Pet-friendly holiday rentals in Bend

Midtown Gem With Cozy Fire and Park Views

Above garage one bedroom/one bath apartment in booming midtown. Open living with a gas fireplace, ac, full-sized kitchen, and gas stove. A large bathroom with a deep tub to relax or let the kids play. The bedroom features a cozy queen bed with a new Tempur-Pedic mattress topper and ample closet space. The east-facing deck is ready to sip your morning coffee while you wake up slowly, grill for an evening in or sit and work with the high-speed wireless as you watch the dog park across the street!

Laverne - Historic Home in Downtown (new hot tub!)

Laverne is a one bedroom historic cottage tucked in between two larger houses, with access from both Georgia Ave and Lava Road. Unique for it's proximity to downtown AND the peaceful residential feel. Mature landscaping with heritage cherry tree, private and sheltered bungalow. Outdoor space includes private deck and hot tub with views; small enclosed front yard. Full kitchen, washer/dryer. Queen Casper in the tiny bedroom. Sleeper sofa in living room. Great natural light. Off street parking.

DogOk. Large Retreat, 3 King Beds. Fire pit

3 Bedroom/2.5 Bath House with King Beds in All bedrooms + Private Den/Office with Queen Bed. Open floor plan downstairs with large kitchen, great room (with fireplace), dining room, and 1/2 bath. Fenced in back yard with large Gas Fire Pit, Outdoor Grill/BBQ area, and plenty of room to relax after exploring Bend. Convenient East Side location, 5 min drive to downtown Bend. Very close/easy walking distance to grocery stores, restaurants, coffee shops, and two very popular food truck lots.

Contemporary Chic, Walk Downtown, Gourmet Kitchen

Featuring classic cottage charm with a contemporary modern twist, The Modern Mill Cottage perfectly embodies the spirit of Bend. This charming two bedroom, one bathroom vacation home is ideal for those Bend explorers who wish to be in the heart of it all. This house is located on a vibrant and eclectic street, situated just two blocks from downtown Bend. You are just a short stroll to all the superb dining, infamous breweries, art galleries, and festivals that make our town so unique.

Downtown with hot tub and fenced-in yard

Light and bright downtown Bend vacation cottage with a landscaped, fenced yard and HOT TUB. Walk to breweries, restaurants, coffee shops , art galleries and the Deschutes river and river trail. One-bedroom, one-bath unit features a separate memory foam queen hide-a-bed in the living room. Private laundry room. Private parking spaces in back. Open floor plan with vaulted ceilings and automated skylight shades. Complete remodel. Pet-friendly (must add pet to the reservation).

Sixties Suite Spot

Escape to our cozy, retro suite, a serene haven centrally located near Pine Nursery Park. Enjoy a tranquil retreat with high-quality amenities, dog-friendly comforts, and snowboard/ski storage. With a semi-private yard featuring Adirondack chairs, easy parking, and a vibrant, photo-ready design, it's perfect for relaxation and adventure. We proudly welcome 2SLGBTQIA+ guests, offering a warm, inclusive environment. Discover a blend of charm and convenience at our unique getaway!

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!

Charming Millhouse w/ hot tub close to everything

Unveil Bend's charm at our centrally located 1945 mill cottage – the adventure nexus! Walk to top restaurants, a grocery store, and embrace the Old Mill District, or catch a Bend Elks game. Deschutes River, and Hayden Homes Amphitheater just a short bike ride or walk away. Conquer Mt. Bachelor in a scenic 30-min drive. Your ultimate Bend basecamp beckons! No pet fee!! No chore list at checkout!! Ski, golf, hike, climb, shop, dine, float .... It's all here

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.

Gorgeous Condo With River View - Pool and Hot Tub

Condo 309/310 is a stunningly remodeled condo here at Bend Riverside Rentals, which we have named 'Deschutes Trail Mix." This condo went through an extensive head to toe remodel and is now ready to host travelers! It can sleep up to six guests, has a full kitchen, two full bathrooms, a washer and dryer, a private patio and comes with access to our indoor heated pool and hot tub! This condo is also pet friendly! Bring up to two pets for an additional fee.

MCM Home in Bend - 5 min from Downtown

Welcome to our home in Bend, OR! Our cozy, newly renovated midcentury modern home is centrally located in charming Midtown Bend. Enjoy a bonfire in the backyard, or relax after a day on the mountain in the elevated living area. Take a stroll with your pup down to Hollinshead Park to enjoy the trees and beauty of the neighborhoods. We are conveniently located: 5 Minutes to Downtown Bend 7 Minutes to Old Mill District 35 Minutes to Mt. Bachelor

Luxury View Condo - Mt Bachelor, Amphitheater

Luxury condo with fast WiFi - a perfect jumping off place for your summer escape. Stunning views of the Cascade Mountains. 21 miles to Mt Bachelor for hiking, mountain biking, or river fun. Easy walking distance to the Deschutes, the Amphitheater, Old Mill + downtown. Secure garage parking for your car and gear. Relax on the deck in the sun after a day outside or working remotely. Watch the sun set over the mountains. That’s pure heaven