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Holiday houses in Bend

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Top-rated holiday rentals in Bend

Guests agree: these stays are highly rated for location, cleanliness and more.

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Bungalow in Old Bend

4.92 out of 5 average rating, 215 reviews

Broadway Bungalow Retreat - 243

Welcome to 243 NW Broadway, a one-bedroom bungalow in the heart of downtown Bend. 243 is the southern unit in a historic triplex with private front and back door access. Full kitchen, king bed (with upgraded 2022 Casper mattress, high thread 100% cotton linen), peaceful sitting room, claw-foot tub, and off street parking. Gas fireplace, Central heat and A/C. Comfortable, private location for Bend exploration. Outdoor space includes large shared backyard with bistro seating and gas grill.

6–13 May

$290 NZD per night

Guest favourite

Apartment in Bend

4.95 out of 5 average rating, 242 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.

28 May – 4 Jun

$235 NZD per night

Guest favourite

Apartment in Bend

4.89 out of 5 average rating, 328 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.

1–8 Apr

$175 NZD per night

Guest favourite

Guesthouse in Bend

4.93 out of 5 average rating, 136 reviews

Private Studio w/ Hot Tub near the Deschutes River

The Fresca Studio has a kitchenette, hot tub, BBQ & bikes. Downtown Bend is a few miles away, McKay cottage, Deschutes River Trail & Sawyer park are a short walk, and all things Bend eat, drink, biking, hiking, skiing are all close by. The studio is separate from the main house w/ a private entry & patio, fully furnished, and easy access to/from the highway and parkway. Not suitable for children under 5y/o, 2 guests only and children are considered guests. No pets. See you soon!

9–14 Jun

$278 NZD per night

Guest favourite

Guest suite in Bend

4.92 out of 5 average rating, 114 reviews

Cozy Queen, Private Bathroom and Entryway

Peaceful, intimate bedroom (outfitted like and referred to as a “studio”) with a generously sized bathroom. Facing a large, sunny community space, enjoy amenities like a coffee maker, heated bathroom floors, log bed, AC and PRIVACY. Experience a welcoming atmosphere, making it effortless for you to focus on what truly matters—creating cherished memories during your stay. This studio features WiFi, washer/dryer, kitchen essentials, TV with streaming, and self-check in.

19–26 Nov

$194 NZD per night

Guest favourite

Cabin in Bend

4.99 out of 5 average rating, 430 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 .

11–18 Nov

$178 NZD per night

Guest favourite

Tiny home in Bend

4.95 out of 5 average rating, 106 reviews

The Sunset Bungalow, cozy, private and sweet.

Come join us for a boutique experience in this one-of-a-kind Bungalow above the high desert! Warm, cozy and private. It's centrally located just 25 minutes from the world renowned Smith Rock and 15 minutes from downtown Bend. The bungalow is peaceful and private, nestled beneath old growth Junipers, surrounded by gardens and a rustic countryside feel, with private bathroom and kitchenette. Includes complimentary organic coffee and lava rock filtered water!

16–23 Oct

$222 NZD per night

Guest favourite

Guest suite in Bend

4.9 out of 5 average rating, 262 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!

3–10 Mar

$193 NZD per night

Guest favourite

Apartment in Bend

4.96 out of 5 average rating, 112 reviews

WALK DOWNTOWN & OLD MILL-1 BLOCK TO THE RIVER-#1

Perfect property for extended stay needs or a few nights visiting in Bend. Bring your toys! A private 5' x 9' locked storage area for your kayaks, bikes, clubs, skis, boards. . ... NO smoking and sorry, no pets. Discounts for extended stays in off season. No room tax for stays of 30 days or more. City of Bend permit and Short Term Operating License No. STR-15-0016

26 Mar – 2 Apr

$212 NZD per night

Guest favourite

Cabin in Old Bend

4.9 out of 5 average rating, 374 reviews

Mill Cabin at Deschutes Dunes River/ beach access

This Mill Cabin is located in one of the most central, westside Bend neighborhoods along the Deschutes River. The modest, no frills two bedroom 1918 cabin was home to some of Bend’s earliest mill workers. It features a rustic theme and most of the basic stuff you'll need for a great stay. The main highlight is LOCATION, the fabulous yard and direct river access.

10–17 Apr

$274 NZD per night

Tiny home in Bend

4.86 out of 5 average rating, 399 reviews

The Garden Airstream no pet fee

Have you ever wanted to stay in an airstream? Have you ever wanted to stay in an airstream in a garden?!? Well we have you covered! Come stay in our newly renovated airstream surrounded by flower beds. Enjoy a little piece of farm life only a few minutes away from all of Bend's wealth of nature activities and charming town vibes, and we're pet friendly also.

12–19 Dec

$195 NZD per night

Guest favourite

Apartment in Bend

4.97 out of 5 average rating, 137 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!

18–25 Oct

$265 NZD per night

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Bend holiday rentals

Free parking on premises

Air conditioning

Stay near Bend's top sights

Old Mill District292 locals recommend

BLOCKBUSTER15 locals recommend

McMenamins158 locals recommend

Pine Nursery Park41 locals recommend

Sawyer Park11 locals recommend

Walmart Supercenter15 locals recommend

Other great holiday rentals in Bend

Guest favourite

Guest suite in Bend

4.9 out of 5 average rating, 134 reviews

New Modern and Cozy Private Studio In The Woods

22–29 Jul

$179 NZD per night

Guest favourite

Guest suite in Bend

4.99 out of 5 average rating, 300 reviews

Old Mill Studio, Walk to Concerts, River, dining!

6–13 Oct

$255 NZD per night

Guest favourite

Bungalow in Bend

4.9 out of 5 average rating, 146 reviews

West Side Bungalow, Hot Tub, One Block to River

6–13 Dec

$300 NZD per night

Guest favourite

Guesthouse in Bend

4.96 out of 5 average rating, 700 reviews

A Couples Getaway in Old NW Bend

13–20 Jan

$255 NZD per night

Guest favourite

Condo in Sunriver

4.91 out of 5 average rating, 180 reviews

Cozy Condo-Pool/Hot Tub. Minutes from Mt Bachelor

30 Jan – 6 Feb

$180 NZD per night

Guest favourite

Guest suite in Bend

4.98 out of 5 average rating, 167 reviews

Good Life Apartment

31 Mar – 7 Apr

$232 NZD per night

Guest favourite

Guesthouse in Bend

4.98 out of 5 average rating, 502 reviews

Live the Pastoral Idyll in a Warm and Inviting Guesthouse

15–22 Feb

$248 NZD per night

Guest favourite

Guest suite in Bend

4.9 out of 5 average rating, 289 reviews

Cozy Studio! Walk to NW Crossing and Shevlin Park

27 Aug – 3 Sep

$209 NZD per night

Quick stats about holiday rentals in Bend

Total rentals
2K properties
Rentals with dedicated workspaces
1.2K properties have a dedicated workspace
Rentals with a pool
350 properties have a pool
Pet-friendly rentals
790 properties allow pets
Family-friendly rentals
1.2K properties are a good fit for families
Total number of reviews
134K reviews

Destinations to explore