Vacation Rentals

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

North Sister Bungalow

Location: Bend, Oregon

Property Type: Cottage

from $99 /nt
1
1
3

Welcome to North Sister Bungalow! The North Sister Bungalow is the largest of the three attached but completely independent homes in this unique and historic triplex. A classic example of early 1900's living, you'll love having Bend at your front door. The grassy back lawn and outdoor dining area are perfect for summer picnics. Enjoy a dedicated parking space and a very charming bungalow home. Perch on your front stoop…...

A sweet craftsman bungalow home IN downtown Bend? This is it! Less than a block to Jackson's Corner, 3 blocks to the river and 4 blocks to downtown Bend. This renewed bungalow home is so charming. Dedicated parking spot, yard and BBQ too! Come stay!

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North Sister Bungalow

Welcome to North Sister Bungalow! The North Sister Bungalow is the largest of the three attached but completely independent homes in this unique and historic triplex. A classic example of early 1900's living, you'll love having Bend at your front door. The grassy back lawn and outdoor dining area are perfect for summer picnics. Enjoy a dedicated parking space and a very charming bungalow home. Perch on your front stoop…

Bedrooms 1
Bathrooms 1
# of Guests 3
Pet Friendly? No

Vintage Awbrey

Location: Bend, Oregon

Property Type: Cottage

from $109 /nt
2
1
6

This spacious and Old Mill home is fully furnished for your Bend getaway! Vintage and modern all at the same time...You will love this completely updated kitchen and the cool, mid century furnishings. This charming vintage-modern home is adorable inside and out. A classic wood burning fireplace will warm and welcome you home on cool nights. This home has central heat too! Original hardwood and modern cork floors rest underfoot.…...

Three blocks to the heart of downtown Bend, this vintage-modern home will be the perfect homebase for your Bend getaway. You'll find a wood burning fireplace, A/C, flatscreen/cable, TV, wifi, bikes and hot tub. You'll be set for your Bend getaway!

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Vintage Awbrey

This spacious and Old Mill home is fully furnished for your Bend getaway! Vintage and modern all at the same time...You will love this completely updated kitchen and the cool, mid century furnishings. This charming vintage-modern home is adorable inside and out. A classic wood burning fireplace will warm and welcome you home on cool nights. This home has central heat too! Original hardwood and modern cork floors rest underfoot.…

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

St Helens Place Cottage

Location: Bend, Oregon

Property Type: Bungalow

from $109 /nt
2
1
4

This lovely home is ready just in time for Memorial Day! Welcome to St Helens Cottage, a sweet, warm and inviting vintage-but-modern home featuring 2 bedrooms (king, queen) and 1 bathroom. DOWNTOWN LOCATION You are a mere 2 blocks from everything downtown...some of Bend's finest restaurants, breweries and entertainment. Take an easy stroll into the very heart of downtown Bend, the Old Mill or the Deschutes River. The best of…...

This sweetly restored cottage home in Bend offers room to roam inside and out! Quiet and peaceful, tucked into the charming historic neighborhoods of downtown Bend. Curl up by the fireplace or relax in the spacious front yard.

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St Helens Place Cottage

This lovely home is ready just in time for Memorial Day! Welcome to St Helens Cottage, a sweet, warm and inviting vintage-but-modern home featuring 2 bedrooms (king, queen) and 1 bathroom. DOWNTOWN LOCATION You are a mere 2 blocks from everything downtown...some of Bend's finest restaurants, breweries and entertainment. Take an easy stroll into the very heart of downtown Bend, the Old Mill or the Deschutes River. The best of…

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

Elderberry Cottage

Location: Bend, Oregon

Property Type: Bungalow

from $119 /nt
3
1
8

Welcome to your cozy and classic cottage for your downtown Bend adventures! You'll love this delightful space! Plenty of space for relaxing and dining for 6 adults... if you can share the 1 bathroom! This bungalow home is comfortable and open, perfect for catching up with friends and family inside and out. The back patios are open and a BBQ is waiting for you too! Grab a book, a friend…...

Tuck into this classic bungalow home...you are only 2 walkable blocks from downtown Bend at the Elderberry Cottage! Classic charms abound...snuggle up in front of the fireplace, make it a movie night on the flatscreen TV, free wifi/cable, & hot tub!

