Vacation Home Rentals By Owner In Bend, OR

$1643.2

Luxury Five Star Reviewed 5 Bedroom Caldera Springs Cabin, Bend, Oregon

Bend, Oregon, United States

* Now with exclusive access to the brand new Forest House pools, waterslides and fitness center*. This Luxury property has 5Br and 4.5 Baths and is located within the high end quiet community of Caldera Springs. Renters receive access to all Caldera Springs exclusive amenities in addition to those from the larger neighboring Sunriver resort (so you get the best from both worlds to maximize the value of your rental). More amenity information below. We have turnkey and professional local property managers with concierge service included with your stay to ensure everything imaginable is taken care of for you. brbrThis 3,948 sq. ft. home is the perfect basecamp for exploring Sunriver and beyond. br Perfect for large groups and family reunions, this home can easily accommodate 8-10 adults (or enjoyable for up to 12 with kids) with its spacious 5 bedrooms and 4.5 bathrooms. The 3 primary suites have king beds and their bathrooms have heated floors and soaking tubs, upstairs there is a 4th Bedroom with a queen bed and a 5th Bedroom called the bunk room with 3 full and 3 twin beds. These two rooms share a full bath with tub shower.brbrEnjoy spending quality time in the expansive great room, with high vaulted ceilings, hickory grey hardwood floors, and large windows to immerse yourself into nature with beautiful forest views. brbrWhile you won't get tired of the beautiful Northwest views, the great room does of course have a large 70 TV with Sonos surround sound, so you can watch TV from the very comfortable sectional with 2 chairs & ottomans while the gas fireplace burns in the background.brbrThe kitchen is a chef's dream, and has a very nice island with granite top and prep sink, a 48 Wolf gas range with dual ovens and a very quiet hood, a Wolf warming drawer and a 48 Subzero fridge, 2 Meile dishwashers, and instant hot water access. brbrAdjacent to the kitchen you will find a massive dining area that can accommodate up to 12, with a small wine fridge and bar counter at your disposal as well. brbrUpstairs has a nice loft with a ping pong table + foosball table and a couch, adjacent is a media room with TV and games/DVD/Cable. This interior hang out area allows you to play from the comfort of the house and not relegated to the garage. brbrThe entire home is wired for Sonos music where our guests can play their own tunes once they down load the app. High speed Wifi Internet and cable are available throughout.brbrWe also have 2 laundry areas for guests (downstairs and upstairs).brbrBeyond the amazing interior features, the back yard has a covered patio, a natural gas BBQ and dining area, a hot tub, and a cozy fire pit and star gazing area as well. The patio has its own music zone. Please note the Hot tub can be accessed from the Primary suite or the patio, it can seat 7.brbrWith your rental comes amenities, amenities, amenities...You get access to all Sunriver Resort's amenities, so you have endless recreation opportunities at your doorstep and concierge service to help you navigate and use them all. If you want to avoid the crowds, stay in the quiet community of Caldera Springs and enjoy complimentary access to the Quarry pool (outdoor infinity pool overlooking a large lake), fitness center, family game room with billiards and shuffleboard, playground, basketball court, bike rentals from the Lake House, Obsidian lake and complimentary rentals of canoes, kayaks, paddle boards etc., golf at Caldera Links, tennis and pickleball, and miles and miles of walking, jogging and bike paths. To gain larger resort amenities, head a few minutes next door to Sunriver where you also get exclusive access to: The Cove Aquatic Center (indoor and outdoor pools, hot tubs, waterslides and The Spotted Frog Cafe & Bar), Crosswater Club, golf and dining, Sunriver Resort tennis courts, and much more. Mt. Bachelor Ski resort is 20 minutes away for winter enjoyment!brbrThere is also a Tesla charger in the 3 car garage along with access to bikes for adults and kids alike (note you can also rent bikes at the lake house for free as well). brbrNO TRAILERS OR CAMPERS/RVs parking on street or driveway. Can park them by the quarry pool house across from the tennis courts.brbrCheck-in is after 4:00 p.m. on the day of arrival. During times of peak occupancy, your property may not be available until 6:00 p.m. Check-out is no later than 10:00 a.m.brbrDCCA#1250

5

Bed

4

Bath

12

Sleeps

$599.98

/ Nightly

Private Vacation Home

Westside Living at Its Best | Hot Tub, EV Charger & Walkable Bend Location

Bend, Oregon, United States

Meet Me on Milwaukee is a beautifully furnished 2-bedroom, 2.5-bath home located in one of Bend's most desirable Westside neighborhoods, offering the perfect blend of comfort, walkability, and Central Oregon adventure. Available for minimum stays of 30 nights, this two-story home is ideal for extended stays, relocations, or seasonal living.brbrJust blocks from Newport Market and within easy walking distance to the Deschutes River, downtown Bend, and some of the area's best coffee shops, restaurants, and breweries, the location truly can't be beat. Whether you're strolling river trails, grabbing a morning latte, or enjoying Bend's vibrant food scene, everything is right outside your door.brbrThe home features a private alley-access garage with an EV charger, making it both convenient and future-friendly. Inside, you'll find thoughtfully designed living spaces with comfortable furnishings and a layout that balances privacy and gathering.brbrStep outside to your lovely private patio, complete with a hot tub—perfect for stargazing at night or unwinding after a day skiing at Mt. Bachelor, or exploring Bend's endless biking, hiking, fishing, and outdoor adventures.brbrAdventure truly awaits at Meet Me on Milwaukee, a peaceful yet perfectly located home base in the heart of Bend's Westside.

