Holiday bungalows in Bend

With a stay at this vacation home in Bend (Old Farm District), you'll be within a 5-minute drive of Old Mill District and Deschutes River. This vacation home is 1.8 mi (2.9 km) from Hayden Homes Amphitheater and 2.6 mi (4.2 km) from Downtown Bend Business Association. Take advantage of recreation opportunities such as a hot tub, or other amenities including complimentary wireless internet access and a picnic area. Limited parking is available onsite. Treat yourself to a stay in this individually decorated vacation home, which features a fireplace and a flat-screen TV. There's a private furnished patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment.

Wake up refreshed in this bright, elegant studio sanctuary overlooking rocky hillside and grassy meadow in a historic friendly neighborhood. Comfy king bed, private entrance, kitchenette, private bath & cozy workspace. Walk to beautiful First Street Rapids Park footbridge (less than 1 min) & Downtown along the Deschutes River Trail passing several parks in 12 minutes. 55" TV with Amazon Fire, ethernet. This is a unique space has charm along with an ideal location. ♥︎The calm, parklike setting makes it hard to believe you are so close to the conveniences of town. Relaxing is inevitable in this private sanctuary where all your needs are met. Please note there is a shared wall with our primary home so some family noise is inevitable when we are home. If you are looking for total silence, you may want to consider a different option.The private entrance to the right side of the home allows for coming and going at any hours. The covered walkway to the door has a table and chairs to enjoy the morning side, or afternoon shade overlooking an empty lot with chickens, trees and open meadow. You'll have access to a kitchenette (with sink, microwave, Keurig machine, ample counter space, picnic supplies, etc.), and a private bathroom (including bathtub).We are generally available to help you out with anything, since we live on the property as well but wish to respect your privacy.This is a special location: Old Bend but not vacation homes all around. You're in a real neighborhood that is smack dab in the middle of Bend. Incredibly convenient with access to highway 97, downtown and the Deschutes River. Our neighborhood has been described as, "The last of the Mohicans" of Bend. There are multi-million dollar houses two houses down, as well as homes that haven't changed since they were built in the 20's. Being 200 yards from the Deschutes River and bordering downtown, the area has seen an explosion in property values and, as such, is enjoying significant upgrades. The First Street Rapids Park has a variety of picnic areas, river access, and one of most northerly footbridges across the river, making it a popular spot for walkers, bikers, kayakers/floaters, and anglers. Please note that we are the only vacation rental on our street -- please respect our neighbors!Bend is certainly not known for it's public transportation, but fortunately there is ample street parking due to a vacant lot next to our home. There is also parking in front of our home.Please note that because the room is attached to our main home and we do share a wall, there are some normal household noises that will come into the room.NO PARTIES. This is a quiet neighborhood and we live next-door. We are happy to share our space and are not unreasonable at all in regards to noise, but amplified music, late night loud voices, slamming doors, etc. are not allowed. We have had 300+ stays without issue, but we like to be transparent about the fact that this is not a suitable location if you are looking for a wild night. Also, please note this is listed as a 'townhouse' as there is a shared wall. While we did go through renovations to reduce sound transmission, there is some amount of noise that does make it into the studio (muted footsteps being the most common). It has not been an issue but we do want to point it out.Please turn the fireplace down several degrees before you leave. The furnace may be used if needed, but we do ask you to use the fireplace if possible.Please remove your shoes before going onto the carpeted areas when possible.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Located in Bend (River West), this vacation home is within a 10-minute drive of Hayden Homes Amphitheater and Old Mill District. This vacation home is 0.3 mi (0.4 km) from Central Oregon Community College and 1.1 mi (1.7 km) from Westside Church. Take advantage of recreation opportunities such as a hot tub, or other amenities including complimentary wireless internet access and concierge services. Free self parking is available onsite. Make yourself comfortable in this air-conditioned vacation home, which features a fireplace. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Digital television is provided for your entertainment.

