50 Best Bend Vacation rentals on Holiday Lettings - Apartments

Close

Bend

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

703 Vacation rentals

24

Bend ski home to rent.

Central Oregon / Bend

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ski
  • Child friendly
  • Air conditioning
Make the most of your mountain getaway when you stay at this 3-bedroom, 2-bathroom vacation rental house in Bend. Up to 7 guests can spread out in over 1,500 square feet of well-appointed living space. Breathe in the fresh air on the back deck as you take in the picture …see more

from $165 / night

$1,155 / week

Book View

Responds fast!
avg. 19 minutes

from $165 / night

13

Vacation home in Bend

Central Oregon / Bend

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
You'll find the comforts of home at the Milwaukee Cottage, an updated vintage Bend cottage meticulously maintained and perfectly situated in Bend's popular westside. (updates to come November 1, 2017 new paint inside/out from ceilings to trim, all new furnishings/furni …see more

from $200 / night

$1,400 / week

Book View

from $200 / night

33

Bend Vacation home rental

Central Oregon / Bend

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
The Central Oregon getaway of your dreams starts with this conveniently located Bend vacation rental! Modern and comfortable, with a private washer/dryer, a lovely deck, and updates throughout, this two-bedroom townhouse is an excellent home base for everything from an …see more

from $95 / night

$665 / week

Book View

Responds fast!
avg. 42 minutes

from $95 / night

(2) Excellent 

34

Vacation guest house in Bend

Central Oregon / Bend

7 28 2 nights min

  • 7 bedrooms
  • Sleeps 28
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
The Bunk+Brew Historic Lucas House is the newest and ONLY affordable destination for the adventure traveler in downtown Bend, Oregon. 2.5 blocks from the Bend Ale Trail, the Lucas House (1910) is also Bend’s first and oldest brick building. Book a room (or bunk), grab …see more

from $656 / night

$4,592 / week

Book View

Responds fast!
avg. 2 hours 21 minutes

from $656 / night

(5) Very Good 

Certificate of Excellence

15

Condo rental in Bend

Central Oregon / Bend

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Air conditioning
This place has it all, super convenient and accessible to all of the amenities you want when you visit Bend. A stone's throw from the Deschutes River and it's miles of walking trails, a 5 minute walk to downtown, quick access to the Bend Parkway, and adjacent to rest …see more

Certificate of Excellence

from $115 / night

$650 - $850 / week

Book View

Responds fast!
avg. 1 hour 30 minutes

from $115 / night

(12) Excellent 

10

Vacation home in Bend

Central Oregon / Bend

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Otterhouse is a riverside, two-story chalet-style home featuring an open floor plan with natural light and vaulted cedar ceilings. In addition to the living room, it has a spacious, warm library\loft as well as a large TV entertainment room. There is a master bedroom up …see more

from $195 / night

$1,200 - $1,520 / week

Book View

Responds fast!
avg. 1 hour 56 minutes

from $195 / night

35

Vacation studio rental

Central Oregon / Bend

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Air conditioning
Settle in for a fun-filled retreat to Bend with this studio condo, boasting a great location close to all the excitement in downtown plus great running and cycling on the Deschutes River Trail. Overlooking the peaceful scenery of Pioneer Park, this condo sits a couple …see more

from $82 / night

$574 / week

Book View

Responds fast!
avg. 42 minutes

from $82 / night

25

Ski log cabin to rent in Bend

Central Oregon / Bend

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Ski
  • Child friendly
  • Pet friendly
This classic log cabin exudes rustic country charm and offers 1,329 square feet of cozy living space. With views of the Deschutes River from all 3 bedrooms, the living room and the lofted patio, this Bend vacation rental cabin invites 7 guests to experience the essence …see more

from $135 / night

$945 / week

Book View

Responds fast!
avg. 19 minutes

from $135 / night

15

Bend Vacation home rental

Central Oregon / Bend

3 10 2 nights min

  • 3 bedrooms
  • Sleeps 10
  • 2 nights min
  • Child friendly
  • Pet friendly
The home is located in a quiet and peaceful setting, just minutes from all the great entertainment and restaurants to be found in downtown Bend. If you like great beer, you are in the right place. At last count, there were 31 micro breweries in town. Spring is a gre …see more