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Sleeps

$533.6

/ Nightly

Private Vacation Home

Hot Tub ~ Fireplace ~ Brand New Furnishings ~ Dog Friendly

Bend, Oregon, United States

This Bend Westside home is the perfect home base for all your adventures! Relax in the hot tub after a day of activities, take advantage of the well stocked kitchen or ride the bikes to one of many restaurants and coffee shops within a mile of the home! brbrBedding Configuration:brbrPrimary Suite: King bed w/ ensuite bathbr2nd bedroom: Queen bedbr3rd bedroom: Bunk Bed-full on bottom, twin on topbrbrThe home is pet friendly (2 pet max) and the pet fee is $40/day (Max $250). brbrBook at least a week and a 10% discount is automatically applied (Excludes Christmas/New Years). brbrVacation Rental Collective has the perfect Bend Vacation Rental, Bend Cabin, Bend AirBnB, or Bend VRBO for you and your group! Whether you're hiking, fishing, biking, skiing at Mount Bachelor, or enjoying Bend’s one-of-a-kind restaurants the Bend Collection has your perfect private lodging accommodations.brbrLCSL202201151

Bed

Bath

Sleeps

$470.62

/ Nightly

Private Vacation Home

Walk to the River! Incredible Home in the ♥ of Old Bend

Bend, Oregon, United States

We're new to VRBO but have all 5⭐️ reviews on other sites! You'll love this home.brbrEntire one bedroom 1st floor guest suite w/ private entrance. Newly renovated, clean, modern w/ a chef's stove & full kitchen on a quiet cul-de-sac in the Heart of Old Bend.brbrWalk from your door to the Deschutes River in minutes, or head to Downtown, Old Mill, or Box Factory: all within easy walking distance. You won't find a better location to explore Bend.brbrHigh speed internet & a standing desk. Electronic locks for easy check-in. Enhanced cleaning procedures. Licensed by the City of Bend.

Bed

Bath

Sleeps

$401.17

/ Nightly

Private Vacation Home

Modern Bend Vacation Home, Old Mill, HOT TUB!

Bend, Oregon, United States

This absolute gem is located in the heart of Bend and is less than 5 minutes from the Old Mill District. Our 3 bed/2.5 bath mountain modern home backs up to the canal and has just about every amenity you could ask for. Such amenities include a private hot tub & back patio, 2 separate living rooms, gourmet fully stocked kitchen, dedicated workspace, high end furniture/artwork, and much more. This home is light and bright with large windows and vaulted ceilings. Come enjoy all Bend has to offer!brbrYou are going to love every inch of this house…between the location and features of the home, you truly can’t beat this spot for your Bend getaway. We are located just 5 minutes from the Old Mill District and Downtown Bend. brbrWhen you enter the home you are immediately greeted by the open layout of the home. First is the great room with comfy furniture, a large smart TV, and a propane fireplace. From there you’ll see the dining area that comfortably seats 6. Any home chef is going to absolutely love the gourmet kitchen…it’s stocked with everything we could think of! Off of the kitchen/dining area is the back patio with a private (brand new) hot tub, as well as a firepit/seating area. Also downstairs is a mudroom, half bathroom, and garage with 6 bikes that guests will have access to. brbrUpstairs is probably my favorite part of the home because of how much natural light there is. The vaulted ceilings and large windows make it incredibly inviting and spacious. When you first walk upstairs you walk into the second living room with a sofa, smart TV with PS4, dedicated work space, board games, etc. Upstairs is also where you will find all 3 bedrooms. The primary bedroom (1 king bed) is incredibly spacious and has its own private balcony and full bathroom. The other 2 bedrooms have 1 queen bed each and also have a balcony that looks out over the canal…these balconies are perfect for your morning coffee! A full bathroom and laundry room are also present on this second level. Guests are going to love the beautiful artwork scattered throughout the home, all from local Central Oregon artists. brbrWe’ve really tried to make this the ideal Bend vacation home…we would love to host you! Please reach out with any questions!brbrWe can host a maximum of 6 occupants INCLUDING CHILDREN AND INFANTS per City of Bend regulations. brbrPlease note that in Central Oregon in the Winter we often have snowy road conditions. To make things simple, we stick to our stated cancellation policy. Please keep this in mind when booking in the Winter months. We also have a similar policy for smoke in the Summer. There’s a chance due to wildfires that there are smokey air conditions during your stay. If evacuations were to take place (extremely rare around here!) then a refund would be given, but other than that we will stick to the stated cancellation policy. Thank you for your understanding!brbr Please note that guests will have to climb stairs as all 3 bedrooms are located upstairs.brbrNO PETS ALLOWED ($750 fine)brbrLINK TO VIDEO TOUR: https://youtu.be/R-QwsT9ySVU si=FhdCOBl_xq-JCAGAbrbrBest equipped kitchen ever. If you like to cook, you’ll be very pleased with the appliances and accessories. - Review from Abram (December 2023)brbrThis home is a gem! Beds were the most comfortable we have slept on in a rental. - Review from Brittney (December 2023)brbrThe house was absolutely beautiful! In a great area, super close to everything! My friend and I enjoyed the hot tub and and everything Bend had to offer!brJoseph has a great book on the counter with suggestions of things to do and see! Would stay here again - Review from Victoria (November 2023)brbrPlease note that we have a ring doorbell by the front door, 2 outdoor security cameras (front and back), and a noise decibel meter in the living room to ensure the safety of our guests, neighbors, and property. brbrWe are located in a small, close-knit community with an active HOA. For this reason, any additional visitors (including dinners or small gatherings) must be approved in writing prior to the visit. Failure to disclose or obtain approval for additional guests will result in a $350 deep-cleaning fee and immediate cancellation of the remainder of the stay without refund.brbrQuiet Hours & Noise Policy - To respect our neighbors and comply with city regulations, no loud parties or events are permitted. This home is equipped with a noise monitoring device (measures decibel levels only, not conversations). Quiet hours are from 10:00 PM to 8:00 AM. Sustained noise levels above 80 dB during quiet hours may result in a $500 fine, in accordance with both City of Bend regulations and our neighborhood policies.brbr**Hot Tub Use Info/Disclaimer:brGuests use the hot tub at their own risk. By booking, you agree to follow all safety and cleanliness rules. Please shower and rinse feet before use, and do not use any soaps, oils, bubble bath, or other products in the tub. Absolutely no glassware near the hot tub. The cover must be removed and replaced properly (video instructions provided), and must remain closed and buckled when not in use. Misuse or damage (including improper cover handling) may result in fees up to $500. No horseplay or standing/sitting on the cover. Children 12 and under are not allowed in the hot tub under any circumstances due to prior incidents. A $150 cleaning fee applies if any food, drinks, bath products, or unauthorized uses are found. By using the hot tub, you assume all risk and agree to hold the property owner and manager harmless from any injury, loss, or damage.brbr**Bicycle Use Info/Disclaimer: brBikes are available as a free perk, but use is at your own risk. No helmets are provided—guests are encouraged to rent them locally. Bikes are not inspected between every stay and are suitable for teens and adults only—no one under 13 may use them. Please use caution and care; you’re responsible for any damage, loss, or injury caused while using the bikes. Locks are provided, but if a bike is stolen, you’ll be responsible for the replacement cost (up to $500). Any damage must be reported within 60 minutes of arrival, and repairs must be made at Bend Velo Bike Shop within one business day (or a fee may apply). You’ll also be responsible for tire repair or replacement if damage occurs. By using the bikes, you agree to hold the property owner and manager harmless from any injury, damage, or loss resulting from their use.