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Elderberry Cottage

Welcome to your cozy and classic cottage for your downtown Bend adventures! You'll love this delightful space! Plenty of space for relaxing and dining for 6 adults... if you can share the 1 bathroom! This bungalow home is comfortable and open, perfect for catching up with friends and family inside and out. The back patios are open and a BBQ is waiting for you too! Grab a book, a friend…

Bedrooms 3
Bathrooms 1
# of Guests 8
Pet Friendly? Yes

Farewell Bend Bungalow…New Listing!

Location: Bend, Oregon

Property Type: Bungalow

from $149 /nt
3
2
6

This lovely home will be available in June 2024! Just in time for summer! We'll have additional photos soon... DOWNTOWN LOCATION This is where all the best neighborhoods meet...downtown, Old Mill, Westside...this is the location you are looking for in Bend. So walkable, you will likely park your car and walk to your concert at the Hayden Homes Amphitheater, walk to your dinner in downtown Bend, walk to the surf…...

Excellent downtown Bend location just steps to Jackson's Corner, the Old Mill and the surf wave. Historic charm and a clean, modern vibe, this lovely home has a king suite that takes up the whole upper floor and 2 main floor queen bedrooms. Welcome!

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Farewell Bend Bungalow…New Listing!

This lovely home will be available in June 2024! Just in time for summer! We'll have additional photos soon... DOWNTOWN LOCATION This is where all the best neighborhoods meet...downtown, Old Mill, Westside...this is the location you are looking for in Bend. So walkable, you will likely park your car and walk to your concert at the Hayden Homes Amphitheater, walk to your dinner in downtown Bend, walk to the surf…

Bedrooms 3
Bathrooms 2
# of Guests 6
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

Cecil Sly

Location: Bend, Oregon

Property Type: Bungalow

from $119 /nt
1
1
4

Welcome to your downtown historic retreat. Cecil Sly is IN Downtown Bend. Fully Furnished with 1 king bed and modern amenities, this historic home is registered with the National Register of Historic Places. Warm, inviting and centrally located, this classic and walkable home is just a few steps to Downtown Bend. Perfect for your next Bend stay. DOWNTOWN LOCATION Downtown Bend is your front yard from this historic perch. Walk…...

Cecil Sly is a Registered Historic home on a quiet treed residential block right at the edge of downtown Bend. Fresh from an early 2018 remodel, this historic home has it all. Amazing location, salt water hot tub, gas fireplace and historic charm.

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Cecil Sly

Welcome to your downtown historic retreat. Cecil Sly is IN Downtown Bend. Fully Furnished with 1 king bed and modern amenities, this historic home is registered with the National Register of Historic Places. Warm, inviting and centrally located, this classic and walkable home is just a few steps to Downtown Bend. Perfect for your next Bend stay. DOWNTOWN LOCATION Downtown Bend is your front yard from this historic perch. Walk…

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

On the River Westside – Waterfront

Location: Bend, Oregon

Property Type: House

from $125 /nt
3
3
6

Welcome to On The River Westside in Bend. Available for monthly stays and longer, this lovely riverfront home will be a peaceful retreat for your stay in Bend. Located on Bend's very popular westside, this home is only a few blocks walk to popular coffee shops and brew pubs. Relish your riverfront perch from the master bedroom hot tub on the outdoor deck. Featured in an issue of Cascade East…...

This lovely home is available for monthly stays and longer. Incredible river views from this lovely waterfront home in the heart of westside Bend. Master hot tub, free internet, HDTV, gas outdoor BBQ, riverfront dining.

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On the River Westside – Waterfront

Welcome to On The River Westside in Bend. Available for monthly stays and longer, this lovely riverfront home will be a peaceful retreat for your stay in Bend. Located on Bend's very popular westside, this home is only a few blocks walk to popular coffee shops and brew pubs. Relish your riverfront perch from the master bedroom hot tub on the outdoor deck. Featured in an issue of Cascade East…

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

Riverside Condo

Location: Bend, Oregon

Property Type: Condo

from $69 /nt
1
2
4

Welcome to the Riverside Condo! Cozy, top floor 2-bed, 2-bath condo in a riverside complex just 2-3 blocks from Downtown Bend! Saunter to the river, play in the park, or cruise to downtown Bend. You'll love having a fully furnished kitchen for cooking, gas fireplace, A/C, and 2 balconies overlooking the common courtyard! DOWNTOWN LOCATION The River Retreat Condo is only a skip to downtown Bend! With the Deschutes River,…...