from $200 / night

$1,200 / week

Book View

from $200 / night

(8) Very Good 

36

Apartment rental in Bend with tennis court

Central Oregon / Bend

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
Located on Bend's westside, a short walk along the Deschutes to the Old Mill district and off the Cascade lakes road to Mt.Bachelor, this cozy, recently upgraded condo in Mount Bachelor Village is a convenient base for any recreation or vacation plans. Features a full …see more

from $150 / night

$900 / week

Book View

from $150 / night

(3) Very Good 

22

Vacation home rental

Central Oregon / Bend

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Enjoy the comfort and serenity waiting for you at this peaceful home with views to the Big Deschutes River. Watch ducks stirring the water or a heron standing nearby. Listen to geese pierce the calm as you absorb the tranquil beauty of this natural setting. With easy ac …see more

from $195 / night

$1,365 / week

Book View

Responds fast!
avg. 1 hour 2 minutes

from $195 / night

25

Vacation home in Bend

Central Oregon / Bend

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
Bring the whole family along to this Deschutes River paradise! The back deck overlooks the river's currents, and the home's secluded location means you can escape from life's worries for a bit. The wood interior evokes a true cabin feel, while you'll have all the comfor …see more

from $250 / night

$1,750 / week

Book View

Responds fast!
avg. 42 minutes

from $250 / night

10

Bend Vacation studio rental

Central Oregon / Bend

Studio 3 2 nights min

  • Studio
  • Sleeps 3
  • 2 nights min
  • Air conditioning
  • Pet friendly
Note: We are new to Tripadvisor so we don't have any reviews yet. However, on one of the other big booking sites we are Superhosts and have hundreds of 5 star reviews. Here's a couple of examples: Megan - March 2017 We stayed here for our 5th anniversary and it was pe …see more

from $75 / night

$525 / week

Book View

Responds fast!
avg. 1 hour 27 minutes

from $75 / night

(63) Excellent 

27

Vacation cottage in Bend

Central Oregon / Bend

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning
Secluded and quite 1 bedroom cottage just a 4 minute walk across Newport Ave bridge to numerous activities and businesses in downtown Bend. ~Immaculate, professionally decorated Cottage. ~Large Bathroom with deep tub, tiled walls and multiple shower heads. Tankless wat …see more

from $169 / night

$1,125 - $1,250 / week

Book View

Responds fast!
avg. 38 minutes

from $169 / night

36

Vacation home in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Sunsets over the cascades and leisurely strolls along the Deschutes River await you at this comfortable house in Bend, which features two master suites and scenic mountain and river views to greet you every morning. Located within easy walking distance of the shops and …see more

from $189 / night

$1,323 / week

Book View

Responds fast!
avg. 42 minutes

from $189 / night

(3) Excellent 

8

Vacation home in Bend

Central Oregon / Bend

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Pet friendly
This house is right on the Deschutes River. You can walk one way to town (through Drake Park), and the other way also along the river to the Old Mill District. There really isn't a better location in Bend. One bedroom with queen bed and a really comfortable queen hid …see more

from $150 / night

$730 - $1,250 / week

Book View

Responds fast!
avg. 3 hours 54 minutes

from $150 / night

(1) Excellent 

16

Bend Vacation home rental

Central Oregon / Bend

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning
This home is located on the desirable, southwest side of Bend in the heart of best recreation activities that Oregon has to offer. Easy access puts Mt. Bachelor skiing, fly fishing on remote lakes, mtn. biking, rafting, kayaking or the Old Mill District & Factory Outlet …see more

from $250 / night

$1,750 - $2,730 / week

Book View

Responds fast!
avg. 2 hours 2 minutes

from $250 / night

50

Vacation home in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
Get ready to live like a local in this gorgeous Deschutes Landing townhome with a lovely interior and great views! Located in the middle of Bend's historic Old Mill District, enjoy Bend from its very heart and leave your worries behind you. Close to everything, with a …see more

from $176 / night

$1,232 / week

Book View

Responds fast!
avg. 42 minutes

from $176 / night

(2) Excellent 

21

Vacation condo with golf nearby in Bend

Central Oregon / Bend

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Very clean, light and comfortable, well furnished one bedroom two full baths/shower/tub. Sleeps 4 very comfortably. Includes all utilities, wifi, basic cable, land line and use of all amenities. Fireplace ( presto log only), balcony with Deschutes Forest views and of …see more