Bed

Bath

Sleeps

$1014.1

/ Nightly

Private Vacation Home

LUXE Home with EPIC Home Theater - Westside Location!

Bend, Oregon, United States

This is a luxury home located at the top of Overturf Butte in Bend, OR. If you're a movie lover, you'll enjoy the studio-quality theater room, with 155 8K screen, 11 channel ATMOS sound, and over 6,400 watts of speaker and subwoofer performance - an IMAX experience in your home.brbrWhen you're not in the theater room, enjoy the gas fire pit overlooking pine trees, or the deck area to socialize (or perhaps just read a book!) with the bird sounds and view. The back area is perfect for family lawn games like bocce ball, badminton, and croquet, which are all provided. Note this is our primary home and there are TWO CATS that will be present (sweet and social, no bite/scratch).brbrThe modern dining room can host up to 10 people with a large kitchen and covered gas grill. An expansive living room and gas fireplace set a nice backdrop to the 12' windows looking out at ponderosa pine trees, Aubrey Butte, and the occasional views of Mt. Jefferson. brbrThe primary bedroom has a king size bed and TempurPedic Hybrid mattress, and the bathroom suite includes a shower area for two, with rain showers and body spray heads for both. Relax with a soak in the large tub. Double vanities make it easy to get ready.brbrThree bedrooms have en suite full bathrooms, and the fourth bedroom has a full adjacent bathroom. All three bedrooms have queen-size, high-quality mattresses.brbrWork remotely in the dedicated office, with 1 gig high-speed internet and two workspaces with docking stations ready for your laptop. A sit/stand desk is available, and high quality video and microphones are there for video conferences. The room also hosts a second TV and reading area.brbrThere is a workout room with a Hydrow rowing machine, Echelon bike, NordicTrack treadmill, and a 5-50 lb weight set. Or use the yoga mat in front of floor-to-ceiling windows letting in the natural light and territorial views for a fantastic workout!brbrBend is an outdoor mecca. Voted #1 multi-sport town by Outdoor magazine and so many others, you're just minutes away from floating the Deschutes River, world-class single-track mountain biking at Phil's Trail, downhill skiing or lift-assisted mountain biking at Mt. Bachelor, nordic skiing at the Meissner trail system, stand-up paddle boarding on the alpine lakes, or hiking anything from the gentle river trail in town to nearby Tumalo Falls or the Cascade Mountains in the Three Sisters Wilderness. Climbers from around the world come for Smith Rock State Park, and for something unique, take a hike through ancient lava caves or make a day trip to Crater Lake National Park, the deepest lake in the United States and one of the clearest in the world (and certainly one of the most photographed!)brbrIn town get ready for the Bend Ale Trail. With more breweries per capita than nearly anywhere else, you're sure to find a brew that is perfect. We have a strong food scene, from food trucks after a day playing, to craft cocktails, wine tasting, and fine dining. Local boutique stores line the streets as you stroll through downtown. And for entertainment, watch a live show at the Tower Theater, Hayden Homes Amphitheater, or one of the many comedy or music venues.br