Brand New NW Modern Home Across From River, Old Mill, and near Downtown! If you Love to Walk, Bike or Float to your Adventure or just chill at a tranquil getaway, THIS IS YOUR PLACE! "The Cabin"The spaceFrom our "Ohana" to yours "The Cabin".Experience Bend's outdoor wonderland nestled in an amazing, sought after quiet wooded neighborhood. "The Cabin" is situated directly across from a Sandy Beach on the Deschutes River Trail, Farewell Bend Park and 3.5 mile Loop Trail with it's enchanting bridges arching over the ever flowing Deschutes River.Short walk out your back gate to the Old Mill District, Parks, Les Schwab Amphitheater, Breweries, Shops, REI, Downtown Bend with all the Festivals and festivities in between. Absolutely the best location for access and peacefulness. It will make you want to move to Bend!"The Cabin" is a brand new NW Modern home built with an abundance of local reclaimed materials and local craftsmen. Natural light cascades throughout with high vaulting ceilings and windows, warm textures and colors envelope you. Enjoy indoor/outdoor living by opening your full glass garage door. It opens up the living space to a large partially covered stamped concrete patio. Your private fully fenced back yard has immediate access to Bend's endless playground and come back home to a peaceful place to re energize. Ideal for up to 4 adults and 2 children. Up to 2 dogs allowed.Your Master suite has a 6' wide opening barn doors. Fall onto a plush Cal-King bed with luxurious linens and pillows. Enjoy a good book, 40" HDTV or coffee in comfort.Bedroom 2 boasts a Queen bed with luxurious linens and memory foam topper. Daydream out the 5' wide opening barn doors through the living space out the wall of glass garage door of what adventure awaits.Full size sleeper in the living room with bedding provided. Perfect for one adult or two kiddos. While not ADA approved, its a 856 sq ft single level home with only one step out onto the back patio. Concrete floors throughout for cleanliness and if anything is needed please just ask. Slippers are highly recommended.Prepare a memorable meal in your fully equipped kitchen with stainless steel appliances and artist quality finishes. Sit down dining for 6 awaits at a beautiful live edge slab wood table and seating for 3 at a quarts slab counter. BBQ out on the gas grill and enjoy the outdoor seating and savor the moment you glimpse a bald eagle soaring over the river fishing.Soak up the morning sun with coffee on your stone patio tucked away in the front yard listening to an array of birds and maybe watch the resident deer stroll by. Step out your back door and relax in the fully fenced back yard and propane fire pit with kids and furry friends alike. With the covered patio and fire pit you'll relish in the natural setting year round. Walk your SUP or bike out your gate to all the wonders Bend has to offer:* Across from Sandy Beach with popular "put in" to float, SUP or Kayak. Farewell Bend with Playground and River Bend Park. Head up the amazing Deschutes River on the enchanting 3.5 mile loop River Trail with falls, rapids and spectacular cliffs. Fly fish, boulder or take a dip. Cross the arching South Canyon Bridge over the ever flowing river and fill your soul with nature.* Head down river approx. 1/2 mile OLD MILL District, Restaurants, Shops, Dog Park, Sand Volleyball Courts, Regal Cinema, REI or take in Les Schwab Amphitheater with its Sunday Free Concerts, Summer Band Series or a Festival.* 2+/- miles to the White Water Park, McKay Park, Pavilion Ice Skating Rink, Mirror Pond, Drake Park, Playgrounds, Downtown Bend and the most Breweries per capita in the State of Oregon. Endless Fun!* 3 to 5 miles of numerous famous Trail Heads, Phil's Trail Complex, 1000+ acre Shevlin Park and upper section Deschutes River Trail. Go Explore!* Within 15 miles of endless Upper Trails, Snow Parks, and Tumalo Falls. Snow shoe or cross country ski under the stars to an awaiting hut with wood stove, jump on a snowmobile for a scenic adventure to Elk Lake for lunch and drinks or a thrilling river rafting trip!* 22 miles to Mt Bachelor with its year round activities and the gateway to spectacular pristine Lakes and awe inspiring Cascade Mountain Range. Outdoor Wonderland!We are always available for any help with ideas for a Great adventure!"Ohana" is the Hawaiian term for family. It is our guiding principle in how we treat our guests. So, from our "Ohana" to Yours, come Stay, Play and Enjoy a little piece of paradise at "The Cabin". Gay friendly getaway.Guest accessOff street parking for two vehicles is located directly in front of "The Cabin".You may also park on the street beside the driveway if needed.Other things to noteDogs are welcome with a 10$ fee per day. You must bring all bedding for them and up to two dogs are allowed. We will have amenities to clean up after them which is strictly enforced. Cleaning up after your pet is a must or a additional 25$ cleaning fee will be added after your departure. Thank you for taking good care of your dog and our lovely place.About pets:Pets allowed: limit 2 total.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:No parties allowed..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 24.About events:No events allowed.

