Cottage rentals near Old Mill District

4.93 out of 5 average rating, 299 reviews

NW Bend Hot Tub+Big Porch w/ Enclosed Yard+Pets OK

Located in the heart of NW Bend in the middle of it all! A short walk to great restaurants + pubs, the river, Amphitheater, Downtown, 3 Parks, The Old Mill -but on a nice quiet street. Well worth the price, it sleeps a comfortable 4 and a cozy 6 with a comfty Queen bed in one room, and pine bunk bed in other room (full bed on bottom and top with cozy mattresses). Large enclosed yard for the pets and patio with Hot tub! The home is well stocked, tastefully furnished with high quality bedding.

4.98 out of 5 average rating, 125 reviews

The Tumalo House

The Tumalo House is located just north of Bend and is situated between Tumalo Cider and Bend Cider. Just across the street from The Bite, the local hang out, this fully renovated 1940's farm house offers 2 bedrooms, sofa bed and 1 bath, and outdoor space with a gas fire pit. This cozy find is only steps from the Deschutes river, 30 minutes from Mt. Bachelor and minutes from Downtown Bend and The Shops at the Old Mill. No matter what brings you here, this home will make you want to stay!

4.98 out of 5 average rating, 124 reviews

Immaculate, secluded Downtown Cottage-EV charger

24 time Airbnb "Super Host" award. 2017/2019 Winner of a "Certificate of Excellence" Exceptional 5 Star reviews for all vacation rentals in the Bend area. The Cottage is constantly being updated including new furniture, appliances, paint, and even painting of the cabinets. A new mini split A/C and Heating system will be installed in August, 2025.These significant investments keep the Cottage fresh and like it was brand new. City of Bend Short Term Rental Operating License: STR-20-0285

4.95 out of 5 average rating, 274 reviews

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.

4.99 out of 5 average rating, 137 reviews

Blue Spruce Cottage, 2/1, Modern, & Clean.

This cottage is located in the heart of Midtown - 20 mIn walk downtown & walking minutes from great food/beer/coffee. You will enjoy a very quiet, newer home, with air conditioning & 2 KING tempurpedic beds, tucked under mature Spruce trees. For active guests a hose is available to wash bikes, washer/drier and indoor racks to dry your clothing. A full kitchen and BBQ for meal prep. Garage is secure and available UPON REQUEST. Lastly, wireless internet is super fast, 300mbs.

4.96 out of 5 average rating, 82 reviews

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!

4.87 out of 5 average rating, 450 reviews

Downtown Bend Home - Walk Anywhere - Firepit- Pets

Riverway Cottage is a charming 2BR/1BA pet-friendly home in Old Bend, just 1/2 block from the Deschutes River. Walk to Downtown, Old Mill, river trails, parks, surf wave, and top breweries. Features include a full kitchen, smart TV, fast Wi-Fi, washer/dryer, fenced yard, BBQ, and fire pit. Private driveway, A/C units, and all essentials included. Ideal for families, couples, work trips, skiers, paddlers, and extended stays. Unbeatable location, comfort, and flexibility.

4.95 out of 5 average rating, 438 reviews

Vintage Pink Hot Tub✓ Walkable✓

Our 105 year-old lovingly restored 1920 cottage is 3 blocks from First Street River Rapids, 25 minutes to Bachelor & 10 minute walk to Town. Centrally located urban setting on a main street. Step back in time, the original charm was painstakingly preserved, with original claw foot with shower and bathtub (which requires adequate mobility) and wood floors. Comforts include: Hot Tub, Gas fireplace, Dishwasher, W/D.

4.95 out of 5 average rating, 361 reviews

Adorable West Side Cottage, Pet Friendly!

Enjoy a cozy and comfortable stay in my 1-bedroom, 2-bathroom home, complete with a bonus room that offers plenty of privacy when needed and a plush futon that allows for two additional guests (best for up to 3 adults or 2 adults and 2 kids, or two couples would work as a well ) Conveniently located within walking distance of Newport Market, Backporch Coffee, Chow, and Spork, it's just five blocks from downtown

4.97 out of 5 average rating, 158 reviews

Cottage in Sunriver

Cozy Home w/River Access, Hot Tub, 7min to Village

Welcome to our Backcountry Basecamp Cottage! Nestled in the heart of the Deschutes National Forest. Our home is a short walk from the crystal-clear waters of the Deschutes River, which you can access through a private neighborhood marina. You can enjoy hiking, floating, kayaking, or skiing and snowshoeing nearby. It is the perfect base camp for exploring all that the area has to offer.

4.99 out of 5 average rating, 122 reviews

Riverfront Cottage epic walkable location on river

Truly one of the best riverfront homes in Bend! This luxury 2 bed, 2 bath cottage sits directly on the Deschutes River with a fenced yard, deck, gazebo, fire pit, kayaks, paddleboards, bikes, and more. Walk to downtown, Old Mill, and Galveston Ave breweries. Pet-friendly, fully updated, and made for cozy, upscale stays. Relax, explore, and enjoy Bend like a local — right on the river.