Bed

Bath

Sleeps

$430.52

/ Nightly

Private Vacation Home

Close, Cute, and Clean! - Hot Tub/Firepit/Bikes/Floats

Bend, Oregon, United States

There's a ton of snow in the mountains still and the days are warming up for springtime fun in Central Oregon!brbrThe perfect basecamp for all of your Central Oregon adventures! Come settle in for exploration and recreation!! 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. Reserve this convenient, comfortable, and centrally located home for your Bend adventures!! brbrSki, bike, paddle, golf, hike, climb, shop, dine...it's all here!brbrSoak in the hot tub or relax next to a patio fire after a fun day of skiing, biking, rock climbing, or hiking! You’ll have the comforts of home in a clean, cozy house that is close to all of the fun and adventure that Bend has to offer!brbrBikes (4 cruisers), float tubes (4), and paddleboards (2 inflatable) are all available for you to use! brbrFor winter sports, there are ski/snowboard racks in the garage. There are also heated boot/glove dryers...just in case your adventures get wet. You will be warm, dry, and ready to go again by morning! brbrMeals can be prepared at home using the full kitchen, with air-fry range, or the outdoor grill. You could also choose delivery, take-out, or eat at one of the many nearby restaurants and breweries that Bend is known for :) You'll also have a dishwasher, toaster, blender, and other standard kitchen appliances. Complimentary coffee is provided and can be used with the drip coffee pot or a French press. Watch movies or videos from your activities on the 50 Roku smart TV. The bluetooth sound bar will fill the house with your music or add excitement to your movies. The wifi is fast, at up to up to 1 Gig download speeds. brbrNeed more tubes or paddleboards Tumalo Creek rents them!brNeed more bikes Bird e-bikes can now be rented and used throughout the Bend area!brbrThis house sleeps up to 4 comfortably with quality, cotton bedding on:brbrBedroom 1: Queen bedbrBedroom 2: Full-over-twin trundle bedbrbrThe attached garage is available for your use and accommodates up to a mid-size vehicle. The driveway accommodates another vehicle for a 2nd off-street parking spot.brbrYou'll also have:brFull-size washer and dryer in dedicated laundry roombrOutdoor games (oversized Jenga and cornhole)brHigh-quality body wash, shampoo, and conditionerbrHair dryerbrExtra folding chairs (indoor and outdoor)

2

Bed

1

Bath

4

Sleeps

$280.16

/ Nightly

Private Vacation Home

Historic Belle Millhouse in Bend, OR. Walk to Downtown.vrbo

Bend, Oregon, United States

Enjoy an entire cottage built in Bend's Mill heyday of 1925, located in the historic Old Town of Bend. Newly restored including refinishing the original fir floor complete with their charming squeaks, and listed on Nat register of historic places. The bungalow comfortably sleeps 2 in the queen bed, and one or 2 adults or children in the second bedroom with a trundle bed with 2 twin mattresses. Just one block walk to the heart of downtown Bend with its restaurants, pubs, galleries as well as visitors center,banks groceries/pharmacy. Historic Drake park on the Deschutes River is an easy stroll. McMenamins Complex with Turkish soaking bath is around the block. Enjoy the fully equipped kitchen, washer and dryer, secure Wi-Fi and cable TV, heat pump and AC for your comfort. Cute gas fireplace. Lockable garage for your gear, ample street parking & full driveway. Bikes for your use. City of Bend short term Rental License No STR- 15-0324

Bed

Bath

Sleeps

$164.99

/ Nightly

Private Vacation Home

Hollinshead - Orchard District, Amazing Yard Next To Hollinshead Park w/Daylight Basement w/Billiards

Bend, Oregon, United States

Welcome to Hollinshead Haven, your serene escape in the heart of Bend. Nestled at the end of a tranquil Mid-Town cul-de-sac and backing onto the lush 16-acre Hollinshead Park, this 3-bedroom, 2.5-bath retreat is perfect for guests seeking a peaceful, long-term stay. Immerse yourself in the natural beauty and charm of Bend with seamless access to local amenities, dining, and shopping.brbrInteriorbr- Bright and spacious living area with plush seatingbr- Wood-burning fireplace for cozy eveningsbr- Large flat-screen smart TV for entertainmentbr- Open kitchen with modern appliances and ample counter spacebr- Deck with BBQ grill and patio furniture for alfresco diningbrbrBedroomsbr- Master Bedroom: King bed, walk-in closet, private bath with tubbr- Bedroom 2: Full bed, high-quality linensbr- Bedroom 3: Full bed, high-quality linensbrbrAmenitiesbr- Pool table and family room on the lower levelbr- Pet-friendly accommodations upon requestbr- Free WiFi throughout the homebr- Wood-burning fireplace for added warmthbr- Washer and dryer for conveniencebr- Secure garage parkingbrbrLocationbr- Situated in a quiet neighborhood at the end of a cul-de-sacbr- Adjacent to Hollinshead Park with off-leash dog park and community gardenbr- Close to coffee shops, restaurants, and shopping optionsbrbrDiscover the perfect balance of relaxation and adventure at Hollinshead Haven. Whether you're here for a family getaway or a retreat with friends, this home offers everything you need for an unforgettable stay. Contact Arrived today to reserve your spot in this idyllic Bend hideaway.

