Holiday rentals in Bend

LOCATION! WALK DOWNTOWN & OLD MILL - #2

Modern one-bedroom with fully equipped kitchen, washer/dryer in unit and designer touches to make your stay feel like home. Maximum of two guests. Ductless heat/air conditioner for your comfort. Free wi-fi, smart TV with HD cable service. Plenty of off-street parking spaces. A private 5' x 9' locked storage for your kayaks, bikes, clubs, skis, boards. .... NO smoking ... and sorry, no pets. No room tax for stays of 30 days or more. City of Bend Short Term Operating License No. STR-15-0016.

| The Chalet | 1+ acre| Remodeled | Quiet |

Discover tranquility in our A-frame cabin nestled among the pines. A rustic haven where the scent of pine fills the air, inviting you to unwind on the porch. Inside, a cozy living space & quaint kitchen offer comfort. Retreat to the loft bedroom, where the soft glow of morning light through pine branches awaits. Whether a romantic escape or family adventure, this cabin is a sanctuary, a respite from the daily rush. Embrace simplicity, enjoy the peace & quiet, and enjoy all the nearby beauty.

River Ridge Getaway - River Trail & Hot Tub

Our peaceful guest suite with private entrance & pool/hot tub access is in Mt Bachelor Village, nestled in the trees above the scenic Deschutes River trail where you can enjoy walking, jogging, floating, kayaking, SUP, surfing, rock-hounding and fishing. It is one of the best locations in town, just off Century Dr on the way up to Mt Bachelor Ski Resort and within walking distance to the The Old Mill, Hayden Homes Amphitheater and Bend's popular west side. Pool (Jun-Sep) & Hot Tub (10am-9pm)

Quiet Escape: Fireplace, 5min to Downtown & River

Relax on the private balconies overlooking the park. After your coffee take a 2 minute walk down to the Deschutes river trail. Or walk 10 minutes and you're in downtown Bend. After a day of outdoor and ski adventures, you'll love the king size bed or relaxing by the fireplace. You'll have super fast wifi with Netflix, and a Smart TV in each room. Looking to stay longer? Send us a message to talk about long term stays and remote working. Locally owned and operated. Book your stay today!

Location! Bungalow River & Beach Access

Welcome to our 1918 Bungalow on Riverfront Street. This simple, no frills one bedroom, one bath sleeps two to three. Enjoy a fully equipped kitchen, floor to ceiling river rock gas fireplace, inviting front porch, back deck with propane BBQ, table/ chairs. The Bungalow has a peek of the river, as it is considered the "guest house" to the larger "main house" it shares the lot with. Enjoy low bank river access to launch your kayak. Park the car and experience the best Bend has to offer.

Black Duck Cabin

Cozy A frame cabin set in a quiet neighborhood among the pine trees just a short walk from the Deschutes River. The Black Duck Cabin is a perfect destination for all of Central Oregon's amazing activities. 10 minute drive to Sunriver Village, 30 minute drive to Mt. Bachelor, 30 minutes to Downtown Bend, 10 minute walk to the Deschutes River, golfing, fishing, hiking, shopping, mountain biking, all a short drive. If you're looking for a rustic, cabin experience this is the place for you!

Tall Pine Tuckaway! Hot tub, EV charge, RV hookup

Welcome to Tall Pine Tuckaway! This sprawling home sits among the peaceful wooded edge of town yet is just a 10-minute drive to Downtown Bend! Perfect for large families or groups, this home has it all - salt water hot tub, firepit patio, landscaped acreage for kids and pets to play, universal EV charger, two living rooms, dedicated office with lightning-fast 1G wifi, and full RV hookups! Bring your trailer and toys and ride directly onto China Hat Road for some excellent off-roading.

Old Mill Charm

Great Location in Old Mill District – Walk to Summer Concerts! ♥ Fenced Backyard ♥ Pet Friendly Nestled in the heart of Bend, Old Mill Charm offers the perfect blend of comfort and convenience. Thoughtfully designed with many amenities to ensure a seamless stay, this charming rental is ideal for relaxing or exploring all that Bend has to offer. There is a tenant in the apartment above the detached garage who does not use the driveway ensuring your privacy.

Near River Trail - Pet-Free - King - Local Hosts

We take pride in maintaining high standards in this spacious studio—our first Airbnb and still one of our most popular. Guests love the proximity to the Deschutes River Trail, just a 10-minute walk to downtown, and First Street Rapids Park two houses away. Then come home and stretch out on the ultra-comfy king bed. Trust the reviews—they say it best! We maintain a low-allergen environment using unscented products and do not allow pets.

Drake Park Cottage in the Heart of Bend

This location can’t be beat! The cottage is steps away from Drake Park and the river as well as walking distance to downtown. Enjoy summer festivals in the park, floating or stand up paddleboard on the river. Located in the historic parks district, this property is quiet and comfortable yet close to all the action. Guests have been coming back year after year to enjoy this unique vacation spot. It’s a gem! SORRY NO PETS and NO SMOKING.

Close, Cute & Clean! *Hot Tub* Bend Adventure Base

Welcome to your Central Oregon adventure base! Book now to enjoy the convenience and comfort of this centrally located Bend home!! 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. Come settle in for exploration and recreation!!

Larkspur Lodge — Cozy, Private Guest Suite

Formerly known as "Chili Powder Inn," Larkspur Lodge offers a cozy and inviting space to relax and enjoy all Bend has to offer! Located in the Larkspur neighborhood on the quieter side of Bend. A quaint, scenic trail is walking distance from the house. Downtown Bend and the Old Mill shops are minutes away. The entrance is private with convenient key-code access.