Holiday rentals with a fire pit in Bend

Modern retreat in central Bend

Enjoy our new custom-built ADU located a block away from the Deschutes River in a quiet residential neighborhood, just a 10-minute walk from downtown along the River Trail. In this modern, bright, and private space, you'll enjoy the luxuries of hardwood floors, waterfall countertops, a built-in workspace, heated tile bathroom floors, a 55" Smart TV, BBQ and fire pit, and endless hot water—plus off-street parking and EV charger. One king bed, one daybed with a trundle, and one queen sleeper sofa.

Private Apartment, Separate Entrance, Spacious

DCCA License #001537 Welcome to the Garden Sweet, a private apartment adjacent to a residential home. Tuscan style living nestled on a beautiful acre. Private and peaceful, yet just minutes to great local dining, shopping and outdoor recreation. The historic downtown and river are an easy 6 minute drive into the heart of old Bend. Spacious 3 room suite-living makes longer stays comfy! No shared interior spaces. Our extensive gardens, gazebos, grills, firepits are shared and open for guest use!

Cozy Studio! Walk to NW Crossing and Shevlin Park

Cozy, soft decor fill this light, bright studio with a private entrance. Shevlin Park and Phil's Trail are minutes away for hiking, running, and mountain biking. Mt. Bachelor is a short 30 minute drive for skiing in the winter and downhill biking in the summer. Smith Rock is a 45 minute drive for hiking and climbing enthusiasts. Shopping and dining are within walking distance at NW Crossing or a a short drive to the Old Mill or Downtown Bend. Mesh Network Wifi, coffee, tea and snacks provided.

Skyliners Getaway

Our tiny log cabin is a cozy getaway, close to hiking, mountain biking, and cross country skiing but only 10 miles from the amenities of Bend Oregon. It is a rustic place, with modern touches, like a gas range, refrigerator, and a gas fireplace. The bathroom is detached from the cabin - steps from the door. It is fully equipped with plumbing and a shower. Our place is perfect for people who love the outdoors with the comforts of home. No children under the age of 12 -- And alas, No Pets.

Game Room | Hot Tub | Easy 2 Bachelor | Old Mill

Looking for a home away from home while in Bend? This house is not just a place to sleep at night, it’s the perfect place to relax and have fun after your day of adventures. Perfect for both families and groups of friends. The game room is always a huge hit with guests, as is the hot tub. The large kitchen table is perfect for dinner as well as game night. Both TVs have surround sound speakers. Great access Bachelor (25 minutes). Close to Old Mill. Trail to the river right from the backyard.

Quail Park Haven in NW! King Beds & Hot Tub

Relax in this peaceful NW Bend home with king beds and access to Quail Park. Enjoy natural light from the skylights and high ceilings. Kick back in the expansive backyard with mature plantings, tall trees and flagstone paths. Multiple patios including a deck off the living room, a paver patio with fire-pit, hot tub, outdoor furniture and gas BBQ. EV charger, HEPA air filter and garage access. No parties or pets please. Trip insurance recommended if illness, weather or smoke may be an issue.

Welcome to Dome Sweet Dome

Your chance to stay in a true-to-name Geodesic Dome! This one-of-a-kind retreat blends comfort with architectural charm. Guests call it cozy, inspiring, and unforgettable — a stay that feels like an experience, not just a place to sleep. Nestled in the First-on-the-Hill neighborhood off Century Drive, the Dome is perfectly positioned for everything Bend has to offer. Whether you’re here for skiing, biking, hiking, or just relaxing, you’ll love how close you are to Bend’s best adventures.

Villa77: Renovated Stay Near Downtown & Old Mill

Newly renovated and thoughtfully designed, our airy apartment in Bend’s Midtown offers a 5-star experience. Enjoy crisp linens, plush towels, and fresh-ground local coffee brewed just the way you like it. Perfectly located near Downtown, the Old Mill District, and Bend’s best shops and eateries, our apartment is a cozy and stylish retreat. After a day of adventure, unwind in comfort at this charming home base! Owned by locals, this is the perfect launch pad for your Bend adventures!

Have a Patio Barbecue at a Pet-Friendly House in Midtown

Stoke the wood stove with another log and stay warm and cozy in a colorful plant-filled living room with stylish mid-century modern furniture. When the weather's nice, go outside to play croquet or corn toss and roast mores around the fire pit under the stars. Each bedroom has cable TV....large fully fenced in yard . Dogs are welcome. Limit of 3 with a $35.00 Pet fee. No cats allowed. Wood provided. There is a smart lock on the front door, you will be given the code before arrival.

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

Welcome to the perfect basecamp for your Central Oregon adventures! The snow is coming!! Book today for your winter adventure in Bend to enjoy this convenient, comfortable, and centrally located 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!!

Historic Old Bend Cottage & Carriage House Spa

This historic Old Town Bend cottage boasts a relaxing setting for unwinding with a lovely cedar hot tub & sauna in its restored carriage house. Walk to the attractions: 0.2 mi. to the best shops and restaurants, and 0.4 mi. to Mirror Pond & Drake Park! Split heating in each room, snow gear storage, boot warmer, grill, and new washer/dryer. Driveway and extra street parking (free). Fast WiFi and a smart TV. The kitchen is fully stocked, and we look forward to hosting you!

Zen w/ Hot Tub, Office, Yard, Dog Friendly, Park

Welcome to your peaceful Bend basecamp, thoughtfully managed by The Home Co.—a local small business focused on clean, well-functioning homes with easy checkouts. This stylish 2-bedroom, 2-bath home is centrally located near Ponderosa Park and Pilot Butte, with easy access to Downtown, the Old Mill, and the Deschutes River. With a fully fenced yard, dedicated office, hot tub, and flexible living space, it’s perfect for families, remote workers, and pet lovers.