Bed

Bath

Sleeps

$404.73

/ Nightly

Private Vacation Home

Downtown Craftsman with Hot Tub

Bend, Oregon, United States

Unwind in your brand-new, private saltwater hot tub, now ready for you to enjoy! Welcome to our fabulous Craftsman, where historic charm has been thoughtfully blended with high-end modern comforts for a luxurious stay—set in what is arguably one of Bend’s very best locations. You’re perfectly positioned within easy walking distance to both Downtown Bend and the Deschutes River, including the beloved 1st Street Rapids Park and miles of scenic river trails.brbrThe main floor features a bright, open layout that flows from the welcoming front porch to the backyard patio. Gather in the living room around the classic Waterford wood stove, relax on the comfortable leather sofas, or enjoy a movie night on the large-screen LED SMART TV, which includes popular streaming apps such as Netflix, Amazon Prime, YouTube TV, Disney+, Hulu, Apple TV, and many others—simply log in to your favorite services and settle in.brbrThe gourmet kitchen is a chef's dream, fully equipped with a chef's refrigerator, gas range, and convection oven. We've stocked it with all the cookware and spices you need for a culinary adventure, along with thoughtful coffee amenities including a Cuisinart drip coffee maker, a bean grinder, and a French press, so you can start each morning exactly the way you like it.brbrRest is guaranteed in our three comfortable bedrooms, all furnished with plush European bedding. The main floor features two inviting bedrooms, while the beautifully finished basement serves as a private third-bedroom suite, complete with two single beds and its own dedicated full bathroom. This separate, lower-level retreat offers additional privacy and flexibility for families, children, or friends traveling together. In total, the home offers two full bathrooms, including one with a charming vintage clawfoot tub, plus a convenient laundry area.brbrThis home is thoughtfully appointed with features for every type of traveler:br- Private Saltwater Hot Tub: Soak your cares away year-round in your exclusive spa.br- Outdoor Stone Fireplace: Gather for cozy evenings under the stars, sharing stories and making memories by the fire.br- Dedicated Workspace: A quiet spot is available for you to catch up on emails or work remotely.br- Family-Friendly: We provide a Pack ‘n Play, children's books, toys, and dinnerware to make your family's stay easier.

Bed

Bath

Sleeps

$589.78

/ Nightly

Private Vacation Home

New! Old Mill Lookout–Mountain Views, Fireplace, Dog Friendly

Bend, Oregon, United States

Perched above the Deschutes River with sweeping views of the Cascade Mountains, Old Mill Lookout offers the perfect blend of modern comfort and unbeatable location. Just steps from the Hayden Homes Amphitheater and minutes from the shops and restaurants of the Old Mill District, this stylish townhome is your front-row seat to the best of Bend.brbrStylish Interiors & Cozy TouchesbrStep into a thoughtfully designed living space featuring rich leather seating, a cozy fireplace, and a Roku-equipped TV—ideal for relaxing evenings after a day of adventure. A dedicated game table invites you to slow down with a game of chess or a puzzle night.brbrThe chef’s kitchen is fully equipped with stainless steel appliances, ample prep space, and a double basin sink—perfect for cooking in or entertaining with ease.brbrOutdoor Living with a ViewbrTake in stunning mountain and river views from not one, but two private balconies. Grill dinner on the gas BBQ or sip your morning coffee while breathing in that crisp, high-desert air.brbrBedrooms & BathroomsbrPrimary Suite (1st floor): King bed with an ensuite bathroom, soaking tub, standalone shower, and balcony access for ultimate relaxation.br2nd Bedroom: (2nd floor) King bed w/ private balconybr3rd Bedroom: (2nd floor) 2 double bedsbrbrExtras You'll Love:br-Private laundry roombr-Fast Wi-Fi for streaming or remote workbr-Garage + driveway parking (2 vehicles)br-Smart home technology for added securitybrbrLocation, Location, Location!br-Steps from Hayden Homes Amphitheater – walk to concerts & eventsbr-Minutes to Old Mill District – boutique shopping, dining & breweriesbr-Close to Bend’s best outdoor adventures – hiking, biking & river activitiesbrbrThings to Know:br-Roku streaming on 3 TVs (bring your login)br-4x4 may be required in winter monthsbr-Propane for the grill providedbr-This home is dog-friendly! We allow a maximum of 2 dogs max and the pet fee is $40/day (for a max $250 per stay)brbrWhether you're here for a concert, a weekend of outdoor adventure, or a relaxing retreat, Old Mill Lookout puts you right where you want to be.brbrBook your stay and experience Bend like a local—mountain views and all.

Bed

Bath

Sleeps

$419.55

/ Nightly

Private Vacation Home

Cozy Farmhouse on 1 acre- Stargaze in the Hot tub

Bend, Oregon, United States

Relax with the whole family at this peaceful farmhouse on 1 acre in central Oregon. This home is a beautifully renovated old barn/house with 4 bdrms, 2.5 baths and every amenity you might need. The property has a private, fenced yard with a hammock, outside eating area, etc..brbrThis home is suitable for families or small groups who will respect the quiet and relaxing nature of the area, my place, and my neighbors. *** THIS HOME IS NOT APPROPRIATE FOR ROWDY GROUPS OR PARTIES!!***