from $165 / night

$1,055 - $1,250 / week

Book View

from $165 / night

(1) Very Good 

2

Bend Vacation apartment rental

Central Oregon / Bend

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Bendgetaway is a privately owned 2 bed/2 bath loft condominium located within the Seventh Mountain Resort near the town of Bend in central Oregon. Central Oregon is known for it's nearly 300 days of sunshine per year! …see more

from $175 / night

$1,225 / week

Book View

from $175 / night

(10) Excellent 

18

Vacation home in Bend

Central Oregon / Bend

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Private garden
Private country setting with mountain views just 5 miles northwest of Bend. This 12 year old home sits on 20 acres of open juniper and pine forest, surrounded by other large, open tracks of land. The setting is lovely and private - like your own, private park with a h …see more

from $250 / night

$1,750 / week

Book View

from $250 / night

34

Vacation home accommodation

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Plan your trip and dive into adventures that surround this convenient Bend condo! Whether you're out on the river whitewater rafting, hiking along the Deschutes River Trail, or exploring the award-winning beer scene, your vacation promises to be one to remember! Locate …see more

from $85 / night

$595 / week

Book View

Responds fast!
avg. 42 minutes

from $85 / night

20

Vacation home in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
Sasquatch Embrace the spirit of outdoor adventure in this beautiful Sunriver home with all the amenities you need for refreshing time away with family and friends. Nestled in pine woods, but bike ride to Sunriver Village and SHARC, this three-bedroom home may become yo …see more

from $122 / night

$794 - $1,711 / week

Inquire View

from $122 / night

(1) Excellent 

12

Bend Vacation home rental

Central Oregon / Bend

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Cute and cozy cottage on the west side of Bend. A short stroll to First Street Rapids foot bridge and the river trail. 10 minute walk to downtown Bend with an assortment of restaurants, night life, and activities throughout the year. Convenient access to the parkway for …see more

from $150 / night

$1,050 / week

Book View

from $150 / night

30

Vacation home in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Pet friendly
This house is perfect for a family getaway in the quiet neighborhoods outside of Sunriver, with a large yard and dog-friendly attitude. The yard boasts patio furniture, a basketball hoop, and everything you need to enjoy all 300 days of sunshine this area sees each year …see more

from $99 / night

$693 / week

Book View

Responds fast!
avg. 42 minutes

from $99 / night

26

Bend ski home to rent.

Central Oregon / Bend

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Ski
  • Child friendly
  • Air conditioning
Enjoy incredible views of the Deschutes River during your stay at 'River Glen Retreat,' a 3-bedroom, 2.5-bathroom vacation rental house in Bend! The 2,500-square-foot home is located on the banks of the river and has large windows which provide guests with unbeatable vi …see more

from $315 / night

$2,205 / week

Book View

Responds fast!
avg. 19 minutes

from $315 / night

30

Vacation home in Bend

Central Oregon / Bend

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Air conditioning
Come enjoy Central Oregon while enjoying the authentic charm of this Old Mill home with mountain views perched above the Old Mill District. You're within biking distance to all the shops, restaurants and theater in the Old Mill District. There are three well appointed …see more

from $185 / night

$1,295 / week

Book View

Responds fast!
avg. 42 minutes

from $185 / night

(1) Excellent 

26

Vacation home in Bend

Central Oregon / Bend

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Classic log cabin charm meets industrial vintage style. Quality natural fibers and stone are used to update this space into a cozy log cabin experience you will soon not forget. Whether listening to the wind in the pine trees or enjoying a warm real log fireplace, the f …see more

from $150 / night

$900 / week

Book View

from $150 / night

(8) Excellent 

35

Vacation home in Bend

Central Oregon / Bend

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
Tucked away on a private acre within the Deschutes National Forest, this home, completely remodeled in 2012, offers a seven-person hot tub, firepit, and barbecue, as well as plenty of indoor amenities to make it ideal for a group of up to nine guests. An ideal location …see more

from $112 / night

$784 / week

Book View

Responds fast!
avg. 42 minutes

from $112 / night

12

Home rental in Bend

Central Oregon / Bend

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Our 3 bedroom 2 bath house, located right near the Old Mill district, is the perfect basecamp for your adventure in Central Oregon. You'll find comfort with 2 Queen beds, 1 California King, an open kitchen & living area, a garage and a fenced yard. Our home is great fo …see more

from $299 / night

$2,000 / week

Book View

Responds fast!
avg. 57 minutes

from $299 / night

36

Bend ski cottage to rent.

