Holiday rentals in Pilot Butte

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!

The Blackberry Cottage

This adorable 1950's cottage is located in the heart of Midtown Bend, within walking distance to local coffee shops, restaurants, parks and Pilot Butte State Park, and less than a mile away from downtown Bend. Two light-filled bedrooms both have double French doors leading out to a large back deck and a fenced, private backyard. A cozy living room, and eat in kitchen make this home the perfect place for a small family or a few friends to share. Serene fenced back yard space with hot tub.

Midtown Getaway- Private entrance and bathroom!

Just over 2 miles from downtown. This is a private room attached to our house with a separate entrance. The room has a double bed, full private bathroom, closet space, a kitchenette, and seasonal access to the outside deck and hammock. Includes heating and cooling controls, a mini-fridge/freezer, microwave, coffee maker, cups, plates, and utensils. Coffee, tea, snacks, ice provided. Great for late night arrivals or early departures! The space is quaint- room & bathroom- 185 sq. ft. total

Bend, Oregon Private Suite; Perfect for 1 or 2

Hey there! Welcome to our place in beautiful Bend, OR! We absolutely love, love, love that we can offer a soft place to land after a day of adventuring in and around our awesome town! This is your spot if you are the order-in and snuggle-up kind; the get up, caffeine-up, and go kind; &/or the mid-day siesta kind. We have had tons of fun focusing on the details that will make your stay blissful and relaxing. From coffee options to Netflix, we've got your basics dialed so you can do you!

*Private Entrance & Deck* 10 min to Downtown Bend!

This tranquil room is sealed off from the main house and comes with a private deck entrance and all the amenities you need to enjoy Bend. 10 min drive/20 min bike ride to downtown. The room boasts an ensuite bath with 2 separate sinks and shower. Large walk-in closet as well. Large screen Smart TV on swivel mount comes with Netflix. Small dining area includes mini fridge, Nespresso machine, toaster, and microwave. Quiet neighborhood close to local dog parks and Pilot Butte state park.

Petite Suite: Midtown Warm & Welcoming This Winter

Welcome to our charming suite in the heart of midtown Bend, just 5 blocks from the beautiful Pilot Butte and only 5 minutes from downtown. Our studio apartment is the perfect choice for those looking for a comfortable and convenient home base for their Bend adventures. The location is ideal for exploring all that Bend has to offer. Take a hike on Pilot Butte, or stroll through the charming streets of downtown. You'll find plenty of shops, restaurants, and cafes nearby to enjoy.

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!

Larkspur Garden Guesthouse

Located in Bend's Midtown and with access to the Larkspur trail that leads to iconic Pilot Butte, this bright, newly built 450 sq. foot apartment balances cozy and modern elements to make your stay in Bend comfortable. Equipped with a full kitchen, a separate room with a queen bed, a deep, relaxing tub, a sofa that converts into a memory foam queen bed, a TV with access to Netflix, and a separate laundry room. Our space is a great option for 2 guests, but it can fit up to 4.

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!

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

Curated Comfort | Quiet, Clean, Beautiful Design

We built this home out of a passion for creating welcoming spaces. Years ago, we renovated a motel on the coast - an experience that sparked our love of hospitality and shapes how we host today. We live around the corner with our kids, a golden retriever, and a few cats. Mike’s a local realtor, and Betsy manages business ops for Bend Fire & Rescue. We love books, music, and helping you discover the best of Bend - trails, eats, and community.

Villa75: Perfect Midtown Location w/ Cozy Fire Pit

Experience Bend like a local! This newly renovated, beautifully landscaped apartment in Midtown offers a 5-star stay with crisp linens, fresh-ground local coffee, and a cozy backyard fire pit. Walk to the best coffee, tacos, bagels, and bakeries, or explore downtown just minutes away. Owned by Bend locals, we’re here to share insider tips to make your stay unforgettable. The perfect launch pad for your Bend adventures!