4

Bed

2

Bath

8

Sleeps

$307.73

/ Nightly

Private Vacation Home

Riverview Executive Retreat | Farewell Bend

Bend, Oregon, United States

Summary:brbrExperience elevated Bend living at Riverview Executive Retreat | Farewell Bend. This luxury furnished 30+ day rental is located across from Farewell Bend Park and steps from the Deschutes River Trail, offering the perfect balance of comfort, location, and lifestyle. Walk or bike to the Old Mill District, downtown Bend, breweries, restaurants, river access, and concerts at Hayden Homes Amphitheater. Designed for extended stays, remote work, relocation stays, and experiencing Bend like a local.brbrbrbrThe Space:brbrThis thoughtfully designed home features modern finishes, comfortable living spaces, and everything needed for a relaxing monthly stay in Bend. Large windows bring in natural light while the surrounding river and park setting create a peaceful atmosphere just minutes from the heart of town.brbrbrbrThe open-concept kitchen, dining, and living areas are ideal for gathering, working remotely, or unwinding after a day outdoors. Guests will enjoy a fully equipped kitchen, comfortable furnishings, high-speed WiFi, and spaces designed to feel both elevated and livable for longer stays.brbrbrbrAs a furnished 30+ day executive rental, the home is well suited for family vacations, relocation stays, traveling professionals, remote work, seasonal Bend living, or those simply looking to experience Bend for an extended period of time.brbrbrbrLocated directly across from Farewell Bend Park and the Deschutes River Trail, guests can easily walk, bike, paddle, or explore some of Bend’s most iconic outdoor spaces right from the front door. The home also offers quick access to Century Drive, making Mt. Bachelor adventures, Cascade Lakes hikes, and mountain biking trails easily accessible year-round.brbrbrbrWhether visiting for work, adventure, or an extended escape, this home offers a comfortable and convenient home base in one of Bend’s most desirable locations.brbrbrbrGuest Access:brbrGuests will have access to the full home, thoughtfully designed with spacious multi-level living ideal for extended stays, families, or groups traveling together.brbrbrbrThe main level features comfortable single-level living with three bedrooms, including a private primary suite located on its own wing of the home for added privacy. The central living space includes a fully equipped kitchen, dining area, and inviting living room with fireplace, all opening to the outdoor balcony.brbrbrbrOn the opposite wing of the main level, guests will find two additional bedrooms and a full shared bathroom.brbrbrbrThe lower level offers additional space to relax and unwind with two more bedrooms, a full bathroom with tub, and a second family room/game room — perfect for movie nights, kids, remote work overflow, or separate gathering space for larger groups.brbrbrbrGuests will also have access to the garage and the home’s convenient location directly across from Farewell Bend Park and the Deschutes River Trail.brbrbrbrThe Neighborhood:brbrLocated in Bend’s highly sought-after Farewell Bend area, this home places you in the center of everything that makes Bend special. Directly across the street, Farewell Bend Park offers river access, open green space, and immediate connection to the Deschutes River Trail — perfect for walking, running, biking, or floating the river during summer months.brbrbrbrJust minutes away, the Old Mill District features some of Bend’s best restaurants, breweries, coffee shops, shopping, and entertainment. Guests can also enjoy concerts and events at Hayden Homes Amphitheater, one of the Pacific Northwest’s premier outdoor music venues, all within easy reach of the home. On many summer evenings, concert music can even be heard and enjoyed right from the balcony, creating a uniquely Bend experience.brbrbrbrThe location also provides quick access to Century Drive, the main route to Mt. Bachelor and the Cascade Lakes, making skiing, snowboarding, hiking, paddleboarding, and mountain biking easily accessible year-round. Despite being close to Bend’s attractions, the neighborhood maintains a peaceful residential feel surrounded by parks, river trails, and outdoor beauty.brbrbrbrGetting Around:brbrOne of the best parts of this location is how easily guests can experience Bend without needing to drive everywhere. The home sits directly across from Farewell Bend Park and the Deschutes River Trail, making it easy to walk or bike to the Old Mill District, Hayden Homes Amphitheater concerts, breweries, restaurants, coffee shops, and nearby parks.brbrbrbrDowntown Bend is just minutes away, while Century Drive provides quick and convenient access to Mt. Bachelor, the Cascade Lakes, hiking trails, mountain biking, and year-round outdoor recreation.brbrbrbrBend is very bike-friendly, and guests can enjoy miles of paved river trails right from the neighborhood. Ride-share services are readily available, though many guests find themselves walking or biking to most nearby attractions. The home also offers easy vehicle access and parking for exploring Central Oregon and beyond.brbrbrbrOther Things to Note:brbrThis is a furnished 30+ day rental designed for extended stays and executive-style living in Bend.brbrThe home is located in a peaceful residential neighborhood directly across from Farewell Bend Park and the Deschutes River Trail.brbrDuring summer concert season, music from Hayden Homes Amphitheater can often be heard from the balcony and outdoor spaces. Many guests enjoy the unique atmosphere and proximity to live music while still being outside the busiest downtown areas.brbrBend is an outdoor-focused community with easy year-round access to hiking, biking, river activities, skiing, and mountain recreation.brbrQuick access to Century Drive makes trips to Mt. Bachelor and the Cascade Lakes especially convenient.brbrPlease be respectful of neighbors, quiet hours, and the residential nature of the neighborhood.brbrSnow and winter weather conditions may occur seasonally, particularly for guests traveling to Mt. Bachelor during winter months.brbrbrbrInteraction with Guests:brbrSecond Base provides professional local management with a boutique, personalized approach. We respect our guests’ privacy while remaining available throughout your stay should anything arise or local recommendations be needed. Guests will enjoy convenient self check-in along with responsive local support during their time in Bend.

Bed

Bath

Sleeps

$1071.28

/ Nightly

Private Vacation Home

Stone - Tetherow, Hot Tub, Gas Fire Pit, BBQ, Executive Retreat

Bend, Oregon, United States

Welcome to the serene Cairn neighborhood of Tetherow, where you'll enjoy a world-class resort experience surrounded by Central Oregon's stunning high desert scenery. This exceptional destination is renowned for its award-winning golf course, fine dining options, and proximity to outdoor adventures like hiking and biking, as well as Mt. Bachelor and downtown Bend. Designed with entertainment in mind, this vacation home's reverse-living floor plan features a spacious upstairs living area, complete with a large kitchen and expansive exterior patio offering elevated views. Retreat to the peaceful ground floor living quarters, featuring an exterior patio with a firepit and hot tub for peace.brbrInteriorbr- Reverse-living floor plan for optimal entertainmentbr- Upstairs open concept living areabr- Spacious kitchen with modern fixturesbr- Large exterior patio with second-story viewsbrbrBedroomsbr- Ground floor living quarters for peaceful restbr- Comfortable and thoughtfully designed spacesbrbrAmenitiesbr- Exterior patio with firepit for cozy eveningsbr- Relaxing hot tub for unwinding after adventuresbrbrLocationbr- Nestled in Tetherow's Cairn neighborhoodbr- Close to award-winning golf course and fine diningbr- Convenient access to hiking, biking, Mt. Bachelor, and downtown BendbrbrPlease note, this home does not have access to Tetherow amenities.