Central Oregon / Bend

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 200 mi
  • Ski
  • Child friendly
This is "The Shed" at the Barnyard. The Shed is where Vintage meets farm life. We have cows,hen chickens, pigs and 2 goats. It is a true farm experience. You can tour the farm or just enjoy The Shed. We are 10 minutes east of Worthy Brewing, 15 minutes from downtown Ben …see more

from $75 / night

$525 / week

Book View

from $75 / night

(8) Very Good 

25

Home rental in Bend

Central Oregon / Bend

1 6 Min stay varies

  • 1 bedroom
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Plan a snowy holiday in this one-bedroom home with a loft and luxury resort attractions at Mt. Bachelor Village. The inviting space is perfect for six guests (four adults) wishing to explore Oregon by river or mountain top! This condo is surrounded by nature. The Desch …see more

from $95 / night

$665 / week

Book View

Responds fast!
avg. 42 minutes

from $95 / night

25

Bend ski cottage to rent.

Central Oregon / Bend

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ski
  • Child friendly
Fall in love with the Beaver State from the comfort of this 1-bedroom, 1-bathroom vacation rental home in Bend. Located on 1.5 gorgeous acres speckled with pine trees, this newly remodeled guest house for 4, complete with a flat-screen cable TV and high-end finishes, is …see more

from $100 / night

$700 / week

Book View

Responds fast!
avg. 19 minutes

from $100 / night

33

Home rental in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
The whole family will find moments to cherish during a stay at this spacious home in Sunriver. Featuring a private hot tub and shared tennis courts and pools accessible with eight SHARC passes, this house is the perfect blend of comfort and tranquility in the outdoor me …see more

from $109 / night

$763 / week

Book View

Responds fast!
avg. 42 minutes

from $109 / night

(7) Excellent 

22

Hotel apartment rental in Bend

Central Oregon / Bend

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Exceptional value @ Mt Bachelor Village Resort this upstairs unit (no elevator) with 2 REAL queen beds. No sofabeds here but there are 2 queen beds and an additional small roll-away single bed. This is a tastefully updated and exceptionally clean unit in a resort sett …see more

from $150 / night

$900 / week

Book View

from $150 / night

28

Vacation home in Bend

Central Oregon / Bend

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
Wake up to majestic views of Central Oregon's Three Sisters at this two-bedroom Bend escape, a beautifully crafted ranch home with a partially shaded deck, a stunning piece of property, and wonderful access to outdoor adventures in summer and winter alike. This welcomi …see more

from $93 / night

$651 / week

Book View

Responds fast!
avg. 42 minutes

from $93 / night

14

Bend ski home to rent.

Central Oregon / Bend

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Ski
  • Child friendly
This three bedroom, two bath with reversed living offers living/kitchen spaces upstairs, a master suite with hot tub, 800 square foot deck for outdoor living, and perfect accommodations for a family or couples sharing a vacation. Enjoy easy access to the Sunriver Villag …see more

from $200 / night

$1,400 / week

Book View

from $200 / night

21

Bend Vacation home rental

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
This piece of country in town at the Old Mill has 2400 sq feet of upscale comfort in a quiet, peaceful, beautiful setting and great location. Bike to the Old Mill, hang out in the Tipi on the 1/4 acre yard, luxuriate in the comfort of this well appointed and spacious ho …see more

from $250 / night

$1,300 - $1,600 / week

Book View

from $250 / night

(5) Excellent 

42

Vacation condo in Bend

Central Oregon / Bend

3 10 1 night min

  • 3 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in beautiful Mount Bachelor Village offering spectacular views of downtown Bend & Old Mill District. This Condo House is 2.0 miles from downtown Bend and 20 miles from the slopes of Mount Bachelor Ski Resort. Nearby activities include downhill & cross-count …see more

from $179 / night

$1,175 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from $179 / night

(2) Very Good 

10

Home rental in Bend

Central Oregon / Bend

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Air conditioning
*FALL/WINTER/SPRING SPECIAL* Normally $150 a night now $125 a night. 4 night minimum. Not available with any other specials or Thanksgiving weekend or Christmas Break or Spring Break. Beautiful, built in 2006, 1800+ SqFt., Luxury 3 Bedroom lodge style v …see more

from $165 / night

$990 - $1,230 / week

Book View

Responds fast!
avg. 2 hours 29 minutes

from $165 / night