Holiday rentals in Pilot Butte

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Top-rated holiday rentals in Pilot Butte

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Guest favourite

Guest house in Bend

4.97 out of 5 average rating, 188 reviews

Midtown gem~light+bright~park view~full kitchen

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!

Guest favourite

Flat in Bend

5.0 out of 5 average rating, 174 reviews

The Guest Nest- quiet convenience in Midtown Bend!

Delightful, comfortable, well-lighted, and close to everything. Your are at "nest level" in my upstairs apartment. Come stay, relax, and rest in The Guest Nest! My goal is to provide a welcoming comfortable place for you to stay when you visit Bend! In return, I request that you treat my Guest Nest with care and respect-- just as you'd want guests in your home to do. No dealing with impersonal rental companies. I clean and manage everything myself and do my best to make it perfect for you.

Guest favourite

Guest suite in Bend

4.98 out of 5 average rating, 122 reviews

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!

Guest favourite

Flat in Bend

4.96 out of 5 average rating, 247 reviews

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.

Guest favourite

Flat in Bend

4.89 out of 5 average rating, 331 reviews

Petite Suite: Springtime Charm in Midtown

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.

Guest favourite

Cabin in Bend

4.99 out of 5 average rating, 431 reviews

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. 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 .

Guest favourite

Guest house in Bend

4.95 out of 5 average rating, 158 reviews

The Outpost Bend

The Outpost is a seperate guest home located on our 10 acre hobby farm. It offers spectacular views of the Cascades, stunning sunsets and a peaceful, private location 15 minutes east of downtown Bend. The property adjoins public land, and is on a quiet country road. Our family lives onsite with our 3 sons, dogs, hens, and sheep. The Outpost has a private driveway, use of basketball court, and a lovely private outdoor seating area. 45 min drive to Mt. Bachelor.

Guest favourite

Guest suite in Bend

4.93 out of 5 average rating, 657 reviews

Orchard District Studio

A cozy studio apartment; this converted garage space has tall ceilings making it feel light and airy. Located in Bend's Orchard District, it is walking distance to Hollinshead Park & Pilot Butte. We are NOT within walking distance to downtown, however it is only a 5 minute drive to downtown & 15 minutes to outdoor recreation opportunities. Hosts live in the main house. LGBQT+ BIPOC friendly.

Guest favourite

Guest suite in Bend

4.9 out of 5 average rating, 263 reviews

CLOSE COUNTRY QUARTERS (Hot Tub and Fire Pit)

COUNTRY QUARTERS is a private suite living space for you and your significant other. If you're looking for a quiet getaway after a busy day recreating or exploring, this lovely suite is just 5 miles east on Hwy 20 from Costco. The suite includes a kitchenette, a separate bedroom, and living room with a hot tub, Fire Pit, summertime water feature, and maybe more comforts than home!

Guest favourite

Flat in Bend

4.97 out of 5 average rating, 139 reviews

Villa77-Cozy Bend Getaway

Newly renovated, our airy apartment in Bend's Midtown district was designed to make your stay feel 5 star: Crisp linens, fluffy towels, fresh-ground local coffee brewed your favorite way. Close to Downtown, the old Mill and all of Bend's best shops and eateries. You won't find a more charming place to land after your day of adventure!

Guest favourite

Farm stay in Bend

4.95 out of 5 average rating, 496 reviews

Historic cabin at Anker Farm

This original settlement cabin, built in 1911, was completely restored and renovated in 2015. Our organic farm [search for Anker Farm], is located 10 min east of downtown Bend, and Mt Bachelor is 45 min away. The cabin has a completely fenced yard and we welcome well behaved dogs with open arms, but no cats.

Guest favourite

Guest suite in Bend

4.93 out of 5 average rating, 651 reviews

Home on the BAYOU dr. - fenced yard with fire pit

One BR guest suite with private entrance, separate LR with a mini fridge, microwave, coffee/tea and private fenced yard with fire pit. Located in SE Bend, 3 miles to downtown, and a short drive to hiking and mtn bike trails. Dog friendly..but please see our dog rules below.