Stay at one few of the remaining homes in the core of downtown Bend. Enjoy the natural light from vaulted ceilings, charming architectural details, original hardwood floors and paintings by local artist Sheila Dunn. Choose from dozens of restaurants, breweries, coffee and shops within blocks. Cross the alley to food trucks and occasional live music at the historic Lucas House or relax in your private walled courtyard. A beautifully restored 1922 home with plants and warm wood throughout.An inviting home with lovely light, attention to detail, character and the historic charm. that comes with carefully cared for homes of this vintage.The entire house is accessible to guests, with two exceptions: the garage and the loft. The laundry is in the closet, in the front room.We live right down the street and are happy to meet our guests, but more often than not, we let you enjoy your privacy for the entire trip.A mixed urban downtown setting with traditional historical homes converted to businesses. In the evening there is often live music or DJs just across the alley at the Bunk and Brew (most people love it!). Please be aware it can be noisy in the backyard or bedroom but should be wrapped up by 10pm. If it is noisy past 10pm please let us know immediately and we will respond to resolve it.The location is extremely walkable and also has easy access to/from the highway 97 (especially southbound).Live music can be heard from the historic Lucas House next door and can vary from acoustic guitar to rock and karaoke. The music should be wrapped up at 10 pm but often goes a bit late. Note that this is an urban setting and comes with urban sounds. It is also close to the highway.Please use the leather three-ring notebook for all kinds of helpful information.NO PARTIES. Noise monitoring devices and exterior cameras on all entrances are in place. All guests must be included in the reservation. Any unauthorized additional guests will be charged a $100 fee, per additional guest, per night. A guest is considered anyone who enters the property for more than 1 hour. Pets not included in the reservation will incur a $200 charge.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.

Welcome to Your Midtown Bend RetreatExperience a warm, inviting single-level home designed with families and pets in mind. This charming 3BR/1BA getaway in Bend's quiet Midtown has been thoughtfully renovated to blend modern comfort with a clean, bright style that helps everyone—from kids to furry friends—feel right at home.Where You'll Sleep:• King Bedrooms: Two serene bedrooms feature plush king-size beds, offering restful sleep after a day of Bend adventures.• Bunk Room: Perfect for kids, the third bedroom includes a fun twin-over-twin bunk bed and a dedicated desk—great for homework or remote work.Living Area:Gather in the spacious living room, where a wood-burning stove adds cozy charm. Air conditioning keeps you comfortable year-round. Enjoy movie nights, games, or curling up with a book while your pet lounges nearby on the comfortable sectional sofa.Kitchen & Laundry:The fully equipped kitchen makes family meals a breeze, with modern stainless steel appliances and ample counter space. From quick breakfasts to gourmet dinners—coffee is absolutely covered! A stacked washer and dryer add convenience for longer stays.Outdoor Spaces:Step into the fully fenced backyard—a private, safe space for pets and kids to play. Share stories around the fire pit or enjoy a relaxed evening under the stars.Guest Access:You'll have private access to the entire single-level home and fenced backyard. Enjoy the convenience of self check-in upon arrival.The Neighborhood:Nestled in a peaceful residential neighborhood in Bend's desirable Midtown, our home offers the perfect balance of tranquility and convenience. You're just a short walk away from local shops, fantastic restaurants, and popular breweries. Don't be surprised if you spot some local deer wandering through nearby wooded areas, adding a touch of natural charm to your stay!Getting Around:Many of Midtown's best attractions are easily accessible on foot. For exploring the wider Bend area, including the mountains and rivers, having a car is recommended. Parking is available on the property.About Your Hosts:We live just down the street and are available if you need anything during your stay. We're happy to answer questions while respecting your privacy and independence!Please Note:This home is in a peaceful residential neighborhood. Parties, events, and large gatherings are not allowed. For security purposes, exterior security cameras monitor the property. We appreciate your respect for the space and community.Book your stay today and enjoy a comfortable, memorable Bend experience for the whole family (and furry friends)!About pets:Pets allowed: dogs (limit 2 total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Newly renovated home with high-end finishes located just 1.5 miles from Downtown Bend. Well stocked for longer stays, this home can host anyone from a romantic couples retreat to a wedding party of 10 getting ready for a night on the town. The downstairs office/movie room has a projector for streaming and a pullout couch that serves as a 4th bedroom. Enjoy the spa-like master suite to unwind, or head outside to the hot tub for some r&r after your day of skiing, climbing, biking, or hiking!Why stay here?~Master Suite: Robes, Parachute linens, couple's shower, bathroom heater, air purifier, walk in closet, insta-hot water!~Kitchen: Caraway cookware, espresso machine, bakeware, spices, drawer microwave, Keurig with complimentary pods, pantry essentials, Kitchen Aid mixer, instant-pot!~Extra features: 1080p projector with Roku and YouTube TV, hot tub and deck, mood lighting, house plants, central AC and heat!Enjoy this newly renovated home with high-end finishes located just 1.5 miles from Downtown Bend. This 3 bed 2.5 bath can host anyone from a romantic couples retreat to a wedding party getting ready for a night on the town. The downstairs office/movie room has a projector for streaming from your laptops, and a pullout couch that serves as a 4th bedroom. Enjoy the spa-like master suite to unwind, or head outside to the hot tub for some r&r after your day of skiing, climbing, biking, or hiking!This home has 3 bedrooms on the second floor, and an office/movie room on the first floor with a pull out couch that can be used as a 4th bedroom when needed. All beds are queen sized aside from the master which features a king. If there are more than 8 guests booked, we will provide an additional air mattress.The kitchen hosts new stainless steal appliances including a 4-burner oven range, full sized fridge, drawer microwave in the kitchen island, high-efficiency dishwasher, countertop toaster oven, and insta-pot. Kitchen island seating, coffee/liquor bar, and duel sliding trash bins make this kitchen a great place to host large gatherings for all occasions. The master suite is a peaceful retreat with south facing windows and plenty of natural light. The private bathroom with vessel sinks, dual shower-head glass enclosure, powder cabinet, independent heating, and mood lighting make the bathroom feel like you've stepped into a private spa. Corner bedroom on second floor features a queen bed with firm mattress and light airy décor. Middle bedroom has a softer mattress and a warm, earthy vibe.There is a wide driveway in front of the garage that fits up to 3 vehicles. There is also street side parking when needed.*Please note that this home has an attached apartment on the right side of the home. This apartment is typically rented out, but there are no common/shared spaces. Apartment has separate entrance*About pets:Pets allowed: limit 3 total.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking allowed: in designated areas.About events:Events allowed: family gatherings, birthday parties, weddings.Maximum event attendees: 20.

