cozy home is a great place to relax and enjoy all that Bend has…...

Welcome to the Aspen House! You'll love this modern cottage with cozy charm and global flair! Bring your adventurous spirit and embrace your amazing location in downtown Bend. Saunter in any direction and you’ll find lots to do in downtown Bend!

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Aspen House

The Aspen House cozy home is a great place to relax and enjoy all that Bend has to offer. A classic Bend millworker’s house at its roots, it's been modernizing while keeping the Old Bend feel. Look for creative reuse and recycled materials and enjoy energy efficient systems to keep you just the perfect temperature. This cozy home is a great place to relax and enjoy all that Bend has…

Bedrooms 2
Bathrooms 1
# of Guests 4
Pet Friendly? No

Bungalow Blue

Location: Bend, Oregon

Property Type: Cottage

from $109 /nt
3
2.5
6

Bungalow Blue is a charming 3 bed, 2 ½ bath home located on Bend’s popular West Side right in the heart of it all! You'll love this quintessential craftsman westside home. Just half a block off of Newport Avenue, Bungalow Blue is tucked into a quiet neighborhood. Welcome to your home just a few steps away from some of Bend’s most popular restaurants, coffee shops, bakeries, grocery, boutiques and more!…...

Sweet cottage home with modern amenities in the heart of westside Bend! Two fireplaces, free wifi, window A/C in summer, gas outdoor BBQ, outside dining, bikes. Walk a block to Newport Ave for some of Bend's best restaurants, cafes & shops.

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Bungalow Blue

Bungalow Blue is a charming 3 bed, 2 ½ bath home located on Bend’s popular West Side right in the heart of it all! You'll love this quintessential craftsman westside home. Just half a block off of Newport Avenue, Bungalow Blue is tucked into a quiet neighborhood. Welcome to your home just a few steps away from some of Bend’s most popular restaurants, coffee shops, bakeries, grocery, boutiques and more!…

Bedrooms 3
Bathrooms 2.5
# of Guests 6
Pet Friendly? Yes

Sugar Plum Cottage

Location: Bend, Oregon

Property Type: Cottage

from $99 /nt
1
1
4

This sweet cottage is a completely refreshed 1910, craftsman bungalow. Welcome to the Sugar Plum Cottage. This fully furnished home has been head to toe remodeled in 2023 and has 1 bedroom (Queen), 1 bathroom and a Queen pull out sleeper sofa. Snuggle in and enjoy the very best Bend has to offer. Just 1 block from the delicious food cart lot and all of the cafes, restaurants and breweries…...

Completely rejuvenated Sugar Plum Cottage in downtown Bend! Wifi, Smart HDTV, propane BBQ, outside seating. Walk a block to food trucks, restaurants and shops. Walk a bit further to concerts and to river float. Come enjoy all Bend has to offer!

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Sugar Plum Cottage

This sweet cottage is a completely refreshed 1910, craftsman bungalow. Welcome to the Sugar Plum Cottage. This fully furnished home has been head to toe remodeled in 2023 and has 1 bedroom (Queen), 1 bathroom and a Queen pull out sleeper sofa. Snuggle in and enjoy the very best Bend has to offer. Just 1 block from the delicious food cart lot and all of the cafes, restaurants and breweries…

Bedrooms 1
Bathrooms 1
# of Guests 4
Pet Friendly? No

Hygge Harmony

Location: Bend, Oregon

Property Type: House

from $109 /nt
2
1.5
6

Welcome to Hygge Harmony, a 1927 westside bungalow that delivers big on style! This light and bright home has two bedrooms (king, king), sleeper sofa (queen) and one full bathroom and one extra shower. You'll love the large bedrooms which are so rare for bungalow homes. Snuggle up in front of either of the 2 gas fireplaces in the master bedroom and kitchen, and the luxury of a hot tub!…...

Fantastic 2 bedroom home with luxury styling! Vintage chandeliers, cozy fireplaces, Viking range...you'll be at home in this gem! Just steps to all 10 Barrel, the food cart lot, all the restaurants and shops on Galveston. This is the heart of Bend!

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Hygge Harmony

Welcome to Hygge Harmony, a 1927 westside bungalow that delivers big on style! This light and bright home has two bedrooms (king, king), sleeper sofa (queen) and one full bathroom and one extra shower. You'll love the large bedrooms which are so rare for bungalow homes. Snuggle up in front of either of the 2 gas fireplaces in the master bedroom and kitchen, and the luxury of a hot tub!…

Bedrooms 2
Bathrooms 1.5
# of Guests 6
Pet Friendly? Yes

Bella Bird Bungalow

Location: Bend, Oregon

Property Type: Cottage

from $119 /nt
3
2
6

The Bella Bird Bungalow is a completely renewed 1910 solar, craftsman cottage. This solar powered, fully furnished home has 3 bedrooms (1 King, 1 Queen, 2 Twins) and 2 bathrooms. Snuggle into your private, sweet bird nest and enjoy the very best Bend has to offer. Delightful details will surprise and charm you in this very sweet westside home. Just 1 block from the delicious food cart lot and all…...

Sweet cottage home with modern amenities in the heart of westside Bend! Outdoor hot tub, wifi internet, HDTV, gas fireplace, gas outdoor BBQ, outside dining, bikes. Walk a block to Galveston Ave for some of Bend's best restaurants, cafes and shops.

Book Now

Bella Bird Bungalow

The Bella Bird Bungalow is a completely renewed 1910 solar, craftsman cottage. This solar powered, fully furnished home has 3 bedrooms (1 King, 1 Queen, 2 Twins) and 2 bathrooms. Snuggle into your private, sweet bird nest and enjoy the very best Bend has to offer. Delightful details will surprise and charm you in this very sweet westside home. Just 1 block from the delicious food cart lot and all…

Bedrooms 3
Bathrooms 2
# of Guests 6
Pet Friendly? No