Holiday rentals with outdoor seating in Bend

4.88 out of 5 average rating, 351 reviews

House on the Hill. West Hills Sleeps 8, dog OK!

Bends Best Westside Location! Dog friendly! Gorgeous private four bedrooms, three full baths. Sleeps ten! Relax in our private Saline Hot Tub. Huge luxury open floor plan and outdoor space. Two minutes to Newport Market and fabulous restaurants. Enjoy our large gourmet open kitchen, rap-around bar, living room, fireplace, and dining room for your family and friends. Huge extra family room with ping pong table. Newly Renovated! Super Comfy beds and pillows! Close to Mt.Bachelor Ski Resort.

4.94 out of 5 average rating, 118 reviews

Halley St Haven in Bend

Two story house in a quiet neighborhood with large back yard (with grill), table tennis, and games for all ages. There's room to roam with 3 bedrooms, a large bonus room with 2 futon sofa-beds, and parking for 5 cars. Well-stocked kitchen and cleaned professionally after each stay. Excellent choice for up to 2 families or 3 couples! Close to recreational activities and amenities: 10 minute walk to the Deschutes river trails, 5 minute drive to Old Mill and 15 minute drive to Mt Bachelor.

4.99 out of 5 average rating, 103 reviews

Guest house in Bend

NEW Tranquil Retreat On Canal

Charming, clean, comfortable, fully renovated guest house on 3 acres, nestled by a canal. A quiet escape near Pine Nursery Park, just 5 miles from downtown and less than 20 minutes from the airport. Enjoy beautiful natural light, vaulted ceilings, large bathtub, and balcony with outdoor seating and a beautiful view. Fully stocked kitchen, washer & dryer, heat & AC, blackout shades, board games, books, amenities for kids, smart TV, and a Blu-ray player for rentals from The Last Blockbuster.

5 out of 5 average rating, 252 reviews

Mountain Bliss: Gateway to Mt. Bachelor and More

When the mountains are calling, Bend is like nothing on earth. Savor the charms of Base Camp throughout the year in this luxurious and spacious cabin (1200 square feet). Celebrate the great outdoors – best experienced through unparalleled adventures at Mt. Bachelor (18 miles), Phil’s trailhead (15 minutes), the Deschutes River (5 minutes) as well as the endless access to hiking, biking, running trails, skiing, golf, breweries, restaurants, coffee shops, and the Hayden Homes Amphitheater.

4.99 out of 5 average rating, 234 reviews

Perfect walkable location, the best Bend Bungalow

The Kingston Bungalow will provide you with a truly authentic Bend experience. Walk to some of the best restaurants, pubs and markets in Bend. Stroll across the river to downtown Bend or use the cruiser bikes and ride to the Old Mill, Drake park or the river wave at McKay park. This home offers easy access to Mount Bachelor and Phil's Trail and many beautiful hikes, river paddles or x-country ski trails. End your day with a soak in the hot tub or cozy up by the fireplace or gas fire pit.

4.99 out of 5 average rating, 269 reviews

Cabin in Sunriver

Sunriver Oasis : Hot Tub,Good Dogs-Ok, SHARC&Bikes

Summer in SunRiver now-Soak in Hot tub -7 nights 10% off-Unwind & Bike, Hike, Ski, Explore, Swim, Stargaze or Netflix on 65”smart TV-Sip cocktails by GAS fireplace & play games. Fun great room for family night. Golf course views. Slumber on 2 king beds or bunk beds Separation of space-privacy w bedrooms DOWNSTAIRS. Play with kids or dog in backyard (non fenced) New Carpet/Paint New A/C HotTub/Wifi & Netflix FoosBall table/Corn hole 8 Bikes 8 swim passes SEASONAL PRICING NO SMOKING

4.92 out of 5 average rating, 123 reviews

Cabin in Sunriver

Modern Cabin Oasis Near Village

Huge April discounts ! Hip cabin centrally located on par 3, off circle 1. Play room with New hot tub. Backyard walking trail and 10 min walk to the village and SHARC. Playroom with toys and electric charging station. Sleeps 8 comes with 5 bikes garage space for kayaks. 8 SHARC passes. Center of all Sunriver action. Its small in the rooms but the common areas are large. The trail in the back gives a feel you are in the center of all the action! It has everything you need in Sunriver.

4.94 out of 5 average rating, 205 reviews

Stunning Mid Century Home by Old Mill, BBQ

Located within a small friendly neighborhood down a private St is this cherished home where each item has been carefully selected and lovingly woven into the gorgeously designed interior. The home features bright, sun-filled living with 4 spacious bedrooms, a gourmet kitchen, a game room/office and a paved patio with a BBQ and fire pit. You’ll be tucked away from the noise of the city yet only mins to Bend's Old Mill, Deschutes River, hiking/bike trails, parks, Mt. Bachelor and more

Superhost

Cabin in La Pine

4.82 out of 5 average rating, 107 reviews

5BR Homestead Entire Lodge / Cabin

Great for small groups. NOT 12 BEDS; Sleeps 12 max with accessory beds. 3800 sq ft, 5 BR, 6 BA, 2 Kitchens, 2 Great rooms and dining areas. Bedrooms each have private entrance, baths & kitchenettes. See floor plan picture with bed arrangements (2 King, 4 Queen, and 5 accessory beds.) Radiant and accessory heat. Outdoor hot tub. Wi-Fi, cable TV. Propane BBQs. 1+ acre. Near fine dining &/or groceries. No parties. Quiet, rural residential subdivision. Dog-friendly for $15/dog/nt, max 2.

4.97 out of 5 average rating, 101 reviews

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).

Superhost

4.83 out of 5 average rating, 201 reviews

Newport Ave Downtown House

Walking distance to the best bend has to offer. River access is right down the street. Downtown just a quick walk out of the front door. Enjoy all Central Oregon has to offer with tons of breweries, local shops and excellent food. Mt Bachelor, waterfalls and numerous lakes all within a half hour drive. Amphitheater is a quick five minute drive away. Large spacious yard to enjoy time with pet or family. Relax and unwind at the days end through the garden path to the hot tub.