Welcome to Kiesow Retreat, a spacious, luxury-modern home for families, groups, and adventure seekers. Enjoy mountain days, river fun, or cozy nights at home — all just minutes from Downtown Bend, Mt. Bachelor, and Deschutes River, and within walking distance to Riley Ranch Nature Reserve.Whether you’re here for outdoor adventure or relaxation, this home combines space, comfort, and entertainment for everyone.Why Guests Love Staying Here2 King Master Suites – perfect for couples or multi-family tripsPrivate Hot Tub + Fire Pit – relax under the starsEpic Game Room – ping pong, air hockey, arcade games & Nintendo SwitchChef’s Kitchen + Coffee Bar – cook, dine & enjoy morningsPet-Friendly + Fenced Yard – bring the whole familyEV Charger – convenient, worry-free chargingComfortably Sleeps 12Designed for comfort and space:• King Suite #1 – spa-inspired ensuite, Smart TV, luxury linens• King Suite #2 – premium bedding & peaceful retreat• Queen Bedroom – warm, stylish & inviting• Bunk Room – full-over-full bunks, perfect for kids & teens• 4 Full Bathrooms – stocked with plush towels & essentialsCook, Gather & RelaxOpen-concept living made for connection:• Fully equipped chef’s kitchen with stainless steel appliances• Coffee bar with Keurig & drip options• Dining table for 10+• Spacious living room with Smart TV & cozy seating• Outdoor BBQ & covered patio (weather permitting)Entertainment for All AgesWhether you’re relaxing or hosting friends and family:• Game room with ping pong, air hockey, arcade games & Nintendo Switch• Private hot tub for post-adventure relaxation• Fire pit for s’mores & evening hangouts• Fast Wi-Fi & Smart TVs for streaming or remote work• Board games & comfortable gathering spacesPrime Bend LocationEnjoy the best of Bend without the crowds:5–10 minutes to Downtown Bend (breweries, dining & shopping)25 minutes to Mt. Bachelor for skiing & snowboardingWalking distance to Riley Ranch Nature Reserve – scenic trails & wildlifeClose to Deschutes River trails, hiking & bikingEasy access to floating, fishing & outdoor adventuresFamily & Pet FriendlyTravel easy with:• Pack ’n Play, high chair, baby bath & safety gate• Fully fenced yard for pets & safe play• Quiet neighborhood for peaceful eveningsGood to Know• Driveway parking for 2 + free street parking• EV charger (bring your own cable)• No smoking | No parties• Quiet hours: 10 PM – 8 AMYour Bend Home BaseFrom mountain adventures to relaxing evenings in the hot tub, Kiesow Retreat offers the perfect blend of luxury, space, and entertainment for families, groups, and adventure-seekers.Book now and experience Bend in comfort.About pets:Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.

Located in Bend (Southern Crossing), this cottage is within a 15-minute walk of Deschutes River and Old Mill District. This beach cottage is 1.3 mi (2.1 km) from Hayden Homes Amphitheater and 2.2 mi (3.5 km) from Downtown Bend Business Association. Make use of convenient amenities, which include complimentary wireless internet access and barbecue grills. Make yourself comfortable in this air-conditioned cottage, which features a fireplace. There's a private balcony. A kitchen is outfitted with an oven, a stovetop, and a microwave. Conveniences include a dryer and an iron/ironing board.