Bed

Bath

Sleeps

$243.33

/ Nightly

Private Vacation Home

Bend Home Near Orchard Park Sleeps 4

Bend, Oregon, United States

Summary:brbrThis Bend home sits one block from Orchard Park and minutes from downtown, Old Mill District, and Mt Bachelor. Bright open living spaces feature new furnishings, a fully equipped kitchen, and a sunny backyard with outdoor dining for 4. Winter brings access to Oregon's largest ski resort in 30 minutes, while summer opens up golf at Widgi Creek and miles of hiking. Great for couples or a small family seeking both adventure and relaxation.brbrbrbrThe Space:brbrThe living room offers plush seating and a large smart TV for streaming. The kitchen has stainless steel appliances, stone countertops, and a circular dining table seating 4. The backyard includes an outdoor dining table for 4.brbrbrbrBedroom 1 has a queen bed, smart TV, and an ensuite half bathroom with single vanity. Bedroom 2 has a queen bed. A full guest bathroom features a single vanity and an accessible shower/tub combo with handrails.brbrbrbr❄️ Winter guests can reach Mount Bachelor Ski Resort in 30 minutes and Wanoga Sno Park in 25 minutes for snowshoeing and cross-country trails. ☀️ Summer brings golf at Widgi Creek Golf Course 15 minutes away and hiking through Cascade Mountain forests.brbrbrbrThe home includes washer and dryer in-unit, WiFi, driveway parking for 2 cars with additional street parking available, mini split AC in the living room and primary bedroom, and a fan in the second bedroom. Pets are not allowed. The fireplace and garage are not available for guest use.brbrbrbrThis rental includes one free ticket, per activity, per day to some of our favorite attractions! After booking you will receive a personal link to book your activities.brbrbrbrbrbrSelf check-in details will be provided before arrival. Driveway parking accommodates 2 vehicles with additional street parking on a first-come, first-served basis. The garage is off-limits to guests. AWD or 4WD is required during winter months for safe travel to ski areas and around Bend in snowy conditions.brbrbrbr Orchard Park is less than a block away, and Midtown Yacht Club Food Truck Lot is just a few blocks further for casual outdoor dining. Downtown Bend and the Old Mill District are under 10 minutes away, offering river walks, Deschutes Brewery, shopping, and dozens of restaurants. Mount Bachelor Ski Resort is 30 minutes west, and Wanoga Sno Park is 25 minutes away. Widgi Creek Golf Course is 15 minutes from the home. Pilot Butte, an extinct volcano with a summit trail, and the High Desert Museum are both short drives south of the property.brbrbrbrGetting Around:brbrBend is located along Highway 97. Mount Bachelor Ski Resort is approximately 30 minutes west via the Cascade Lakes Scenic Byway. Downtown Bend and the Old Mill District are under 10 minutes by car. Wanoga Sno Park is 25 minutes away. Widgi Creek Golf Course is 15 minutes from the home. Redmond Municipal Airport is about 20 minutes north on Highway 97.brbrbrbrOther Things to Note:brbr• Pets: Not allowed — a fine will be assessed at checkout if evidence of a pet is foundbrbr• Washer/Dryer: In-unitbrbr• Parking: 2 cars maximum in driveway, additional street parking available first-come, first-servedbrbr• AWD or 4WD required during winter monthsbrbr• Mini split AC available in living room and primary bedroom; second bedroom has a fan onlybrbr• Fireplace is not available for guest usebrbr• Garage is off-limits to guestsbrbrbrbrAs our valued guest, your rental includes one free ticket, per activity, per day to some of our favorite attractions including a Ghost Tour, Museum Tickets, Canoeing, and more! After booking you will receive a personal link to book your activities.

Bed

Bath

Sleeps

$393.71

/ Nightly

Private Vacation Home

New Listing! Bend Home ~ Hot Tub ~ Dog Friendly

Bend, Oregon, United States

Welcome to our serene vacation rental just on the outskirts of Bend, where you can enjoy the best of both worlds – minutes away from the vibrant city life while reveling in the tranquility of our quiet retreat.brbrThe rental encompasses the west half of the house, ensuring complete privacy as it is separated by a locked door. Inside, you'll find a well-equipped kitchenette, a cozy living room, a comfortable master bedroom, and an additional bedroom featuring a set of bunk beds. For those who need to work during their stay, we have provided a desk and office chair, creating a convenient workspace.brbrStep outside to the patio, where you'll discover a soothing hot tub and inviting outdoor furniture, perfect for unwinding under the starry night sky. The fully fenced backyard is a haven of tranquility, offering a peaceful space to relax and rejuvenate.brbrThroughout your stay, you won't need to share any common areas with other guests, except for the front parking area. Once you arrive, all the amenities and features listed are exclusively for your enjoyment.brbrWe know that your furry friends are a part of your family, and we're delighted to welcome up to two dogs per stay. The backyard is thoughtfully fenced, providing a safe and secure play area for your pets. brbrSo, come and experience the best of Bend while enjoying the comforts of our tranquil rental. Book your stay now and make unforgettable memories in this blissful retreat.brbrPet Fee: $40/night up to $250. No cats allowed. 2 dog max.brbrBedding Configuration:brbrBedroom One: King BedbrBedroom Two: Bunk beds

2

Bed

1

Bath

4

Sleeps

$342.48

/ Nightly

Private Vacation Home

Glendale Forest Retreat - Fireside Nights

Bend, Oregon, United States

Tucked away in a peaceful setting next to Sunriver, this spacious 4-bedroom, 2- bathroom home offers a tranquil and comfortable retreat. Perfect for families or groups, it features an inviting open layout and beautiful details throughout. Enjoy relaxing moments by the fire pit and explore the surrounding nature, all while having the comfort of modern living, with a staircase leading to an elevated living space.