Great top floor condo in a riverside complex! Just 3 blocks to downtown Bend! Saunter to the river, play in the park, amble downtown...Fully furnished kitchen for cooking, 2 balconies overlooking the big park-like grounds.

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Riverside Condo

Welcome to the Riverside Condo! Cozy, top floor 2-bed, 2-bath condo in a riverside complex just 2-3 blocks from Downtown Bend! Saunter to the river, play in the park, or cruise to downtown Bend. You'll love having a fully furnished kitchen for cooking, gas fireplace, A/C, and 2 balconies overlooking the common courtyard! DOWNTOWN LOCATION The River Retreat Condo is only a skip to downtown Bend! With the Deschutes River,…

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

Khaya

Location: Bend, Oregon

Property Type: House

from $129 /nt
3
2.5
6

Welcome to Khaya, a LEED certified, solar powered home that is as serious about its carbon footprint as it is about the comforts of home! Khaya will spoil you with its luxurious touches. Your toes will love the heated floors and your senses will delight in the soaring ceilings and plentiful natural light. So spacious, modern and comfortable! DOWNTOWN LOCATION This amazing location on Newport Avenue is within a one-minute…...

Eco smart, solar powered, LEED certified home in the heart of Bend..Walk to downtown, just about everywhere! Heated floors underfoot, soaring ceilings overhead and 3 king bedrooms welcome you to your best Bend getaway yet!

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Khaya

Welcome to Khaya, a LEED certified, solar powered home that is as serious about its carbon footprint as it is about the comforts of home! Khaya will spoil you with its luxurious touches. Your toes will love the heated floors and your senses will delight in the soaring ceilings and plentiful natural light. So spacious, modern and comfortable! DOWNTOWN LOCATION This amazing location on Newport Avenue is within a one-minute…

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

Hygge Harmony

Location: Bend, Oregon

Property Type: Bungalow

from $126 /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

Sunshine Daydream – New listing!

Location: Bend, Oregon

Property Type: Bungalow

from $99 /nt
1
1
4

Ready just in time for summer! Welcome to your downtown Bend retreat. Sunshine Daydream is IN Downtown Bend. This sweet and completely redone 1941 cottage is fully furnished with 1 queen bed, 1 sleeper sofa and modern amenities. This home is perfect exploring all of downtown Bend! DOWNTOWN LOCATION Sunshine Daydream is right on the edge of bustling downtown Bend. You can walk anywhere downtown in just a few minutes.…...

Sweet Sunshine Daydream is tucked away right on the edge of downtown Bend. Walk 1/2 a block to start your exploration of downtown restaurants, shops and more! This sweet gem is the perfect basecamp for a Bend adventure.

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Sunshine Daydream – New listing!

Ready just in time for summer! Welcome to your downtown Bend retreat. Sunshine Daydream is IN Downtown Bend. This sweet and completely redone 1941 cottage is fully furnished with 1 queen bed, 1 sleeper sofa and modern amenities. This home is perfect exploring all of downtown Bend! DOWNTOWN LOCATION Sunshine Daydream is right on the edge of bustling downtown Bend. You can walk anywhere downtown in just a few minutes.…

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

The Sweet Spot

Location: Bend, Oregon

Property Type: House

from $120 /nt
3
3
6

Welcome to this modern 3-bed, 3-bath home in the heart of Bend! Ample room to spread out and enjoy you private oasis in downtown Bend. This amazing 2 story perch is light and bright and above it all. The upstairs living area centers around a beautiful and modern kitchen and kitchen island. So perfect for coffee and planning another day in beautiful Bend. Each of the 3 bedrooms has its…...

This urban beauty is perfectly placed on one of the best corners of downtown Bend. This light and bright home is modern and fresh. Hot tub, 2nd floor balcony, 2 living spaces, 3 car garages. Walk a block to the river, downtown or the Old Mill.

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The Sweet Spot

Welcome to this modern 3-bed, 3-bath home in the heart of Bend! Ample room to spread out and enjoy you private oasis in downtown Bend. This amazing 2 story perch is light and bright and above it all. The upstairs living area centers around a beautiful and modern kitchen and kitchen island. So perfect for coffee and planning another day in beautiful Bend. Each of the 3 bedrooms has its…

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