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Bath

Sleeps

$429.24

/ Nightly

Private Vacation Home

Mountain View Retreat on 10 Private Acres, Minutes from all things Bend!

Bend, Oregon, United States

In a perfect location, this property strikes just the right balance of having everything easily accessible, yet very secluded with a breathtaking view of Mt. Bachelor! The Old Mill District, Drake Park, the road to Mt. Bachelor, and the shops and restaurants in Rustic Downtown Bend are all conveniently close by. The property is set at the end of the road on 10 Private Acres, biking trails literally in the backyard!brbrThis picture perfect home is updated with modern finishes in all the areas where it counts. The open-concept main level has a gorgeous new kitchen with a large island that seats 4, new appliances for all your cooking needs and a dining table for 6 adjacent to the kitchen. Flowing from the kitchen/dining area, is a great room with vaulted ceilings, comfortable furniture and views in every direction! An expansive deck for relaxing and gathering. Perfect indoor/outdoor living that lets in tons of natural light.brbrThe well thought out floor plan has a generously sized first floor master suite, attached master bathroom and oversized closet with a private patio. 2 well appointed bedrooms upstairs, a full bath and futon for additional sleeping needs.brbrThe garages below are available to store bikes, boats and all the toys to enjoy everything Central Oregon has to offer!brbrSo many thoughtful amenities, from the whole house WiFi, to AC, and a pellet stove for cozy winter nights. There are many options for entertainment within the house itself. All three flat screens are smart TVs, with multiple streaming apps available. Board games, puzzles, cards and poker chips are just a few of the provided entertainments.brbr The beautifully landscaped property also offers a variety of outdoor spaces and activities, such as a horseshoe pit, corn hole, a hot tub that seats 6, and a fire pit with lots of seating! There is a large BBQ, which is protected by a covered area, and can be used in any season. In the warmer seasons there is a large outdoor patio dining table and lots of other outdoor seating.brbrWeddings and large events are not permitted at this home - the home is very private - but noise travels - if you are looking for a party place - this house will not be a good fit.br

3

Bed

2

Bath

7

Sleeps

$325.26

/ Nightly

Private Vacation Home

Walk To Downtown & The Last Blockbuster from recently renovated home. 3 Bed/2ba

Bend, Oregon, United States

Welcome to Bend! Whether it's biking, hiking, skiing, fishing, playing in the water or just drinking great beer; I know that you will enjoy it all from the centrally located Olney Ave Re:Treat 2.0. With renovation completed in June 2018, you will find a warm, modern ambiance that is perfectly situated less than 1 mile from the heart of Bend. This is a perfect space for a family retreat, a group of friends, or a family looking for the comfort of a home while away. - Now get out and play!brbrEven though this is mentioned in several parts of the listing, it occasionally it gets overlooked; there is a mother in law apartment over the back area of the house where other guests may stay. There are no shared spaces and separate entrances. I do ask all guests to respect each others vacations by observing quiet hours between 10:00pm - 7:00am. Thank you.

3

Bed

2

Bath

6

Sleeps

$106.67

/ Nightly

Private Vacation Home

Bend's Darling Bungalow - Walk to Old Downtown & River + Fire Pit

Bend, Oregon, United States

♡ LOCATION ♡brbrCharming 2BR/2BA bungalow located in Old Town Bend! Enjoy a stroll to local breweries, shops, and restaurants, or explore the nearby river trail for fishing, rafting, and biking to the Old Mill for concerts. With cozy living spaces and a private backyard featuring a fire pit, this spot is ideal for unwinding after a day filled with adventure.brbrCheck our IG @bendsdarlingbungalow for more pictures and info! brPlease note, all bookings must go through the VRBO platform.brbrPROPERTY DESCRIPTIONbr♡ Charming House in an Ideal LocationbrbrThis property is a complete house located in a fantastic area known for its excellent walkability and opportunities to explore Bend. It features two bedrooms, a fully equipped kitchen, a cozy living room, and a private outdoor space complete with a fire pit.brbr♡ The Perfect Base for Your StaybrbrWhether you’re planning a romantic getaway or a family adventure, this delightful home serves as the perfect foundation for your visit. Nestled in a prime location, it offers a unique chance to discover everything Bend has to offer. The two bedrooms are tastefully decorated, boasting plush bedding and ample storage to make you feel at home, ensuring a restful night’s sleep after a day of adventures.brbr♡ Modern ConveniencesbrbrThe contemporary bathroom comes stocked with essentials for your convenience, allowing you to enjoy a refreshing start to your day. The fully equipped kitchen is a delight for any cooking enthusiast, inviting you to prepare delicious meals with all the appliances and utensils you need at your fingertips.brbr♡ Relaxation AwaitsbrbrAfter a day of exploring the vibrant local scene, unwind in the cozy living room. Whether you’re curling up with a favorite book, watching a movie, or simply enjoying some quiet time, this space is designed for relaxation. The private outdoor area is a true treasure, complete with a fire pit—perfect for stargazing at night or savoring a morning coffee while taking in the crisp, fresh air.brbr♡ Explore Local AttractionsbrbrWith its prime location, you’ll find yourself just steps away from charming local cafes, unique shops, and scenic hiking trails. This home is an ideal spot for experiencing the diverse attractions and natural beauty that Bend has to offer, promising a memorable stay for all who visit.

2

Bed

2

Bath

4

Sleeps

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